As the third-largest city in the US, Chicago quite literally has something for everyone—from world-class restaurants, museums, theater, and comedy to thousands of acres of parks, biking trails, and beaches.
Summer in the city is perfection, as three million residents collectively shed their heavy coats and embrace the sun with long walks along Lake Michigan and outdoor dining that pops up everywhere—seemingly overnight—as soon as the weather warms up. (For what it’s worth, there’s plenty to do in winter too, including museums, ice skating, cozy restaurants, and jazz clubs.)
Chicago manages to be a big city with an endearing Midwestern vibe, so whether you’re visiting with family, on a romantic getaway, or with a group of friends, there really is an activity for every kind of trip.
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Day 1
The best of Chicago
Start your day with coffee in the Loop, the heart of downtown Chicago. Cafecito serves excellent Cuban coffee and breakfast sandwiches, or small The Goddess & Grocer chain is a safe bet for coffee and breakfast to go.
Take a mid-morning Chicago Architecture Center River cruise, a picturesque way to see the city and get acquainted with its sights and history. The boat tour ends at Michigan Avenue, where you’re steps away from the Art Institute of Chicago and Grant Park, a giant park in the center of the city with a theater and fountains, sometimes called the “front yard of Chicago.”
Spend a few hours at the art museum. Then, grab a Chicago-style hot dog at Millennium Park, a smaller park on the north side of Grant Park, and visit Cloud Gate (popularly known as The Bean), an art sculpture that reflects the city and is popular for selfies. If you’re up for it, head across the street to the Chicago Cultural Center to see the stunning stained-glass Tiffany dome––the largest in the world.
After all that sightseeing, stop for a drink at Cindy’s Rooftop, the rooftop bar in the Chicago Athletic Association Hotel with views across Lake Michigan. Visiting when it’s cooler? The lobby bar is also nice and cozy in the winter when you can settle in by a fireplace and warm up with a mulled wine or coffee.
From here, you have plenty of options for dinner. Restaurants in the Loop or River North are an easy walk, or you could take an Uber or public transit to the many restaurants and bars in the West Loop.
In River North, visit the city’s oldest steakhouse, Gene & Georgetti, for a traditional Chicago experience or Avli for modern Greek cuisine and people-watching. In West Loop, Top Chef–winner Joe Flamm dishes up excellent Italian-Croatian cuisine at Rose Mary, or you can grab one of the country’s most famous burgers at Au Cheval.
Post-dinner, see a Broadway show, listen to live music at one of the city’s many jazz clubs, such as Andy’s Jazz Club, Untitled, or the Green Mill, or go dancing downtown or in the Northalsted neighborhood (also known as Boystown).
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Day 2
Gold Coast, Lincoln Park, and the Lake
On day two, you’ll explore Chicago’s North Side, starting in the Gold Coast neighborhood, known for gorgeous historic mansions and high-end shopping. Make your way from the Loop to the Gold Coast via Michigan Avenue, window-shopping along the way.
Grab coffee and a pastry at the Restoration Hardware cafe (don’t miss the giant chandelier), and spend some time strolling the neighborhood. Dearborn and State are especially pretty streets.
Rent a Divvy bike (or take public transit), and ride north along the Lakefront Trail to Lincoln Park. If it’s hot outside, you might want to stop for a bit at Oak Street Beach or North Avenue Beach. Once in Lincoln Park, you can visit the free Lincoln Park Zoo and Lincoln Park Conservatory.
Then, grab lunch at one of the dozens of Lincoln Park restaurants, ranging from pizza to fine dining. Gorge on deep-dish pizza at Pequod's, Middle Eastern food at Galit (which also has a fantastic wine list), or go all out with a tasting menu at Esmé or Alinea, widely regarded as one of the best restaurants in the world.
From here, you have options. Catch a Cubs game at Wrigley Field, a comedy show at The Second City, or continue north to the Andersonville neighborhood, where you can support local shops and restaurants along Clark Street.
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Day 3
Museum Campus and Navy Pier
After your day spent exploring several of Chicago’s neighborhoods and the lakeshore, day three is all about museums.
Museum Campus is a 57-acre park along Lake Michigan home to some of the city’s biggest attractions. Don’t miss the Field Museum, one of the world’s largest natural history museums; Shedd Aquarium, a huge indoor aquarium and research center with daily shows; and the Adler Planetarium, the first planetarium in the US and now a museum to all things space (don’t miss the immersive movies in the Sky Theater).
All three are large and take at least two hours to walk through, so pick one or two and stop for a break in between at the museum cafes or food stands on the lawn outside.
After that, head over to Navy Pier, a 3,300-foot-long lakefront attraction featuring games, rides, shopping, and dining. To get there, you can walk or bike along the lake, take a bus, or even a water taxi in the summer. Once at the pier, you can ride the Centennial Wheel and eat Chicago-style pizza. Navy Pier is ideal for people traveling with kids, as it also has a children’s museum and front-row seats to watch the boats pass by.
If Navy Pier isn’t your thing, head to Wicker Park instead. Here you can join Chicagoans on the always-busy patio at Big Star, drink some of the world’s best cocktails at The Violet Hour, shop local bookstores and boutiques, and take in the historic architecture.
How to spend several more days in the city, when to visit, where to stay, and more: Find it all online.
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With local expert:
Rebecca Holland
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Rebecca Holland is a freelance travel and food writer who has lived around the Middle East for the past decade, in Jordan, Iraq, and now Dubai. She wants everyone to visit this part of the world for the history, hospitality, and especially the food! She writes for AFAR, Food & Wine, The Guardian, and more, and is the founder of Curiosity Magazine.
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