50 fun things to do this winter in Chicago!

Chicago is a wonderful city with endless opportunities for entertainment and recreation (and I am not just saying this as a native!). The Windy City’s world-class museums, cultural attractions, and amazing architecture are the standouts of this great city. Unfortunately, many tourists never consider visiting the city outside of the summer season due to the frigid temps and frequent snowstorms. I was just in the city for the record breaking 2025 Thanksgiving storm where the city saw a foot of rare early snow. Heavy snow is not the norm in December and most of the time you will just need to bundle up.

While I love the summer scene (especially the beautiful lakefront path, free concerts, and beaches), many of the best attractions are located indoors. And, in my opinion, the festive outdoor attractions are worth braving the cold, bundled up of course! Growing up in the Chicagoland area, I always preferred the winter months as most tourists were long gone. I love ice skating and attending all the fun & festive winter events. After visiting other great cities like Philly and NYC during the cold months, I have to say “Sweet Home Chicago” is still number one for me.

Honestly, you are missing out if a winter vacation has never crossed your mind! As a local of 20+ years and now a frequent visitor, I have come up with my favorite things to do over the long and frigid winter months. This season can be long and tiresome, so it helps to have some fun events and activities to look forward to. Benefits of visiting this time of year include a quieter atmosphere with fewer crowds and more local charm, plus discounted hotels and attractions, and lots of special Christmas events. I have included a mix of popular tourist attractions plus a few hidden gems. Enjoy!

1. Visit The Art Institute

The Art Institute of Chicago is one of the world’s best art museums. The impressive collection include a number of iconic works including: A Sunday on La Grande Jatte, a self portrait of Van Gogh, American Gothic, and Nighthawks. Visiting any time of the year is a once in a lifetime experience, however, visiting during the holiday season is even more special. The beautiful lions out front wear festive wreaths for the “Annual Wreathing of the Lions” event. This event takes place the day after Thanksgiving: 2025 marks the 30th anniversary.

Special holiday displays (Neapolitan Crèche), festive decor, and choir performances add an extra festive touch during the season. On a budget? Visit Thursday nights for free admission (5-8pm for Illinois residents).

• Address: 111 S. Michigan Avenue
• Admission: $32 per adult, $26 for seniors and teens, $14 for children under 14
• Discounts: Visit Thursday nights for free (5-8pm) for Illinois residents

2. Ice skate in Millennium Park

Ice skating at the McCormick Tribune Rink at Millennium Park is one of my favorite winter activities in the city. There is nothing better then heading downtown on a brisk, snowy winter day, and taking in the spectacular city architecture while skating along to holiday music. I love how you can see the gorgeous Cloud Gate reflective sculpture while you are skating. I also love skating here at night – it’s super festive with the city tree in the background (see my cover photo).

This is one of the few city rinks I’ve ever seen offering free admission (your only cost outside of holiday periods will be skate rentals, unless you own a pair). Bonus – free skating lessons are offered weekend mornings. I would love to take one of these lessons one of these days! Snacks, coffee, and hot cocoa available for purchase. Best of all, I love that you can walk to many of the best holiday activities from here including Macy’s on State Street and Christkindlmarket.

• Address: 55 N. Michigan Avenue
• Admission: $17 with skate rentals. Online reservations required.
• Discounts: Free with your own skates (Mon-Thurs and the first session on weekends, $5 otherwise)

3. Take a stroll down Michigan Avenue

Michigan Avenue is home to the world famous Magnificent Mile shopping district. There are so many great shops and restaurants, plus lovely holiday decorations this time of year. I recommend a stop at Water Tower Place, an upscale 8 floor shopping center located at 835 N. Michigan Ave.

Dining options on this famous street include everything from fancy steakhouses and Italian restaurants to casual gems like Frankie’s by the Slice. Shopping includes a mix of luxury shops like Bvlgari and Gucci to casual sports shops like the Cubs and Blackhawks team store. I love stopping by Fannie Mae for their amazing mint meltaways and foil wrapped chocolates. On a side note, there is a large American Girl store that is super popular with tourists (I see so many tourists carrying multiple bags on any visit).

Also, if you are in town, be sure to check out the Magnificent Mile Holiday Lights Festival, which takes place every November. This popular, festive event include many activities: a parade, concerts, and a fireworks show over the Chicago River.

Address: N. Michigan Avenue

4. Experience an authentic Italian dinner at The Rosebud

A winter visit to the city would not be complete for me without a delicious Italian dinner at my favorite restaurant, The Rosebud. My dad introduced this restaurant to me many years ago and I return frequently on any trip back home. This upscale restaurant located in the Little Italy neighborhood features a spectacular menu, a romantic setting, and impeccable service.

Try the Cheese Ravioli or Chicken Parmesan for a real treat. Also, they are known for their lasagna (I wish they offered a vegetarian version, but my dad loves it!). On an interesting side note, this charming restaurant was Frank Sinatra’s favorite: imagine that!

Address: 1500 W. Taylor Street

5. Be amazed at Lincoln Park ZooLights Festival

Take advantage of this festive display of over 2 million lights, held annually each year at beautiful Lincoln Park Zoo. This free event features multiple themed holiday activities including ice carving demonstrations, carolers, and a synchronized music and light show. The ice carvings are absolutely fantastic; these artists really have a unique talent. I could watch them carve all day.

Strolling is the perfect holiday and date night activity: sipping a hot cocoa in hand while taking in the wonder of all the dazzling lights is really one of the best things to do in the city in December. While I prefer Brookfield Zoo by day, I prefer Lincoln’s colorful light display.

• Pricing: Admission now ranges from $7-12. Mondays are free with reservation. Tickets released a week prior at 11am.
• Dates: Late November – early January
• Address: 2001 N. Clark Street

6. Visit the spectacular dinosaur & mummy exhibits at The Field Museum

Most of you have probably heard about the famous Field Museum. Reading about this museum is much different than actually seeing the incredible dinosaur fossils in person. Most impressive, this museum is home to “Sue,” the most complete T-Rex fossil at ~90%. I recommend a break from shopping in the cold, brisk air to tour this incredible museum. I also love the Inside Egypt exhibit which features an incredible burial chamber.

If you plan on visiting The Field & the Shedd, along with other Chicago museums and attractions, you should definitely look into a combined attraction discount from CityPass. Fortunately, I visited these museums a lot as a kid thanks to the Public Library’s wonderful free pass check out program offered to city locals.

• Address: 1400 S. Lakeshore Drive
• Pricing: $30 for nonresidents, $21 for residents
• Discounts: Free for Illinois residents on Wednesdays

7. Dine at The Walnut Room

For years, I have wanted to dine at this beautiful restaurant located at Macy’s on State Street. We lucked out for the 2025 season thanks to a last minute reservation cancellation (we joined the waiting list over a month in advance). This longtime favorite opened way back in 1907 on the seventh floor of Macy’s. It was the first restaurant to open in a department store which is pretty cool.

Historical significance aside, everyone wants a reservation here during the holiday season. Seats are extremely hard to get and you need to reserve your spot right after reservations open to the public sometime in late September. The highlight here is dining alongside a gorgeous 45 foot Christmas tree (known as The Great Tree). The theme changes yearly but we were lucky enough to visit for the 2025 season where they featured an incredible Marshall Field’s theme. As a Chicago native, it will always be Marshall Field’s to me so this was a special trip down nostalgia lane. I love that they recently renamed the restaurant the Marshall Field’s Walnut Room.

As for the food, it’s surprisingly decent. They are known for their signature pot pie, but I went with the mushroom ravioli and have to say, I was impressed. Even better is their decadent Fannie Mae cheesecake which is very worthy of the $10 price tag.

• Address: 111 N. State Street
• Reservations: Required to see the tree. They open in late September
• Tree lighting: November 1st
• Decorations: November 1st – January 11th

8. Visit the Wild Reef Exhibit at the Shedd Aquarium

The famous aquarium known as the Shedd is one of the top tourist attractions downtown. I’ve visited many top notch aquariums and this is still my favorite. Being a Chicago native, I went through the hassle of attempting to get a free pass for this one at the library every summer (it was never available!). You will see all sorts of marine life, but best of all is the gorgeous lakeside location.

Over 25,000 animals call the Shedd home. The Wild Reef is a spectacular exhibit, which features numerous varieties of sharks. The exhilarating feel of getting so close to the sharks can’t be topped. Also you will get to see 8 beluga whales which is pretty cool as only a few US aquariums house whales.

The museum is in a great location, and thus, there is plenty to do before or after your visit. You can learn more about the Museum Campus by visiting the official city website.

• Address: 1200 S. Lakeshore Drive
• Pricing: $20 for Chicago residents. Nonresident pricing ranges from $38-42 depending on the date
• Discounts: You can get discounts by booking in advance and visiting outside of peak season

9. See a show

The historic Chicago Theater (est in 1921) is conveniently located in the center of all the action on State Street. Today, this is a great place to see a comedy show or music event. The Oriental and Cadillac Palace Theater are the top spots in the city for catching a Broadway production. These beautiful theaters offer a number of holiday productions. Past productions have included Elf The Musical and Rudolph the Red Nosed Reindeer: The Musical. I was lucky enough to see Wicked year a few years back.

Update: The Oriental, which opened in 1926, is now the James M. Nederlander Theatre. Upcoming winter 2025 productions include: The Neil Diamond Musical, Elf the Musical, and A Magical Cirque Christmas.

Address: 175 N. State Street (Chicago Theater) 24 (Oriental) & 151 (Cadillac) W. Randolph Street

Upcoming Broadway productions

10. Cheer on the Chicago Bulls

The 1990’s era Bulls were so dynamic that they helped to popularize the sport throughout the world. With 6 NBA championships led by Jordan, nothing will ever compare. One of my fondest childhood memories was attending the 1998 Bulls Championship Rally in Grant Park. I’ve been to several Bulls games during the height of their popularity which I’ll never forget.

While nothing compares to the Jordan era, attending a game is a fun way to beat the cold for a few hours. With games running several times a week, from October-April, you should have no problem fitting one into your itinerary!

Mike is a huge fan of the Bulls, Jordan, and basketball in general (he even played in college for a few years). He was quick to get his picture next to this Jordan photo opp at the Willis Tower. You can enjoy a tour through the city’s sports history at the Willis Tower interactive museum. I really loved all the nostalgic photo opps here!

• Address: 1901 W. Madison Street
• NBA season: October – April
• Visit the Bulls website for times and ticket prices

11. See the Chicago River dyed green

It took me forever, but I finally made it out to the iconic downtown St. Patrick’s Day festival. I grew up attending the fun (but totally crazy) southside Irish parade in Beverly. I always wanted to see the dyeing of the river green in person, but somehow never made it. This was a really cool experience, and as someone who loves everything shamrock, I would definitely plan a return visit.

This tradition started way back in 1962 and continues to draw tourists from all over. Whether you are Irish, love St. Pat’s days festivals, or you are simply looking for something fun to do in March (when the weather can still be wacky), I totally recommend putting this one on your bucket list. There is also the long running city parade and tons of local Irish pubs to enjoy afterwards. You can read more about my experience attending this amazing festival for full details.

12. Enjoy amazing views from one of the world’s tallest buildings

The iconic Skydeck at the Willis Tower (it will always be Sears to us locals!) offers amazing views from 1353 feet in the air. For a long time, the Sears was the tallest building in the world. Sears claimed the title for 25 years (after opening in 1972). Today, Burj Khalifa takes the title at a whopping 2716 feet!

The views are truly amazing, especially from the glass ledge look out. The wait can be so long, but really worth it for the incredible views and photo opportunities. You will see guests doing many crazy poses on the glass – be creative and think of something totally unique for the perfect city photo memento! I really loved the entire experience – I only wish I would have planned a visit sooner. It’s super pricey, but worth it in my opinion.

According to the Willis website, the glass you will stand upon (that is if you are not afraid of heights) is only 1.5 inches thick! Although a bit scary, it’s really cool to be able to look beneath your feet at the city hustle and bustle 103 floors below!

Ferris Bueller‘s Day Off fans take note – you can take your pic at the exact same windows that Ferris, Cameron, and Sloane stuck their head against. “In the word of Ferris: “Anything is peaceful from one thousand, three hundred, and fifty-three feet.” You can read more about my experience and see more pics on my Skydeck post.

• Address: 233 S Wacker Drive
• Pricing: Adult tickets start at $32, children start at $24

13. See It’s a Wonderful Life at Hollywood Blvd/Palms

Hollywood Blvd/Palms Cinema is a unique dinner & movie theater concept located in the suburbs (Woodridge and Naperville). The lobby was modeled after Grauman’s Chinese Theater at the Hollywood Walk of Fame in L.A. which is pretty cool. Both theaters frequently offer special celebrity hosted events, including meet and greets.

During recent years, they have screened “It’s a Wonderful Life” hosted by Karolyn Grimes, who played Zuzu Bailey in the film. A few years back, I attended a fun throwback to the 80’s which included a meet and greet with Corey Feldman. Films included iconic 80’s gems The Goonies, Stand by Me, License to Drive, and The Lost Boys. What a fabulous lineup! I got to take a picture with one of my favorite 80’s celebs after seeing a few of my favorite movies, so this was a really fun trip down nostalgia lane for me.

These festive events give you the opportunity, not only to meet your favorite celebrities, but also learn some background information about filming process and the opportunity to mingle with other fans.

• Address: 1001 W. 75th St. (Woodridge location) 352 Illinois 59 (Naperville location)
• Ticket info: Pricing ranges from $6-9 for tickets. Food is comparable to a chain like Chilis.
• Showtimes and the food menu

14. See the Chicago Bears play at Soldier Field

Chicago is easily one of the best sports cities in America. Locals are very passionate about all of their teams especially the Cubs and Bears. It’s always more fun attending a game when the fans are truly there for the love of the game and their home city. Watching a football game on TV just isn’t the same as seeing one in person. You are not a true Bears fan until you have roughed through the cold to cheer on your team.

Visit the Bears website for information on this year’s schedule and ticket prices. Side note – while Mike is a big Bears fan, I have always been a Patriots fan. It’s just not the same without Brady and Belichick though.

Update: I am not too happy about the new stadium plans in Arlighting Heights. The new stadium is set to open in 2029.

Address: 1410 Museum Campus Drive

15. Shop at Macy’s on State Street

I always make my way over to Macy’s on State Street during the holiday season. First off, the beautiful window displays are located here. Second, I really love browsing the massive holiday shop. There are so many beautiful Christmas trees and ornaments to browse through. I love exploring the Fannie Mae gift sets and just browsing around enjoying the decor.

I would consider walking through the store a holiday activity in an of itself. Also, this store is pretty big at 7 floors so you can do some pretty heavy duty shopping here. On a side note, they had some cool old time glass ornaments on display on my last visit.

Address: 111 N. State Street

16. Shop til you drop at Illinois’ largest mall

Woodfield Mall, located in the northwest suburbs, is one of the largest malls in the US. I love shopping here during the holiday season because I have access to a wide range of both high end and casual shops. It’s also decorated beautifully. While malls are going out of fashion in many parts of this country, this one is still going strong which is a great thing. I love shopping in person and this mall has been so active and festive during my last few visits. I love that they have a Garrett’s Popcorn shop in the middle of the mall (they offer the cutest holiday gift tins).

In addition, there are a number of other shopping, dining, and entertainment options in Schaumburg: the perfect area for a full day shopping spree! Major chain restaurants include P.F. Changs and The Cheesecake Factory. I find the Nordstrom store especially beautiful this time of year. Plus, their mint mocha is so much better than Starbucks.

Address: 5 Woodfield Ctr. Schaumburg

17. Order some deep dish pizza from Giordano’s

New York vs. Chicago: who has the better pizza? The debate will never end in our lifetime. It depends on your preference for thick or thin crust pizza. Deep dish pizza lovers will be more than satisfied with the numerous pizzerias (both in the city and suburbs) serving up the popular dish.

Giordano’s is one of the most popular restaurant chains the area, with locations throughout the city and suburbs. Personally, I prefer thin crust but will occasionally indulge in deep dish. While many tourists don’t know this – the south side of the city is home to some fabulous local pizza joints including Barracos, Palermo’s and my personal favorite, Vito & Nick’s.

18. Enjoy a stroll around Brookfield Zoo

Brookfield Zoo, located just 20 minutes outside of the city, is one of the biggest and best zoos in the country. There are many wonderful exhibits here: a fantastic underwater polar bear viewing area, a great dolphin show, and an indoor primate area are a few of the top sights to check out. On a side note, admission and parking are quite pricey, so I recommend a membership if you live in the area.

I like that there are plenty of indoor attractions so you can still enjoy a winter visit. When you get cold, just hop inside one of the many fantastic exhibits or see the fabulous dolphin show (separate tickets required). I haven’t checked it out yet, but the zoo recently opened a new indoor exhibit called Bramsen Tropical Forests.

The Holiday Magic light spectacular is when the zoo really shines although it doesn’t compare to Lincoln’s festive event. It’s a winter wonderland with over a million dazzling LED lights. Caroling, Santa visits, special holiday treats, and ice carvings round out a memorable holiday evening out.

• Address: 8400 31st St, Brookfield
• Pricing: $30 for adults, $25 for seniors, $21 for kids under 11. Parking is $17-20.
• Holiday Magic: Late November – early January.

19.See the holiday windows on Macy’s on State Street

I never walk around downtown without visiting Macy’s on State Street. I can’t leave without grabbing a box of those delicious Frango mints (which are just as fantastic as Fannie Mae’s famous mint meltaways). The theme changes every year, so you can always look forward to something new. This long running tradition started way back in the 1870’s when Macy’s was still Marshall Field’s.

2025’s theme was “The Most Wonderful Stories Start Here.” The theme incorporates some nostalgic Marshall Field’s elements which is pretty great for those of us who grew up in the city seeing the windows before Macy’s took over. As I mentioned earlier, dining at The Walnut Room is a fantastic experience if you can score reservations. 2025 marks the 118th anniversary of the tree lighting.

• Address: 111 N. State Street
• Opening date: November 1st
• Admission: Free

20. Treat yourself to a rainbow cone

The best ice cream cone I’ve ever had in my life is the same one I enjoyed as a kid. The iconic rainbow cone includes 5 slices (not scoops) of fresh ice cream. The hardest part is figuring out which flavor you like best: chocolate, strawberry, pistachio, orange sherbert, or Palmer House Vanilla? My favorite? Definitely the Palmer House!

Who says you can only enjoy ice cream in the summer? Not the Original Rainbow Cone’s OG location on Western Ave. A long time seasonal only business, a few years ago they decided to stay open all year, so you no longer have to wait for the summer to taste the city’s best treat. There are now a few other locations (including one at Navy Pier), unfortunately, they are only open seasonally.

Address: 9233 S Western Avenue

21. See a holiday classic at the historic Tivoli Theater

Tivoli Theater, located in suburban Downer’s Grove, is a beautiful downtown restored historic theater. Various holiday classics such as “A Christmas Story” “Christmas Vacation” and “White Christmas” screen during the holiday season. I recommend arriving early to participate in a sing along with the Wurlitzer Theater Pipe Organ.

The theater opened way back in 1928, so there is some historical value there. It’s architecturally beautiful and much different than visiting your ordinary strip mall theater. Overall, it is a really special experience, so much so that I try to get over here at least once if my visit falls during any of their showings.

The last movie I saw here was “Christmas Vacation,” one of my personal favorites. What a fantastic experience, especially with the old time vibe and red curtains! The classic decor, red velvet seats, and beautiful holiday decor add to the ambiance.

• Address: 5201 Highland Ave. Downers Grove
• Date: Starts in mid December
• Pricing: $6-9

22. Take unique pictures by the Cloud Gate sculpture

Referred to as “the Bean” by locals, Millennium Park’s popular Cloud Gate art piece is a fun spot to take pictures, due to the reflective nature of the sculpture. This artistic beauty really stands out, especially with the beautiful cityscape in the background. It was designed by international artist Anish Kapoor in 2006.

This is a hot spot with tourists and it is always busy. I recommend visiting as early in the day as possible to enjoy fantastic photographs without all the crowds. Afterwards, I like to head over to the beautiful ice rink I mentioned earlier. The city tree is also just a few steps away. I love that you can see the city reflection in the sculpture as you skate.

Address: 201 E. Randolph Street

23. Stroll downtown Naperville

Naperville is home to one of the most charming downtowns in the suburbs. The quaint neighborhood features a variety of upscale shops, restaurants, and attractions. If you get cold, stop in the one of the area’s many coffee or tea shops.

The winter season is the perfect time to check out a new restaurant. Although there are many to choose amongst, La Sorella di Francesca really stands out.  This charming Italian restaurant features the most delicious Italian dishes, a lively atmosphere, and unique decor. Mike and I planned many dates to this charming historic district when we lived in neighboring Lisle.

Other great restaurants that I recommend include: Lou Malnati’s (I love their lasagna), Rosebud (a suburban location of the iconic downtown restaurant), and Quigley’s Irish Pub.

Downtown Naperville directory

24. Go shopping at Oakbrook Center, one of the state’s nicest outdoor shopping centers

This upscale shopping center in the western suburbs is beautiful during the holiday season.  Plenty of lights and a large Christmas tree light up the dark winter nights. This is the best place to do any luxury shopping: anchors include Neiman Marcus, Macy’s, and Nordstrom. I was sad to see Lord & Taylor go, but there are plenty of great options. Maggiano’s is my favorite restaurant on-site. The ambiance is so festive for the holidays and I love their 2 for 1 deal.

I’m not a McDonald’s fan, however, fans will appreciate the modern look of this location. This McDonald’s is the fanciest I have ever set foot in; here you will find a Wi-Fi center, a modern fireplace, flat screen TVs, and an overall urban design scheme.

Address: 100 Oakbrook Center

25. Check out the foodie scene

This is easily one of the top food cities in the country. You can find almost any type of food imaginable here, really the options are endless. Besides pizza, the city is also known for Italian beef sandwiches, gyros, pierogies, hot dogs, Garretts popcorn, and the iconic Original Rainbow cone. Pictured above is an amazing Eggplant Parmesan dish at Rocco’s Little Italy Tinley Park, one of my favorite suburban Italian restaurants.

Address: Varies

26. Enjoy the views from the John Hancock Observatory

The John Hancock is an amazing architectural wonder. Like the Willis, you can also enjoy fantastic views here, via the 94th floor of the 360 Observation Deck. Tickets start at just 30 bucks, so it’s much cheaper than the Willis and you still get to enjoy great views of the city and Lake Michigan.

Although most famous for the grand views of the city from its’ observatory, it is also home to the highest ice rink in the world! The skating season typically starts in early January and ends in April. To save some money on pricey skate rentals, bring your own skates that you can use over and over again.

Update: The ice rink is sadly closed. However, you can enjoy a drink at CloudBar or a ride on Tilt, the highest thrill ride in the city.

• Address: 875 N. Michigan Avenue
• Pricing: Starts at $30
• Visit the Hancock website for more info

27. Hunt for vintage treasures at the Kane County Flea Market

This year-round flea market in St. Charles has been around for over 40 years. Antique collectors will have a blast checking out the variety of vendors found at this local favorite. Wolff’s Flea Market in Rosemont is another one of my favorites. It’s really massive and you can find anything here. This one has been going strong since 1991 and is open seasonally, sometime from late July through October.

Address:  525 S Randall Rd, St. Charles (Kane) 6920 Mannheim Rd, Rosemont (Wolff’s)

28. Enjoy some local Chicago style southside pizza

The Southside is home to some of the city’s best pizza joints. This may come as a surprise to many tourists, but the city is not known just for its’ deep dish. Thin crust is also popular especially on the Southside. I actually prefer thin crust as I think deep dish is a bit too heavy. In addition, do some exploring of your own; there are many local treasures to check out.

What better way to warm up over the cold winter months than by enjoying hot delicious square cut pizza. It’s a toss up between Fox’s (best of the suburbs) and Vito & Nick’s (the best in the city) for me. Palermo’s and Barraco’s are also amazing southside choices.

29. Warm up with a visit to a historic Wrigleyville pub

Take a break from the cold at one of many lively pubs, located in the trendy Wrigleyville neighborhood located in Lakeview and home to the Cubs. An annual favorite, the 12 Bars of Xmas Pub Crawl, takes you to favorites like Cubby Bear, John Barleycorn, and Casey Moran’s.

30. Take a winter stroll along the lake

The Lakefront Path provides over 36 miles of amazing views of Lake Michigan. Dozens of fantastic photo opportunities await you with each passing mile. I love biking here during the summer months but it’s also a nice place for a quiet winter stroll. Take advantage of the peacefulness that comes along with the changing weather. Just bundle up and grab a hot drink or dinner afterwards! I recommend parking at a garage near Millennium Park.

Address: Lake Shore Drive

31. Shop, dine, and explore State Street

This iconic street is an architectural wonder with many sightseeing opportunities plus restaurants and shopping to enjoy. Most famously, you can explore the gigantic Macy’s store. If you are looking for a bite, the Berghoff is the city’s most iconic German dining experience.

You will also find a number of attractions including: The Chicago Theater, Museum of Illusions, the Riverwalk, Medieval Torture Museum, Verse Immersive, and the Chicago Cultural Center. Block 37 is a five story complex featuring an AMC theater, Zara, Five Iron Golf, and a few restaurants.

32. See the “Christmas Around the World” exhibit at The Museum of Science and Industry

This unique annual event held at Chicago’s top science museum features trees from every culture. Take your time browsing through over 50 beautifully decorated trees, each with their own unique ethnic design. This event runs from mid November-early January each year.

Tip: The Museum of Science and Industry is part of the City Pass deal, where you will receive up to 50% off 5 great attractions. You will also get VIP admission. This is a real steal at just $98 a person and well worth it if you are already planning to visit more than 3 museums.

• Address: 5700 S. Lakeshore Drive
• Dates: Early November – early January
• Pricing: $26 for adults, $15 for children ages 3-11

33. Attend Navy Piers Winter Wonderland event

Navy Pier offers numerous attractions year-round including shops, restaurants, firework shows, and the ever popular scenic Ferris Wheel ride. You can enjoy dinner at an iconic favorite like Harry Caray’s Tavern or Giordano’s or treat yourself to a slice of pizza at Frankie’s. If you have a sweet tooth, you will definitely want to order one of the crazy milkshakes from JoJo’s.

The pier also hosts an annual “Winter Wonderfest” event, complete with ice skating, live entertainment, rides, and more! This event is perfect for the entire family!

• Address: 600 E. Grand Avenue
• Winter event details

34. Marvel at the gorgeous Christmas Tree

The beautiful annual tree truly is a sight to behold. While the tree stood for many years at Daley Plaza (from 1966-2015), it is now located at Millennium Park. While the tree at Daley is so nostalgic for me, I love the new location by the ice rink. It’s so much fun to skate alongside one of the prettiest trees in the country. 2025 marks the 112th anniversary of the lighting.

• Address: Millennium Park
• Tree lighting: November 21st (2025 date)
• Display dates: November 21st – January 11th (2025 dates)

35. Take advantage of the snowy forests & parks: go sledding!

Most winters see plenty of snow, at least enough for a few visits to the local sledding hill. Some of the best places to sled are located within the Cook County forests. Swallow Cliff in Palos Park is home to an enormous hill which provides ideal sledding conditions! This area used to be famous for their toboggan slides, however, they were demolished a few years ago. However, the large hills still remain; so get over there this winter season for a snow filled fun day!

Address: 11918 S. Lagrange Rd. Palos Park

36. Enjoy a treat at a local bakery

There are so many wonderful bakeries throughout the city. One of my favorites is Weber’s, a long running favorite since 1920. It’s one of the oldest bakeries in the city and everything is made from scratch. They serve a lot of holiday treats, but the best is their iconic Cinnamon bread (you will not find better anywhere else).

If you are looking for something more modern, I recommend Goddess and the Baker downtown. The pastry selection is amazing and they also serve great breakfast burritos. Recently, I enjoyed an amazing Pumpkin Chocolate danish here.

Address: 7055 W Archer Ave (Weber’s)

37. Get back to nature at the Little Red Schoolhouse

This is a beautiful little oasis in the suburbs which I have been visiting for years. It’s such a wonderful escape from both the city and suburban congestion. I’ve been coming here for years and it never gets old. In addition to taking a peaceful walk around several miles of wooded trails, you can also browse through the recently remodeled nature center.

It’s open all year (except Thanksgiving, Christmas Day & New Year’s Day), so you can get out there for a little fresh winter exercise when you need a break from the stuffy indoor heat. An invigorating winter walk will help you stay in shape and burn off all those extra holiday calories!

• Address: 9800 Willow Springs Road Willow Springs
• Admission: Free
• Hours: 8am-5pm (4 in winter)

38. Shop for unique German goods at Christkindlmarket

It can be a very long wait (I waited an hour this year), but Christkindlmarket is an iconic holiday tradition. It’s one of the largest German Christmas markets in the US and it attracts a lot of foot traffic each year. At this outdoor German market, you can feast on perogies, potato pancakes, pretzels, and sausages. You can shop for gorgeous old world glass ornaments.

The vibe is festive and holiday cheer is all around. Live music accompanies you most nights as you stroll around. I especially love sipping a hot cocoa on a cold winter night in a cute souvenir mug.

• Address: 50 W. Washington Street
• Dates: November 21st – December 24th (2025 dates)
• Admission: Free (extra costs for food and shopping)

39. See a show at the Museum of Science and Industry

Every show I have seen at the Museum of Science and Industry has been truly fantastic. The Omnimax, located inside the museum, is a huge 5 story domed theater. This type of film projection is the largest in the world. Various nature/space related documentaries have shown here over the past few years.

• Address: 5700 S. Lakeshore Drive
• Pricing: $32 for admission and 1 show ($20 for kids), $40 for admission and 2 shows ($28 for adults)

40. Get your cocoa fix

Nothing sounds better than a hot cocoa on a cold winter’s day. With the temps ranging into the 30 degrees and lower range for months on end, warming up with a cozy drink always sounds like a good idea. Mindy’s is super popular with a long line but the cocoa is considered the best in the city. Katherine Anne Confections in Logan Square serves drinking chocolates and espresso drinks plus they offer a tempting assortment of truffles.

Shown above is the 2025 souvenir cup from Christkindlmarket. At this wonderful holiday market, you can dine, shop, drink cocoa, and enjoy live entertainment all in one place.

Address: Varies

41. Take a self guided tour of John Hughes filming locations

The Breakfast Club, Pretty in Pink, Ferris Bueller, Weird Science, Uncle Buck, & Planes and Trains – I have always been a huge fan of John Hughes and wouldn’t even know which one to pick as my favorite. I have seen all of his movies countless times. I prefer to watch old classics of the 80’s any day over a trip to the theater. Planes and Trains is on my holiday lineup up every year without question. Many of these old school classics filmed in the Chicagoland area.

Hughes was from one of the Northern suburbs and always preferred to film close to home. I finally decided to take a self-guided tour of some of the iconic houses featured in his films after years of wanting to do so. It was definitely a nostalgic trip down memory lane!

Check out my Hughes movie filming locations post for details on where to find each one.

42. Stay at a fancy hotel

Wintertime is often the best time of the year to score a great deal at a luxurious hotel. My favorite upscale lodging choice is Kimpton. Kimpton Grey is a gorgeous 4 star property in the Loop. I scored a room here for under 200 bucks in late November.

It’s located within walking distance to Millennium Park and offers numerous amenities including: free morning coffee from La Colombe, an evening wine reception, and a wonderful rooftop lounge and bar called Boleo. On a side note, they decorate beautifully for the holidays. And, bonus points for allowing all pets to stay for free – my 2 cats enjoyed their luxurious stay!

Address: 122 W. Monroe Street

43. Skate on a unique ribbon shaped rink

One of the most unique things to do during the winter season is skate on the ribbon shaped rink at Maggie Daley Park. While there are numerous city rinks, this new one is particularly impressive as you skate along a unique quarter of a mile ribbon shaped path surrounded by trees. Great city views in the background and easy access to other city attractions make this one totally bucket worthy.

• Address: 337 E. Randolph Street
• Pricing: $17-23
• Discounts: Bring your own skates for free admission for the 11am session on Mon-Fri and free admission on the 8am session on weekends.

44. Enjoy a relaxing escape at Lake Katherine

Lake Katherine is a beautiful, small 85 acre park where you can escape the southwest suburbs congestion. It’s a great alternative to shopping and dining. Pick a warmer winter day, bundle up, and enjoy the quaint views of the lake, woods, and waterfall. A little bit of light exercise will brighten your mood during the long bleak winter months.

• Address: 7402 Lake Katherine Drive
• Pricing: Admission is free
• Hours: 9am-5pm (4 on Thursdays). The nature center is closed on Sundays.

45. Find a local park to go cross country skiing or snowshoeing

Not only are cross country skiing and snowshoeing incredibly fun winter activities, they burn a lot of calories! Did you know that cross country skiing is one of the top cardio activities, right behind running and basketball?! To me, there is nothing that says winter more than getting out to a snowy park and skiing in the serene winter setting.

To find a park that offers cross country skiing, visit the Parks District website. Tip: I recommend purchasing your own pair of snowshoes. Rentals can get quite pricey, especially if you plan on making snowshoeing a regular winter activity.

46. See the famous McCallister Home Alone house

The Christmas season is the perfect time to head out to Chicago’s North Shore to see the famous Home Alone house. If you are like me, I am sure you have seen this movie countless times. I am a native and for some reason it took me more than 30 years to finally drive over to see the iconic house. It still looks exactly the same from the outside. Unfortunately, the inside has been completely remodeled. If you ask me, I would have left it exactly the same right down to that gorgeous green tile in the kitchen!

Check out my experience visiting the house for more details.

Address: 671 Lincoln Ave, Winnetka

47. Volunteer at the McDonald’s Thanksgiving Parade

Although not as iconic as New York’s popular Macy’s Thanksgiving Day Parade, this festive Windy City parade still holds its’ own. What better way to be a part of all the action then volunteering to carry one of the balloons down historic State Street?

Mike & I had a blast several years ago, and would love the opportunity to take part in this fantastic event again. Mark your calendars – 2025’s parade will air on November 27th, from 8:00-11:00am on WGN. Visit the Chicago Festivals website for a volunteer application, along with additional information on the parade.

Address: State Street (Congress to Randolph)

48. Treat yourself to a delicious breakfast at Wildberry

Wildberry, an outstanding restaurant located downtown on Randolph St., serves up an enticing breakfast menu. They are most well known for their creative pancakes (S’mores, tiramisu, gluten free Honey-Cakes, etc), but also serve French toast, omelettes, and burritos. Service is outstanding, prices are affordable, and the location can’t be beat (Millennium Park). I like to dine here before walking along the lakefront or skating at the Millennium rink.

Address: 130 E. Randolph Street

49. Holiday shop at Orland Square

I have been to a lot of malls throughout the country, but I always come back to fantastic Orland Square Mall! There is just something about this mall around the holidays that make it perfect – the cheerful atmosphere, nice layout, variety of shops, and festive decor make it the ideal suburban stop for all your holiday shopping.

You don’t have to stop with the mall as Orland Park is home to some of the best shopping in the Southwest suburbs. Here you will find dozens of strip malls, complete with any store you can imagine. Don’t worry, there are plenty of restaurants in the area if you need to take a break from the crowds. Papa Joe’s is a great casual, local Italian choice. This is one of my favorite Italian restaurants in the city. The food is delicious and the dining room is gorgeous.

Address: 288 Orland Square Drive Orland Park (the mall), 14459 LaGrange Rd (Papa Joe’s)

50. Enjoy lunch at a fun themed restaurant

There are a handful of entertaining restaurant choices for those seeking more than your average meal. Dining out somewhere with a really eclectic vibe makes for a more special experience. After all, what is the point of dining out if you are not going to have a memorable time? Medieval Times is a dinner/show experience featuring fun medieval style games.

Hard Rock Cafe is always fun, no matter which city you visit. I love the rock n’ roll vibe and the food is surprisingly good for a chain. This Hard Rock is decorated beautifully around the holidays, making it the perfect place to stop for a fun, festive lunch or dinner before heading off to your other activities. The Twisted Mac and Cheese is out of this world! Also their Jumbo Platter (those spring rolls!) is worth every calorie! Update: This Hard rock is unfortunately closed. Ed Debevic’s is a long running favorite where you can dine 50’s style with the addition of snarky servers.

Address: Varies