50 fun things to do this winter in Chicago!
Chicago is a wonderful city with endless opportunities for entertainment and recreation. Chicago’s world-class cultural attractions and amazing architecture are the standouts of this great city. Unfortunately, many tourists never consider Chicago to be a winter vacation destination due to the frequent snow storms and frigid temperatures. Luckily, many of the best attractions are located indoors, and the festive outdoor attractions are worth braving the cold, bundled up of course!
Do you think of Chicago as a summer only destination? You are missing out big time if a winter vacation has never crossed your mind! In Chicago, there is plenty of fun to be had year-round! As a long time former resident, I have come up with some of my favorite things to do over the long and frigid winter months. In fact, I actually prefer the winter months due to the quieter atmosphere and abundance of tranquil dreary, snowy days. Fewer crowds, discounted hotels and attractions, and a laid-back appeal are just some benefits of visiting over the winter season.
Whether you are a local looking for new interesting activities this winter, or a tourist planning a winter getaway, you are bound to find a few ideas for winter fun on my list. What are your favorite Chicago winter activities? Feel free to give your own suggestions in the comments below!
1. Visit The Art Institute
The Art Institute of Chicago is one of the world’s best art museums. Visiting at any time of the year is a once in a life experience, however, visiting during the holiday season is even more spectacular! The beautiful lions out front wear festive wreaths during the holiday season! On a budget? Visit Thursday nights for free admission (5-8pm for Illinois residents). Special holiday displays (Neapolitan Crèche), festive decor, and choir performances add an extra festive touch during the season.
Address: 111 S. Michigan Ave. Chicago, IL 60603
2. Ice skate in Millennium Park
Ice skating at the McCormick Tribune Rink at Millennium Park is one of my favorite winter past times in the city. There is nothing better then heading downtown on a brisk, snowy winter day, and taking in the spectacular Chicago architecture while skating along to holiday music. Great prices for a city rink! One of the few city ice rinks you will find offering free admission (your only cost will be skate rentals, unless you own a pair). Bonus – free skating lessons are offered weekend mornings. Snacks, coffee, and hot cocoa available for purchase.
Address: 55 N. Michigan Ave. Chicago, IL 60601
3. Take a stroll down Michigan Avenue
Michigan Avenue: home to the world famous Magnificent Mile shopping district. How could you not want to spend your holiday season shopping along this beautiful street, complete with prestigious shops, amazing restaurants, and scenic holiday decor?! Definitely plan for a stop at Water Tower Place, an upscale 8 floor shopping center located at 835 N. Michigan Ave.
In addition, 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 Ave. Chicago, IL 60610
4. Experience an authentic Italian dinner at The Rosebud
A winter visit to Chicago would not be complete without a delicious Italian dinner at my favorite restaurant, The Rosebud. This upscale restaurant located in Chicago’s Little Italy neighborhood features a spectacular menu, a romantic setting, and impeccable service. Try the Cheese Ravioli or Chicken Parmesan. On an interesting side note, this charming restaurant was Frank Sinatra’s favorite: imagine that!
Address: 1500 W. Taylor St. Chicago, IL 60607
5. Be amazed at Lincoln Park ZooLights Festival
Take advantage of this festive display of over 2 million lights, held annually each year at Chicago’s 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. Strolling around Zoo Lights is the perfect holiday and date night activity: strolling around with a hot chocolate 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.
Update: Admission is now $5. Mondays are free.
Address: 2001 N. Clark St. Chicago, IL 60614.
6. Visit the spectacular dinosaur & mummy exhibits at The Field Museum
Most of you have probably heard about Chicago’s famous Field Museum. Reading about this museum is much different than actually seeing the incredible dinosaur fossils in person. Home to “Sue,” the most complete fossil, The Field Museum is tops on my list of must-dos in the city. Take a break from shopping in the cold, brisk Chicago air to tour this incredible museum! 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.
Address: 1400 S. Lakeshore Drive Chicago, IL 60605
7. Explore The Museum of Science & Industry
History buffs will appreciate the German submarine, replica coal mine, and the Apollo 8 spacecraft exhibits found at this large museum. One of my favorite exhibits, The Henry Crown Space Center, includes fantastic interactive displays. Also be sure to schedule a show at the Omnimax, a 5 story domed theater.
Also, be sure to add this one to your holiday bucket list. Tourists & locals alike will be awed by the spectacular, seasonal “Christmas Around the World” exhibit featuring dozens of trees, decorated to represent each unique culture.
Address: 5700 S. Lakeshore Drive Chicago, IL 60637
8. Visit the Wild Reef Exhibit at the Shedd Aquarium
The Shedd Aquarium in Chicago is one of the best you will ever visit. This grand aquarium features a large display of all kinds of marine life, not to mention a fantastic location on the lake! Over 25,000 animals call the Shedd home. The Wild Reef is a spectacular exhibit, which features numerous different varieties of sharks. The exhilarating feel of getting so close to the sharks can’t be topped! The museum is in a great location, and thus, there is plenty to do before or after your visit.
Address: 1200 S. Lakeshore Drive Chicago, IL 60605
9. See a Broadway production at the The Ford Oriental or Cadillac Theater
The Oriental and Cadillac Place Theater are the top spots in Chicago 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. 2022 highlights include The Lion King and Annie the Musical.
Address: 24 & 151 W. Randolph St. Chicago, IL 60601
10. Cheer on the Chicago Bulls
The 1990’s era Chicago 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 memories was attending the 1998 Bulls Championship Rally in Grant Park. Nonetheless, it’s still an exciting experience to attend a live basketball game. Visiting Chicago during the winter season will give you the perfect opportunity to see one of Chicago’s most beloved teams live in action. With games running several times a week, from October-April, you should have no problem fitting one into your itinerary! Visit the Chicago Bulls site for times and ticket prices.
Address: 1901 W. Madison St. Chicago, IL 60612
11. Book your tickets at The Chicago Theater
Various plays, concerts, comedy shows, and other events are scheduled year-round at this historic State Street theater. One of the best times of the year to plan a visit is during the holiday season: what better way to get out of the cold than spending your evening at this architectural wonder?
Address: 175 N. State St. Chicago, IL 60601
12. 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. Ed Debevics, a lively 50’s style diner, is another option.
Hard Rock Cafe is always fun, no matter which city you visit. Great music, decor, and fun entrees are awaiting you at this rock themed chain! Hard Rock Cafe 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!
Address: 63 W. Ontario St. Chicago, IL 60654
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 Chicago suburbs (Woodridge and Naperville). These 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. Recently, 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!
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.
Tip: You can usually find discounted tickets on Groupon. Recent deals have included 2 tickets for $9 or 4 for $18.
Address: 1001 W. 75th St.(Woodridge location) 352 Illinois 59 (Naperville location)
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. Recent polls have placed Chicago on the list of top 10 cities with the most passionate NFL fans. 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 Chicago Bears fan until you have roughed through the cold to cheer on your team. Visit the Chicago Bears website for information on this year’s schedule and ticket prices.
Address: 1410 Museum Campus Drive Chicago, IL 60605
15. Shop at Water Tower Place
A walk down the Magnificent Mile would not be complete without paying a visit to Chicago’s grand 8 floor shopping center extraordinaire . Water Tower features a unique architectural design, a number of high end specialty shops, and a convenient central location.
Address: 835 N. Michigan Ave. Chicago, IL 60611
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. In addition, there are a number of other shopping, dining, and entertainment options in Schaumburg: the perfect area for a full day shopping spree!
Address: 5 Woodfield Ctr. Schaumburg, IL 60173
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 Chicago pizzerias serving up the popular dish. Giordano’s is one of the most popular restaurant chains the area, with locations throughout the city and suburbs. Search for your nearest location on the Giordano’s website. I prefer thin crust pizza. Unknown to many tourists, Chicago (esp the Southside) is also known for their amazing thin crust. pizza. Vito & Nick’s pizzeria is my favorite pizza in the entire country – just try it, you will not be dissapointed.
18. Enjoy a festive night at Brookfield Zoo’s Holiday Magic celebration
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. The Holiday Magic light spectacular is when the zoo really shines. Here you will be treated to a winter wonderland, complete with over a million dazzling LED lights. Caroling, Santa visits, special holiday treats, and ice carvings round out a memorable holiday evening out.
19. Visit Macy’s on State Street
I never leave Chicago without visiting Macy’s on State Street. I can’t leave without grabbing a box of those delicious Frango mints (which by the way are far better than Fannie Mae!) The holiday season is not complete without seeing the iconic holiday window displays and decor of the Walnut Room. The Walnut Room, located on the 7th floor, is one of Chicago’s most famous restaurants, and a must visit during the festive holiday season. Although Macy’s is still a holiday tradition, any loyal Chicago resident still prefers the original, Marshall Field’s.
Address: 111 N. State Street Chicago, IL
20. Take a horse drawn carriage ride downtown
Scenic horse drawn carriage rides which travel the streets of downtown Chicago operate year-round, however, taking a ride during the holiday season, surrounded by all the lights, makes for a far more memorable (and romantic) experience. A romantic ride along Chicago’s scenic Magnificent Mile is the perfect way to surprise your date! Visit the Antique Coach & Carriage website for information on operating times and prices.
Address: 806 N. Michigan Ave. Chicago, IL 60610
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. Arrive early to participate in a sing along with the Wurlitzer Theater Pipe Organ.
We recently went to a showing of “Christmas Vacation.” 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, IL 60515
22. Take unique pictures by the Cloud Gate sculpture
Referred to as “the Bean” by locals, Millennium Park’s popular Cloud Gate sculpture 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. Every tourist should plan for a viewing of this masterpiece! I recommend visiting as early in the day as possible to enjoy fantastic photographs without all the crowds! Afterwards, lace up your skates at one of the country’s most scenic ice rinks.
Address: 201 E. Randolph St. Chicago, IL 60601
23. Stroll downtown Naperville
Naperville is home to one of the most charming downtowns in the Chicagoland area. The quaint downtown neighborhood features a variety of upscale shops, restaurants, and attractions. Strolling around this small section of town is a great option anytime of the year, even during the winter season. If you get cold, stop in the one of the area’s many coffee or tea shops: David’s Tea and Adagio Tea are both excellent choices.
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.
24. Go shopping at Oakbrook Center, one of the state’s nicest outdoor shopping centers
This beautiful, upscale shopping center in the Chicago suburbs is a delight during the holiday season. Plenty of lights and a large Christmas tree light up the dark winter nights. Plenty of great anchor stores, such as Neiman Marcus, Nordstroms, Macy’s, and Lord & Taylor call Oakbrook Center home.
Maggiano’s is an excellent choice for those craving great Italian in a nice setting. 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 Oakbrook IL 60523
25. Check out the foodie scene
Chicago 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, Chicago is also known for Italian beef sandwiches, Portillo’s hot dogs, Garretts popcorn, and the iconic Original Rainbow cone, an ice cream specialty featuring 5 trademark flavors (Orange Sherbet, Pistachio, Palmer House, Strawberry, and Chocolate). Pictured above is an amazing Eggplant Parmesan dish at Rocco’s Little Italy Tinley Park, one of my favorite suburban Italian restaurants.
26. Go ice skating at the John Hancock Observatory
The John Hancock is an amazing architectural wonder. 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! Take the opportunity to skate 1000 feet in the air on the 94th floor of this iconic landmark, while taking in to die for views of the city. The skating season typically starts in early January and ends in April. Visit the John Hancock website for information regarding dates and prices. To save some money on pricey skate rentals, bring your own skates that you can use over and over again.
Address: 875 N. Michigan Ave. Chicago, IL 60611
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.
Address: 525 S Randall Rd, St. Charles, IL 60174
28. Enjoy some local Chicago Southside Pizza
The Southside of Chicago 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. Here’s a few great pizza places to check out on your visit: Fox’s (Orland Park), Vito & Nick’s (Chicago), Barraco’s (Evergreen Park), and Palermos (Oak Lawn) to name a few. 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 Chicago style pizza?
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 of Chicago. An annual favorite, the 12 Bars of Xmas Pub Crawl, takes you to favorites like Cubby Bear, John Barleycorn, and Casey Moran’s. Visit the Wrigleyville website for a full listing of pubs, restaurants, and attractions in the area.
30. Take a winter stroll along the lake
The Chicago Lakefront Path provides over 18 miles of amazing views of Lake Michigan. Dozens of fantastic photo opportunities await you with each passing mile. Take advantage of the peacefulness that comes along with the changing weather. Just bundle up and grab a hot drink or dinner afterwards!
Address: Lake Shore Drive Chicago, IL
31. Explore the Wicker Park neighborhood
Chicago’s trendy Wicker Park neighborhood is home to many great restaurants, popular bars, and great shops. There are plenty of fun indoor activities to keep you busy during the cold season. Be sure to check out Mindy’s Hot Chocolate, an area favorite! I also recommend visiting The Wormhole Coffee, which is a really eclectic shop featuring lots of 80’s nostalgia including the Back to the Future car.
Address: Wicker Park is located northwest of the loop
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 Chicago 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 Chicago, IL 60637
33. Attend Navy Piers Winter Wonderland event
Navy Pier offers a host of attractions year-round including shops, restaurants, firework shows, and the ever popular scenic Ferris Wheel ride. They also host 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 Ave. Chicago, IL 60611
34. Marvel at the gorgeous Christmas Tree
The beautiful annual tree truly is a sight to behold. 2022 marked the 109th year of the annual holiday tradition. See the beautiful tree in Millennium Park and then enjoy a fabulous night of ice skating in a gorgeous city setting. While the tree stood for many years at Daley Plaza (from 1966-2015), it is now located at Millennium Park.
Address: Millennium Park
35. Take advantage of the snowy forests & parks: go sledding!
Most Chicago 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, IL 60464
36. Take skyline photography
The winter is an ideal time to get out there and photograph the magnificent skyline; no doubt one of the country’s finest. If you can brave the cold, you will enjoy some crowd free photos.
37. Take a walk around the trails at Little Red Schoolhouse
A beautiful oasis in the Chicago suburbs, Little Red is a local favorite for escaping the city and suburban congestion. 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, IL 60480
38. Attend fun & festive holiday themed activities
Planning your visit during the holidays is sure to be a blast as Chicago goes all out during the Christmas season. In addition to the Lincoln Park ZooLights festival & the Mag Mile Lights Festival events listed above, you also have Christkindlmarket (a German shopping village), the grand downtown tree, Navy Pier’s Winter Wonderland, Brookfield Zoo’s ZooLights, and much more!
You are bound to have a festive time with an endless supply of events & activities to choose from! Visit my Best Holiday Activities in Chicago post for more holiday entertainment ideas.
39. See an IMAX show at the Museum of Science and Industry
Every show I have seen at Chicago’s 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 Chicago, IL 60637
40. Visit The Hershey’s Chicago candy store
Treat yourself to a delicious cup of Hershey’s Hot Chocolate after a long day shopping along Chicago’s gorgeous Magnificent Mile. I ran into this cute shop randomly, and I’m glad I found it! Hershey’s is a great place to stock up on unique candy souvenirs for all those with a sweet tooth on your holiday shopping list!
Address: 822 N. Michigan Ave. Chicago, IL 60611
41. Grab a hot chocolate and window shop downtown
The festive winter setting is perfect for a stroll downtown. Beautiful lights and decor, horse & carriage rides, special holiday markets, and more add to the holiday ambiance. Another bonus comes with the quieter atmosphere as the city sees much less tourism during the winter months. There is such a drastic difference between crowds in the winter vs. summer months. I try to get out and ice skate at Millennium on a weekday morning/afternoon for the fewest crowds as insane lines often form quickly on the weekends!
Address: N. Michigan Ave. Chicago 60611
42. Explore unique space exhibits at the Adler Planetarium
The Adler is one of the premier planetariums in the country. Interesting space exhibits and incredible shows in The Grainger Sky Theater make for a full day of learning and fun! Afterwards, be sure to snap a bunch of pictures outside. The planetarium patio is the absolute best spot in the city for skyline photography (the cover photo was taken here!).
Address: 1300 South Lake Shore Drive Chicago, IL 60605
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 rinks throughout Chicagoland, 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 St. Chicago, IL 60601
44. Enjoy a relaxing escape at Lake Katherine
Lake Katherine is a beautiful, small 85 acre park in the Chicago suburbs. 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, Palos Heights, IL 60463
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 Chicago 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. Take a self guided tour of movie filming locations
Many classics such as The Breakfast Club, Home Alone, Sixteen Candles, My Best Friends Wedding, Ferris Bueller, Home Alone and more have filmed in various locations in and around the city. Why not take a tour of all your favorite films from the 80’s or 90’s? An entertaining and free activity to perk up the boring winter season!
Address: The National Film Institute lists all the addresses for these movies and more.
47. Volunteer at the McDonald’s Thanksgiving Parade
Although not as iconic as New York’s popular Macy’s Thanksgiving Day Parade, this festive Chicago 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 – this year’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 in Chicago’s downtown on Randolph St., serves up an enticing breakfast menu. You will find specialty pancakes (S’mores, tiramisu, gluten free Honey-Cakes, etc), French toast creations, omelettes, and more! Service is outstanding, prices are affordable, and the location can’t be beat (Millennium Park).
Address: 130 E. Randolph St. Chicago, IL 60601
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.
Address: 288 Orland Square Drive Orland Park, IL 60462
50. Find a local park district ice rink
Most neighborhood rinks are free to skate, and only charge a few dollars or so for skate rentals. One of my favorite suburban rinks is Orland Park’s Winter Wonderland ice rink, located at Centennial Park. The rink is large, almost never crowded, and provides a quiet park like setting. As a bonus, skate rentals are super cheap! Visit The Orland Park website for information on this season’s operating dates and times.
Address: 15600 West Ave. Orland Park, IL 60462
Just for Fun
And just for fun, here are some of my favorite gift ideas for Chicago lovers.
11 Chicago Themed Gifts for Christmas, Birthdays, Etc.
MLB Chicago Cubs Fleece Blanket – The perfect winter gift for Cubs fan. Keep cozy all season long!
Chicago-Opoly – A fun monopoly style game for residents and locals! I received this as a Christmas gift and I just love it!
Chicago snowglobe – Anyone who collects snowglobes will love this one which includes a replica of the Chicago skyline.
Chicago Canvas wall decor – You really can’t go wrong with a classic picture of the Chicago skyline. Absolutely beautiful and perfect for locals and visitors who love the city.
Michigan Avenue puzzle – This 1000 piece puzzle is really hard and will take forever to complete – but that’s just part of the fun! A beautiful photo awaits you upon your completion. This 4D Chicago puzzle is pretty cool as well.
Kurt Adler Chicago Christmas Ornament – This beautiful glass Chicago skyline ornament is the perfect addition to your Christmas tree. Also makes a great stocking stuffer.
NFL Chicago Bears tumbler – This travel tumbler is really the perfect gift for any Chicago Bears fan. I bought it for my bf last Christmas and he loves to bring it with on any road trip!
Chicago Bears Christmas ornament – This gift is just perfect for the die hard Chicago Bears fan just hoping to someday see their team in the Superbowl again! Also take a look at this Chicago Bears nutcracker – I received this as a stocking stuffer years back and I still display it every year!
Chicago Bears winter hat – Fashionable and functional at the same time!
Chicago wine glass – I just love the line of Lolita hand painted wine glass. If you have ever been in a Hallmark store, you have probably seen them too. This Chicago themed version, featuring memorable sights such as Wrigley Field, Michigan Ave, and Navy Pier is amazing.