Fun activities for couples in Chicago

Popular activities for couples in Chicago

Experience Chicago on this world famous tour. .

Chicago River 90-Minute Architecture Tour

1.5 hours

4.7
9646 reviews

$44.00

Experience Chicago's amazing history and architecture.

Chicago River 45-Minute Architecture Tour from Magnificent Mile

1 hour

4.6
2950 reviews

$28.00

Skydeck - Willis Tower Admission

0.5 to 1.5 hours

4.2
1779 reviews

$44.00

Flyover in Chicago

0.5 hour

4.7
489 reviews

$38.03

Chicago Architecture River Cruise

1 to 1.5 hours

4.8
15757 reviews

$39.00

Lineup with Capone and Dillinger!

Chicago Crime and Mob Bus Tour

1.5 to 2 hours

4.5
3194 reviews

$49.00

Taste deep-dish pizza, a Chicago-style hot dog, Italian beef, Garrett’s popcorn & the original 1893 brownie on our top-rated Chicago Food Tours—the ultimate Chicago Culinary Tour experience!

Chicago Favorites Ultimate Food and Walking Tour

3 hours

4.8
1967 reviews

$84.99

Total Chicago: From Architecture to Food

Chicago in a Day: Food, History & Architecture Walking Tour

4.5 hours

4.9
1156 reviews

$100.95

Chicago City Minibus Tour

2 hours

4.9
517 reviews

$49.95

Chicago Pizza Tour

Chicago Pizza Tour

3.5 hours

4.8
458 reviews

$89.00

Medieval Torture Museum Ticket with Audio Guide and Ghost Hunting

1.5 hours

4.8
967 reviews

$35.83

Chicago Craft Brewery Barrel Bus Tour

4 hours

4.8
340 reviews

$99.60

Original Chicago Architecture Interiors Tour: Dazzling Interiors

2 hours

4.9
1498 reviews

$35.00

Chicago Architecture Tour: Underground Pedway and the Loop

2 hours

4.8
402 reviews

$35.00

Haunted Chicago: Crime and Ghosts Walking Tour

1.5 hours

5
54 reviews

$35.00

Chicago Loop District Food Tour with Deep Dish & Beef Sandwich

3 hours

4.9
874 reviews

$84.99

Our favorite recruits

Chicago's Original Gangster Tour by Bus

2 hours

4.7
117 reviews

$48.00

African American Heritage Tour of Chicago

4 hours

4.4
127 reviews

$125.00

Chicago Mobs and Haunts Walking Tour

1.5 to 2 hours

4.7
389 reviews

$34.00

Delicious Donuts & City Sights: Chicago's Original Donut Tour

2 hours

4.9
1390 reviews

$70.00

Tips for couples visiting Chicago, Illinois

When is the best time to visit Chicago?

The best time to visit Chicago is during the Spring months of April to June and the Fall months of September to October. These periods of the year provide mild and pleasant weather, making them optimum for outdoor activities such as bicycling, sailing, or rowing on Lake Michigan. Additionally, these periods tend to be less crowded than the peak summer months.

What are some fun activities for couples in Chicago?

  • Explore The 606 Trail and Bloomingdale Trail

  • Go Kayaking on Lake Michigan

  • Take an Architectural River Cruise

  • Visit the Shedd Aquarium

  • Explore The Garfield Park Conservatory

What are some romantic date ideas in Chicago?

  • Take a walk along the Lakefront Trail, admiring the skyline of the city and stopping to watch the sunset.

  • Explore the winding canals and pathways of Millenium Park.

  • Visit the iconic Willis Tower Skydeck and take in the breathtaking views of the city skyline.

  • Take a historical walking tour and learn about the city’s rich history.

  • Go ice-skating at Maggie Daley Park’s ice skating ribbon and enjoy dinner afterward at Park Grill.

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