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Chicago Travel Guide

Here’s How to Best Experience Chicago’s Lakefront

Despite its four-season climate, Chicago’s waterfront is enjoyable all year round.

Hugging the shores of one of the five Great Lakes (hello, Lake Michigan!) and boasting some of the world’s tallest skyscrapers has led to one of Chicago’s most famed assets: its lakefront view. There are 26 blissful miles of scenic lakefront as well as the 18-mile Lakefront Trail. Whether you’re at sea level or several stories up, the view is amazing: On a clear day you can see up to four states (Illinois, Indiana, Michigan and Wisconsin) from a skyscraper (yes, really!).

A visit to the Windy City is not complete unless you do one of the following: drink or dine at a rooftop bar, lounge, or restaurant; relax or swim at the beach; or bicycle, run or walk along a lakefront path.

Here’s how to view and experience Chicago’s lakefront—whether you have a day or a week. Fortunately, these can be done year-round, thanks to, for example, glass-enclosed indoor spaces high in the sky or the knowledge that dressing in layers means you don’t have to wait for perfect weather to take a walk.

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Skyscraper Tours

There are two major high-rises in downtown Chicago open to the public that offer experiences. Note that these are not for the faint of heart, or for those who are skittish about heights. These are among the highest towers in the world, after all.

The former Sears Tower—referred to as Willis Tower since 2009—was built in 1973 and deemed the world’s tallest building until 1998. Today it’s the 25th tallest building worldwide and the fourth tallest in the Western Hemisphere. However, it remains Chicago’s tallest building. Spanning 110 stories, it was designed by Bruce Graham and Fazlur Rahman Khan.

A glass-enclosed balcony juts out four feet from Willis Tower on the 103rd floor, giving a hint of what it might be like to soar like a bird above the Chicago skyline. The adjacent Skydeck is another way to take in the view—and a less scary one, at that. On the same floor is an interactive experience that talks about the building’s history.

Sharing the same design duo, 875 North Michigan Avenue (called the John Hancock Center until 2018) is a 100-story building. At the time of its 1968 construction, it was the second-tallest building in the world. While you can no longer dine at the building’s 95th-floor restaurant, which used to be a way to side-step the building’s tourist attractions and still get a killer view, there are two ways to soak up the view. At the 360 Chicago observation deck on the 94th floor, which is also home to TILT—a glass-enclosed motion ride that lasts between two and three minutes and literally tilts forward.

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Chicago has nearly two dozen public beaches, from Juneway Beach on the North Side to Calumet Beach on the South Side, spanning 26 miles. These are all free to visit although it’s important to know they are only staffed by lifeguards between Memorial Day and Labor Day, and swimming outside of these months is strongly discouraged. If water conditions are rough, a red flag will be placed on the beach, urging people to stay out of the lake. Year-round, the water temperature can be quite cool. Eight of the beaches are wheelchair-accessible. Although they’re open year-round, between November and April you may have to swap out a T-shirt and shorts for a down jacket and layers of clothing.

A few beaches have restaurants or bars, including Oak Street Beach, with Whispers at Oak Street Beach serving seafood-inspired eats like ahi tuna nachos and shrimp tacos; and Dock at Montrose Beach, where off-beat apps like pierogis and cheese curds are available seasonally at Montrose Beach, as well as live music some nights. Both restaurants serve alcoholic drinks, too.

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Rooftop Bars, Lounges, and Restaurants

Within the last decade, Chicago has nearly exploded with new rooftop spots to soak up the view. Many proprietors understand this is a four-season city. This translates to quite a few indoor-outdoor spaces where you can bask in the sun during summer or cozy up by the indoor fire in winter. Many also have heat lamps or misters outside to make things more comfortable.

Sable at Navy Pier Chicago, Curio Collection by Hilton opened in 2021 and its rooftop bar (Offshore Rooftop) literally juts out into the water on the easternmost point of Navy Pier, providing unobstructed views. Guinness World Records dubbed this the world’s largest rooftop. Further North, in Lincoln Park, The J. Parker (at Hotel Lincoln, across from Lincoln Park, which hugs Lake Michigan) serves an all-day menu as well as weekend brunch. If you’re downtown, Cindy’s at Chicago Athletic Association boasts a glass-enclosed arched roof and open-air terrace on its 13th floor, across from Millennium Park. It’s open for lunch and dinner daily, along with weekend brunch, and late-night drinks and snacks. All three of these bars operate year-round.

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Lakefront Hikes and Bicycle Rides

Chicagoans don’t shy away from the outdoors. Year-round, you’ll see people out running and walking. Bicycling heats up during spring, summer and fall, unless one has invested in fat tires and the roads aren’t icy or slick on a particular winter day. Some great ways to access the lakefront are the Lakefront Trail (from Ardmore in the North to 71st Street on the South Side) and the 313-acre Grant Park (just east of the Loop, it includes Buckingham Fountain, Millennium Park and the Art Institute of Chicago and is where former President Obama gave his acceptance speech in 2008). Divvy Bikes is a city-wide, shared-bicycle program that rents out bicycles, e-bikes and scooters. Once you’ve downloaded the app onto your smartphone you can access one through docking stations located around Chicago.