A field guide · Chicago

Chicago in a Weekend

Deep dish, jazz and some of the best architecture in America. A two-day loop from the Loop to Wrigleyville.

12 placesLast updated Nov 1, 2026
1

Lou Malnati's Pizzeria

Chicago
Food

“Deep-dish with a buttercrust; allow about 40 minutes to bake.”

#deep dish#pizza
2

Portillo's

Chicago
Food

“Chicago-style hot dogs and Italian beef, dipped or dry.”

#hot dogs#italian beef
3

Au Cheval

Chicago
Food

“Fulton Market diner famous for its cheeseburger; waits can be long.”

#burgers#west loop
4

The Berghoff

Chicago
Food

“German restaurant in the Loop since 1898.”

#historic#loop
5

Intelligentsia Coffee Broadway

Chicago
Coffee

“The roaster's original Lakeview coffeebar, opened in 1995.”

#lakeview
6

The Green Mill

Chicago
Drinks

“Uptown jazz club and cocktail lounge with nightly live sets.”

#jazz#historic
7

The Art Institute of Chicago

Chicago
Sights

“World-class collection; don't miss the Impressionist galleries.”

#museum
8

Cloud Gate

Chicago
Sights

“"The Bean" in Millennium Park; best at sunrise or after dark.”

#free#photo spot
9

Chicago Riverwalk

Chicago
Outdoors

“Stroll the river past the downtown skyline; boat tours leave nearby.”

#walk#architecture
10

Skydeck Chicago

Chicago
Sights

“Glass ledges 103 floors up in Willis Tower.”

#views
11

Wrigley Field

Chicago
Sights

“The Cubs' ivy-covered ballpark, open since 1914; tours run year-round.”

#baseball#historic
12

Lincoln Park Zoo

Chicago
Outdoors

“Free zoo on the lakefront, open daily.”

#free#family

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