We’ve said it before and we’ll say it again, summer is Chicago’s best season and Lake Michigan just might be the season’s best attraction. This week’s Bucket List brings you seven ways to enjoy the lake. Whether you set out for one of the city’s 24 beaches, hit the 18-mile Lakefront Trail or head out on the 148-foot topsail schooner named Windy, there will be no shortage of ways to add sun, sand and freshwater to your summer forecast.
Paste Travel’s Bucket List columnist Lauren Kilberg is a Chicago-based freelance writer. Her travels have found her camping near the Pakistani border of India and conquering volcanoes in the Philippines.
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Chicago is home to more than 25 miles of lakefront with 24 different beaches scattered along Lake Michigan. One of the most popular is North Avenue Beach in Lincoln Park, It's base camp for the city's annual Air and Water Show and is home to a bar and grill for when a day in the sun leaves you needing to refuel. Oak Street Beach in Chicago's Gold Coast/Streeterville neighborhood is another favorite, especially among those who enjoy playing or watching volleyball. Kathy Osterman Beach, also called Hollywood Beach, in Edgewater is a favorite among the city's LGBTQ community. Pet owners flock to Montrose Beach, which is home to the city's only dog-friendly section of sand. It's also one of Chicago's largest beaches and includes a popular full-service eatery.
Photo by arch2452, CC BY-NC-ND 2.0
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The 18-mile long Lakefront Trail (LFT) stretches north to south from Ardmore Street (5800 N. Sheridan Road) to 71st Street (7100 S. South Shore Drive) along Lake Michigan. In addition to gorgeous lake and skyline views, the trail takes you by beaches, harbors, gardens, recreation areas, playgrounds, nature sanctuaries, as well as several of the city's best parks and a variety of neighborhoods from Hyde Park to Edgewater. Chicagoans use the trail for leisure, exercise and as a means of commuting. If you're setting out to tackle LFT in its entirety, there are washrooms, snack shops and drinking fountains all along the way.
Photo by Susan Smith, CC BY-NC-ND 2.0
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Windy isn't just a word used to describe Chicago's weather or politics, it's also the name of the 148-foot topsail schooner that sets sail on Lake Michigan. This tall ship is an homage to the trade shipping days of the Great Lakes. There are a handful of tours offered, like pirate-themed and firework cruises. Windy departs from Navy Pier and trips last between 60 and 75 minutes.
Photo by Bart Heird, CC BY-NC-ND 2.0
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Chicago offers plenty of options for those looking to dine with lake views, but a few options take it even further by setting up shop right on the lakefront. This beach eateries aren't your average concessions stand either. They offer chef-driven menus, fancy cocktails, as well as live concerts and more. The Dock at Montrose Beach offers a full menu of American fare, cocktails and a roster of nighttime concerts and luaus. Caffe Oliva, run by the same team at The Dock, is located in Olive Park at Ohio Street Beach and serves Mediterranean fare and cocktails. It also hosts a lobster night and has cabanas for rent. Oak Street Beach Food and Drink (pictured) serves up surf and Chicago-inspired food and drinks like beach tacos, hotdogs, margaritas and beach bum punch right at water's edge in Chicago's Gold Coast/Streeterville neighborhood. Waterfront Café offers lakeside dining without the sand. The cafe is located in the coach house of a historic Sheridan Road mansion in Berger Park on Chicago's North Side. One of the city's most iconic and popular lakefront dining options is Castaways Bar and Grill. You can't miss it, it's located at the equally popular North Avenue Beach in an ocean liner-inspired building. The ground level houses an ice cream cafe and walk-up snack shop, while the open-air roof deck serves a full food and drink menu.
Photo by John W. Iwanski, CC BY-NC 2.0
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Water sports are one of the best ways to enjoy Lake Michigan up close and personal, especially for those who prefer to keep active. Kayak Chicago, an outfitter and tour operated, offers kayak and paddle board lessons, as well as guided tours out on the lake. Options include a skyline paddle perfect if you're out for city views, sunset on the lake for those seeking something scenic, paddle boarding along the shoreline, a fireworks float and more.
Photo by niXerKG, CC BY-NC 2.0
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Each summer, Chicago hosts the country's largest free air and water exhibition. 2017 marks the 59th year for the Air and Water Show. For two days in August, Lake Michigan and the Chicago skyline play backdrop to some jaw-dropping thrills. While the show can be seen along the Chicago lakefront between Fullteron and Oak Street, North Avenue Beach is the epicenter of activity. The show features the U.S. Navy Blue Angels every other year, along with the U.S. Air Force Thunderbirds, U.S. Army Golden Knights parachute team, U.S. Navy Leap Frogs and many more.
Photo by Jonathan Parker, CC BY-NC-ND 2.0
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If sunbathing is just too passive a way to enjoy Chicago's lake, then Seadog is for you. This popular adrenalin-packed speedboat whisks you by some of Chicago's best lakeside sites. The 30-minute lakefront tour includes a high-speed trip along Chicago's shoreline. It departs from Navy Pier and brings you by the Magnificent Mile, Museum Campus and plenty of landmarks in between. As an added bonus, Seadog tours are BYOB--as in bring your own booze, not boat.
Photo by Michel Curi, CC BY 2.0