All 22 on the map
Every stop in 3 days in Chicago: a three-day itinerary, pinned where it actually is. Tap a marker to see which one it is.
Day one: the river and Millennium Park
The architecture cruise in the morning, then a short cab ride to Taylor Street for an Italian beef at Al's Beef, the 1938 original, then back downtown for the Bean and the Art Institute. Book the boat and the museum ahead.
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.
Al's Beef
Al's has been slicing Italian beef since 1938, and Taylor Street is the original stand. Order it dipped with hot giardiniera, and lean over the counter while you eat.
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.
Day one, night: pasta and live music in the West Loop
Handmade pasta at Monteverde, then Lazy Bird, a basement lounge with live bands Thursday to Saturday.
Monteverde
Sarah Grueneberg's West Loop pasta house, where pastas are rolled in view all day; she won the James Beard Best Chef award for it. Order two pastas for the table.
Lazy Bird
A mid-century cocktail lounge in the basement of The Hoxton, with live bands Thursday to Saturday (9 to midnight, with a cover) and vinyl sets on Sundays.
Day two: the Museum Campus and the Skydeck
Pick two of the three lakefront museums and book timed tickets, then go up the Willis Tower near sunset.
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.
Willis Tower Skydeck
Up 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 the blues
Deep dish at Pequod's, then about 15 minutes' walk to Kingston Mines, where two stages trade blues sets until late.
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).
Kingston Mines
Running since 1968 and billed as the city's biggest, longest-running blues club, with two stages trading sets late into the night, every night of the week. There's food, so settle in.
Day three: Pilsen, The 606 and Bucktown
Start at the free National Museum of Mexican Art (closed Mondays) and the murals on 18th Street, with carnitas for lunch. Then head up to Bucktown and walk The 606 west to Margie's Candies for a sundae.
National Museum of Mexican Art
Free admission, and a permanent collection reaching back 3,600 years, with a big Day of the Dead show each fall. Closed Mondays; walk the murals along 18th Street afterward. The first Wednesday of each month it stays open until 8.
Carnitas Uruapan
Michoacán-style carnitas sold by the pound since 1975, with tortillas, salsas and chicharrón. The Pilsen counter opens early, and the best cuts are gone by mid-afternoon.
The 606 (Bloomingdale Trail)
An old elevated rail line turned 2.7-mile trail linking Bucktown, Wicker Park, Humboldt Park and Logan Square. Ramps sit at most cross streets; walk or bike it late afternoon in fall.
Margie's Candies
Family-owned since 1921, with chocolates still dipped in-house and sundaes big enough to share, hot fudge on the side. The Bucktown original keeps its old booths; a second shop is in Ravenswood.
Day three, night: Logan Square
Keep going west to Logan Square for dinner at Mi Tocaya Antojería and a martini at Best Intentions.
Mi Tocaya Antojería
Diana Dávila's Logan Square restaurant, cooking from her family's travels across Mexico: regional plates you won't find elsewhere in town. The burrito suizo is a Wednesday special. Tuesdays take half off bottles of wine.
Best Intentions
Brothers Chris and Calvin Marty's Logan Square bar, back since 2023 and a 2025 James Beard nominee: dive comfort, sharp classics (the martini runs two parts gin to one vermouth) and frozen drinks, a smashburger and duck-fat matzo ball soup, plus a patio.
A fourth day: Hyde Park
Take the Metra Electric from Millennium Station: breakfast at Valois Cafeteria, the Museum of Science and Industry, Frank Lloyd Wright's Robie House (tours Thursday to Monday) and a walk in Jackson Park.
Valois Cafeteria
A Hyde Park cafeteria since 1921 under its 'See Your Food' sign, opening at 6 a.m., and a regular stop for Barack Obama when he lived nearby. Know your order before you reach the counter: omelets in the morning, meatloaf later on.
Museum of Science and Industry
Tour the captured U-505 submarine, ride down into the replica coal mine and watch chicks hatch. Plan most of a day, and know some exhibits carry an extra ticket. Catch a film in the five-story domed theater.
Robie House
Frank Lloyd Wright's 1910 Prairie-style house on the University of Chicago campus. Tours run Thursday to Monday, 10 to 3. An outdoor audio tour comes in eight languages.
Jackson Park
Olmsted and Vaux's lakefront park, home of the 1893 World's Fair, with the Garden of the Phoenix and Yoko Ono's SKYLANDING on Wooded Island. The Museum of Science and Industry anchors its north end.
Getting around
Downtown is walkable. For the rest, a CTA 3-day pass covers every 'L' and bus ride, or tap a contactless card or phone at the turnstile. The Pink Line goes to Pilsen, the Blue Line to Bucktown and Logan Square, and the Metra Electric to Hyde Park in under 20 minutes.
In winter
The river cruises run spring to fall, and The 606 is a cold walk. In winter, swap the cruise for the free Tiffany dome at the Chicago Cultural Center, across from Millennium Park, and The 606 for Garfield Park Conservatory, a glasshouse that stays tropical all winter (free; reserve a time).
Want more?
Less time? See one day or 48 hours in Chicago. Where to stay and how to get in from the airport: first time in Chicago.
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