Date Ideas in Chicago, IL

  • TripBuzz discovered 110 different types of activities for couples in the Chicago area, including Theaters (like The Chicago Theatre), Parks (like Millennium Park), Neighborhoods (like Michigan Avenue) and Sports Stadiums (Professional) (like US Cellular Field), and much more.
  • We discovered a total of 483 date ideas in or near Chicago, Illinois, including 437 fun or romantic activities in nearby cities within 25 miles like Skokie, Oak Park, Lombard and Des Plaines.
  • TripBuzz discovered 110 different types of activities for couples in the Chicago area, including Theaters (like The Chicago Theatre), Parks (like Millennium Park), Neighborhoods (like Michigan Avenue) and Sports Stadiums (Professional) (like US Cellular Field), and much more.
  • We discovered a total of 483 date ideas in or near Chicago, Illinois, including 437 fun or romantic activities in nearby cities within 25 miles like Skokie, Oak Park, Lombard and Des Plaines.
Showing 1-10 of 986
0.0 Miles
During the wine tasting participants will have an opportunity to expand a scope of wine varietals
0.7 Miles
97% 5605 votes
Boat Cruise Southeast corner of Michigan & Wacker, Chicago, IL 60604 MoreLess Info
With volunteer tour guides detailing the rich scenery along the river, Chicago Architecture Foundation River Cruises provide the tourist and the local alike with an in depth look at the city's evolution over the decades. Tours begin in early Spring and end in late Fall.
0.8 Miles
95% 1340 votes
Boat Tours 400 North Michigan Ave, Chicago, IL 60611 MoreLess Info
Wendella Sightseeing Boats is Chicago's family owned, original architecture tour. Featuring various cruises such as the River Experience and Summer Fireworks, Wendella showcases Chicago's history and landmarks with a special touch for adults through Beer & BBQ and Wine & Cheese cruises.
0.5 Miles
94% 765 votes
Theaters 175 N. State Street, Chicago, IL 60601 MoreLess Info
The Chicago Theatre is a seven story, 3,600 seat performance venue that features a “Chicago” marquee and a pipe organ. Visitors of this site who are interested in learning about its history can go on guided tours.
1.0 Miles
90% 8242 votes
Scenic Walks N Michigan Ave, Chicago, IL 60611 MoreLess Info
The Magnificent Mile is a shopping district that features stores like Jimmy Choo and Chanel. Visitors of this site will be able to enjoy the Magnificent Mile Lights Festival during the holiday season.
2.3 Miles
88% 1744 votes
Comedy Clubs 1616 N Wells St, Chicago, IL 60614 MoreLess Info
For over fifty years The Second City has been entertaining its audience with comedy sketches and short scenes with a focus on improvisation, seven nights a week. Second City features open cabaret-style table seating for added social interactivity.
1.7 Miles
86% 388 votes
Beaches 1000 North Lake Shore Drive, Chicago, IL 60611 MoreLess Info
Oak Street Beach offers guests the opportunity to hike and swim in the waters of Lake Michigan. The location, which is often a site for beach volleyball games, also provides places for guests to purchase beer and cocktails.
0.4 Miles
82% 702 votes
Jazz/Blues Bars 700 South Wabash, Chicago, IL 60605 MoreLess Info
Buddy Guy's Legends is a blues bars that features performances from the likes of Larry Carlton and The Nu Blu Band. Visitors of the site can order classic bar food items like buffalo wings, oysters, gumbo, and crab cakes.
0.1 Miles
84% 182 votes
Theaters Bank of America Theater, Chicago, IL MoreLess Info
Created by Matt Stone and Trey Parker, the team behind Comedy Central's South Park, The Book of Mormon is a musical that offers a satirical look at The Church of Latter-Day Saints. The plot involves two Mormon missionaries being sent to Uganda.
0.5 Miles
87% 246 votes
Theaters 151 W Randolph St, Chicago, IL 60602 MoreLess Info
Featuring a marquee sign with the word “Palace”, the Cadillac Palace Theatre is a Broadway performance venue. The location has hosted productions like The Color Purple, The Producers, and The Pirate Queen.
3.6 Miles
86% 159 votes
Theaters 2540 N Lincoln Ave, Chicago, IL 60614 MoreLess Info
The Apollo Theater Chicago is a performance venue that hosts performances from folks like Million Dollar Quartet. This theater is quite small, providing an intimate feel and quality seats to its guests.
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