Chicago · 2-day itinerary
2 Days in Chicago: A Weekend for Grown-Ups
Two days is enough to fall for Chicago. See it from the river, eat very well twice and hear the city's music in one of its oldest rooms.
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Day 1: River and rooftops
Arrive by early afternoon for the cruise.
Afternoon
Chicago Architecture Center River Cruise
112 E. Wacker Dr (riverfront)
The best 90 minutes you'll spend in Chicago (March to November).
A 90-minute cruise aboard First Lady down all three branches of the river, with a docent covering 50-plus buildings and the bascule bridges. The single best introduction to the city. The 2026 season runs mid-March to late November.
Sunset
LH Rooftop
LondonHouse, Michigan Ave bridge
Right above the Michigan Avenue bridge.
A tri-level rooftop above the Michigan Avenue bridge with river, lake and Magnificent Mile views. Busy in summer; lovely in the late afternoon.
Dinner
Joe's Seafood, Prime Steak & Stone Crab
60 E. Grand Ave, River North
Stone crab and prime steak in River North.
The Chicago partnership with Miami Beach's Joe's Stone Crab: prime steaks, seafood and cracked stone crab claws in a classic, bustling dining room.
Late
The Drifter
Beneath Green Door Tavern, Orleans & Huron
A tiny Prohibition-era speakeasy under the Green Door Tavern (Wednesday to Saturday).
A tiny speakeasy in a real Prohibition-era basement under the 1921 Green Door Tavern, with cocktails, live entertainment and burlesque. Open Wednesday to Saturday evenings.
Day 2: Laughs and jazz
A comedy institution and the jazz lounge Capone used to visit.
Day
Art Institute of Chicago
Michigan Ave at Millennium Park
A couple of hours with the Impressionists.
One of the great art museums in the world, strongest in Impressionism and American art. Pick a wing or two and pace yourselves.
Evening
The Second City
1616 N. Wells St, Old Town
The mainstage revue in Old Town.
The improv and sketch theatre that launched generations of comedians. The mainstage revue runs two shows on Friday and Saturday nights.
Late
The Green Mill
Broadway, Uptown
A short ride north to Uptown. Cash only.
The legendary jazz lounge (Al Capone's booth is still there), with live music seven nights a week. Cash only, no reservations, and a serious listening room.
Everything here was checked in September 2026. Club line-ups, cruise seasons and performance calendars change, so confirm before you go.
Questions people ask
What should adults do in Chicago in 2 days?
Take the architecture river cruise, have a sunset drink at LH Rooftop or Cindy's, spend a morning at the Art Institute, see the Second City and finish with jazz at the Green Mill.