Christmas in Chicago!

Note: Please refer to my holiday bucket list post for a full breakdown of all the fun and festive activities in the city. Also, keep in mind that there is so much to do this time of year even if the sun isn’t shining. After many years of living in and visiting the city, I made a comprehensive guide to the best winter activities. This is actually my favorite time of year. As long as you bundle up, it’s a magical time of year with so many festive events, beautiful lights, and amazing ice skating rinks to enjoy.

Chicago will always be one of my favorite cities to spend the holiday season in. I love the brisk weather, old- school Italian restaurants, abundant snow, and long lineup of festive events. This year for the holidays, Mike and I decided to drive in to visit family. In my opinion, it is the best city to spend the holidays in due to the wintry weather and holiday traditions combining to form the perfect festive ambiance. We were excited to be back after several years living out West.

There are always plenty of events going on in what I believe is one of the top 3 downtowns in the US. Surprisingly, the weather was incredibly mild for this time of the year. We did not get any snow our entire trip! Below I have listed some highlights of our Christmas vacation. On the top of our list was visiting our favorite zoo, Brookfield. I have been coming here since I was a kid and have never found a better zoo. The dolphin show is so amazing and the indoor Tropic World primate exhibit is unparalleled. They also put on an extravagant light show so you can enjoy taking in the lights and then warming up in the indoor exhibits.

Brookfield Zoo Lights

For this “Holiday Magic” event, 2 million multi colored lights decorate the zoo. There is also a laser show, carolers, ice carving demonstrations, and more. The nice thing about this event is that you can still check out all the indoor animal exhibits, of which Brookfield is home to some of the best in the country.

We saw the dolphin show, which was done holiday style to the background of Christmas music. Brookfield’s dolphin show is one of the top zoo exhibits in the country. I have been attending this show since I was a kid and it is always the same (wonderful) no matter how many times I come back. The trainers are so talented and you can tell that they really love their job. The show is so amazing and I am totally impressed no matter how many times I see it. Yes, it’s worth the small extra fee!

Tropic World, a primate exhibit and one of the largest indoor exhibits in the country, is one not to be missed. Another great new-ish attraction is the Great Bear Wilderness, which includes a fantastic underwater polar bear viewing area. We were lucky enough to see the brown bear swimming even though it is considered quite rare.

There is a nice tram ride that takes you around the zoo. During Zoo Lights, the tram is a nice way to cover the entire zoo in a short period of time, making it a great choice for those not tolerant of extreme cold. I love walking around and then also taking the tram just to enjoy the ride.

Hollywood Palms movie theater

Hollywood Blvd. and its’ sister company, Hollywood Palms, is a unique dinner and movie theater concept located in the suburbs of Woodridge and Naperville.  The theater is stylish and features décor and memorabilia from all different films. The lobby at the Hollywood Palms location was modeled after Grauman’s historic theater at the Walk of Fame in L.A. The creative menu features entrees and appetizers with movie themed names. I enjoyed a healthy veggie filled “Roger Rabbit wrap.”

Surprisingly, the food is really good – much, much better than typical movie theater selections. Here you can order all sorts of fun appetizers, full size entrees, desserts, and even a bucket of beer! The waiters are very fast and efficient taking your order right before the movie starts and usually getting it out before the movie starts or shortly after. The seats are very comfortable and the theater is clean. They also frequently host celebrity events.

We attended a special holiday screening of “It’s a Wonderful Life” hosted by Karolyn Grimes who plays ZuZu in the film. We got to meet Karolyn after the film and she was super nice and we paid a little extra for an autographed movie photo. Before the screening she also shared some personal stories from way back in the filming days. It was so interesting to hear about the filming process from someone actually in the movie. It’s so different than just reading facts online.

In addition to It’ a Wonderful Life, Hollywood also screens a few other holiday classics including White Christmas. As one of my personal favorites, I would love to see this next year (I love the music!). Check the website for upcoming celebrity events and make sure to get advance tickets as they get very crowded.

Update: I actually prefer Hollywood Blvd., the original theater. They have more movie memorabilia and the ambiance is a bit more old-school. Also, Hollywood Palms went through an ownership change in 2015 so it isn’t the same.

Festive downtown fun

Downtown looks gorgeous around the holidays, and thus, we had to walk around at least one day during our trip. We conveniently took “The L” train into the downtown area. First, we walked around Millennium Park. There is some neat architecture here including Cloud Gate aka “the bean,” which is a unique sculpture which allows you to see your own reflection and that of the city behind you. As expected, this city landmark draws a ton of tourism. Even during the winter you can expect crowds since it is located right next to the skating rink.

Update: Here is a new pic from our Thanksgiving trip to the city in winter of 2025. As you can see in this pic, not much has changed! I recommend stopping by for a quick photo before ice skating/seeing the tree. What a gorgeous artistic sculpture in one of the country’s best cities.

There is also a very busy ice rink which features great views of the city skyline in the background. It’s such a picture-perfect Hallmark movie-like setting to skate with the beautiful cityscape in the background. This is definitely a Christmas in the city movie-like setting if ever there was one.

We arrived an hour before opening and there was already a huge line of people waiting. I have been ice skating for several years (and I am still not good), but I absolutely love skating right before Christmas. As a bonus, this is one of the only free city rinks anywhere in the US. There is a rental fee, but it’s free if you bring your own. I purchased my own skates a while back and they have easily paid for themselves after just one winter season. Definitely invest in a pair if you live in or near the city and plan on visiting often.

Update: On our recent 2025 winter trip, we enjoyed a skating session at Millennium with the beautiful tree in the background. This was our first time back in the city in a long time so it was a blast. Seeing the gorgeous tree in the background while skating was such a magical festive experience. Seriously, this is one of the most gorgeous urban rinks around. I like skating here both day and night, but nighttime is so much more romantic.

For this trip, we booked a room at the Kimpton Gray which is conveniently walkable. I just threw my skates over my shoulders and walked right over. Note: This is an amazing hotel. They decorate beautifully, offer free coffee in the morning, and the rooms are so nice. I highly recommend for an awesome Christmas stay.

Next, we walked The Magnificent Mile – I really enjoy walking this shopping district located on Michigan Avenue during the holidays as the atmosphere is so festive. I haven’t been on this street in years so it was a great time. Every tree is lighted and the stores are decorated beautifully. I also like to walk a few blocks over to State Street to see the Macy’s Christmas themed windows.

As a Chicago native, I grew up seeing the famous Marshall Fields windows. Once Macy’s took over, it was never the same. Even though the magic is not really there anymore (the windows just are not as whimsical), it’s a long running tradition to add to your bucket list. Whenever I am back in the city for the holidays, I still push through the crowds to see what the theme will be this year.

From the windows, you can walk over and see the Grand Christmas Tree and visit Christkindlmarket, a German Christmas market where you can browse all sorts of amazing handcrafted ornaments and decor. You can order a cocoa in the cutest souvenir mug (the design changes yearly).

Update: Here are some new pictures of Michigan Ave., the iconic Window displays (2025’s theme was a nostalgic Marshall Fields throwback), and the grand tree by its’ new Millennium location. We also finally enjoyed an iconic hot cocoa in a souvenir mug at Christkindlmarket (we just browsed around in the past). This year’s mug was a cute heart shaped mug (to be honest, I was hoping for one of the cute boots!).

The windows were very whimsical and nostalgic this year with a retro Marshall Fields theme. I remember so many people lining up to see these windows in the old days. Seriously, there were rows of people waiting to get a view. This year, we just walked right up and took any pictures we wanted. I wonder if this is because there was a major storm on the way (we got hammered with almost a few of snow just after Thanksgiving!).

Here is a view of the colorful Christmas tree at Daley Plaza. Update: In 2019, the tree moved to Millennium park. The city tree was located at Daley Plaza for almost 50 years, so it is sort of sad that they moved it. On the bright side, it is now located closer to the ice rink if you plan on skating.

Update: We finally saw the new tree location at Millennium. This is something I wanted to do for years but just never made my way around to it. Even though I’m a bit nostalgic about the old Daley location, I have to admit the new tree looks fabulous. And it’s kind of fun and extra festive to see it while skating.

We also finally made reservations for dinner at The Walnut Room which is something I’ve wanted to do for years. It’s really pricey, but worth it for the festive experience. The festive 45 foot tree hangs from the ceiling which is a bit different. Tables surround the tree and even the tables in the back still have a decent view (note you can’t pick your seat as it is random).

You can get up and walk around and photograph the tree too. There is a photo spot for those not dining too which is nice. I loved the theme for 2025 – Marshall Fields! I grew up in the city with this department store so this nostalgic throwback was pretty special; I guess I lucked out with the timing.

For my main course, I ordered a delicious Wild Mushroom ravioli and capped the experience with a slice of Franco Mint cheesecake I’ve been dying to try for years. The food was fabulous, especially that cheesecake! Really, it wasn’t much more expensive than dining at any other restaurant. Here are a few pictures of our dining experience.

Definitely take some time to walk around the store. The holiday decorations are so magical this time of year. Even if you aren’t dining at the restaurant, it’s totally worth a walk through. They really do a good job keeping the holiday magic alive in a time when most stores are giving up and decreasing the decor year by year.

Orland Square

This large mall in the Southeastern suburbs, has always been my favorite amongst the variety of options available throughout the metro. Orland Square is a very large mall with 2 floors featuring both upscale and casual stores. There is always a lot of security around and it is always up kept and clean.

My only problem with this mall is that the food court is horrible. However, there are dozens of restaurants and other shopping centers located nearby. In addition, a new Dave and Buster’s entertainment center is opening next year. They also opened a Cheesecake Factory in recent years which is pretty cool.

Other great malls in the suburbs include Oakbrook Center and Woodfield Mall in Schaumburg. Woodfield is massive – you can really shop til you drop here. The place is gorgeous and it is decorated beautifully for the holidays (epsecially Nordstroms). There are a lot of great chain restaurants including: P.F. Changs and Cheesecake Factory. I love that there is a Garretts popcorn stand (I like to pick up some special holiday tins here).

Where we dined

We also visited several restaurants on our trip, some downtown and a few in the suburbs as we were staying with family members. Check out some of my favorite gems in the southwest suburbs:

Fox’s

Fox’s is a local family run pizza place which has been in business for decades. I love Fox’s – it is one of my favorite restaurants on the South side (besides Vito & Nick’s which is even better). We have been ordering take out pizza from them for decades.

This was my first time dining inside the Orland Park location, and I have to say I was pleased! Great entertainment (live music and dancing), tasty food, and a lively unique atmosphere made for a really fun weekend family dinner. If you are looking for some excellent super thin crust Chicago style pizza, Fox’s is one of your best bets!

Oak Lawn Family Restaurant

Oak Lawn Family Restaurant is one of the hidden gems on the Southside. All the locals know that the Oak Lawn Family restaurant is the best casual diner style restaurant this side of Chicago. I like it because it is always consistent – every-time I come back I always receive the same great service, great food, and a comfortable atmosphere. It never changes!

We had so much food leftover the next day – the portions are huge so bring your appetite! Lots of options on the menu including all day breakfast and delicious stir fry dishes. It’s one of the best family restaurants around. Update: This restaurant has recently closed, but don’t worry there are plenty of great local restaurants throughout the suburbs.

My replacement choice: Papa’s Joes, a local Italian gem in Orland Park.

Hard Rock Cafe

I always try to visit different Hard Rock locations on every trip as I like the touristy vibe, plus I collect all the glasses. This downtown location is a bit dull compared to others, nevertheless, the food was good as always (I love their spicy twisted mac and cheese) and it was decorated nicely for the holidays. Update: Unfortunately this Hard Rock is closed.