Chicago · 4-day itinerary
4 Days in Chicago: The Unhurried Grown-Up Version
Four days lets you add Chicago's culture heavyweights (Frank Lloyd Wright's studio, the opera or the Symphony) to the music and restaurants, without ever rushing.
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Day 1: River North
Start gently near the hotel.
Sunset
360 CHICAGO and CloudBar
94th floor, 875 N. Michigan Ave
The 94th-floor view with a CloudBar cocktail.
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
Rush Street steak.
A Rush Street steakhouse since 1989 with white-jacketed servers, a busy bar and giant desserts. Noisy, clubby and very Chicago.
Late
The Drifter
Beneath Green Door Tavern, Orleans & Huron
A speakeasy under a 1921 tavern.
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: The river and Andy's
Architecture by boat, jazz by candlelight.
Afternoon
Chicago Architecture Center River Cruise
112 E. Wacker Dr (riverfront)
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
City Winery at the Riverwalk
Chicago Riverwalk, between Dearborn and State
Wine on 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
Reserve for one set.
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.
Day 3: Oak Park and the opera
Wright in the morning, a big night of music after.
Morning
Frank Lloyd Wright Home and Studio
Oak Park, about 30 minutes west
The one-hour Home and Studio tour; book ahead.
Wright's own house and studio, seen by one-hour guided tour, plus a neighbourhood walk past his other early homes. Advance tickets recommended.
Dinner
Monteverde
1020 W. Madison St, West Loop
Hand-made pasta in the West Loop.
Sarah Grueneberg's pasta-focused Italian restaurant, with pasta made by hand in the middle of the room. Ten years in and still one of the city's most wanted tables.
Evening
Lyric Opera of Chicago
Civic Opera House, Wacker Dr
A short ride to the Civic Opera House. Or the Chicago Symphony at Symphony Center.
Grand opera in the 1929 Civic Opera House. The 2026/27 season opens with Don Giovanni (October 10 to November 1, 2026); check the calendar for your dates.
Day 4: Art and blues
The Art Institute and a late night in Lincoln Park.
Day
Art Institute of Chicago
Michigan Ave at Millennium Park
Take your time.
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
Over Millennium Park.
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 in the West Loop.
Stephanie Izard's shared-plates restaurant that helped turn Randolph Street into a restaurant row. Big flavours, lively room.
Late
Kingston Mines
2548 N. Halsted St, Lincoln Park
Two stages of blues every night of the year.
Chicago's oldest and largest continuously running blues club: two rooms, two stages and two bands every night of the year. It goes late.
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 to add to a longer Chicago trip?
A morning in Oak Park for Frank Lloyd Wright's Home and Studio, a night at the Lyric Opera or the Chicago Symphony, and a late blues set at Kingston Mines.