While most tourists visit Chicago in the summer months, there’s no need to spend a wintertime visit to Chicago trapped in the hotel! So, bundle up to brave the cold and check out this sample itinerary for a way to spend a fun-filled long weekend.
The itinerary below assumes arrival on Thursday night with 2.5-3 full days in Chicago, but can easily be adjusted to two full days and a different arrival day/time though some of the activities are specific to a weekend day, so plan accordingly. You will also want to grab tickets in advance where possible – things sell out fast!
For a longer list of year-round Chicago activities, be sure to check out my post Chicago Weekend Itinerary: a List of Fun Things to Visit in the Windy City. You’ll get a complete list of top entertainment, professional sports, and other activities to build your ideal itinerary.*
Full Day 1: Friday
Highlights include wandering the Magnificent Mile, Espresso Martini flight at Starbucks Reserve, and Lincoln Park Zoo Lights
- 9AM: Coffee & Breakfast at Doma or Cafecito
- Alternative best breakfast sandwiches around Chicago:, though they may require you to travel via Uber/Lyft
- 10AM: Shop the Stores along the Magnificent Mile (~2 hours), all lit up for the holidays!
- Wintrust Magnificent Mile Lights Festival is on November 23, 2024. Expect tree lighting, and family-friendly activities.
- 12PM: Lunch at Eataly – wander around the two-story store for stocking-stuffers and eat lunch at one of the three restaurants upstairs-I’ve never needed a reservation for lunch
- Alternatives if you already have an Eataly in your city:
- Macy’s Walnut Room – decorated for the holidays
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- Francesca’s on Chestnut – haven’t been here, but it’s on my list to try due to the phenomenal reviews regarding the fresh pasta
- Alternatives if you already have an Eataly in your city:
- 1:30PM: Dessert: Seasonal Espresso Martini flight at the top of Starbucks Reserve Roastery Bar
- There is always a line, but it moves really fast, it’s worth the wait! Take the escalators all the way to the top to get to the bar
- 2:00PM: Two Options
- Museum of Science and Industry: Christmas Around the World exhibit (Nov 16-Jan 6) or choose another museum to explore
- Break Time: Nap/Read at the hotel if you need some downtime
- 6:00PM: Make your way to Lincoln Park Zoo for the Lincoln Park Zoo Lights – buy your tickets in advance – at least a week before to get the day/time you want! Also, be sure to grab some of the spiked hot chocolate
- Alternative option: Chicago Botanic Gardens
- 8:00PM: Dinner at Gemini (10-minute walk) or Pequod’s Pizza is my favorite deep dish pizza, hands down, but can be up to a 2 hour wait (8-minute car ride, 35-minute walk)
- Optional: dessert at the Chocolate Bar lobby of the Peninsula (Friday / Saturday nights – 7pm-11pm, $65/person)
Full Day 2: Saturday
Highlights include a delicious brunch, ice skating, ChrisKindlmarket, High tea, and It’s a Wonderful Life play to round out a very full day.
- 9:30AM: Brunch
- Beatrix (Fulton Market District), most locals agree the one in Fulton Market District is better than the one in River NorthWildberry PancakesPurple Pig – I have a friend that when she comes to Chicago only eats here. I personally was not wowed by my experience, but it does have a devoted following with 4.6 stars rated by 6.5k people on Google
- The Chicago Diner – all vegetarian/vegan restaurant serving breakfast comfort foods that will convert any meat eater
- 11AM-12:00PM: Maggie Daley, Ice Skating ribbon, instead of a rink, skate in a loop outdoors totally unique experience! – make reservation ahead of time! Skate for 1 hour, then head over to the ChristKindlmarket
- 12:00-1:00PM: Stroll through the ChrisKindlmarket in Milliennium Park: drink a delicious hot chocolate (it’s worth the $$ if you love hot chocolate) or gluwein (aka mulled wine), and other treats like the viral croissant rolls from 2023. Be sure to check out the Millennium Park Christmas tree near the Bean!
- Note: normally there is another Chriskindlmarket outside of Wrigley which is a better set up, since you get to go into the stadium (additional fee is worth it to make s’mores!), but the NHL Winter Classic is being held at Wrigley field on December 31st so this market was canceled. Also, with this itinerary, sticking close to Millennium Park makes more sense.
- 1:30PM: Three activity options:
- 1) Un-Tea at Sofitel (Saturdays and Sundays only, $55/person) – a high tea that includes sandwiches and small desserts. I have not tried this one, but it’s on my bucket list. Let me know in the comments if you tried it out!
- OR….
- 3) Choose another museum based on your interests and eat dinner at Girl and the Goat before the show.
- Art Institute of Chicago
- Field Museum
- Medieval Torture Museum
- Museum of Contemporary Art
- Chicago History Museum
- Adler Planetarium
- And many more…..
- 1) Un-Tea at Sofitel (Saturdays and Sundays only, $55/person) – a high tea that includes sandwiches and small desserts. I have not tried this one, but it’s on my bucket list. Let me know in the comments if you tried it out!
- 7:30PM: It’s a Wonderful Life a play that feels like you are watching a radio program and will get you into the holiday spirit. (Tickets $25-$65). Additional show time at 7:30PM, can work dinner plan around this. Popular activities-buy tickets in advance!
- Alternative live performances:
- See the Nutcracker performed by the Joffrey Ballet – they have incorporated the 1893 Chicago World’s Fair into the story making it a unique experience!
- Alternative live performances:
- Optional: Finish out your evening with Karaoke at Brando’s Speakeasy, I’ve only visited the one in the Loop, but I’m sure both locations are great!
Half Day: Sunday
Highlights include a delicious brunch, and option to take a boat tour. If you have additional time, check out the list of Notable Christmas/Cold Weather Activity Mentions.
- 10AM: Brunch at the Duck Inn – The Duck Inn – let them know in advance you want a whole roasted duck, their specialty!
- Alternative: Kanela Old Town, grab pastries to take home from La Fournette, a delicious French bakery next door
- 12:00PM Optional Activity: If you have time Architecture Boat Tour, I really like Chicago Architecture Center they generally have an indoor area, and you can buy a warm drink at the bar. Be sure to buy tickets in advance
- ??: Depart Chicago
Notable Christmas/Cold Weather Activity Mentions:
- Morton Arboretum Illumination Tree Lights – this is a bit of a hike from downtown Chicago, best if you have access to a car
- Chicago Botanic Garden – this is also a bit of a hike from downtown Chicago, best if you have access to a car
- Royal Palms Shuffleboard (see pic below)
- Stay in the Hotel at Midtown where guests of the hotel have access to the luxurious Midtown Athletic Club
- The Shops at Northbridge – 4 stories of department stores if you don’t want to shop outdoors on Mag Mile
- Peninsula Hotel Sky Ice Skating Rink
- Other Live Performances
- A Christmas Carol – Goodman Theatre
- Irving Berlin’s White Christmas – Marriott Theatre
- Christmas with the King: Brandon Bennett Sings Elvis – Marriott Theatre
- Hip Hop Nutcracker – CIBC Theater
- Fairytale of New York – Broadway Playhouse at Water Tower Place
- Chicago Symphony Orchestra
- Check out which Professional Sports teams may have games while you are in town: NHL, NBA, NFL
Favorite Wintertime Restaurants:
- Chicago Winery
- Au Cheval – for one of the alleged best burgers in Chicago – a hot topic among locals
- La Fournette – for delicious French breakfast pastries
- Lost Larson (2 locations) – for delicious breakfast pastries and good coffee
- Oromo Coffee – Turkish coffee shop with Turkish pastries
- 20 Michelin rated restaurants and 45 Bib Gourmand restaurants – reservations generally required well in advance. Some of my Michelin faves are Moody Tongue, El Ideas, and Topolobampo
- Tortello’s for fresh pasta
- Bloom for gourmet vegan that will convert any meat eater (Wicker Park)
- Moody Tongue Bar, lots of the same bites that can be found on the restaurant’s tasting menu, but without the commitment of the pricier fixed menu – great for dinner (Chinatown)
- Note: the area around this restaurant looks shady AF at night for some reason, but I’ve never had any issues, especially just hopping into an uber/Lyft – still trust your gut, remain vigilant.
- Logan Square Restaurants– my favorite neighborhood in Chicago, will give you a more Chicago local experience:
- Daisies for fresh pasta – named one of most exciting places to eat in US by NY Times
- Lula Café – always has a line waiting for brunch, every day of the week
- Giant – best for 2
- Longman & Eagle – rotating farm to table menu, great whiskey collection, can also stay at the inn here apparently
- Scofflaws – best for cocktails, but they also serve decent pub food. Cozy with two fireplaces and lots of mismatched seating
Final Thoughts
Chicago has many wonderful activities to get into for the holiday season. You could easily spend a full week exploring all that this beautiful city has to offer. Let me know in the comments which activities are your favorites!
