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Every place in First time in Chicago: what to do, eat and where to stay, pinned where it actually is. Tap a marker to see which one it is.
The 10 things to see
If you only see ten things in Chicago, see these. Book the cruise, the museums and the Skydeck 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.
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.
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.
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.
Navy Pier
Ride the Centennial Wheel, board a lake or architecture cruise from the docks and stay for summer fireworks. It's tourist-heavy; walk out to the end of the pier for the best views. Check the calendar for free fireworks through the year.
Lincoln Park Zoo
Free, open all 365 days and running since 1868. Gates open at 8 a.m. and the animal houses at 10; families head for the Farm-in-the-Zoo. Parking costs, so bike or bus in. In winter, ZooLights dates sell out.
Wrigley Field
The Cubs' home since 1914, with ivy on the outfield walls, a center-field scoreboard still changed by hand, and rooftop seats across Waveland and Sheffield. No game on? Take a guided ballpark tour, then a beer in Wrigleyville.
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.
What to eat
Deep dish, an Italian beef dipped with hot giardiniera, a char-grilled hot dog with no ketchup, breakfast at the old start of Route 66, and the dinner everyone books.
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).
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.
The Wieners Circle
Char-grilled hot dogs and cheese fries in Lincoln Park, famous for counter staff who trade insults with the bar crowd. After midnight is the full show; daytime is tamer.
Lou Mitchell's
A diner on Jackson since 1923, at the old start of Route 66, handing doughnut holes and Milk Duds to the line. Breakfast and lunch Wednesday to Sunday until 2; closed Monday and Tuesday.
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.
Where to drink
A rooftop over Millennium Park, a tiki bar down an alley, a 1907 jazz lounge and Buddy Guy's own blues club.
Cindy's
The glass-topped rooftop of the Chicago Athletic Association hotel, looking over Millennium Park to the lake; in winter the terrace keeps fires going.
Three Dots and a Dash
An underground tiki bar reached down an alley off Hubbard, pouring rum drinks in elaborate mugs alongside pupu snacks. Bring a crowd for the Treasure Chest, a giant shared rum punch. The Bamboo Room inside is a separate tasting bar.
The Green Mill
Uptown's 1907 jazz lounge, a Capone-era hangout with music every night. Sunday's Uptown Poetry Slam started here, and late jam sessions run past 1 a.m. on Fridays and Saturdays.
Buddy Guy's Legends
Buddy Guy's own club in the South Loop since 1989: blues nightly, Cajun food, and his January residency. Buy tickets ahead for big nights.
Where to stay in Chicago
River North and the Magnificent Mile: the most hotels, restaurants and bars, a short walk from the river and Michigan Avenue. The easiest pick for a first trip.
The Loop: next to Millennium Park, the Art Institute and the cruise docks, and a walk from the Museum Campus. Quieter at night.
Streeterville: by Navy Pier and the lake, a few blocks east of Michigan Avenue.
The West Loop: the city's restaurant row, a short ride west of downtown.
Lincoln Park and Old Town: leafier and quieter, near the zoo, the lakefront and Second City, about 15 minutes north of downtown.
Getting in from the airport
From O'Hare, the Blue Line runs to the Loop in about 45 minutes, day and night. From Midway, the Orange Line takes about 25. Tap a contactless card or phone at the turnstile; there's no ticket to buy.
When to go
June through September is the city at its best: the lakefront, the patios and a festival nearly every weekend. September and October are milder and less crowded. Winter is cold, but the museums, the Christmas lights and the restaurants are all still going, and hotels cost less. More in Chicago in winter.
A few things to know
- Book the river cruise and the Skydeck ahead in summer; both sell out on weekends.
- Lou Mitchell's is closed Monday and Tuesday.
- "Cooler by the lake" is real: bring a layer for the lakefront, even in July.
- The 'L' beats a cab downtown at rush hour.
Want more?
Ready to plan the days? Try one day, 48 hours or 3 days in Chicago. Bringing kids? Chicago with kids.
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