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17 Best Activities for a Christmas Girls Weekend in Chicago

My mom and I took an incredible girls trip to Chicago in December for an amazing kickoff to the Christmas season. We made some priceless memories and thoroughly enjoyed ourselves–of course my mom is the best travel buddy ever. Here are our votes for 17 Best Activities for a Christmas Girls Weekend in Chicago!

1. Take the Amtrak!!

We took the Amtrak to Chicago, which was a wonderful way to avoid traffic chaos and end up right downtown with easy access to everything we wanted to see. Amtrak is an easygoing and comfortable way to travel, with huge seats, friendly attendants and  sometimes a hilarious commentary from the overhead speakers about exactly WHEN you can visit the snack car. Don’t forget to walk around the old part of the beautiful Union Station in downtown Chicago, with its richly decorated barrel vault ceiling, old carved wood benches, and giant Christmas tree. www.amtrak.com

Union Station

2. Visit Maggiano’s Little Italy

Sit down and relax to enjoy delicious Italian comfort food in a warm and welcoming old world environment. Decked out with Christmas lights and playing old-fashioned Christmas music, this restaurant a few blocks off the Magnificent Mile was a great introduction to our Christmas girls weekend in Chicago. Try the Fra Diavolo (a bit spicy, but amazing shrimp), the famous Rigatoni D (very creamy!), and of course the Dessert Sampler (definitely shareable!). https://www.maggianos.com/locations/illinois/chicago/516-n-clark-st./

Fra Diavolo at Maggiano’s Little Italy
Rigatoni D at Maggiano’s Little Italy

3. Stay at the Hampton by Hilton off Magnificent Mile

Located just off the Magnificent Mile, this clean and modern hotel was a very comfortable place to call home for a few days. They serve a great breakfast and the amenities like pool and fitness room are very nice and come with a terrace view. Beds and pillows are GREAT!! https://www.hilton.com/en/hotels/chidmhx-hampton-chicago-downtown-magnificent-mile/?eventId=EV_20091103171624810984

4. Picture Yourself with Golden Wings at the Plaza of the Americas

On our first full day, we headed down the Magnificent Mile, pausing to take a picture in front of the famous golden wings at the Plaza of the Americas. This is a great photo op if you ever had a secret desire to sprout giant golden wings. Who doesn’t?

5. Eat at Wildberry Pancakes and Cafe

We ate at the wonderful Wildberry Pancakes and Cafe for breakfast in our next foodie stop on our Christmas Girls Weekend in Chicago. Come hungry, you will certainly leave extremely full. I had heard it was really popular and the food did not disappoint. Try the Signature Berry Bliss Pancakes or the Blueberry Danish Pancakes. With mascarpone and crème anglaise between and topping every pancake, and a berry coulis over the top, you don’t really need syrup and the are probably the best pancakes ever.

To add some protein, the skillets are fantastic. Try the Garden Skillet for some tasty veggies or the Butcher Block for equally tasty meats! You can add any of the Signature Pancakes as a side to the skillets for an additional charge. One of our top meals on our list of 17 Best Activities for a Christmas Girls’ Weekend in Chicago! https://wildberrycafe.com/

Signature Berry Bliss at Wildberry’s
Blueberry Danish Pancakes at Wildberry’s
Garden Skillet at Wildberry’s

6. See the Bean and Explore Millennium Park

After breakfast, we walked through Millennium Park to see the Cloud Gate, aka The Bean. This has got to be one of the most fun pieces of public art ever. Whether making yourself dizzy in the reflecting dome on the underside of the Bean, or taking selfies in any part of the mirror, The Bean brings out the kid in everyone.

Millennium Park offers so much to see, even in the winter, so don’t miss this spot on your next Christmas Girls Weekend in Chicago. The famous Crown Fountain, featuring 1000 faces of ordinary Chicagoans, isn’t running water during the winter, but the faces are still amazing. Maggie Daley Park offers an amazing Skating Ribbon which winds through a section of park with a perfect ribbon of ice.

A more conventional skating rink in the front of Millenium Park is a hilarious people-watching opportunity, as everyone clings to the rail for dear life. We even tried out the playground! And the BP Pedestrian Bridge,  silver-scaled and winding gently over the road and through the park like a giant snake, is unforgettable. https://www.chicago.gov/city/en/depts/dca/supp_info/millennium_park.html

Cloud Gate, aka The Bean
BP Pedestrian Bridge
Crown Fountain
Skating at Millenium Park

7. Visit the Famous Downtown Macy’s

A Christmas Girls Weekend in Chicago wouldn’t be complete without a visit to the old downtown Macys with its glamorous Christmas displays and giant tree in the famous Walnut Room. While the Christmastime story windows on State Street are somewhat scaled down from the old days, they still put on a pretty glorious show inside and out. Make sure to see the spectacular arched mosaic ceiling and visit the Walnut Room to eat lunch and see the famous 45-ft tree. https://macysrestaurants.com/walnut-room/

Macys Christmas Windows
Macys Walnut Room

8. Stroll through the Christkindlmarkt

Chicago is known for its Christkindlmarkt, the largest European style Christmas market outside of Germany. You can’t have a Christmas Girls Weekend in Chicago without stopping at this famous and magical spot! A giant nativity welcomes you to a lovely and bustling square filled with Christmas cheer. Spiced Gluhwein (wine), cider, hot chocolate, brats, and giant pretzels will keep you well filled as you shop for amazing  ornaments and warm and cozy hats and scarves, among other holiday wares. https://www.christkindlmarket.com


9. Visit the Chicago Art Institute

A trip to the famous Chicago Art Institute makes a busy day of tourism complete. You can marvel at the incredible Thorne Miniature Rooms, 68 tiny and perfect views of historic rooms in various countries and eras, or sit on a bench surrounded by an entire room of Monet landscapes. The glorious Tiffany window on the landing of the grand staircase will stop you in your tracks, and don’t forget a picture with the iconic guarding lions out front! https://www.artic.edu

Chicago Art Institute
Tiffany Window at Chicago Art Institute

10. Eat at Ema

Supper at Ema, an upscale Mediterranean small-plate restaurant, rounded out the day. Sharing makes this place really fun, so try it with friends. They recommend two plates per person but we found that we couldn’t quite make it through and we were quite hungry—so two is more than enough! Try the fantastic Spicy Toothpick Lamb—best dish of the night—and the Brussels Sprouts with pumpkin seeds and a sherry glaze. Other favorites were the Chicken Kefta Kabob (basically crispy chicken meatballs) and Crispy Potatoes. https://www.emachicago.com

Crispy Brussel Sprouts at Ema
Crispy Potatoes at Ema
Toothpick Lamb at Ema

11. Visit the Palmer House Hotel

Nothing is open until about 11 am, so plan a slow start to the day. On a tour of the best Christmas trees in the city on the Christmas Girls Weekend in Chicago, don’t miss the Palmer House Hotel’s spectacular Gilded Age lobby and magnificent tree. It’s a very old hotel that is still absolutely gorgeous, especially at Christmas time. https://www.palmerhousehiltonhotel.com

Palmer House Lobby

12. Eat Chicago Deep Dish Pizza at Giordanos

Giordano’s Pizza was the first food stop of the day for some famous Chicago deep dish pizza. The Lunch Pronto special is a 6” personal deep dish pizza (also a thin crust option) and salad, and the salads are delicious. Chicago deep dish pizza is made upside down, with the toppings, cheese, and THEN sauce atop a thick buttery crust. It was tasty but not as spectacular as some of the less-traveled stops on the food tour of Chicago. Italian is very good here!

Deep Dish Pizza at Giordanos

13. Explore the Gold Coast

Walking north to the Gold Coast area, we saw some spectacular historic Chicago mansions and very upscale shopping. You can’t miss exploring this area on your next Christmas Girls Weekend in Chicago. Try Aritzia and Restoration Hardware, which is a destination in itself.

Restoration Hardware Atrium

A. Leonides Chocolate

A must-try experience is the fantastic Leonidas Chocolate near the Gold Coast neighborhood. Try Noir-et-noir hot chocolate and the adorable walnut chocolates. This is some of the best hot chocolate ever, anywhere. But it’s very very dark! https://www.leonidas-cafe.com

Noir-et-Noir Hot Chocolate at Leonides
Chocolates at Leonides

B. Aritzia

A fascinating and very soft and fuzzy upscale clothing store, both of us girls decided this place was an excellent discovery!! We definitely wanted to buy most of the store’s contents… https://www.aritzia.com/us/en/store?StoreID=aritzia-rush-street-chicago


C. Restoration Hardware

Restoration Hardware is a furniture and design icon housed in a beautiful old 5 story brownstone building with a glass conservatory in the middle, housing the famous 3 Arts Cafe. This is an extremely upscale restaurant in carefully curated and spectacularly decorated surroundings, where you can eat sitting on the famous Restoration Hardware luxurious couches after shopping 5 floors of show-stopping furnishings for your own mansion.

14. Shop and Eat on North Clark St. in Lincoln Park

A. Stanley Gallery

As evening falls, keep heading north to Lincoln Park for the ZooLights. The restaurants and shops across from the Lincoln Park Zoo on North Clark St are definitely worth a visit, especially the quirky and magical Stanley Gallery, a vintage light shop in the very old fashioned style. Have a conversation with the memorable proprietor Kenneth Stanley (46 years in the business and counting as of 2022) about the old days of Chicago, and he will recommend his favorite restaurants in the neighborhood. http://www.stanleygalleries.com

Stanley Gallery

B. Vanille Cafe and Patisserie

Before or after Lincoln Park ZooLights, stop to warm up in Vanille cafe and patisserie for some really good loose-leaf tea and very pretty patisserie. It’s very festive and feminine, a good place to sit and eat decadent chocolate and sip tea or coffee. https://www.vanillepatisserie.com


15. Eat at Riccardo Enoteca

The highlight of Italian food in Chicago was definitely Riccardo Enoteca, an unassuming and completely authentic tiny Italian restaurant in Lincoln Park on North Clark St. I cannot recommend this amazing and undiscovered gem highly enough. It’s quiet and cozy and the food is pure Italy. Try the Fettucine Alla Bolognese, and their table bread is perfection. https://riccardoenoteca.com

Riccardo Enoteca
Fettuccine alla Bolognese at Riccaro Enoteca

16. Walk through Zoo Lights

Lincoln Park ZooLights is one of the must-do Christmas activities on a Christmas Girls Weekend in Chicago in December. Stroll through the spectacularly lighted Lincoln Park Zoo which is completely decked out in animated Christmas lights and coordinated music. You might even see a sleeping lion… Don’t forget to get tickets online for a half hour entry slot. The tour takes about 45 min-1 hr walking. https://www.lpzoo.org/winter-wonders-at-the-zoo/

Zoo Lights

17. Shop on the Magnificent Mile

Shopping on the famous Magnificent Mile is an important stop on your Christmas Girls Weekend in Chicago. From the extravagant fashions of Neiman Marcus to Saks Fifth Ave to Cartier to UGG and UnderArmour, there is something for every taste.

A. Ghirardelli Cafe

Don’t forget hot chocolate and a brownie at the beautiful Ghirardelli cafe! After all the walking and shopping, it will warm your soul!

Ghirardelli Cafe

B. Tru Food Kitchen

For a light and healthy food option, True Food Kitchen right off the Magnificent Mile will give you new energy for more shopping! With a fun hipster vibe and fresh ingredients, it will hit the spot without crashing any diets. Try the Korean Noodle Bowl or the Ancient Grains Bowl with steak. The steak is fantastic in pretty much any of the bowls. For drinks—if you like ginger!—try the O.G., a zingy and refreshing drink of honey, ginger, and lime.

Korean Noodle Bowl at Tru Food Kitchen
Ancient Grains Bowl at Tru Food Kitchen

To Wrap It Up!

Chicago in December is a place for Christmas magic in the city. It’s the perfect place to take a girls’ holiday, with something for every taste. This city is sure to bring out the kid in all of us, and make some fantastic and tasty memories! I hope you’ve enjoyed our picks for 17 Best Activities for a Christmas Girls Weekend in Chicago.

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