One day in Chicago: a one-day itinerary

Morning: breakfast and the architecture cruise

Breakfast at 8 at Lou Mitchell's (closed Monday and Tuesday), then walk east through the Loop, about 30 minutes, to the cruise dock by the Michigan Avenue bridge. Book the boat ahead.

1. L

   Lou Mitchell's

   West LoopClassic dinerEssentials list

   A diner on Jackson since 1923, at the old start of Route 66, handing doughnut holes and Milk Duds to the line. Breakfast and lunch Wednesday to Sunday until 2; closed Monday and Tuesday.

   (312) 939-3111loumitchells.com

   Map
2. C

   Chicago Architecture Center River Cruise

   LoopArchitecture boat tourEssentials list

   The Chicago Architecture Center's 90-minute trip aboard First Lady, with a docent covering roughly 50 buildings. There's a bar on board, and boats sell out spring to fall.

   (312) 922-3432architecture.org

   Map

Lunch: an Italian beef on Taylor Street

A short cab ride southwest of the dock to the stand that has sliced Italian beef since 1938. Order it dipped, with hot giardiniera, then cab back to Michigan Avenue.

1. A

   Al's Beef

   Little ItalyEssentials list

   Al's has been slicing Italian beef since 1938, and Taylor Street is the original stand. Order it dipped with hot giardiniera, and lean over the counter while you eat.

   (312) 226-4017alsbeef.com

   Map

Afternoon: the Bean and the Art Institute

Walk down Michigan Avenue to Cloud Gate, then give the Art Institute next door two or three hours. Book its timed ticket ahead.

1. M

   Millennium Park

   LoopPark & Cloud GateEssentials list

   Free and open daily from 6 a.m.: walk under Cloud Gate (the Bean), wade into Crown Fountain in summer, and catch free concerts at Frank Gehry's Pritzker Pavilion.

   (312) 742-1168chicago.gov

   Map
2. A

   The Art Institute of Chicago

   LoopLandmark art museumEssentials list

   Seurat's Grande Jatte, Hopper's Nighthawks and Wood's American Gothic all hang here. Book a timed ticket online, then join a free daily tour or plot your own route through the galleries. The café serves a rotating pick from the city's restaurants.

   (312) 443-3600artic.edu

   Map

Sunset: a drink over Millennium Park

Across Michigan Avenue from the park, on the roof of the Chicago Athletic Association hotel.

1. C

   Cindy's

   Loop$$$Cocktail Bars list

   The glass-topped rooftop of the Chicago Athletic Association hotel, looking over Millennium Park to the lake; in winter the terrace keeps fires going.

   (312) 792-3502cindysrooftop.com

   Book on OpenTableMap

Dinner: deep dish, or the West Loop

Deep dish at Pequod's in Lincoln Park, a short cab ride north, or book ahead for Girl & the Goat on Randolph Street.

1. P

   Pequod's Pizza

   Lincoln ParkDeep-dish pizzaEssentials list

   Pan pizza ringed with cheese baked dark and crunchy against the pan, the edge regulars fight over. It's a sports bar on Clybourn, a long-standing favorite of the city's chefs, and the kitchen runs until 2 a.m. most nights (midnight on Sunday).

   (773) 327-1512pequodspizza.com

   Map
2. G

   Girl & the Goat

   West LoopNew AmericanEssentials list

   Stephanie Izard's 2010 original: shareable plates from a wood-fired kitchen, with her sautéed green beans a fixture. Sunday brunch runs 10 to 2.

   (312) 492-6262girlandthegoat.com

   Map

Late: jazz in a 1907 lounge

Take the Red Line north to Lawrence for music every night at one of Al Capone's old haunts.

1. G

   The Green Mill

   UptownEssentials list

   Uptown's 1907 jazz lounge, a Capone-era hangout with music every night. Sunday's Uptown Poetry Slam started here, and late jam sessions run past 1 a.m. on Fridays and Saturdays.

   (773) 878-5552greenmilljazz.com

   Map

In winter

The river cruises run spring to fall. In winter, go up the Willis Tower Skydeck in the morning instead, and add the Tiffany dome at the Chicago Cultural Center, free and across from Millennium Park. Cindy's keeps fires going on its terrace, and from late November the city's Christmas tree stands in the park: see Christmas lights in Chicago.

Want more?

Staying longer? See 48 hours in Chicago or 3 days in Chicago, and what to know on a first visit.

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