59 days in Chicago Itinerary

59 days in Chicago Itinerary

Created using Inspirock Chicago route maker

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

Route & dates

View / edit route

1
Chicago
— 58 nights

58
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Get some cultural insight at The Magnificent Mile and The Art Institute of Chicago. Relax by the water at Silver Beach County Park and Ohio Street Beach. Explore Chicago's surroundings by going to Shabbona Lake State Park (in Shabbona), Lemon Creek Winery (in Berrien Springs) and The Sandwich Fair (in Sandwich). Plan for a day of cool, family-friendly fun on the 12th (Mon) at Six Flags Great America. There's still lots to do: experience rural life at Bengtson's Pumpkin Farm, kick back and relax at Lions Park Beach, stroll through Kathy Osterman Beach, and engage your brain at Museum of Science and Industry.

To see traveler tips, ratings, other places to visit, and other tourist information, read Chicago tour builder app .

In September in Chicago, expect temperatures between 78°F during the day and 61°F at night. Finish up your sightseeing early on the 18th (Sun) so you can travel back home.

Things to do in Chicago

Parks Outdoors Beaches

Side Trips

Oak Park, South Bend, Lake Geneva, Saint Joseph, Naperville
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

4 days in Chicago BY A USER FROM UNITED STATES April, teens, slow & easy, hidden gems PREFERENCES: April, teens ATTRACTION STYLE: Hidden gems PACE: Slow & easy 3 days in Chicago BY A USER FROM UNITED STATES June, teens, kids, popular sights PREFERENCES: June, teens, kids ATTRACTION STYLE: Popular sights PACE: Medium 10 days in Chicago BY A USER FROM SPAIN April, slow & easy, popular & hidden gems PREFERENCES: April ATTRACTION STYLE: Popular & hidden gems PACE: Slow & easy 16 days in Chicago BY A USER FROM PHILIPPINES April, teens, fast-paced, popular sights PREFERENCES: April, teens ATTRACTION STYLE: Popular sights PACE: Fast-paced 1 day in Chicago BY A USER FROM UNITED STATES April, teens, kids, popular sights PREFERENCES: April, teens, kids ATTRACTION STYLE: Popular sights PACE: Medium 4 days in Chicago BY A USER FROM UNITED STATES April, teens, kids, popular sights PREFERENCES: April, teens, kids ATTRACTION STYLE: Popular sights PACE: Medium 5 days in Chicago BY A USER FROM UNITED STATES March, teens, historic sites, museums, hidden gems PREFERENCES: March, teens, historic sites, museums ATTRACTION STYLE: Hidden gems PACE: Medium 3 days in Chicago BY A USER FROM UNITED STATES April, kids, popular & hidden gems PREFERENCES: April, kids ATTRACTION STYLE: Popular & hidden gems PACE: Medium 5 days in Chicago BY A USER FROM UNITED STATES June, teens, popular & hidden gems PREFERENCES: June, teens ATTRACTION STYLE: Popular & hidden gems PACE: Medium 11 days in Chicago BY A USER FROM DENMARK August, teens, kids, beaches, shopping, popular sights PREFERENCES: August, teens, kids, beaches, shopping ATTRACTION STYLE: Popular sights PACE: Medium 4 days in Chicago BY A USER FROM UNITED STATES April, teens, kids, popular sights PREFERENCES: April, teens, kids ATTRACTION STYLE: Popular sights PACE: Medium 60 days in Charlotte, Chicago & Las Vegas BY A USER FROM IRELAND June, outdoors, relaxing, romantic, beaches, shopping, popular sights PREFERENCES: June, outdoors, relaxing, romantic, beaches, shopping ATTRACTION STYLE: Popular sights PACE: Medium
View more plans