Weekend Hive

Chicago weekend plan

★ Editor’s pick

Date Night in Chicago: The Perfect Weekend Plan

A romantic Chicago weekend itinerary — great food, a little culture, and somewhere to linger after dark.

Numbered pins trace the route in order; a stop without a known location isn’t shown.

SaturdaySat, May 30

≈ 9 hrs · 5 stops

Morning

museum
9:00 AM
11:00 AM
Adler Planetarium

Adler Planetarium

Immerse in sky shows and space artifacts at the historic planetarium.

1300 S DuSable Lake Shore Dr

Directions

≈ 10 min walk

museum
11:00 AM
1:00 PM
Field Museum

Field Museum

See SUE the T. rex and natural history wonders nearby.

1400 S DuSable Lake Shore Dr

Directions

Afternoon

≈ 20 min walk

museum
1:00 PM
3:00 PM
Art Institute of Chicago

Art Institute of Chicago

Explore world-class art from Impressionists to American Gothic.

111 S Michigan Ave

Directions

≈ 20 min walk

restaurant
3:00 PM
4:30 PM
Lou Malnati's Pizzeria

Lou Malnati's Pizzeria

Enjoy classic deep-dish pizza with buttery crust and sausage patty.

439 N Wells St

Directions

≈ 30 min by transit

bar
4:30 PM
6:00 PM
Green Mill Cocktail Lounge

Green Mill Cocktail Lounge

Sip cocktails in a historic jazz club once frequented by Al Capone.

4802 N Broadway

Directions

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Built from Weekend Hive’s verified local listings — use Directions on any stop to open it in Google Maps.