25 days in Chicago Itinerary

25 days in Chicago Itinerary

Created using Inspirock Chicago trip planner

Make it your trip
1
Chicago
— 24 nights

S M T W T F S
22
23
24
25
26
27
28
29
30
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19

Chicago

— 24 nights

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Your day by day itinerary now includes Shedd Aquarium as well as Adler Planetarium. You'll explore the less-touristy side of things at Chicago Riverwalk and Lakefront Trail. Get outdoors at Starved Rock State Park and Indiana Dunes National Park. Explore the numerous day-trip ideas around Chicago: Milwaukee (Milwaukee Art Museum, Historic Third Ward, &more), Lake Geneva (Geneva Lake Shore Path & Geneva Lake) and Saint Joseph (Silver Beach Carousel, Silver Beach County Park, &more). The adventure continues: examine the collection at Richard H. Driehaus Museum, take a tour by water with Boat Tours & Water Sports, pause for some serene contemplation at Basilica of the Sacred Heart, and contemplate the waterfront views at Lake Michigan.

To see maps, where to stay, reviews, and other tourist information, go to the Chicago trip itinerary planning website.

September in Chicago sees daily highs of 78°F and lows of 61°F at night. Finish your sightseeing early on the 19th (Sat) so you can travel back home.

Things to do in Chicago

Parks · Outdoors · Museums · Beaches

Side Trips