5 days in Chicago Itinerary
5 days in Chicago Itinerary
Created using Inspirock United States Trip Planner
Route & dates
View / edit route
Chicago
— 4 nights
Find places to stay »
Edit
View full calendar
4
nights
Chicago
4
nights
©
Windy City
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.You'll discover tucked-away gems like Silver Beach County Park and Starved Rock State Park. Do some cultural sightseeing at The Magnificent Mile and The Art Institute of Chicago. There's lots more to do: tour the pleasant surroundings at Millennium Park, take in panoramic vistas at Skydeck Chicago - Willis Tower, pause for some photo ops at Cloud Gate, and see the interesting displays at The Field Museum.
For more things to do, reviews, ratings, and more tourist information, read Chicago itinerary planner.
July in Chicago sees daily highs of 85°F and lows of 68°F at night. Finish your sightseeing early on the 14th (Fri) so you can travel back home.
Things to do in Chicago
Side Trips
Silver Beach County Park, Starved Rock State Park
Accommodations
Get expert advice on where to stay in Chicago.
Find places to stay »
Highlights from your plan
©
Silver Beach County Park
1:30pm, Tue Jul 11
©
The Art Institute of Chicago
2:00pm, Mon Jul 10
©
Millennium Park
5:00pm, Mon Jul 10
Similar Plans
6 days in Chicago
BY A USER FROM UNITED STATES
August, kids, culture, outdoors, relaxing, romantic, historic sites, museums, popular
PREFERENCES: August, kids, culture, outdoors, relaxing, romantic, historic sites, museums
ATTRACTION STYLE: Popular
PACE: Medium
6 days in Chicago
BY A USER FROM CANADA
August, kids, outdoors, beaches, historic sites, museums, fast-paced, popular
PREFERENCES: August, kids, outdoors, beaches, historic sites, museums
ATTRACTION STYLE: Popular
PACE: Fast-paced
8 days in Chicago
BY A USER FROM MEXICO
September, kids, culture, outdoors, romantic, historic sites, museums, shopping, popular
PREFERENCES: September, kids, culture, outdoors, romantic, historic sites, museums, shopping
ATTRACTION STYLE: Popular
PACE: Medium
6 days in Chicago
BY A USER FROM UNITED STATES
July, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, fast-paced, popular & hidden gems
PREFERENCES: July, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping
ATTRACTION STYLE: Popular & hidden gems
PACE: Fast-paced
6 days in Chicago
BY A USER FROM UNITED STATES
September, outdoors, relaxing, romantic, beaches, historic sites, popular
PREFERENCES: September, outdoors, relaxing, romantic, beaches, historic sites
ATTRACTION STYLE: Popular
PACE: Medium
6 days in Chicago
BY A USER FROM SPAIN
July, kids, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, popular
PREFERENCES: July, kids, culture, outdoors, relaxing, beaches, historic sites, museums, shopping
ATTRACTION STYLE: Popular
PACE: Medium
6 days in Chicago
BY A USER FROM UNITED STATES
June, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, popular & hidden gems
PREFERENCES: June, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping
ATTRACTION STYLE: Popular & hidden gems
PACE: Medium
6 days in Chicago
BY A USER FROM MEXICO
June, culture, relaxing, romantic, historic sites, museums, shopping, popular
PREFERENCES: June, culture, relaxing, romantic, historic sites, museums, shopping
ATTRACTION STYLE: Popular
PACE: Medium
6 days in Chicago
BY A USER FROM UNITED STATES
June, culture, outdoors, relaxing, historic sites, museums, popular
PREFERENCES: June, culture, outdoors, relaxing, historic sites, museums
ATTRACTION STYLE: Popular
PACE: Medium
4 days in Chicago
BY A USER FROM UNITED STATES
July, teens, kids, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, popular
PREFERENCES: July, teens, kids, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping
ATTRACTION STYLE: Popular
PACE: Medium
8 days in Chicago
BY A USER FROM UNITED STATES
July, teens, outdoors, slow & easy, hidden gems
PREFERENCES: July, teens, outdoors
ATTRACTION STYLE: Hidden gems
PACE: Slow & easy
7 days in Chicago
BY A USER FROM UNITED STATES
July, culture, outdoors, relaxing, historic sites, museums, popular
PREFERENCES: July, culture, outdoors, relaxing, historic sites, museums
ATTRACTION STYLE: Popular
PACE: Medium
View more plans
