8 days in Chicago Itinerary

8 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
— 7 nights

7
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Give yourself a bit of retail therapy at The Magnificent Mile and Chicago Cultural Center. Your inner history buff will appreciate Ernest Hemingway Birthplace and Basilica of the Sacred Heart. You'll find plenty of places to visit near Chicago: Cantigny Park (in Wheaton), Willow Springs (Little Red Schoolhouse & Centennial Bike Trail) and Panhandle Pathway (in Winamac). There's still lots to do: admire the masterpieces at The Art Institute of Chicago, get a new perspective on nature at Field Museum, trek along Geneva Lake Shore Path, and admire the landmark architecture of Frank Lloyd Wright Home and Studio.

To see other places to visit, reviews, maps, and more tourist information, read our Chicago road trip website .

In October in Chicago, expect temperatures between 65°F during the day and 49°F at night. Finish up your sightseeing early on the 12th (Sat) so you can travel back home.

Things to do in Chicago

Parks Trails Outdoors

Side Trips

Oak Park, South Bend, Lake Geneva, Willow Springs, White River State Trail
Highlights from your plan
The Art Institute of Chicago ©
The Art Institute of Chicago
Field Museum ©
Field Museum
Museum of Science and Industry ©
Museum of Science and Industry

Similar Plans

9 days in United States BY A USER FROM SOUTH KOREA June, teens, kids, popular sights PREFERENCES: June, teens, kids ATTRACTION STYLE: Popular sights PACE: Medium 10 days in Continental USA BY A USER FROM INDIA August, teens, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, popular & hidden gems PREFERENCES: August, teens, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Medium 30 days in United States BY A USER FROM UNITED KINGDOM July, culture, outdoors, relaxing, romantic, historic sites, museums, wildlife, popular sights PREFERENCES: July, culture, outdoors, relaxing, romantic, historic sites, museums, wildlife ATTRACTION STYLE: Popular sights PACE: Medium 9 days in Chicago BY A USER FROM MEXICO December, kids, popular sights PREFERENCES: December, kids ATTRACTION STYLE: Popular sights PACE: Medium 10 days in Cleveland & Chicago BY A USER FROM CANADA August, culture, romantic, beaches, historic sites, museums, shopping, popular & hidden gems PREFERENCES: August, culture, romantic, beaches, historic sites, museums, shopping ATTRACTION STYLE: Popular & hidden gems PACE: Medium 13 days in Chicago BY A USER FROM UNITED KINGDOM October, relaxing, romantic, wildlife, slow & easy, hidden gems PREFERENCES: October, relaxing, romantic, wildlife ATTRACTION STYLE: Hidden gems PACE: Slow & easy 7 days in Chicago BY A USER FROM MEXICO December, kids, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, popular & hidden gems PREFERENCES: December, kids, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Medium 10 days in Chicago BY A USER FROM UNITED KINGDOM September, popular sights PREFERENCES: September ATTRACTION STYLE: Popular sights PACE: Medium 9 days in Chicago BY A USER FROM SOUTH AFRICA August, popular sights PREFERENCES: August ATTRACTION STYLE: Popular sights PACE: Medium 9 days in Chicago BY A USER FROM UNITED KINGDOM September, popular sights PREFERENCES: September ATTRACTION STYLE: Popular sights PACE: Medium
View more plans