All 15 on the map
Every stop in 48 hours in Chicago: a two-day itinerary, pinned where it actually is. Tap a marker to see which one it is.
Day one, morning: the architecture cruise
The 90-minute cruise leaves from the dock by the Michigan Avenue bridge; book it ahead. Lunch is a block north, at The Purple Pig.
Chicago Architecture Center River Cruise
The Chicago Architecture Center's 90-minute trip aboard First Lady, with a docent covering roughly 50 buildings. There's a bar on board, and boats sell out spring to fall.
The Purple Pig
Mediterranean small plates off Michigan Avenue: the crispy pig's ears with kale and a fried egg are the signature, along with the fried deviled egg, charcuterie cured in-house and an Italian-heavy wine list. Open daily 11 to 10. Happy hour, Sunday to Wednesday 2 to 5, is only at this Michigan Avenue room.
Day one, afternoon: Millennium Park and the Art Institute
Walk down Michigan Avenue to the Bean and the Art Institute. Across the street, the Chicago Cultural Center is free, under the world's largest Tiffany dome.
Millennium Park
Free and open daily from 6 a.m.: walk under Cloud Gate (the Bean), wade into Crown Fountain in summer, and catch free concerts at Frank Gehry's Pritzker Pavilion.
The Art Institute of Chicago
Seurat's Grande Jatte, Hopper's Nighthawks and Wood's American Gothic all hang here. Book a timed ticket online, then join a free daily tour or plot your own route through the galleries. The café serves a rotating pick from the city's restaurants.
Chicago Cultural Center
The old central library, crowned by two stained-glass domes, one of them the world's largest Tiffany dome, with free concerts, films and exhibitions through the week. Admission is free; start in Preston Bradley Hall.
Day one, night: the Riverwalk and the West Loop
At dusk, walk the Riverwalk west, then cross into the West Loop: dinner on Randolph Street and cocktails at Kumiko, the 2025 James Beard winner for Outstanding Bar, a few blocks away.
Chicago Riverwalk
A mile and a quarter of riverside path below street level, lined with wine bars, kayak rentals and boat docks. Duck into the McCormick Bridgehouse museum to see a bridge's gears up close.
Girl & the Goat
Stephanie Izard's 2010 original: shareable plates from a wood-fired kitchen, with her sautéed green beans a fixture. Sunday brunch runs 10 to 2.
Kumiko
Julia Momosé's Japanese dining bar in the West Loop, the 2025 James Beard winner for Outstanding Bar: precise cocktails like the Pepperberry Tonic, spirit-free pairings and an omakase-style tasting, with a whisky bar downstairs and a daytime café.
Day two, morning: the Museum Campus
Three museums on one lakefront peninsula, about 25 minutes' walk south of Millennium Park. Pick two, book timed tickets, and walk out past the Adler for the skyline.
Field Museum
SUE, the most complete T. rex yet found, anchors a natural-history museum begun with the 1893 World's Fair collections; Máximo, a cast of a 122-foot titanosaur, now fills the main hall. Open 9 to 5; buy timed tickets ahead, as weekends sell out.
Shedd Aquarium
Belugas, sea otters and a walk-around Caribbean reef, with Lake Michigan filling the Oceanarium's back windows. Reserve a timed entry online; weekday mornings are quietest.
Adler Planetarium
America's first planetarium (1930), with dome shows inside and the city's widest skyline view from the lawn out front. Open late on Wednesdays, 4 to 10 p.m.
Day two, afternoon: 103 floors up
Book a time slot near sunset on a clear day.
Willis Tower Skydeck
LoopEssentials listUp 103 floors in the Willis (Sears) Tower, step into The Ledge, a glass box hung out over Wacker Drive. Book a timed ticket and aim for a clear evening near sunset. Check tonight's antenna color on its site.
Day two, night: deep dish and Second City
An early deep dish at Pequod's, a short ride to the Second City revue in Old Town, then a drink at Old Town Ale House across the street.
Pequod's Pizza
Pan pizza ringed with cheese baked dark and crunchy against the pan, the edge regulars fight over. It's a sports bar on Clybourn, a long-standing favorite of the city's chefs, and the kitchen runs until 2 a.m. most nights (midnight on Sunday).
The Second City
Sketch and improv since 1959, the stage behind Belushi, Murray, Fey and Colbert. The mainstage revue plays Old Town, and a second revue plays the smaller stage next door most nights.
Old Town Ale House
A dive since 1958 across from Second City, its walls hung with the owner's satirical portraits, and a bar Anthony Bourdain loved. Cash only (there's an ATM); comics drift in after shows.
Arriving Friday night
Go straight to jazz at The Green Mill in Uptown, or to rum drinks at Three Dots and a Dash, the tiki bar down an alley in River North. After midnight, The Wieners Circle in Lincoln Park is the late-night hot dog.
In winter
The river cruises run spring to fall. In winter, take the Skydeck on day one instead, and give day two's afternoon to Garfield Park Conservatory, a free glasshouse that stays tropical all winter (reserve a time). Cindy's, the rooftop over Millennium Park, keeps fires going on its terrace.
Getting around
Day one is all on foot. On day two, walk or take a cab to the Museum Campus, and a cab or the Brown Line to Lincoln Park and Old Town at night. Tap a contactless card or phone at any 'L' turnstile.
Want more?
With a third day, add the neighborhoods: see 3 days in Chicago. Short on time? One day in Chicago.
Common questions
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