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Chicago

Date Ideas: 10 Things to Do Together in Chicago

Ten date ideas in Chicago, from live comedy and ping-pong to a distillery tour and a night under the planetarium dome.

A shared activity gives a date somewhere to go beyond the same dinner reservation or bar. These ten Chicago ideas range from sketch comedy and rooftop drinks to a lakefront walk, live jazz, and a garden trip north of the city.

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The Second City

The glass-fronted building with a red Second City sign on its facade, a revolving door and a crowd on the sidewalk below.
Photo courtesy of The Second City

Laugh at the same sketches on a date at The Second City, a theater known for sketch and improv shows, with drinks to accompany the performance.

Current listings include 8pm shows on the Mainstage and e.t.c. stage. Buy tickets for the show that appeals to you both through the theater's website.

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230 W North Ave
Reservations

Tickets by showtime on the website

Visit website

$$

SPiN Chicago

A large room with several ping pong tables under pipes and track lighting, with seating along the walls.
Photo courtesy of SPiN Chicago

Play a few rounds together at SPiN Chicago, a ping-pong social club with bookable tables, cocktails, and a kitchen.

Table time has been listed at $29 an hour Monday through Thursday, or $10 on Friday and Saturday nights after 10pm. Confirm the address before heading over, since sources conflict on the current location.

$

Koval Distillery

A deck with black umbrellas and tables beside an ivy-covered wall.
Photo courtesy of Koval Distillery

Learn about spirits together at Koval Distillery, where a tour takes you past copper pot stills on the production floor before a guided tasting of three spirits.

Tours cost $12 per person and last 45 minutes. The Classic Tour runs Saturday at 1pm and Sunday at 2pm; the Whiskey Tour runs Saturday at 3pm. Book ahead for weekends, which can sell out, and note that tastings are for guests 21 and older.

$

Lincoln Park Zoo

A child pressing a hand to the glass as a penguin swims past in an underwater viewing tank.
Photo courtesy of Lincoln Park Zoo

Meet the animals on a free daytime date at Lincoln Park Zoo, which is open 365 days a year.

The grounds open at 8am and buildings at 10am. For an after-dark outing in December, ZooLights brings holiday lights to the grounds.

Chicago Botanic Garden

An aerial view of a circular hedge garden surrounded by water and a curving white footbridge.
Photo courtesy of Chicago Botanic Garden

Take a short trip north of the city to wander Chicago Botanic Garden in Glencoe. Its 385 acres give you plenty of space for an outdoor outing together.

Nonmembers need tickets, with free admission days for Illinois residents each year. Parking fees still apply on free days, and tickets must be secured in advance.

Navy Pier

An aerial view of the pier with a Ferris wheel, buildings and boats on the blue lake under a bright sun.
Photo courtesy of Navy Pier

Keep a date moving with a lakefront walk at Navy Pier, stopping at attractions along the way. The 3,300-foot pier makes an out-and-back stroll more than a mile long.

Ride the 200-foot Centennial Wheel for a view over the lake. The pier also hosts more than 245 free public programs each year, so check what is on before your visit.

$$$

Geja's Cafe

A marshmallow on a long fork catching fire over a copper fondue pot.
Photo courtesy of Geja's Cafe

Share a fondue pot over dinner at Geja's Cafe in Lincoln Park. Start with Swiss Gruyere cheese fondue, then choose an entree fondue with shrimp, scallops, lobster, chicken, or beef. Belgian flaming chocolate fondue finishes the meal, accompanied by a classical or flamenco guitarist.

Small curtains shelter the booths, with little light beyond the fondue flames. An average meal costs $35 and up per person, and reservations require a credit card.

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340 W Armitage Ave, Chicago, IL 60614
Reservations

Accepted; credit card required; $25 per person no-show fee

Cindy's Rooftop

A glass-roofed dining room with striped banquettes, wooden tables and hanging globe lights.
Photo courtesy of Cindy's Rooftop

Have drinks with a view at Cindy's Rooftop, a restaurant and bar on the 13th floor of the Chicago Athletic Association hotel. A glass atrium covers the terrace overlooking Millennium Park and Lake Michigan.

Reservations are encouraged and open 14 days ahead, though walk-ins are welcome. Friday and Saturday hours extend until 12am.

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12 S Michigan Ave, Chicago, IL 60603
Reservations

Encouraged, available 14 days ahead; walk-ins welcome

Visit website

$

Green Mill

A saxophonist in a gray jacket and patterned tie smiling beside a microphone on a stage.
Photo courtesy of Green Mill

Let live jazz provide the soundtrack to a date at Green Mill, a historic club with music every night. Nightly sets run, for example, from 8pm to midnight.

Late Friday and Saturday sets run from 1am to closing, with a $5 cover.

$$

Adler Planetarium

The planetarium's domed stone building at the top of a staircase with a person leaping on the steps, under a bright sky.
Photo courtesy of Adler Planetarium

Spend a Wednesday evening at Adler Planetarium on Museum Campus, when hours run late and Illinois residents get free admission. Add a dome show if you want more to see together.

General admission starts at $25 for adults and $13 for children, with dome shows charged separately. Buy timed-entry tickets online.

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