21 days in Chicago Itinerary

21 days in Chicago Itinerary

Created using Inspirock Chicago Trip Planner

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

Route & dates

View / edit route

1
Chicago
— 20 nights

20
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Escape the urban bustle at Lakefront Trail and Oak Street Beach. Let the collections at The Art Institute of Chicago and Field Museum capture your imagination. Explore Chicago's surroundings by going to Grand Mere State Park (in Stevensville), Michigan City (Stateline Blueberries & Shady Creek Winery) and Weko Park (in Bridgman). Plan for a day of cool, family-friendly fun on the 22nd (Wed) at Six Flags Great America. The adventure continues: take a stroll through The Magnificent Mile, get up close and personal with brilliant marine life at Shedd Aquarium, enjoy the sand and surf at Ohio Street Beach, and get curious at Museum of Science and Industry.

To see reviews, ratings, and other tourist information, you can read our Chicago trip planning website .

If you are flying in from Mongolia, the closest major airports are Chicago Midway International Airport, Chicago O'Hare International Airport and South Bend Regional Airport. In June in Chicago, expect temperatures between 32°C during the day and 20°C at night. Finish your sightseeing early on the 24th (Fri) to allow enough time to travel back home.

Things to do in Chicago

Parks Outdoors Beaches

Side Trips

Michigan City, Geneva, Naperville, Lynfred Winery, Horseshoe Hammond
Find places to stay Jun 3 — 24:
Highlights from your plan
The Magnificent Mile ©
The Magnificent Mile
The Art Institute of Chicago ©
The Art Institute of Chicago
Field Museum ©
Field Museum

Similar Plans

23 days in United States BY A USER FROM GERMANY April, popular & hidden gems PREFERENCES: April ATTRACTION STYLE: Popular & hidden gems PACE: Medium 22 days in Chicago BY A USER FROM INDIA May, kids, relaxing, historic sites, museums, shopping, popular sights PREFERENCES: May, kids, relaxing, historic sites, museums, shopping ATTRACTION STYLE: Popular sights PACE: Medium 24 days in United States BY A USER FROM SAUDI ARABIA July, kids, popular sights PREFERENCES: July, kids ATTRACTION STYLE: Popular sights PACE: Medium 24 days in United States BY A USER FROM HONG KONG July, teens, outdoors, beaches, popular & hidden gems PREFERENCES: July, teens, outdoors, beaches ATTRACTION STYLE: Popular & hidden gems PACE: Medium 25 days in New Orleans, Memphis & Chicago BY A USER FROM GERMANY March, culture, beaches, historic sites, museums, popular sights PREFERENCES: March, culture, beaches, historic sites, museums ATTRACTION STYLE: Popular sights PACE: Medium 23 days in Chicago & Florida BY A USER FROM SOUTH AFRICA October, kids, relaxing, popular sights PREFERENCES: October, kids, relaxing ATTRACTION STYLE: Popular sights PACE: Medium 25 days in New Orleans, Memphis & Chicago BY A USER FROM ARGENTINA July, culture, beaches, historic sites, museums, popular sights PREFERENCES: July, culture, beaches, historic sites, museums ATTRACTION STYLE: Popular sights PACE: Medium 25 days in United States BY A USER FROM INDIA June, popular & hidden gems PREFERENCES: June ATTRACTION STYLE: Popular & hidden gems PACE: Medium 22 days in United States BY A USER FROM AUSTRALIA December, teens, popular sights PREFERENCES: December, teens ATTRACTION STYLE: Popular sights PACE: Medium 25 days in United States BY A USER FROM AUSTRALIA November, popular & hidden gems PREFERENCES: November ATTRACTION STYLE: Popular & hidden gems PACE: Medium 24 days in United States BY A USER FROM AUSTRALIA September, teens, kids, outdoors, historic sites, shopping, popular sights PREFERENCES: September, teens, kids, outdoors, historic sites, shopping ATTRACTION STYLE: Popular sights PACE: Medium
View more plans