The best things to do in Chicago: a local's plan for 1, 2 or 3 days

If you only have one day

Start with breakfast at Lou Mitchell's in the West Loop, a Chicago institution since 1923 that still hands out doughnut holes while you wait. Walk east to the river for the Chicago Architecture Center River Cruise — it is the single best introduction to the city, the skyline's greatest buildings explained from the water.

Spend the afternoon downtown. Millennium Park has Cloud Gate, the sculpture everyone calls the Bean, and The Art Institute of Chicago is right next door: the Impressionists and American Gothic make an easy half-day. Then walk the Chicago Riverwalk, where the patios and bars sit at water level below the bridges.

For dinner, Girl & the Goat in the West Loop is the hard-to-book one, so reserve ahead. Finish at The Green Mill in Uptown, a 1907 jazz club that was one of Al Capone's haunts and still has music most nights.

Two days: the lakefront

Day two belongs to the Museum Campus, three institutions on one lakefront peninsula. Pick two: Field Museum for Sue the T. rex, Shedd Aquarium for the belugas and the view from the Oceanarium windows, or Adler Planetarium, which has arguably the best postcard skyline view in the city out front.

In the evening, go up — Willis Tower Skydeck puts you on The Ledge, glass boxes 1,353 feet above the street — or go to The Second City in Old Town, the improv stage that launched Belushi, Murray, Fey and Colbert.

Three days: the neighborhoods

Chicago is a city of neighborhoods, and the third day is for getting out of downtown. In Pilsen, the National Museum of Mexican Art is free and one of the largest collections of its kind in the country; walk the murals along 18th Street afterwards.

Then head northwest to The 606, a 2.7-mile elevated trail on an old rail line, and stop at Margie's Candies in Bucktown, a century-old ice-cream parlor where the Beatles stopped in 1965. If the Cubs are home, Wrigley Field is the most Chicago way to spend an afternoon; if not, Lincoln Park Zoo is free and one of the last of its kind in the country.

Late at night, The Wieners Circle serves char-dogs and cheese fries with famously rowdy banter.

What to eat

• Pequod's Pizza — the caramelized-crust deep dish many locals argue is the city's best. Get the pan pizza.
• Al's Beef — the original Italian beef. Order it dipped, hot, and eat it standing up.
• Xoco — Rick Bayless's casual spot for tortas, caldos and fresh churros in River North.
• The Purple Pig — Mediterranean small plates on the Magnificent Mile.

For the newest openings, see the best new restaurants in Chicago this fall.

Where to drink

Chicago happy hours are one of the city's best deals — oysters, discounted wine and a cheap bar menu at rooms that cost a fortune at dinner. We keep a list of the best Chicago happy hours by neighborhood, with what's on right now. For a night out, start with the best cocktail bars in Chicago, grouped by neighborhood so you can walk between them.

What's on while you're here

Summer is festival season — street fests most weekends and big shows in the parks. October brings the Chicago International Film Festival and the Arts in the Dark Halloween parade; November and December bring the Magnificent Mile Lights Festival, the city's Christmas tree lighting and light shows across town. For the dates on the week you visit, see things to do in Chicago this weekend, updated every day.

Getting around

The CTA's 'L' trains go most places a visitor needs: the Blue Line runs from O'Hare to the Loop in about 45 minutes, and the Orange Line from Midway in about 25. Tap a contactless card or phone at the turnstile. Downtown is walkable, Divvy bikes are everywhere along the lakefront, and the Lakefront Trail runs 18 miles along the water.

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 mild and less crowded. Winter is cold — really cold — but the museums, the lights and the restaurants are all still open, and hotel prices drop.

Save the plan — and bring people

The Chicago Essentials pack drops all 25 of these onto your map in Whosly for free. Turn any of them into a plan, text the link, and see who's in — friends RSVP without the app.

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