If you’re spending Christmas break in Chicago—or you’re looking for ways to make the city feel extra magical between Christmas and New Year’s—you’re in the right place.
I’ve done this season enough times to know two things are true: Chicago goes all out for the holidays, and you don’t have to freeze the whole time to have fun. From twinkling lights and cozy museums to winter walks and even heated boat cruises on the river, here are my favorite ways to spend Christmas break in the city.
🎯 Quick Answer: The best things to do over Christmas break in Chicago include ZooLights at Lincoln Park Zoo (free, runs through January 5), ice skating at Millennium Park ($16 skate rental), the Museum of Science and Industry’s Christmas Around the World exhibit ($21.95), and a heated Duffy boat cruise on the Chicago River with Chicago Boat Company (from $250 for 90 minutes). Most holiday attractions run through New Year’s Day, making the week between Christmas and January 1st perfect for festive activities.
⭐ Quick Picks: Best of Christmas Break in Chicago
🏆 Best Free Activity:
ZooLights at Lincoln Park Zoo
👨👩👧👦 Best for Families:
Museum of Science & Industry
💑 Best Date Night:
Duffy Boat Cruise
📸 Most Instagrammable:
Millennium Park Ice Skating
🎭 Best Indoor Escape:
Chicago Cultural Center (free!)
☕ Best Cozy Experience:
Hot Chocolate Mini Tour
📋 In This Guide: 15 Things to Do
- Christkindlmarket
- ZooLights at Lincoln Park Zoo
- Millennium Park Ice Skating
- Duffy Boat Cruise
- Chicago Cultural Center
- Museum of Science & Industry
- Chicago Riverwalk Walk
- Holiday Shows & Concerts
- Garfield Park Conservatory
- Navy Pier
- Day Trip to Oak Park
- Hot Chocolate Tour
- Magnificent Mile Shopping
- Shedd Aquarium
- Winter Neighborhood Walk
↓ Jump to Comparison Table | ↓ Jump to FAQ
1. Wander Christkindlmarket (Yes, Even After Christmas)
📍 Location: Daley Plaza, 50 W Washington St, Chicago, IL 60602
🕐 Hours: 11am–8pm Sun–Thu, 11am–9pm Fri–Sat (check dates—usually ends Dec 24)
💰 Cost: Free admission
🌐 Website:christkindlmarket.com
Most people think Christkindlmarket is only for early December—but depending on the year and location, it often runs right up to Christmas Eve. I love going during the last week because it still feels festive, but the crowds can be a little more manageable.
Grab a warm drink (the glühwein is a must), browse handcrafted ornaments and gifts, and soak in the atmosphere. It’s one of those spots that instantly makes Chicago feel like Europe in winter.
💡 Pro Tip: Visit during weekday lunches for the smallest crowds. The Raclette (melted cheese on bread) is my go-to—worth every calorie.
2. See the City Lit Up at ZooLights (Lincoln Park Zoo)
📍 Location: Lincoln Park Zoo, 2001 N Clark St, Chicago, IL 60614
🕐 Hours: 4:30pm–9pm (runs through January 5, 2025)
💰 Cost: FREE (parking $20–$40)
🌐 Website:lpzoo.org/zoolights
🅿️ Parking: Zoo lot or street parking; consider CTA bus/Brown Line to Armitage
ZooLights is one of my favorite Chicago holiday traditions—millions of lights, festive music, and that cozy “winter night out” feeling. It’s fun with kids, surprisingly cute for date night, and honestly, I’m happy just walking around with a hot drink in hand.
The zoo transforms into a winter wonderland with animal-shaped light displays, illuminated tunnels, and holiday music everywhere. Best part? It’s completely free (one of the only free major light displays in Chicago).
💡 Pro Tip: Weeknights between Christmas and New Year’s are the sweet spot—festive but not shoulder-to-shoulder. Grab hot cocoa at the Café Brauer before you start walking.
3. Ice Skate at Millennium Park (or Just Watch)
📍 Location: McCormick Tribune Ice Rink, 55 N Michigan Ave, Chicago, IL 60601
🕐 Hours: 12pm–8pm daily (through early March, weather permitting)
💰 Cost: FREE to skate; $16 skate rental (or bring your own)
🌐 Website:chicagoparkdistrict.com
Skating with the Chicago skyline behind you and the Bean nearby is one of those classic Chicago moments. Even if you don’t skate, it’s worth stopping by to watch, grab a photo, and then duck into a nearby café to warm up.
The rink is free to use if you bring your own skates, and rentals are reasonable at $16. It’s right in the heart of downtown, making it easy to combine with other Loop activities.
💡 Pro Tip: Arrive right at noon when the rink opens for the shortest wait. After skating, warm up at Wildberry Pancakes & Café (about a 5-minute walk) or Stan’s Donuts.
4. Cruise the Chicago River in a Heated Duffy Boat
📍 Location: Chicago Boat Company, 1501 N Kingsbury St, Chicago, IL 60642
🕐 Hours: Various departure times; book in advance
💰 Cost: From $250 for 90 minutes (seats up to 10 people)
🌐 Website:thechicagoboatcompany.com
📞 Phone: (312) 757-6262
If you want something festive but more intimate than a big Chicago tour boat, a holiday Duffy boat cruise is such a fun way to experience the city during Christmas break.
Chicago Boat Company offers private, electric Duffy boats that are fully enclosed and heated—so you stay warm while cruising past the skyline and holiday lights along the Chicago River. You can bring your own drinks, snacks, and even plug in a holiday playlist, which makes this feel more like a floating living room than a traditional tour.
Why I love this during Christmas break: it works for families, small groups, or a festive date night—and it feels special without being over-the-top touristy. Split between 6-10 people, it’s surprisingly affordable.
💡 Pro Tip: Book a sunset cruise (around 4pm in late December) for the best combination of daylight skyline views and evening lights. Bring blankets for extra coziness!
5. Pop Into the Chicago Cultural Center (Free + Gorgeous)
📍 Location: 78 E Washington St, Chicago, IL 60602
🕐 Hours: 10am–5pm daily
💰 Cost: FREE
🌐 Website:chicagoculturalcenter.org
This is one of the most underrated winter stops in the city—and it’s completely free. The Tiffany stained-glass dome is absolutely stunning (it’s the world’s largest!), and during the holiday season you can often catch seasonal displays or performances that feel special without being hectic.
It’s also right across from Millennium Park, making it an easy warm-up stop before or after skating.
💡 Pro Tip: Don’t miss the Preston Bradley Hall dome—it’s straight out of a European palace. Stop by the visitor center to check for free concerts happening that day.
6. See “Christmas Around the World” at the Museum of Science and Industry
📍 Location: 5700 S DuSable Lake Shore Dr, Chicago, IL 60637
🕐 Hours: 9:30am–4pm daily (extended hours during holidays)
💰 Cost: $21.95 adults, $12.95 kids 3-11 (online advance purchase)
🌐 Website:msichicago.org
🅿️ Parking: $25 onsite garage
If you want peak holiday vibes without worrying about the weather, this is a perfect Christmas break activity. The “Christmas Around the World” display features over 50 decorated trees representing countries and cultures from around the globe—plus a four-story Grand Tree in the rotunda.
This exhibit has been running since 1942, making it one of Chicago’s longest-running holiday traditions.
💡 Pro Tip: Buy tickets online in advance for a discount and skip the ticket line. Plan 3-4 hours if you want to explore the rest of the museum too (the coal mine and submarine are family favorites).
7. Walk the Chicago Riverwalk (Winter Edition)
📍 Location: Runs along the Chicago River between Lake Shore Dr and Lake St
🕐 Hours: Open 24/7 (some vendors closed in winter)
💰 Cost: FREE
🌐 Website:chicagoriverwalk.us
I know the Riverwalk is usually a summer thing—but I actually love it during Christmas break because it’s quieter and feels more peaceful. Bundle up, grab a warm drink, and enjoy the city lights reflecting off the water.
Most of the restaurants and vendors are closed in winter, but that’s part of the appeal—it feels like you have the city to yourself.
💡 Pro Tip: Time your walk for dusk (around 4:15pm in late December) when the city lights are starting to glow but it’s not fully dark yet. The Wrigley Building lit up across the river is magical.
8. Catch a Holiday Show or Concert
📍 Popular Venues: Goodman Theatre, Chicago Theatre, Auditorium Theatre, Symphony Center
💰 Cost: Varies ($30–$150+ depending on show)
🌐 Tickets:broadwayinchicago.com or individual venue sites
Christmas break is one of the best times of year for live entertainment in Chicago—Broadway-style shows, holiday concerts, and smaller theater performances. If you want one “special night out” during break, make it this.
Popular options include: A Christmas Carol at Goodman Theatre, The Nutcracker at Joffrey Ballet, and Chicago Symphony Orchestra’s holiday concerts. Book early—these sell out.
💡 Pro Tip: Book one big show, then plan dinner nearby before or dessert after. The theater district has plenty of options within walking distance.
9. Warm Up Inside Garfield Park Conservatory
📍 Location: 300 N Central Park Ave, Chicago, IL 60624
🕐 Hours: 9am–5pm Wed–Sun (closed Mon–Tue in winter)
💰 Cost: FREE (donations appreciated)
🌐 Website:garfieldconservatory.org
🅿️ Parking: Free lot onsite
When winter starts to feel a little long, this place feels like a reset. It’s warm, lush, and honestly one of the quickest ways to go from “Chicago winter” to “tropical greenhouse” in under an hour.
The conservatory is one of the largest in the nation, featuring six different garden rooms including a fern room, palm house, and children’s garden. It’s completely free and perfect for all ages.
💡 Pro Tip: Time your visit for mid-morning when it’s least crowded. The Palm House is genuinely tropical—you’ll want to take off your coat.
10. Visit Navy Pier in Winter Mode
📍 Location: 600 E Grand Ave, Chicago, IL 60611
🕐 Hours: 10am–8pm (hours vary by attraction)
💰 Cost: Free entry; individual attractions vary ($15–$25)
🌐 Website:navypier.org
🅿️ Parking: $30–$40 (or take CTA)
Navy Pier is a totally different experience in winter—still fun, but calmer and less touristy. The Centennial Wheel often runs through the holidays (weather permitting), and there are plenty of indoor attractions if it’s freezing outside.
Indoor options include the Chicago Children’s Museum, Crystal Gardens (a botanical garden under glass), and various restaurants and shops.
💡 Pro Tip: The Centennial Wheel at sunset is gorgeous—and way shorter lines than summer. Check the website before you go to confirm winter hours.
11. Take a Day Trip to Oak Park
📍 Location: Oak Park, IL (9 miles west of downtown Chicago)
🕐 Getting There: 25 min on CTA Green Line to Oak Park stop
💰 Cost: Free to explore; Frank Lloyd Wright Home tours $18–$40
🌐 Website:visitoakpark.com
If you want a break from downtown crowds, Oak Park is an easy day trip with a totally different vibe. Between historic Frank Lloyd Wright architecture, local shops on Lake Street, and cozy cafés, it’s a great “slow day” during Christmas break.
This is the town where Ernest Hemingway grew up and where Frank Lloyd Wright developed his Prairie style—plenty of history mixed with charming small-town shopping.
💡 Pro Tip: Take the Green Line—parking can be tricky. Grab lunch at Hemmingway’s Bistro or Buzz Café, both local favorites.
12. Do a Chicago Hot Chocolate “Mini Tour”
☕ Top Hot Chocolate Spots:
* Mindy’s Bakery – 1623 N Milwaukee Ave (rich, European-style)
* Xoco – 449 N Clark St (Mexican hot chocolate)
* Stan’s Donuts – Multiple locations (classic + donuts)
* Sawada Coffee – 112 N Green St (matcha option too)
* The Dearborn – 145 N Dearborn St (upscale, boozy options)
Christmas break is the perfect excuse to sample your way through the city—cozy cafés, bakeries, and dessert spots. I like pairing this with a neighborhood walk so it feels like an outing, not just a sugar mission.
Make it a “mini tour”—pick 2-3 spots in the same neighborhood and walk between them. The hot chocolate at Xoco (Rick Bayless’s spot) is genuinely life-changing.
💡 Pro Tip: Combine a Wicker Park walk with stops at Mindy’s and Sawada—they’re about 10 minutes apart and the neighborhood is great for browsing.
13. Shop the Magnificent Mile After Christmas
📍 Location: Michigan Ave from the Chicago River to Oak Street
🕐 Hours: Store hours vary (most 10am–8pm)
💰 Cost: Free to walk; shopping varies (great post-holiday sales!)
🌐 Website:themagnificentmile.com
Post-Christmas shopping on the Mag Mile is calmer than the holiday rush—and the deals are usually better. It’s also one of the prettiest times to see the holiday lights without shoulder-to-shoulder crowds.
Major stores include Water Tower Place, Nordstrom, Apple, and dozens more. The holiday window displays often stay up through early January.
💡 Pro Tip: Walk the Mile at night when the lights are on—it’s genuinely magical. Start at Oak Street and walk south toward the river for the best views.
14. Spend an Afternoon at Shedd Aquarium
📍 Location: 1200 S DuSable Lake Shore Dr, Chicago, IL 60605
🕐 Hours: 9am–5pm daily (6pm on weekends)
💰 Cost: $29.95–$44.95 adults; $24.95–$39.95 kids 3-11 (varies by package)
🌐 Website:sheddaquarium.org
🅿️ Parking: $30 Soldier Field North Garage
If the weather is miserable (it happens), Shedd is one of the best indoor options. It’s fun for all ages, and it’s an easy way to turn a cold afternoon into something memorable.
Don’t miss the Oceanarium dolphin shows, the penguin habitat, or the Caribbean Reef exhibit. Plan for 2-3 hours minimum.
💡 Pro Tip: Illinois residents get free admission on select days—check the website. Combine with a quick walk to the Adler Planetarium next door for skyline views.
15. Take a Chicago Winter Neighborhood Walk
🚶 Best Winter Walk Neighborhoods:
* Lincoln Park – Classic Chicago charm, brownstones, cozy cafés
* Wicker Park – Shopping, coffee, vintage stores
* The Loop – Iconic holiday sights, architecture
* Andersonville – Swedish bakeries, unique shops
* Old Town – Historic streets, great restaurants
Sometimes the best thing to do is the simplest: pick a neighborhood and walk. During Christmas break, the city feels reflective and calm—lights linger, storefronts glow, and you can actually enjoy the vibe without rushing.
Choose your mood: Lincoln Park for classic Chicago charm, Wicker Park for shopping and coffee stops, or the Loop for iconic holiday sights.
💡 Pro Tip: Andersonville is my sleeper pick—the Swedish bakeries (try Ann Sather or Svea) make it extra cozy during the holidays, and it’s way less crowded than downtown neighborhoods.
Quick Comparison: All 15 Activities at a Glance
| Activity | Cost | Best For | Indoor/Outdoor |
|---|---|---|---|
| Christkindlmarket | Free entry | Couples, Foodies | Outdoor |
| ZooLights | Free | Families, All ages | Outdoor |
| Millennium Park Skating | Free ($16 rental) | Couples, Families | Outdoor |
| Duffy Boat Cruise | From $250/group | Date night, Small groups | Indoor (heated) |
| Cultural Center | Free | Architecture lovers | Indoor |
| MSI Christmas Trees | $21.95+ | Families | Indoor |
| Riverwalk Walk | Free | Couples, Photography | Outdoor |
| Holiday Shows | $30–$150+ | Special night out | Indoor |
| Garfield Conservatory | Free | Families, Nature lovers | Indoor |
| Navy Pier | Free entry ($15-25 rides) | Families, Tourists | Both |
| Oak Park Day Trip | Free–$40 | Architecture, History | Both |
| Hot Chocolate Tour | $5–$10/stop | Foodies, Anyone | Indoor |
| Mag Mile Shopping | Free (shopping varies) | Shoppers | Both |
| Shedd Aquarium | $29.95+ | Families | Indoor |
| Neighborhood Walk | Free | Anyone | Outdoor |
Activities by Type
🆓 Free Things to Do
| ZooLights | Lincoln Park Zoo | Through Jan 5 |
| Cultural Center | Downtown Loop | Daily 10am–5pm |
| Garfield Conservatory | West Side | Wed–Sun 9am–5pm |
| Millennium Park Skating | Downtown | Free (rental $16) |
👨👩👧👦 Best for Families with Kids
| Museum of Science & Industry | Hyde Park | $21.95+ (plan 3-4 hrs) |
| Shedd Aquarium | Museum Campus | $29.95+ (plan 2-3 hrs) |
| ZooLights | Lincoln Park | Free |
| Navy Pier | Streeterville | Free entry (rides extra) |
Frequently Asked Questions
The best thing to do over Christmas break in Chicago is ZooLights at Lincoln Park Zoo—it’s free, family-friendly, and runs through January 5th. For a unique experience, book a heated Duffy boat cruise with Chicago Boat Company to see the skyline lights from the river.
Free things to do during Christmas break in Chicago include ZooLights at Lincoln Park Zoo, ice skating at Millennium Park (bring your own skates), the Chicago Cultural Center with its stunning Tiffany dome, Garfield Park Conservatory, and walking the Magnificent Mile to see holiday lights.
The best indoor activities in Chicago during winter include the Museum of Science and Industry’s Christmas Around the World exhibit ($21.95), Shedd Aquarium ($29.95+), Chicago Cultural Center (free), Garfield Park Conservatory (free), and holiday shows at venues like the Goodman Theatre or Chicago Symphony Orchestra.
Final Thoughts
Christmas break in Chicago doesn’t have to be stressful or over-planned. Pick a few “big” experiences (ZooLights, a museum, maybe a show), mix in a couple cozy indoor stops (hot chocolate, conservatory), and leave room for wandering. That’s when Chicago feels the most magical.
The week between Christmas and New Year’s is one of my favorite times to be in the city—the holiday rush is over, but the lights and festive feeling linger. Enjoy it!