Itinerary: Three Days in Chicago

You could easily spend several days, even weeks, in Chicago and not see half of what the city has to offer. Heck, I've lived here for years and still haven't seen and done everything I'd like. You'll never "see it all", but you can see and do quite a bit in three short days. Here's my suggested plan for a long weekend, arriving on a Thursday and leaving Sunday night, with how to get from one stop to the next.

It assumes a hotel in River North or near the Magnificent Mile, which puts most of this within walking distance or a short L ride. If you're coming in the colder months, our spring long weekend version swaps in more indoor options.

Getting in and getting around

From O'Hare, the Blue Line takes about 40 minutes to the Loop and runs all night. From Midway, the Orange Line takes 20 to 25 minutes. Our airports page has the details. Buy a 3-Day CTA pass for $15 from the vending machines at either airport. It covers the $5 O'Hare fare and every train and bus in this plan, so you won't think twice about hopping on the 151 for eight blocks. On a nice day, a Divvy bike is the best way up and down the lakefront. The transportation page covers the rest.

Day 1: art, a drink up high, and jazz

Drop your bags and head for the Art Institute on Michigan Avenue at Adams. On Thursdays it stays open until 8pm, and that evening is the time I'd pick to go. The old free Thursday evenings for everyone are gone. Illinois residents still get in free on some Thursday evenings, which our free museum days page tracks. Everyone else pays full price, so give it at least three hours to make it worth it. Note that it's closed Tuesdays and Wednesdays.

Then head north up Michigan Avenue, over the river and past the stores of the Magnificent Mile, to the black X-braced tower at 875 North Michigan, which everyone still calls the Hancock. It's about a 35-minute walk, or 10 minutes on the 151 bus. The old move was a cocktail at the Signature Lounge on the 96th floor, but the Signature Room and its lounge closed in September 2023. Now the drink comes with a ticket. CloudBar sits inside the 360 CHICAGO observation deck on the 94th floor, and the Sip & View ticket, from $44, includes one drink. Get there about an hour before sunset and stay while the lights come on.

For dinner, pick your budget. If you want a splurge, book one of the Michelin-starred restaurants weeks ahead, since most sell prepaid tickets. If you'd rather not spend that, try a BYOB restaurant and bring your own bottle.

After dinner, take the Red Line from the Chicago stop (at State and Chicago) north to Lawrence, about 20 minutes, for the Green Mill at 4802 N. Broadway in Uptown. The room dates to the 1930s, and it's cash only, with no reservations. Keep your phone away and your voice down during sets, or you'll be told to. The Red Line runs 24 hours, so getting back isn't a problem. More options are on our nightlife page.

In summer, you have a second choice. The free Grant Park Music Festival plays the Pritzker Pavilion in Millennium Park on Wednesday, Friday and Saturday evenings, and Ravinia in Highland Park has ticketed lawn concerts with a Metra stop at its gate. Bring your own wine and a picnic to either.

Day 2: parks, a market and the lake

Friday or Saturday, get up early. Walk to Millennium Park before 8am, when you can get a photo of the skyline in Cloud Gate (the Bean) without a crowd in it. Walk past the Crown Fountain's two glass towers, then south through Grant Park to Buckingham Fountain, about 15 minutes on foot.

If it's a Saturday (or a Wednesday), catch the 151 bus on Michigan Avenue north to Lincoln Park for the Green City Market, at the south end of the park at 1817 N. Clark St., 7am to 1pm in the warm months. Graze your way through it instead of eating lunch. The free Lincoln Park Zoo is a short walk north and is open every day. From the zoo, walk east to North Avenue Beach, where the Park District has lifeguards from the Friday before Memorial Day through Labor Day. Bring a picnic, or rent a Divvy and ride the Lakefront Trail back south toward the skyline.

If it's Friday, swap the market for lunch at Russian Tea Time, 77 E. Adams St., across the street from the Art Institute. It's been there since 1993, and its afternoon tea runs 11am to 4:30pm every day. Then take the 151 north to the zoo and the beach in the afternoon.

For dinner, stay in River North. Quartino, 626 N. State St., does Italian small plates and pizza, and it's still an easy dinner for a group. Frontera Grill, 445 N. Clark St., is where Rick Bayless started in 1987, and it's on Michelin's Bib Gourmand list. His starred tasting room, Topolobampo, is in the same building if you want the bigger night. Both are covered in our River North guide.

Day 3: classic Chicago

If you're a baseball fan, you can't leave Chicago without a day at Wrigley Field. The Cubs play at home from spring through September, and the Red Line's Addison stop is right outside the park. Our Cubs games page covers tickets, and where to eat and drink near Wrigley covers the rest of the afternoon.

If you're more into culture, spend the morning at the Shedd Aquarium, where the Oceanarium has beluga whales, Pacific white-sided dolphins and sea otters with an underwater viewing level. Take the 146 bus down Michigan Avenue to the Museum Campus. The Field Museum and the Adler Planetarium are next door, but pick one more at most. Doing all three in a morning is too much. If you're seeing several, compare prices with a discount pass first. Our museums guide has the rest.

For lunch, eat a Chicago-style hot dog or a slice of deep dish. Pizzeria Uno, 29 E. Ohio St., says the style was born there in 1943, and Giordano's has a location in the Loop. Our pizza guide compares them.

In the afternoon, take the Chicago Architecture Center river cruise. It's 90 minutes, starts at $57, and runs from mid-March to late November from the southeast corner of the Michigan Avenue Bridge at Wacker Drive. Arrive 30 minutes early. The guides are volunteer docents who can fill you in on more Chicago history than you could ever remember. See our sightseeing tours page for other ways to see the city.

From the boat dock, you have two ways to finish. Walk east along the Riverwalk and up to Navy Pier, about 20 minutes, for a ride on the Centennial Wheel. It's 196 feet tall and replaced the old Ferris wheel in 2016. In summer, the pier's free fireworks go off at 10pm on Saturdays and 9pm on Wednesdays. Or walk about 25 minutes southwest to the Willis Tower Skydeck (the Sears Tower until 2009), where The Ledge sticks out from the 103rd floor. The nearest L stop is Quincy, and Union Station is across the river if you're leaving by train.

With a fourth day, get out of downtown. Our guide to neighborhoods you can reach by L is a good place to start.

Photo by MD1111