Chicago · 3-day itinerary
3 Days in Chicago: A Grown-Up Itinerary
Three days in Chicago gives you the city's three great pleasures: its buildings, its music and its restaurants. Each day below pairs one of each, and every evening stays in a single part of town.
- Day 1
- River cruise, Riverwalk wine, Andy's Jazz Club
- Day 2
- Art Institute, Cindy's, Girl & the Goat, Buddy Guy's
- Day 3
- 360 CHICAGO, Gibsons, the Green Mill
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Day 1: The river and River North jazz
The best introduction to the city, then its most welcoming jazz club.
Afternoon
Chicago Architecture Center River Cruise
112 E. Wacker Dr (riverfront)
90 minutes on the river with a docent. The 2026 season runs mid-March to late 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.
After the cruise
City Winery at the Riverwalk
Chicago Riverwalk, between Dearborn and State
A glass by the water a short stroll along the Riverwalk.
A riverside wine garden and restaurant pouring its own wines on tap, with a retractable glass enclosure for cooler days. An easy sunset glass after the architecture cruise.
Dinner and jazz
Andy's Jazz Club
11 E. Hubbard St, River North
Dinner with a set; reservations are required and good for one show.
A jazz club since 1951 with dinner and several sets a night. Reservations are required and good for one show; the room clears between sets.
Nightcap
Three Dots and a Dash
435 N. Clark St (alley entrance)
Through the alley to the tiki bar, or the quieter Bamboo Room inside.
A subterranean tiki bar reached through an alley, with elaborate rum drinks. The 16-seat Bamboo Room inside is the quieter, serious-rum option.
Day 2: Art, the park and the West Loop
A slow museum day and a lively dinner.
Day
Art Institute of Chicago
Michigan Ave at Millennium Park
Pick a wing or two (Impressionists, American art) rather than everything.
One of the great art museums in the world, strongest in Impressionism and American art. Pick a wing or two and pace yourselves.
Sunset
Cindy's
Chicago Athletic Association, 12 S. Michigan Ave
Across the street, 13 floors up, looking over Millennium Park and the lake.
A 13th-floor glass-atrium restaurant and terrace looking over Millennium Park and the lake. Fire pits in winter, open-air seats in summer.
Dinner
Girl & the Goat
809 W. Randolph St, West Loop
Shared plates on Randolph Street's restaurant row.
Stephanie Izard's shared-plates restaurant that helped turn Randolph Street into a restaurant row. Big flavours, lively room.
Late
Buddy Guy's Legends
700 S. Wabash Ave, South Loop
Live blues in the South Loop, a short ride back.
The blues club Buddy Guy opened in 1989, with Cajun and soul food and live blues most nights. Buddy himself traditionally plays a run of shows each January.
Day 3: Up high, then Uptown
The skyline from the 94th floor and the city's most legendary jazz room.
Afternoon
360 CHICAGO and CloudBar
94th floor, 875 N. Michigan Ave
The 94th-floor deck and a drink at the CloudBar. TILT is optional (and extra).
The 94th-floor observation deck in the former John Hancock Center, with an 18-seat CloudBar for a cocktail with the view. TILT, which leans you over the edge, is extra.
Dinner
Gibsons Bar & Steakhouse
1028 N. Rush St, Gold Coast
A classic, noisy Rush Street steakhouse.
A Rush Street steakhouse since 1989 with white-jacketed servers, a busy bar and giant desserts. Noisy, clubby and very Chicago.
Late
The Green Mill
Broadway, Uptown
A cab up to Uptown. Cash only, no reservations; arrive by 7:30 on weekends for a booth, or later for standing room.
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
Is 3 days enough for Chicago?
Yes for a first visit: enough for the architecture river cruise, the Art Institute, a skyline view and three great nights of food and music.
When does the Chicago architecture river cruise run?
The Chicago Architecture Center River Cruise aboard First Lady runs from mid-March to late November in 2026 (March 15 to November 22), with several departures a day.