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
9071 reviews

$45.00

Chicago Architecture River Cruise

1.5 hours

4.8
15385 reviews

$44.43

Experience Chicago's amazing history and architecture.

Chicago River 45-Minute Architecture Tour from Magnificent Mile

1 hour

4.6
2658 reviews

$28.00

Skydeck - Willis Tower Admission

0.5 to 1.5 hours

4.2
1697 reviews

$44.00

Lake Michigan Skyline Cruise in Chicago

1 hour

4.4
876 reviews

$32.50

360 panoramic views of Lake Michigan at sunset.

Lake Michigan Sunset Cruise in Chicago

1.5 hours

4.5
1472 reviews

$45.00

Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

1.5 hours

4.7
519 reviews

$45.00

Experience Chicago and Lake Michigan on this world famous tour.

Chicago Lake and River Architecture Tour

1.5 hours

4.6
2259 reviews

$45.00

Lineup with Capone and Dillinger!

Chicago Crime and Mob Bus Tour

1.5 to 2 hours

4.5
3056 reviews

$49.00

Tastes of Chicago

Chicago Favorites Ultimate Food and Walking Tour

3 hours

4.8
1805 reviews

$84.99

Chicago River 90-Minute Architecture Boat Tour

1.5 hours

4.8
1580 reviews

$37.00

Flyover in Chicago

0.5 hour

4.7
437 reviews

$38.03

Learn About Chicago's Great Architecture on a Boat Tour

Chicago Seadog River & Lake Architectural Tour

1.5 hours

4.4
259 reviews

$44.03

Chicago Architectural River Cruise

1.5 hours

4.6
792 reviews

$50.00

City Cruises Chicago: Premier Plus Brunch Cruise on Chicago River

2 hours

4.6
46 reviews

$109.90

Chicago City Tour with Architecture River Cruise Option

2 to 4 hours

4.7
682 reviews

$48.95

Chicago City Minibus Tour

2 hours

4.9
434 reviews

$47.95

Total Chicago: From Architecture to Food

Chicago in a Day: Explore Food, History, and Iconic Architecture

4.5 hours

4.9
1092 reviews

$100.95

Cultural Centers Tiffany Dome

Chicago Architecture and True Crime History Tour

1.5 to 2 hours

4.9
182 reviews

$35.00

Field Museum

Field Museum of Natural History Admission Tickets

4 hours

4.5
468 reviews

$29.00

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.

Disclosure: Our content is reader-supported. We may, at no additional cost to you, earn a small commission if you click through and make a purchase from some links on this page. Read Full Disclosure.