16 days in Chicago Itinerary

16 days in Chicago Itinerary

Created using Inspirock Chicago itinerary planner

Make it your trip
1
Chicago
— 15 nights

S M T W T F S
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
1
2
3

Chicago

— 15 nights

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Step out of the city life by going to Fishing Charters & Tours and Hawthorn Hollow - Nature Sanctuary and Arboretum. Head to The Magnificent Mile and Ernest Hemingway Birthplacefor some retail therapy. Venture out of the city with trips to Weko Beach Park (in Bridgman), Bender Park Waterfront (in Oak Creek) and Silver Beach County Park (in Saint Joseph). Next up on the itinerary: admire the masterpieces at The Art Institute of Chicago, hike along Little Red Schoolhouse, get curious at Field Museum, and grab your bike and head to Busse Woods Trail System.

To find other places to visit, maps, traveler tips, and other tourist information, read our Chicago trip planner.

In July, plan for daily highs up to 83°F, and evening lows to 67°F. Wrap up your sightseeing on the 30th (Tue) to allow time to travel back home.

Things to do in Chicago

Parks · Outdoors · Wildlife · Trails

Side Trips