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
Adler Planetarium
Immerse in sky shows and space artifacts at the historic planetarium.
1300 S DuSable Lake Shore Dr
↳ ≈ 10 min walk
Field Museum
See SUE the T. rex and natural history wonders nearby.
1400 S DuSable Lake Shore Dr
Afternoon
↳ ≈ 20 min walk

Art Institute of Chicago
Explore world-class art from Impressionists to American Gothic.
111 S Michigan Ave
↳ ≈ 20 min walk

Lou Malnati's Pizzeria
Enjoy classic deep-dish pizza with buttery crust and sausage patty.
439 N Wells St
↳ ≈ 30 min by transit

Green Mill Cocktail Lounge
Sip cocktails in a historic jazz club once frequented by Al Capone.
4802 N Broadway
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Built from Weekend Hive’s verified local listings — use Directions on any stop to open it in Google Maps.