2 days in Chicago Itinerary

2 days in Chicago Itinerary

Created using Inspirock Chicago travel route maker

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

Route & dates

View / edit route

1
Chicago
— 1 night

1
night
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Your day-by-day itinerary now includes Chicago River, The Escape Game Chicago, The Chicago Theatre, and other attractions you added. Start off your visit on the 10th (Thu): contemplate the waterfront views at Chicago River, take a leisurely stroll along Navy Pier, make a trip to Millennium Park, then make a trip to Cloud Gate, and finally see a show at The Chicago Theatre. Get ready for a full day of sightseeing on the 11th (Fri): get your game on at The Escape Game Chicago, then take in panoramic vistas at 360 Chicago Observation Deck, then get to know the fascinating history of Chicago Riverwalk, and finally take in panoramic vistas at Skydeck Chicago - Willis Tower.

For where to stay, ratings, more things to do, and other tourist information, you can read our Chicago road trip planning tool .

October in Chicago sees daily highs of 65°F and lows of 49°F at night. Wrap up your sightseeing on the 11th (Fri) early enough to travel back home.

Things to do in Chicago

Theme Parks Parks Nightlife
Highlights from your plan
Millennium Park ©
Millennium Park
Skydeck Chicago - Willis Tower ©
Skydeck Chicago - Willis Tower
Navy Pier ©
Navy Pier

Similar Plans

6 days in Chicago BY A USER FROM PUERTO RICO October, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, popular sights PREFERENCES: October, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular sights PACE: Medium 5 days in Chicago BY A USER FROM BRAZIL September, culture, outdoors, relaxing, romantic, historic sites, museums, shopping, popular & hidden gems PREFERENCES: September, culture, outdoors, relaxing, romantic, historic sites, museums, shopping ATTRACTION STYLE: Popular & hidden gems PACE: Medium 5 days in Chicago BY A USER FROM BELGIUM August, culture, relaxing, historic sites, museums, shopping, wildlife, slow & easy, popular & hidden gems PREFERENCES: August, culture, relaxing, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Slow & easy 3 days in Chicago BY A USER FROM MALAYSIA October, culture, outdoors, relaxing, romantic, historic sites, museums, shopping, popular & hidden gems PREFERENCES: October, culture, outdoors, relaxing, romantic, historic sites, museums, shopping ATTRACTION STYLE: Popular & hidden gems PACE: Medium 3 days in Chicago BY A USER FROM UNITED STATES October, kids, culture, outdoors, relaxing, historic sites, museums, shopping, popular sights PREFERENCES: October, kids, culture, outdoors, relaxing, historic sites, museums, shopping ATTRACTION STYLE: Popular sights PACE: Medium 3 days in Chicago BY A USER FROM MALAYSIA October, culture, outdoors, relaxing, romantic, historic sites, museums, shopping, popular sights PREFERENCES: October, culture, outdoors, relaxing, romantic, historic sites, museums, shopping ATTRACTION STYLE: Popular sights PACE: Medium 5 days in Chicago BY A USER FROM UNITED STATES October, culture, outdoors, relaxing, romantic, historic sites, museums, shopping, popular sights PREFERENCES: October, culture, outdoors, relaxing, romantic, historic sites, museums, shopping ATTRACTION STYLE: Popular sights PACE: Medium 4 days in Chicago BY A USER FROM MEXICO October, kids, culture, outdoors, romantic, shopping, wildlife, fast-paced, popular sights PREFERENCES: October, kids, culture, outdoors, romantic, shopping, wildlife ATTRACTION STYLE: Popular sights PACE: Fast-paced 6 days in Chicago BY A USER FROM CANADA October, culture, outdoors, relaxing, beaches, historic sites, museums, hidden gems PREFERENCES: October, culture, outdoors, relaxing, beaches, historic sites, museums ATTRACTION STYLE: Hidden gems PACE: Medium 9 days in Chicago BY A USER FROM UNITED KINGDOM August, teens, kids, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, popular sights PREFERENCES: August, teens, kids, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping ATTRACTION STYLE: Popular sights PACE: Medium 4 days in Chicago BY A USER FROM UNITED STATES November, outdoors, relaxing, romantic, beaches, wildlife, popular & hidden gems PREFERENCES: November, outdoors, relaxing, romantic, beaches, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Medium 6 days in Chicago BY A USER FROM TURKEY November, culture, relaxing, romantic, historic sites, museums, popular & hidden gems PREFERENCES: November, culture, relaxing, romantic, historic sites, museums ATTRACTION STYLE: Popular & hidden gems PACE: Medium
View more plans