60 days in Chicago Itinerary

60 days in Chicago Itinerary

Created using Inspirock Chicago trip itinerary planner

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

Route & dates

View / edit route

1
Chicago
— 59 nights
Edit
View full calendar

59
nights
Chicago

Chicago ©

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Change things up with these side-trips from Chicago: Baha'i House of Worship (in Wilmette), Evanston (Halim Time & Glass Museum, Merrick Rose Garden, & more) and Illinois Holocaust Museum & Education Center (in Skokie). Next up on the itinerary: admire the masterpieces at The Art Institute of Chicago, take a leisurely stroll along Navy Pier, enjoy breathtaking views from 360 Chicago Observation Deck, and get to know the resident critters at Lincoln Park Zoo.

To see traveler tips, maps, more things to do, and more tourist information, use the Chicago journey planner.

In December, daily temperatures in Chicago can reach 38°F, while at night they dip to 26°F. Finish your sightseeing early on the 29th (Wed) so you can travel back home.

Things to do in Chicago

Museums Parks Historic Sites

Side Trips

Evanston, Dixon, South Bend, Oak Park, Lake Geneva
Highlights from your plan
The Art Institute of Chicago ©
The Art Institute of Chicago
1:30pm, Sun Dec 1
Millennium Park ©
Millennium Park
4:00pm, Sun Dec 1
Museum of Science and Industry ©
Museum of Science and Industry
11:00am, Tue Dec 31

Similar Plans

5 days in Chicago BY A USER FROM UNITED STATES November, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife, popular & hidden gems PREFERENCES: November, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Medium 6 days in Chicago BY A USER FROM UNITED STATES December, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife, popular & hidden gems PREFERENCES: December, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Medium 6 days in Chicago BY A USER FROM MEXICO October, culture, outdoors, relaxing, romantic, historic sites, museums, shopping, popular & hidden gems PREFERENCES: October, culture, outdoors, relaxing, romantic, historic sites, museums, shopping ATTRACTION STYLE: Popular & hidden gems PACE: Medium 5 days in Chicago BY A USER FROM UNITED STATES December, culture, outdoors, relaxing, beaches, historic sites, shopping, wildlife, popular & hidden gems PREFERENCES: December, culture, outdoors, relaxing, beaches, historic sites, shopping, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Medium 5 days in Chicago BY A USER FROM UNITED STATES November, culture, outdoors, relaxing, romantic, historic sites, museums, wildlife, fast-paced, popular sights PREFERENCES: November, culture, outdoors, relaxing, romantic, historic sites, museums, wildlife ATTRACTION STYLE: Popular sights PACE: Fast-paced 11 days in New York City, District of Columbia & Chicago BY A USER FROM PHILIPPINES December, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, popular sights PREFERENCES: December, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular sights PACE: Medium 22 days in United States BY A USER FROM AUSTRALIA March, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, popular & hidden gems PREFERENCES: March, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Medium 5 days in Chicago BY A USER FROM UNITED STATES November, teens, kids, culture, relaxing, historic sites, museums, shopping, popular sights PREFERENCES: November, teens, kids, culture, relaxing, historic sites, museums, shopping ATTRACTION STYLE: Popular sights PACE: Medium 32 days in United States BY A USER FROM AUSTRALIA October, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, popular sights PREFERENCES: October, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular sights PACE: Medium 3 days in Chicago BY A USER FROM UNITED STATES January, culture, relaxing, historic sites, museums, shopping, popular & hidden gems PREFERENCES: January, culture, relaxing, historic sites, museums, shopping ATTRACTION STYLE: Popular & hidden gems PACE: Medium 29 days in United States BY A USER FROM UNITED KINGDOM August, culture, outdoors, relaxing, romantic, beaches, historic sites, shopping, wildlife, popular sights PREFERENCES: August, culture, outdoors, relaxing, romantic, beaches, historic sites, shopping, wildlife ATTRACTION STYLE: Popular sights PACE: Medium
View more plans
See also: