Illinois, US, United States · Trip plan
3 days in Chicago at Christmas
Christkindlmarket, skyscraper skylines and deep-dish pizza.
- Best time
- Nov – Dec, May – Sep
- Ideal length
- 3 days
- A day, mid-range
- $300 per person
- Trip for two
- about $1,800
Planning a 3-day trip to Chicago at Christmas? Here's a day-by-day Chicago at Christmas itinerary with what it costs, where to stay and how to get there, ready to follow or make your own.
Why go now
From mid-November the Christkindlmarket fills Daley Plaza and the Magnificent Mile's lights switch on: a classic US Christmas break.
Chicago is America's architecture capital, a lakefront city of museums, blues clubs and some of the country's best food.
- Jan
- Feb
- Mar
- Apr
- May: a good time to go
- Jun: a good time to go
- Jul: a good time to go
- Aug: a good time to go
- Sep: a good time to go
- Oct
- Nov: a good time to go
- Dec: a good time to go
December: -6 to 2°C, windy.
Don't miss
Best things to do in Chicago at Christmas
- 01
Christkindlmarket
A German-style Christmas market downtown.
- 02
Millennium Park
The Bean and skating at the McCormick Tribune rink.
- 03
Architecture river cruise
Chicago's skyline from the water.
- 04
Art Institute
Seurat, Hopper and Van Gogh.
Day by day
Chicago at Christmas itinerary for 3 days
- D1
Day 1: Millennium Park
- Morning
- See your reflection in the Bean (Cloud Gate) and skate at the McCormick Tribune rink.
- Afternoon
- Art Institute of Chicago: Seurat's 'A Sunday Afternoon', Hopper's 'Nighthawks' and more.
- Evening
- Christkindlmarket in Daley Plaza, then deep-dish pizza.
Buy Art Institute tickets online.
- D2
Day 2: Skyline and the Magnificent Mile
- Morning
- Step onto the glass ledge at the Skydeck in Willis Tower.
- Afternoon
- Walk the Magnificent Mile for holiday window displays and lights.
- Evening
- Live blues at Kingston Mines or Buddy Guy's Legends.
The wind off the lake is bitter; wrap up.
- D3
Day 3: Museums and home
- Morning
- Visit the Field Museum to meet SUE the T. rex, or Navy Pier's winter wonderland.
- Afternoon
- Lunch of an Italian beef sandwich.
- Evening
- Fly home.
Allow 45 minutes to O'Hare by train.
Shorter or longer
Chicago at Christmas in 2, 3 or 5 days
2 days in Chicago at Christmas
Follow days 1 to 2 above and leave out “Museums and home”. Start early each day and book the main sights ahead.
5 days in Chicago at Christmas
Slow down with a free day for a spa, a cooking class or simply wandering, then add 1 day in New York at Christmas.
What it costs
Chicago at Christmas trip budget
| Style | Per person, a day | 3 days for two |
|---|---|---|
| Budget | $150 | $900 |
| Mid-range | $300 | $1,800 |
| Luxury | $700+ | $4,200 |
Stay, food, local transport and entry fees; travel to Chicago at Christmas is extra. Rough guides from recent prices, so check before you book.
Where to stay
Best hotels in Chicago at Christmas for every budget
What to eat
Food to try in Chicago at Christmas
Deep-dish pizza
At Lou Malnati's or Giordano's.
Chicago hot dog
With all the toppings, no ketchup.
Italian beef
A dripping sandwich.
Getting there
How to reach Chicago at Christmas
- Travel
- O'Hare and Midway airports, both linked to the Loop by the 'L' train.
- Getting around
- The 'L' trains and walking.
- Dress for wind chill; it's cold off the lake.
- Architecture cruises run until mid-November.
Before you go
What to pack for Chicago at Christmas
- Power bank and charging cables
- Passport and visa printouts
- Clothes that cover shoulders and knees for temples
- A forex card or some local cash
- Travel insurance
Good questions
Chicago at Christmas trip FAQs
How many days are enough for Chicago at Christmas?
3 days are enough to see the highlights: Christkindlmarket, Millennium Park, Architecture river cruise. Add a day or two if you like a slower pace.
How much does a 3-day Chicago at Christmas trip cost?
Roughly $150 a day per person on a budget, $300 mid-range and $700+ for luxury, not counting travel to get there. For two people mid-range, that's about $1,800 for 3 days.
What is the best time to visit Chicago at Christmas?
Nov – Dec, May – Sep. From mid-November the Christkindlmarket fills Daley Plaza and the Magnificent Mile's lights switch on: a classic US Christmas break.
Where should I stay in Chicago at Christmas?
Budget: HI Chicago (The Loop), from about $60 a night. Mid-range: Hotels on Michigan Avenue (Magnificent Mile), from about $250 a night. Luxury: The Langham, Chicago (River North), from about $600 a night.
How do I reach Chicago at Christmas?
O'Hare and Midway airports, both linked to the Loop by the 'L' train.
Is 2 days enough for Chicago at Christmas?
Yes, if you focus: follow days 1 to 2 of the itinerary above and skip "Museums and home". 3 days is the comfortable length.
What is the weather like in Chicago at Christmas?
December: -6 to 2°C, windy.
What food should I try in Chicago at Christmas?
Deep-dish pizza: At Lou Malnati's or Giordano's. Chicago hot dog: With all the toppings, no ketchup. Italian beef: A dripping sandwich.
How do I get around Chicago at Christmas?
The 'L' trains and walking.
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