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12 weird ways to be on the water in Chicago this summer

Written by
Laura Rote

We live for summer in Chicago—lounging on beaches and sipping on the best margaritas. But sometimes you just want to try something new, maybe even make a little splash. This season, we’ve come up with a dozen ways you can experience the city’s waterways a bit differently, from exploring shipwrecks (say what?!) to walking on water.

1. Show the lake who’s boss, and rent a pontoon boat. If you can drive a car, you can captain one of these guys. Chicago Electric Boats, 300 N State St (312-644-6411, $150/hr and up.

2. Prep for next year’s America’s Cup—hey, you’re a fast learner—with sailing classes. Beginners will master the keelboat first. Seabreeze Sail, Columbia Yacht Club, 111 N Lake Shore Dr (312-878-7587, $450.

3. Flyboard. What? Flyboard! It’s kind of like a snowboard, but you’re soaring and bouncing across the water. Chicago Water Sport Rentals, 31st Street Harbor, 3155 S Lake Shore Drive (312-924-7994, $149/20 mins.

4. Put on your swimsuit and floppy hat for Time Out Chicago’s Yacht Party Series. Anita Dee Yacht Charters, 200 N Breakwater Access ( June 16, July 21, Aug 18; $30/each, $70/series.

5. Rent a jet ski and explore North Avenue Beach at a different speed. 1600 N Lake Shore Drive (312-600-8679, $85 and up.

6. Take the water taxi to Chinatown for a cheap way to explore the Chicago River with the wind in your hair. Ogilvie/Union stop, NW Water St between Washington and Madison Sts ( $8/all-day pass.

7. View the magical city skyline at night—from a boat. Get the crew together to rent a vessel after dark. You can also experience the Navy Pier fireworks from a 40-foot powerboat. Chicago Boat Rentals, 111 N Lake Shore Drive (773-236-7245, Mon at 6:30pm; $599 for up to 11 people.

8. Take the whole family for a pirate-themed tour of Lake Michigan on the Tall Ship Windy from Navy Pier. Ahoy, matey! 600 E Grand Ave (312-451-2700, $10 and up.

9. Understand how the city’s skyline has changed over the years when the experts at Chicago Architecture Foundation explain from aboard a boat. Chicago Architecture Foundation River Cruise, southeast corner of the Michigan Avenue Bridge at Wacker Dr ( $44.

10. Walk on water when you rent a stand-up paddleboard at Montrose Beach. Kayak Chicago, 4400 N Lake Shore Dr (312-852-9258, $20/hour, $80/day.

11. Speed across Lake Michigan before entering the Chicago River for a guided tour of the city's architectural attractions, including the Lyric Opera and Willis Tower. The 75-minute tour departs from Navy Pier all summer. 888-636-7737,; $33.95.

12 Take the plunge. If you’re certified, you can explore shipwrecks in Lake Michigan or dive in with a recurring scuba trip from Windy City Diving. Burnham Harbor, Dock EC Slip 21, 1350 S Linn White Dr (630-209-2445, $95 and up.

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