Neighborhood 48H guide
The Loop: Where to Stay & What to Do in 48 Hours
The Art Institute, Millennium Park’s Bean, the Riverwalk and a rooftop above Michigan Avenue.
The Loop is Chicago’s downtown, named for the ‘L’ tracks that circle it. Michigan Avenue faces Millennium Park and the Art Institute, and the Riverwalk runs along its northern edge. It is busy on weekdays and quieter at night.
Photo gallery
Photo: Ken Lund from Reno, Nevada, USA · CC BY-SA 2.0 · Wikimedia Commons 
Photo: Tony Hisgett from Birmingham, UK · CC BY 2.0 · Wikimedia Commons 
Photo: Roman Boed from The Netherlands · CC BY 2.0 · Wikimedia Commons
Why stay here
The big sights are walkable, and every ‘L’ line meets here.
Who it's for: First-timers, architecture fans and museum-goers.
Pros
- Walk to Millennium Park and the Art Institute
- Every ‘L’ line
- Architecture boat tours leave nearby
Cons
- Quiet late at night
- Business-hotel pricing on weekdays
- Few neighborhood restaurants
48H in the Loop
Art, the Bean, the river and a rooftop.
10:00 – Art Institute of Chicago
Book a timed ticket; give it at least three hours.
13:30 – Millennium Park
Cloud Gate (the Bean) and Crown Fountain, free.
15:30 – Chicago Riverwalk
Walk the river west from Michigan Avenue; architecture boat tours leave along here.
18:30 – Cindy’s rooftop
Rooftop bar on the Chicago Athletic Association, facing Millennium Park.
Named recommendations
Real places with links to their official site or a Maps place page. We do not invent hours, prices, or ratings.
Drink
Drink
Cindy’s
12 S Michigan Ave
Rooftop bar on the Chicago Athletic Association hotel with Millennium Park views.
Photo: Tony Hisgett from Birmingham, UK · CC BY 2.0 · Wikimedia Commons Official site / map →
See / do
See / do
Art Institute of Chicago
111 S Michigan Ave
One of the great US art museums, guarded by its two bronze lions.
Photo: Ken Lund from Reno, Nevada, USA · CC BY-SA 2.0 · Wikimedia Commons Official site / map →
Outdoors
Outdoors
Millennium Park
201 E Randolph St
Cloud Gate, Crown Fountain and free summer concerts at the Pritzker Pavilion.
Official site / map →Outdoors
Chicago Riverwalk
Wacker Dr, along the river
Riverside path with cafés and boat-tour docks below street level.
Photo: Roman Boed from The Netherlands · CC BY 2.0 · Wikimedia Commons Official site / map →
Where to stay
Specific named properties—not vague city-wide searches. Expedia stays use tracked Creator links; others open the hotel's official site.
Roam48 may earn a commission when you book a stay through Expedia or Vrbo links on this page, at no extra cost to you. All commercial stay links use rel="sponsored nofollow".
Hotel · Expedia
Chicago Athletic Association
12 S Michigan Ave
Restored 1893 Venetian Gothic club facing Millennium Park, with Cindy’s on the roof.
Check rates on Expedia →Hotel · Expedia
Kimpton Gray Hotel
122 W Monroe St
Boutique hotel in the restored 1894 New York Life Insurance Building.
Check rates on Expedia →
Vacation rentals
Prefer an apartment or whole home in this neighborhood? Browse Vrbo listings for The Loop.
Chicago requires short-term rentals to be registered with the city, and some buildings and precincts ban them. Look for the city registration number on the listing before you book.
Browse vacation rentals in The Loop on Vrbo →Other ways to spend 48 hours in Chicago
- River North — Marina City’s corncob towers, deep-dish pizza, a Portillo’s Italian beef and hotel rooftops.
- Magnificent Mile / Streeterville — Michigan Avenue’s shops, the 1869 Water Tower, the Billy Goat Tavern and Navy Pier.
- Gold Coast — Astor Street mansions, Oak Street Beach and the Drake’s Palm Court.
- West Loop / Fulton Market — Randolph Street’s Restaurant Row: Au Cheval’s burger, Girl & the Goat and Fulton Market’s old warehouses.
- Wicker Park — The six-way corner at North, Damen and Milwaukee, Big Star tacos, Myopic Books and The 606 trail.
- Lincoln Park — The free Lincoln Park Zoo, the glass Conservatory, Pequod’s pan pizza and late-night blues at Kingston Mines.
- Lakeview / Wrigleyville — Wrigley Field’s red marquee, Murphy’s Bleachers and a hotel across the street from the ballpark.
- South Loop / Museum Campus — The Field Museum, Buckingham Fountain and live blues at Buddy Guy’s Legends.
- Hyde Park — Frank Lloyd Wright’s Robie House, the Museum of Science and Industry, the new Obama Presidential Center and Promontory Point.