Fun activities for couples in Chicago

Popular activities for couples in Chicago

Explore Chicago's legendary architecture and history.

Chicago River 90-Minute Architecture Tour

1.5 hours

4.7
10811 reviews

$45.00

Chicago River Cruise

Chicago Architecture River Cruise

1 to 1.5 hours

4.8
16871 reviews

$39.00

Join us in the daytime or evening for City lights and breathtaking views

Chicago River 45-Minute Architecture Tour from Magnificent Mile

1 hour

4.6
3532 reviews

$28.00

Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

1.5 hours

4.6
704 reviews

$46.00

See Chicago's magnificent skyline at night!

Chicago By Night River and Lake Cruise

1.5 hours

4.4
422 reviews

$50.00

Flyover in Chicago

0.5 hour

4.7
698 reviews

$27.95

Lake Michigan Skyline Cruise in Chicago

0.5 to 1 hours

4.4
944 reviews

$32.50

This tour cruises the Chicago River and Lake Michigan.

Chicago Lake and River Architecture Tour

1.5 hours

4.6
2423 reviews

$45.00

360 panoramic views of the Chicago skyline at sunset.

Lake Michigan Sunset Cruise in Chicago

1.5 hours

4.5
1673 reviews

$45.00

Skydeck - Willis Tower Admission

0.5 to 1.5 hours

4.2
1899 reviews

$44.00

Photo Ops Off the Bus

Chicago Crime and Mob Bus Tour

1.5 to 2 hours

4.5
3510 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
2266 reviews

$84.99

Chicago River 90-Minute Architecture Boat Tour

1.5 hours

4.8
1865 reviews

$37.00

Chicago Architectural River Cruise

1.5 hours

4.6
853 reviews

$50.00

A picture of Chicago Chinatown’s landscape shows vibrant streets, iconic arches, and rich culture—everything guests explore on our Chinatown Food Tours. Food Tours in Chinatown bring it all to life.

Chicago's Chinatown Food and Walking Tour

3 hours

4.9
784 reviews

$79.99

Historical and Architectural Chicago Fireboat River & Lake Cruise

2 hours

4.9
456 reviews

$47.00

Chicago Gangsters and Ghosts Walking Tour

2 hours

4.7
134 reviews

$38.00

The Field Museum

Field Museum of Natural History Admission Tickets

4 hours

4.5
577 reviews

$29.00

City Cruises Chicago: Premier Plus Brunch Cruise on Chicago River

2 hours

4.5
81 reviews

$84.74

You get to name your new Exclusive Scent

Chicago Perfume Making Classes on Magnificent Mile

1.5 hours

4.8
87 reviews

$85.00

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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