Date Night Ideas in Chicago.
Unforgettable spots, cozy cocktail hideaways, and romantic experiences for couples.
Updated for right now · 16 dated listings
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Upcoming Events & Happenings
Sunday Market at Jefferson
Come out and enjoy a Sunday in the park. Listen to live music and shop your way through a variety of vendors selling produce, meats, baked goods, dairy products
Icon For Hire: Scripted 15 Year Anniversary Tour
Music at Bottom Lounge, Chicago. Featuring Lauren Babic.
Sleeping With Sirens: An Ending In Itself Tour
Rock at The Salt Shed Indoors (Shed), Chicago. Featuring Rain City Drive, Shyeye.
The Second City's: Pandemonium, Please Hold
Arts & Theatre at Second City-Chicago: Mainstage, Chicago.
Streetlight Manifesto: The Presence of the Past Tour
Rock at House of Blues Chicago, Chicago. Featuring Dave Hause.
ChiTown Drive-In Presents - Sinners
One ticket per vehicle for up to 6 adults. All spaces have excellent views of our large screen. You may face forward or back your car into your space. Spots are
Nate Mercereau presents Fantastic Thoughts with Carlos Niño & Austin Williamson
New Age at Three Top Lounge, Chicago.
ChiTown Drive-In Presents - Halloween (the 1978 Original!)
One ticket per vehicle for up to 6 adults. All spaces have excellent views of our large screen. You may face forward or back your car into your space. Spots are
She Wants Revenge
Rock at House of Blues Chicago, Chicago. Featuring Rosegarden Funeral Party.
ChiTown Drive-In Presents - Obsession (2026)
One ticket per vehicle for up to 6 adults. All spaces have excellent views of our large screen. You may face forward or back your car into your space. Spots are
The Best of The Second City
Arts & Theatre at Second City-Chicago: Mainstage, Chicago.
ChiTown Drive-In Presents - Michael
One ticket per vehicle for up to 6 adults. All spaces have excellent views of our large screen. You may face forward or back your car into your space. Spots are
Hand-Picked Venues & Spots in Chicago
Willis Tower
Soar to the highest US observation deck
The Willis Tower, originally known as the Sears Tower, is a 110-story, 1,451-foot skyscraper in Chicago's Loop. Designed by Bruce Graham and Fazlur Rahman Khan,
Art Institute of Chicago
World-class art museum
The Art Institute of Chicago is a private nonprofit art museum in Grant Park, founded in 1879. It ranks among the oldest and largest art museums in the United S
John Hancock Center
Sky-high views and thrill-seeking TILT platform
The John Hancock Center, officially 875 North Michigan Avenue, is a 100-story skyscraper in Chicago's Magnificent Mile district. Designed by Bruce Graham and Fa
Millennium Park — Cloud Gate
Bean + skyline plaza
Cloud Gate is a public sculpture by Anish Kapoor, serving as the centerpiece of Grainger Plaza at Millennium Park in Chicago. Built between 2004 and 2006, its 1
Grant Park
Chicago's front yard with iconic fountain and museums
Grant Park is a large 319-acre urban park in the Loop community area of Chicago's central business district. Originally called Lake Park, it was renamed in 1901
Museum of Contemporary Art Chicago
Modern art by the lake
The Museum of Contemporary Art Chicago is one of the world's largest contemporary art venues, established in 1967 near Water Tower Place in the Near North Side.
Lincoln Park
Lakefront park with zoo, museums, and beaches
Lincoln Park is Chicago's largest public park, stretching seven miles along Lake Michigan on the city's North Side. Named after President Abraham Lincoln, it fe
Chicago Theatre
Iconic 1921 theater with landmark marquee
The Chicago Theatre, originally the Balaban and Katz Chicago Theatre, opened in 1921 on North State Street in the Loop. It served as the flagship for the Balaba
Navy Pier
Lakefront pier
Navy Pier is a 3,300-foot-long pier on the shoreline of Lake Michigan in Chicago’s Streeterville neighborhood. It spans over 50 acres of shops, restaurants, liv
Museum Campus
America's first planetarium and four other major attractions
Museum Campus is a 57-acre park in Chicago along Lake Michigan. It encompasses five major attractions: the Adler Planetarium, America's first planetarium; the S
Civic Opera House
Second-largest opera auditorium in North America
The Civic Opera House, part of the Art Deco Civic Opera Building that opened in 1929, seats 3,276 in its main performance space. This venue, originally built fo
The Second City
Improv comedy powerhouse since 1959
The Second City is an improvisational comedy enterprise and the oldest continuously operating improv theater troupe based in Chicago. Founded in 1959, it has be
Harris Theater
Underground theater hosting dance and music
The Harris Theater is a 1,499-seat performing arts venue located along the northern edge of Millennium Park in Chicago. Built in 2002–2003, it sits largely unde
Biograph Theater
Historic theater where John Dillinger was gunned down
The Biograph Theater on Lincoln Avenue originally opened as a movie theater in 1915, but now hosts live stage productions. It was designated a Chicago Landmark
Symphony Center
Home to Chicago Symphony Orchestra
Symphony Center is a music complex at 220 South Michigan Avenue in Chicago’s Loop, designed by architect Daniel Burnham. It includes the 2,522-seat Orchestra Ha
Chicago Picasso
Untitled monumental sculpture by Picasso
The Chicago Picasso is an untitled monumental sculpture by Pablo Picasso in Daley Plaza. Installed in 1967, this 50-foot-tall, 162-ton COR-TEN steel Cubist scul
Recently Concluded in Chicago
The Brokes, St. Marlboro
Reggies Rock Club
CircuitMOM & Uncle Present Haunted Hollywood ft Erik Vilar and Ed Wood
House of Blues Chicago
Tank and The Bangas - The Last Balloon Tour with Ariel J. and Zeus
Thalia Hall
Shawn James – Flew Too Close To The Sun Tour
Bottom Lounge
Authority Zero w/ Counterpunch
Reggie's Music Joint
Authority Zero, Counterpunch, the Run Around, Bad Year
Reggies Music Joint
Frequently Asked Questions
What are unique date night ideas in Chicago?
Try a candlelit dinner terrace, an intimate underground jazz lounge, a scenic sunset overlook, or an interactive evening cocktail workshop.