5 days in Chicago Itinerary

5 days in Chicago Itinerary

Created using Inspirock United States route planner

This plan was created by another user.  Make it your plan

Route & dates

View / edit route

1
Chicago
— 4 nights

4
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Get a sense of the local culture at The Magnificent Mile and The Field Museum. The adventure continues: admire the masterpieces at The Art Institute of Chicago, appreciate the extensive heritage of Millennium Park, get in on the family fun at Navy Pier, and get curious at Museum of Science and Industry.

For reviews, other places to visit, photos, and other tourist information, use the Chicago trip planner.

Expect a daytime high around 38°F in December, and nighttime lows around 26°F. Finish up your sightseeing early on the 21st (Fri) so you can travel back home.

Things to do in Chicago

Museums Parks Zoos & Aquariums

Side Trip

Ernest Hemingway Birthplace
Highlights from your plan
The Art Institute of Chicago ©
The Art Institute of Chicago
Millennium Park ©
Millennium Park
The Magnificent Mile ©
The Magnificent Mile

Similar Plans

7 days in Chicago BY A USER FROM UNITED STATES October, teens, kids, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, popular sights PREFERENCES: October, teens, kids, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular sights PACE: Medium 6 days in Chicago BY A USER FROM BRAZIL September, culture, outdoors, relaxing, romantic, historic sites, museums, shopping, popular & hidden gems PREFERENCES: September, culture, outdoors, relaxing, romantic, historic sites, museums, shopping ATTRACTION STYLE: Popular & hidden gems PACE: Medium 8 days in Chicago BY A USER FROM UNITED KINGDOM September, outdoors, historic sites, museums, wildlife, popular sights PREFERENCES: September, outdoors, historic sites, museums, wildlife ATTRACTION STYLE: Popular sights PACE: Medium 7 days in Chicago BY A USER FROM UNITED STATES September, culture, outdoors, relaxing, historic sites, museums, shopping, popular sights PREFERENCES: September, culture, outdoors, relaxing, historic sites, museums, shopping ATTRACTION STYLE: Popular sights PACE: Medium 8 days in Chicago & Miami BY A USER FROM BRAZIL November, culture, relaxing, romantic, beaches, historic sites, museums, wildlife, slow & easy, popular & hidden gems PREFERENCES: November, culture, relaxing, romantic, beaches, historic sites, museums, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Slow & easy 3 days in Chicago BY A USER FROM UNITED STATES September, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife, fast-paced, popular sights PREFERENCES: September, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular sights PACE: Fast-paced 4 days in Chicago BY A USER FROM UNITED STATES November, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife, fast-paced, popular sights PREFERENCES: November, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular sights PACE: Fast-paced 6 days in Chicago BY A USER FROM AUSTRALIA July, culture, relaxing, historic sites, museums, shopping, popular sights PREFERENCES: July, culture, relaxing, historic sites, museums, shopping ATTRACTION STYLE: Popular sights PACE: Medium 6 days in Chicago BY A USER FROM SOUTH AFRICA December, teens, kids, slow & easy, popular sights PREFERENCES: December, teens, kids ATTRACTION STYLE: Popular sights PACE: Slow & easy 6 days in Chicago BY A USER FROM UNITED STATES September, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, popular sights PREFERENCES: September, culture, outdoors, relaxing, romantic, beaches, historic sites, museums ATTRACTION STYLE: Popular sights PACE: Medium 7 days in Chicago BY A USER FROM UNITED STATES September, culture, historic sites, museums, shopping, popular & hidden gems PREFERENCES: September, culture, historic sites, museums, shopping ATTRACTION STYLE: Popular & hidden gems PACE: Medium 7 days in Chicago BY A USER FROM QATAR November, culture, outdoors, relaxing, romantic, historic sites, museums, shopping, popular sights PREFERENCES: November, culture, outdoors, relaxing, romantic, historic sites, museums, shopping ATTRACTION STYLE: Popular sights PACE: Medium
View more plans