29 days in Chicago Itinerary

29 days in Chicago Itinerary

Created using Inspirock Chicago trip builder

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

Route & dates

See / edit route

1
Chicago
— 28 nights
Find places to stay »
Edit
See full calendar

28
nights
Chicago

Chicago ©

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Get out of town with these interesting Chicago side-trips: National Shrine of St. Therese (in Darien), Bengtson's Pumpkin Farm (in Homer Glen) and Cowles Bog (in Chesterton). Plan for a day of cool, family-friendly fun on the 30th (Tue) at Six Flags Great America. There's lots more to do: admire the masterpieces at The Art Institute of Chicago, take a leisurely stroll along Navy Pier, take in panoramic vistas at Skydeck Chicago - Willis Tower, and wander the streets of The Magnificent Mile.

For more things to do, where to stay, and other tourist information, refer to the Chicago holiday maker site .

If you are flying in from Israel, 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. Finish your sightseeing early on the 30th (Tue) so you can travel back home.

Things to do in Chicago

Parks Outdoors Historic Sites

Side Trips

Oak Park, South Bend, Saint Joseph, Illinois, Oak Brook
Find places to stay Oct 2 — 30:
Hotels on TripAdvisor
Homes on Airbnb
Highlights from your plan
The Art Institute of Chicago ©
The Art Institute of Chicago
1:30pm, Tue Oct 2
Millennium Park ©
Millennium Park
2:30pm, Fri Oct 12
Wrigley Field ©
Wrigley Field
2:00pm, Wed Oct 24

Similar Plans

32 days in United States BY A USER FROM UNITED KINGDOM July, teens, culture, outdoors, beaches, historic sites, shopping, wildlife, slow & easy, popular sights PREFERENCES: July, teens, culture, outdoors, beaches, historic sites, shopping, wildlife ATTRACTION STYLE: Popular sights PACE: Slow & easy 7 days in Chicago BY A USER FROM UNITED STATES October, teens, kids, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, popular sights PREFERENCES: October, teens, kids, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular sights PACE: Medium 32 days in United States & Tokyo BY A USER FROM PAKISTAN May, kids, outdoors, relaxing, romantic, beaches, museums, shopping, popular sights PREFERENCES: May, kids, outdoors, relaxing, romantic, beaches, museums, shopping ATTRACTION STYLE: Popular sights PACE: Medium 60 days in Chicago & Manila BY A USER FROM PHILIPPINES October, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, slow & easy, popular sights PREFERENCES: October, culture, outdoors, relaxing, beaches, historic sites, museums, shopping ATTRACTION STYLE: Popular sights PACE: Slow & easy 4 days in Chicago 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 32 days in United States BY A USER FROM UNITED KINGDOM July, teens, culture, outdoors, beaches, shopping, wildlife, popular sights PREFERENCES: July, teens, culture, outdoors, beaches, shopping, wildlife ATTRACTION STYLE: Popular sights PACE: Medium 27 days in United States BY A USER FROM AUSTRALIA June, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, popular sights PREFERENCES: June, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular sights PACE: Medium 32 days in Chicago BY A USER FROM UNITED STATES September, kids, historic sites, museums, popular sights PREFERENCES: September, kids, historic sites, museums ATTRACTION STYLE: Popular sights PACE: Medium 36 days in United States & Vancouver BY A USER FROM AUSTRALIA April, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, popular sights PREFERENCES: April, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular sights PACE: Medium 3 days in Chicago BY A USER FROM UNITED STATES September, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife, fast-paced, popular sights PREFERENCES: September, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular sights PACE: Fast-paced 4 days in Chicago BY A USER FROM UNITED STATES November, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife, fast-paced, popular sights PREFERENCES: November, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular sights PACE: Fast-paced 18 days in Chicago BY A USER FROM UNITED STATES September, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, wildlife, hidden gems PREFERENCES: September, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, wildlife ATTRACTION STYLE: Hidden gems PACE: Medium
See more plans
See also: