8 days in Chicago Itinerary

8 days in Chicago Itinerary

Created using Inspirock United States trip planner

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

Route & dates

View / edit route

1
Chicago
— 7 nights

7
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Eschew the tourist crowds and head to Silver Beach County Park and Carpenter Creek Cellars. Head to The Magnificent Mile and Manteno Antique Mallfor some retail therapy. Explore the numerous day-trip ideas around Chicago: Prarie States Winery (in Genoa), Tom's Farm Market and Greenhouse (in Huntley) and John Deere Historic Site (in Grand Detour). Next up on the itinerary: explore the world behind art at The Art Institute of Chicago, enjoy breathtaking views from Skydeck Chicago - Willis Tower, hike along Starved Rock State Park, and appreciate the extensive heritage of Millennium Park.

To see ratings, where to stay, traveler tips, and other tourist information, you can read our Chicago holiday app .

If you are flying in from Croatia, the closest major airports are Chicago Midway International Airport, Chicago O'Hare International Airport and South Bend Regional Airport. In November in Chicago, expect temperatures between 11°C during the day and 1°C at night. Finish your sightseeing early on the 30th (Fri) so you can travel back home.

Things to do in Chicago

Parks Outdoors Historic Sites

Side Trips

South Bend, Carpenter Creek Cellars, Geneva Lake Shore Path, Silver Beach County Park, Ernest Hemingway Birthplace
Highlights from your plan
The Art Institute of Chicago ©
The Art Institute of Chicago
Millennium Park ©
Millennium Park
John Deere Historic Site ©
John Deere Historic Site

Similar Plans

10 days in Chicago BY A USER FROM URUGUAY November, kids, culture, outdoors, relaxing, historic sites, shopping, popular sights PREFERENCES: November, kids, culture, outdoors, relaxing, historic sites, shopping ATTRACTION STYLE: Popular sights PACE: Medium 10 days in Racine & Chicago BY A USER FROM UNITED STATES December, kids, culture, outdoors, relaxing, romantic, beaches, historic sites, wildlife, fast-paced, popular sights PREFERENCES: December, kids, culture, outdoors, relaxing, romantic, beaches, historic sites, wildlife ATTRACTION STYLE: Popular sights PACE: Fast-paced 10 days in Chicago BY A USER FROM UNITED STATES November, culture, outdoors, historic sites, wildlife, popular sights PREFERENCES: November, culture, outdoors, historic sites, wildlife ATTRACTION STYLE: Popular sights PACE: Medium 11 days in Chicago BY A USER FROM UNITED STATES October, culture, outdoors, relaxing, historic sites, popular & hidden gems PREFERENCES: October, culture, outdoors, relaxing, historic sites ATTRACTION STYLE: Popular & hidden gems PACE: Medium 9 days in Chicago BY A USER FROM ISRAEL June, culture, historic sites, wildlife, popular sights PREFERENCES: June, culture, historic sites, wildlife ATTRACTION STYLE: Popular sights PACE: Medium 9 days in Chicago BY A USER FROM UNITED STATES February, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, popular & hidden gems PREFERENCES: February, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping ATTRACTION STYLE: Popular & hidden gems PACE: Medium 9 days in Chicago BY A USER FROM UNITED STATES November, culture, outdoors, relaxing, historic sites, fast-paced, popular & hidden gems PREFERENCES: November, culture, outdoors, relaxing, historic sites ATTRACTION STYLE: Popular & hidden gems PACE: Fast-paced 9 days in Chicago BY A USER FROM UNITED STATES July, culture, relaxing, historic sites, shopping, popular sights PREFERENCES: July, culture, relaxing, historic sites, shopping ATTRACTION STYLE: Popular sights PACE: Medium 9 days in Chicago BY A USER FROM UNITED STATES July, culture, outdoors, relaxing, romantic, museums, shopping, wildlife, popular & hidden gems PREFERENCES: July, culture, outdoors, relaxing, romantic, museums, shopping, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Medium 10 days in Chicago BY A USER FROM URUGUAY November, culture, outdoors, historic sites, shopping, popular sights PREFERENCES: November, culture, outdoors, historic sites, shopping ATTRACTION STYLE: Popular sights PACE: Medium 10 days in New York City & Chicago BY A USER FROM SWITZERLAND November, culture, outdoors, relaxing, romantic, historic sites, museums, shopping, wildlife, fast-paced, popular sights PREFERENCES: November, culture, outdoors, relaxing, romantic, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular sights PACE: Fast-paced 7 days in Chicago BY A USER FROM GUATEMALA November, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife, popular sights PREFERENCES: November, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular sights PACE: Medium
View more plans