10 days in Chicago Itinerary

10 days in Chicago Itinerary

Created using Inspirock Chicago holiday planner

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

Route & dates

View / edit route

1
Chicago
— 9 nights

9
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Explore Chicago's surroundings by going to South Bend (University of Notre Dame & Basilica of the Sacred Heart), Bengtson's Pumpkin Farm (in Homer Glen) and Chicago Botanic Garden (in Glencoe). The adventure continues: explore the world behind art at The Art Institute of Chicago, take in panoramic vistas at Skydeck Chicago - Willis Tower, get to know the fascinating history of Millennium Park, and make a trip to The Magnificent Mile.

To see traveler tips, reviews, more things to do, and tourist information, refer to the Chicago trip maker tool .

If you are flying in from Canada, the closest major airports are Chicago Midway International Airport, Chicago O'Hare International Airport and South Bend Regional Airport. In October, daily temperatures in Chicago can reach 21°C, while at night they dip to 11°C. Wrap up your sightseeing on the 21st (Sun) early enough to travel back home.

Things to do in Chicago

Museums Parks Childrens Museums

Side Trips

Oak Park, South Bend, Horseshoe Hammond, Chicago Botanic Garden, Bengtson's Pumpkin Farm
Highlights from your plan
The Art Institute of Chicago ©
The Art Institute of Chicago
Millennium Park ©
Millennium Park
Wrigley Field ©
Wrigley Field

Similar Plans

11 days in Schaumburg & Chicago BY A USER FROM SINGAPORE October, culture, outdoors, relaxing, romantic, shopping, popular sights PREFERENCES: October, culture, outdoors, relaxing, romantic, shopping ATTRACTION STYLE: Popular sights PACE: Medium 14 days in United States BY A USER FROM UNITED STATES November, culture, outdoors, beaches, historic sites, shopping, wildlife, hidden gems PREFERENCES: November, culture, outdoors, beaches, historic sites, shopping, wildlife ATTRACTION STYLE: Hidden gems PACE: Medium 60 days in United States BY A USER FROM UNITED KINGDOM June, teens, kids, culture, outdoors, relaxing, beaches, historic sites, museums, wildlife, popular & hidden gems PREFERENCES: June, teens, kids, culture, outdoors, relaxing, beaches, historic sites, museums, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Medium 18 days in United States BY A USER FROM FRANCE October, outdoors, relaxing, beaches, shopping, slow & easy, popular sights PREFERENCES: October, outdoors, relaxing, beaches, shopping ATTRACTION STYLE: Popular sights PACE: Slow & easy 15 days in United States BY A USER FROM UNITED STATES September, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, popular & hidden gems PREFERENCES: September, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Medium 31 days in United States BY A USER FROM UNITED STATES September, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, popular & hidden gems PREFERENCES: September, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Medium 18 days in United States BY A USER FROM UNITED STATES 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 22 days in Chicago BY A USER FROM THAILAND January, culture, relaxing, beaches, historic sites, museums, shopping, hidden gems PREFERENCES: January, culture, relaxing, beaches, historic sites, museums, shopping ATTRACTION STYLE: Hidden gems PACE: Medium 9 days in Chicago & Islamorada BY A USER FROM UNITED STATES July, culture, outdoors, relaxing, romantic, shopping, wildlife, popular & hidden gems PREFERENCES: July, culture, outdoors, relaxing, romantic, shopping, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Medium 20 days in Chicago BY A USER FROM GHANA September, teens, kids, culture, relaxing, romantic, historic sites, shopping, popular sights PREFERENCES: September, teens, kids, culture, relaxing, romantic, historic sites, shopping ATTRACTION STYLE: Popular sights PACE: Medium 27 days in Chicago BY A USER FROM THAILAND January, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, popular sights PREFERENCES: January, culture, outdoors, relaxing, beaches, historic sites, museums, shopping ATTRACTION STYLE: Popular sights PACE: Medium 4 days in Chicago BY A USER FROM UNITED STATES October, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, wildlife, fast-paced, popular & hidden gems PREFERENCES: October, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Fast-paced
View more plans