Ready-made trips · United States
Chicago in 4 days
An architecture river cruise and the Magnificent Mile, the Art Institute and Millennium Park.
Open the plan to change anything: swap stops, swap or add days, and keep your own copy to share.
- Length
- 4 days
- Best time
- May to September
- Pace
- Moderate
- Day trips
- None, all in the city
Four days in Chicago: Willis Tower, Fulton Market and the Blues; The Architecture Cruise and the Magnificent Mile. Each full day is one our team has planned, to be walked in order around usual opening hours, with lunch and dinner suggestions close to the stops.
Day by day
1Art Institute of ChicagoArrival
- When you arriveArt Institute of ChicagoWorld-class art museum.Tip: Home to genuinely significant Impressionist and American art, including Grant Wood's American Gothic — one of the best collections in the US.
Lunch nearby: Terzo Piano or Giordano’s
Dinner: The Purple Pig or Lou Malnati’s River North
2Willis Tower, Fulton Market and the Blues
- MorningWillis Tower SkydeckGlass ledge viewpoint.Tip: The glass 'Ledge' boxes extending from the building are the highlight — not for those uneasy with heights, offering a genuinely vertigo-inducing view straight down.
- AfternoonFulton MarketThe old meatpacking district, now the city’s restaurant row.Tip: Time Out Market has a dozen of the city’s chefs under one roof.
- EveningKingston MinesChicago’s biggest blues club, with two stages and bands until late.Tip: Two stages alternate, so the music never stops.
Lunch nearby: Au Cheval or Time Out Market Chicago
Dinner: R.J. Grunts
3The Architecture Cruise and the Magnificent Mile
- MorningChicago River Architecture CruiseBoat tour of skyline.Tip: The Chicago Architecture Center’s own cruise has the best guides; sit on the open top deck.
- AfternoonMagnificent MileShopping boulevard.Tip: Chicago's premier shopping street — genuinely worth a walk for the architecture and skyline views alone, even without shopping plans.
- Evening360 ChicagoThe observation deck of the former John Hancock Center, with the tilting TILT windows.Tip: Go at sunset; the bar on the 96th floor has the same view for the price of a drink.
Lunch nearby: The Purple Pig or Giordano’s
Dinner: Lou Malnati’s River North or Portillo’s
4A Last Morning at Millennium ParkLast morning
- Before you leaveMillennium ParkHome of The Bean.Tip: Home to the famous 'Bean' sculpture (Cloud Gate) — genuinely popular for photos, so early morning offers a calmer experience.
Lunch nearby: Giordano’s or Terzo Piano
Dinner: The Purple Pig or Lou Malnati’s River North
Where to stay
The Loop
Downtown among the skyscrapers, by Millennium Park and the Art Institute.
Every L line meets here; the Blue Line runs to O’Hare.
River North & Streeterville
North of the river, by the Magnificent Mile and Navy Pier.
Red Line and many buses.
West Loop
The restaurant district of Fulton Market and Randolph Street.
Green and Pink Lines at Morgan.
Everything in the plan is ready to book
The full plan has a map of each day, directions between stops, opening hours, restaurant choices, hotels in these areas and tickets, tours and trains linked to book with the provider you choose.
Open the full plan →Want different dates, a slower pace or something specific? Plan your own Chicago trip in about a minute.