Weekend Hive

Chicago weekend plan

★ Editor’s pick

A Foodie Weekend in Chicago: Where to Eat & Drink

For people who plan trips around meals — a delicious Chicago weekend of markets, restaurants, and bars.

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

SaturdaySat, May 30

≈ 4.5 hrs · 3 stops

Morning

bar
9:00 AM
10:30 AM
Scofflaw

Scofflaw

Sip gin-focused cocktails by the fireplace at Scofflaw, a cozy Logan Square bar.

3201 W Armitage Ave

Directions

≈ 15 min walk

bar
10:30 AM
12:00 PM
The Whistler

The Whistler

End the night with craft cocktails and live jazz at The Whistler, a tiny Logan Square gem.

2421 N Milwaukee Ave

Directions

Afternoon

≈ 10 min by transit

restaurant
12:00 PM
1:30 PM
Pequod's Pizza

Pequod's Pizza

Grab a legendary caramelized-crust pan pizza at Pequod's, a local favorite for deep dish.

2207 N Clybourn Ave

Directions

SundaySun, May 31

≈ 5.5 hrs · 3 stops

Morning

food
8:00 AM
10:30 AM
Wicker Park Farmers Market

Wicker Park Farmers Market

Browse local produce and artisan goods at the Wicker Park Farmers Market.

Wicker Park, 1425 N Damen Ave · Wicker Park

Directions

≈ 25 min by transit

bar
9:00 AM
9:30 AM
Green Mill Cocktail Lounge

Green Mill Cocktail Lounge

Catch live jazz at the historic Green Mill, a 1907 Uptown club with Al Capone lore.

4802 N Broadway

Directions

≈ 40 min by transit

food
11:00 AM
1:30 PM
Street Foods of Pilsen Food Tour

Street Foods of Pilsen Food Tour

Taste your way through Pilsen's celebrated Mexican food scene on a guided food tour.

5 Rabanitos, 1758 W 18th St · Pilsen

Directions

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