Date Ideas in Chicago

400 S DuSable Lake Shore Dr, Chicago, IL 60605, USA

Lakefront Park

Classic talk-and-walk date energy that does not feel forced.

4.9

(175)

Best near sunset

Lurie Garden

Scenic, low-pressure, and easy to pair with coffee or drinks after.

220 E Monroe St, Chicago, IL 60601, USA

(293)

Chicago Botanic Garden

Scenic, low-pressure, and easy to pair with coffee or drinks after.

1000 Lake Cook Rd, Glencoe, IL 60022, USA

(7,815)

$$$

The Art Institute of Chicago

Built-in conversation starters without needing a full itinerary.

111 S Michigan Ave, Chicago, IL 60603, USA

(37,613)

Excellent indoor backup

The Jetty | Riverwalk

Classic talk-and-walk date energy that does not feel forced.

260 W Wacker Dr, Chicago, IL 60606, USA

(351)

Best near sunset

Garfield Park Conservatory

Scenic, low-pressure, and easy to pair with coffee or drinks after.

300 N Central Park Ave, Chicago, IL 60624, USA

(10,363)

Romantic Tip✨ Surprises

“If you want the date to feel thoughtful, send one short “I picked this because it seemed like your vibe” text before you go.”

🌹🎨

6300 S Cornell Ave, Chicago, IL 60637, USA

Osaka Garden

Scenic, low-pressure, and easy to pair with coffee or drinks after.

4.7

(1,224)

111 W Illinois St, Chicago, IL 60654, USA

TARY

Short, low-stakes, and easy to turn into something longer.

4.7

(924)

Great daytime opener

715 S Dearborn St, Chicago, IL 60605, USA

Cafe Deko

Short, low-stakes, and easy to turn into something longer.

4.5

(340)

Great daytime opener

820 N Franklin St, Chicago, IL 60610, USA

Nomad-Chicago

Short, low-stakes, and easy to turn into something longer.

4.4

(229)

Great daytime opener