42 days in Chicago Itinerary

42 days in Chicago Itinerary

Created using Inspirock Chicago travel planner

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

Route & dates

View / edit route

1
Chicago
— 41 nights

41
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Do some cultural sightseeing at The Field Museum and Swedish American Museum. Step out of the city life by going to Bender Park Waterfront and Fishing Charters & Tours. Explore Chicago's surroundings by going to Little Red Schoolhouse (in Willow Springs), Pontiac (Livingston County Courthouse, Pontiac-Oakland Automobile Museum, & more) and Kankakee (French Heritage Museum at The Stone Barn, Kankakee Railroad Museum, & more). There's lots more to do: appreciate the extensive heritage of Millennium Park, explore the world behind art at The Art Institute of Chicago, identify plant and animal life at Deer Grove Forest Preserve, and enjoy the sand and surf at Silver Beach County Park.

For more things to do, reviews, photos, and more tourist information, use the Chicago vacation builder site .

If you are flying in from Norway, the closest major airports are Chicago Midway International Airport, Chicago O'Hare International Airport and South Bend Regional Airport. June in Chicago sees daily highs of 32°C and lows of 20°C at night. Cap off your sightseeing on the 30th (Tue) early enough to travel back home.

Things to do in Chicago

Parks Wildlife Outdoors

Side Trips

Joliet, Pontiac, Ottawa, Valparaiso, Utica
Highlights from your plan
Field Museum ©
Field Museum
The Art Institute of Chicago ©
The Art Institute of Chicago
The Magnificent Mile ©
The Magnificent Mile

Similar Plans

49 days in Boulder City & Chicago BY A USER FROM UNITED STATES June, outdoors, relaxing, historic sites, popular sights PREFERENCES: June, outdoors, relaxing, historic sites ATTRACTION STYLE: Popular sights PACE: Medium 60 days in Chicago & Orlando BY A USER FROM MOLDOVA August, kids, relaxing, beaches, popular sights PREFERENCES: August, kids, relaxing, beaches ATTRACTION STYLE: Popular sights PACE: Medium 4 days in Chicago BY A USER FROM UNITED STATES October, relaxing, romantic, historic sites, museums, popular & hidden gems PREFERENCES: October, relaxing, romantic, historic sites, museums ATTRACTION STYLE: Popular & hidden gems PACE: Medium 60 days in United States BY A USER FROM INDIA May, kids, outdoors, relaxing, romantic, shopping, wildlife, popular & hidden gems PREFERENCES: May, kids, outdoors, relaxing, romantic, shopping, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Medium 13 days in United States BY A USER FROM SINGAPORE May, culture, outdoors, relaxing, romantic, beaches, historic sites, slow & easy, popular & hidden gems PREFERENCES: May, culture, outdoors, relaxing, romantic, beaches, historic sites ATTRACTION STYLE: Popular & hidden gems PACE: Slow & easy 6 days in Chicago BY A USER FROM KUWAIT August, kids, relaxing, beaches, historic sites, shopping, popular sights PREFERENCES: August, kids, relaxing, beaches, historic sites, shopping ATTRACTION STYLE: Popular sights PACE: Medium 6 days in Chicago BY A USER FROM UNITED STATES May, outdoors, relaxing, romantic, beaches, historic sites, museums, wildlife, popular & hidden gems PREFERENCES: May, outdoors, relaxing, romantic, beaches, historic sites, museums, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Medium 1 day in Chicago BY A USER FROM UNITED STATES June, relaxing, romantic, slow & easy, popular sights PREFERENCES: June, relaxing, romantic ATTRACTION STYLE: Popular sights PACE: Slow & easy 4 days in Chicago BY A USER FROM UNITED STATES June, culture, relaxing, romantic, historic sites, museums, popular & hidden gems PREFERENCES: June, culture, relaxing, romantic, historic sites, museums ATTRACTION STYLE: Popular & hidden gems PACE: Medium 5 days in Chicago BY A USER FROM UNITED STATES July, culture, relaxing, romantic, historic sites, museums, popular & hidden gems PREFERENCES: July, culture, relaxing, romantic, historic sites, museums ATTRACTION STYLE: Popular & hidden gems PACE: Medium 3 days in Chicago BY A USER FROM UNITED STATES May, culture, relaxing, romantic, historic sites, museums, fast-paced, popular sights PREFERENCES: May, culture, relaxing, romantic, historic sites, museums ATTRACTION STYLE: Popular sights PACE: Fast-paced 18 days in Chicago BY A USER FROM UNITED STATES May, culture, relaxing, historic sites, museums, slow & easy, popular & hidden gems PREFERENCES: May, culture, relaxing, historic sites, museums ATTRACTION STYLE: Popular & hidden gems PACE: Slow & easy
View more plans