Chicago Date Ideas

The legendary improv and sketch comedy theater that launched the careers of Tina Fey, Steve Carell, and dozens of other comedy icons. The Mainstage hosts original revues, while the smaller stages feature emerging talent. Ten Dollar Comedy shows offer a budget-friendly entry point. Shows run nightly.

Art Deco jazz club with a storied speakeasy past dating back to Prohibition -- Al Capone's favorite hangout. Live jazz seven nights a week with a small cover charge. The Sunday night Uptown Poetry Slam, running since 1986, is the longest-running poetry slam in the country. Cash only. No talking during performances.

One of the oldest and largest art museums in the country, home to iconic works including Grant Wood's American Gothic, Georges Seurat's A Sunday on La Grande Jatte, and Edward Hopper's Nighthawks. The Modern Wing designed by Renzo Piano is worth visiting for the architecture alone. Children under 14 always free. Chicago teens under 18 also free.

The iconic 1921 movie palace with the famous marquee sign is a Chicago landmark. Now hosts concerts, comedy shows, and special events. The 1-hour theatre tour ($32) explores the ornate French Baroque interior, grand staircase, and backstage areas. One of the most photographed buildings in Chicago.

Frank Gehry-designed outdoor concert pavilion in Millennium Park hosting free concerts all summer. The Summer Music Series runs select Mondays and Thursdays from June through August. The Grant Park Music Festival offers free classical concerts from June to August. The Chicago Jazz Festival over Labor Day weekend is also free. Bring a blanket and picnic on the Great Lawn.

The oldest continuously operating blues club in Chicago, open since 1968. Two stages with live blues bands playing simultaneously every night until the early morning hours. Open until 5am on Saturdays. A must-visit for blues fans and one of the few late-night music venues in the city.

Intimate stand-up comedy club two doors down from Second City on Wells Street. Features touring national headliners and strong local acts. One of the premier stand-up rooms in the Midwest. Shows typically Thursday through Sunday with occasional weeknight specials. Two-drink minimum.

Legendary improv theater and training center that helped pioneer long-form improvisation. Multiple stages host nightly shows including the long-running Improvised Shakespeare Company. Also offers improv classes for all levels. More experimental and performer-driven than Second City, with lower ticket prices.

Tony Award-winning ensemble theater company founded in 1974 by Gary Sinise, John Malkovich, and others. Known for visceral, emotionally intense productions. The new in-the-round Ensemble Theater opened in 2022. One of the most respected regional theaters in the country. Rush tickets and student discounts often available.

The Chicago outpost of the famous LA comedy chain, featuring a 311-seat theater with a 100-seat balcony, full bar, and state-of-the-art sound. Hosts touring national headliners and local favorites. Shows most nights of the week with tickets starting around $16. One of the larger dedicated comedy rooms in the city.

Beloved indie music venue and bar that has been a cornerstone of Chicago's underground music scene since 1992. Capacity of 400 with a no-frills dive bar vibe. Hosts everything from experimental noise to indie rock to electronic music. Many free Monday shows. One of the most respected small venues in the country.

A century-old bar tucked in an industrial pocket of Bucktown that served as a Prohibition-era hangout. Now one of Chicago's most intimate and eclectic live music venues, hosting alt-country, folk, rock, comedy, and literary events. Capacity around 100 -- shows sell out fast. A true Chicago institution with fiercely loyal regulars.

Located in the Second City complex on Wells Street, UP Comedy Club hosts stand-up, touring acts, and variety shows in a more traditional comedy club format. A good complement to Second City's improv shows. Part of the Old Town comedy corridor with Zanies just down the block. Tickets typically run $15-40.