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27 days in Chicago Itinerary

Created using Klarna Trips Chicago travel planner
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Start from...
1
Chicago
— 26 nights
End at...
Thu, Jan 19 - Tue, Feb 14 Edit
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Chicago — 26 nights

The Art Institute of Chicago ©

Windy City

Explore the numerous day-trip ideas around Chicago: The Promenade Bolingbrook (in Bolingbrook), South Bend (Grotto of Our Lady Lourdes, Basilica of the Sacred Heart, &more) and Romeoville (The Beller Museum & Mistwood Golf Club). There's much more to do: explore the world behind art at The Art Institute of Chicago, enjoy breathtaking views from 360 Chicago Observation Deck, make a trip to Skydeck Chicago - Willis Tower, and learn about wildlife with up-close encounters at Lincoln Park Zoo.

To find photos, other places to visit, reviews, and more tourist information, use the Chicago online visit planner.

Expect a daytime high around 32°F in January, and nighttime lows around 18°F.
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Things to do in Chicago
Museums · Historic Sites · Parks · Outdoors
Side Trips
Oak Park, Milwaukee, Evanston, South Bend, Hammond
Find places to stay Jan 19 — Feb 14:
Find places to stay with best proximity to your trip
Highlights from your trip
The Art Institute of Chicago ©
Must see
The Art Institute of Chicago
4.8
Shedd Aquarium ©
Must see
Shedd Aquarium
4.1
Millennium Park ©
Must see
Millennium Park
4.8
See timeline

Top Chicago tours

BOOK WITH VIATOR Chicago Architecture River Cruise
4.8
Duration: 1h 15min
Tours from $50 ›
BOOK WITH VIATOR Gangsters and Ghosts Tour in Chicago
4.8
Duration: 2h
Tours from $35 ›
Likely to sell out BOOK WITH VIATOR 90-Minute Chicago River Architecture Tour
4.7
Duration: 1h 30min
Tours from $42 ›
BOOK WITH VIATOR Chicago Crime and Mob Bus Tour
4.5
Duration: 1h 30min - 2h
Tours from $46 ›
Likely to sell out BOOK WITH VIATOR Chicago Lake and River Architecture Tour
4.7
Duration: 1h 30min
Tours from $42 ›
BOOK WITH VIATOR Big Bus Chicago Hop-On Hop-Off Tour
4.0
Duration: 1h
Tours from $49 ›
BOOK WITH VIATOR Chicago Favorites Ultimate Food & Walking Tour
4.8
Duration: 3h
Tours from $80 ›
Likely to sell out BOOK WITH VIATOR Chicago Sunset Cruise
4.5
Duration: 1h 30min
Tours from $42 ›
BOOK WITH VIATOR Lake Michigan Skyline Cruise in Chicago
4.4
Duration: 40min
Tours from $35 ›
See all tours

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