5 days in Chicago Itinerary

5 days in Chicago Itinerary

Created using Inspirock United States trip itinerary planner

You are viewing a shared plan.  Customize plan

Route & dates

View / edit route

Chicago
— 4 nights

5
days
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Chicago is known for museums, historic sites, nightlife, zoos & aquariums, and childrens museums. Your plan includes some of its best attractions: explore the world behind art at The Art Institute of Chicago, admire nature's wide array of creatures at Lincoln Park Zoo, wander the streets of The Magnificent Mile, and take in panoramic vistas at Skydeck Chicago - Willis Tower.

To find ratings, traveler tips, more things to do, and tourist information, you can read our Chicago trip planner .

Expect a daytime high around 39°F in December, and nighttime lows around 28°F. Finish your sightseeing early on the 3rd (Wed) so you can travel back home.

Things to do in Chicago

Museums Parks Zoos & Aquariums

Side Trip

Horseshoe Hammond Casino
Highlights from your plan
The Art Institute of Chicago ©
The Art Institute of Chicago
Millennium Park ©
Millennium Park

Similar Plans

6 days in United States BY A USER FROM ARGENTINA January, teens, kids, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, popular & hidden gems PREFERENCES: January, teens, kids, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Medium 8 days in Chicago BY A USER FROM TURKEY May, teens, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, popular PREFERENCES: May, teens, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular PACE: Medium 7 days in Chicago BY A USER FROM CANADA December, culture, outdoors, relaxing, romantic, historic sites, museums, shopping, wildlife, popular & hidden gems PREFERENCES: December, culture, outdoors, relaxing, romantic, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Medium 7 days in Chicago BY A USER FROM CANADA December, culture, outdoors, relaxing, romantic, historic sites, museums, shopping, wildlife, fast-paced, popular PREFERENCES: December, culture, outdoors, relaxing, romantic, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular PACE: Fast-paced 4 days in Chicago BY A USER FROM PAKISTAN February, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, fast-paced, hidden gems PREFERENCES: February, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Hidden gems PACE: Fast-paced 9 days in Chicago BY A USER FROM UNITED STATES December, culture, outdoors, romantic, beaches, historic sites, museums, popular & hidden gems PREFERENCES: December, culture, outdoors, romantic, beaches, historic sites, museums ATTRACTION STYLE: Popular & hidden gems PACE: Medium 6 days in Chicago BY A USER FROM UNITED STATES November, culture, relaxing, romantic, historic sites, museums, fast-paced, hidden gems PREFERENCES: November, culture, relaxing, romantic, historic sites, museums ATTRACTION STYLE: Hidden gems PACE: Fast-paced 4 days in Chicago BY A USER FROM UNITED STATES December, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, popular & hidden gems PREFERENCES: December, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Medium 8 days in Chicago BY A USER FROM UNITED STATES April, culture, outdoors, historic sites, museums, slow & easy, popular & hidden gems PREFERENCES: April, culture, outdoors, historic sites, museums ATTRACTION STYLE: Popular & hidden gems PACE: Slow & easy 9 days in Chicago BY A USER FROM BRAZIL May, culture, outdoors, relaxing, historic sites, museums, popular & hidden gems PREFERENCES: May, culture, outdoors, relaxing, historic sites, museums ATTRACTION STYLE: Popular & hidden gems PACE: Medium 6 days in Chicago BY A USER FROM UNITED STATES December, culture, outdoors, historic sites, museums, wildlife, fast-paced, popular PREFERENCES: December, culture, outdoors, historic sites, museums, wildlife ATTRACTION STYLE: Popular PACE: Fast-paced 6 days in Chicago BY A USER FROM TRINIDAD AND TOBAGO February, culture, outdoors, relaxing, historic sites, museums, shopping, popular PREFERENCES: February, culture, outdoors, relaxing, historic sites, museums, shopping ATTRACTION STYLE: Popular PACE: Medium
View more plans