16 days in Chicago Itinerary

16 days in Chicago Itinerary

Created using Inspirock Chicago trip planner

Make it your trip
1
Chicago
— 15 nights

S M T W T F S
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28

Chicago

— 15 nights

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Venture out of the city with trips to Milwaukee (Basilica of St. Josaphat, Chudnow Museum of Yesteryear, &more), South Bend (Grotto of Our Lady Lourdes, Basilica of the Sacred Heart, &more) and Saint Joseph (Whirlpool Compass Fountain & Silver Beach Carousel). There's lots more to do: admire the masterpieces at The Art Institute of Chicago, get curious at Museum of Science and Industry, enjoy breathtaking views from 360 Chicago Observation Deck, and learn about wildlife with up-close encounters at Lincoln Park Zoo.

To find photos, ratings, other places to visit, and other tourist information, you can read our Chicago trip tool.

If you are flying in from Canada, the closest major aiports are Chicago Midway International Airport, Chicago O'Hare International Airport and Gary Chicago International Airport. In September, plan for daily highs up to 30°C, and evening lows to 19°C. Cap off your sightseeing on the 27th (Fri) early enough to travel back home.

Things to do in Chicago

Museums · Parks · Historic Sites · Fun & Games

Side Trips