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

Written by
Laura Rote
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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, chicagoelectricboats.com). $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, seabreezesail.com). $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, chicagowatersportrentals.com/rentals/flyboard-rentals). $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 (timeout.com/chicago). 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, jetskischicago.com). $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 (chicagowatertaxi.com/chinatown). $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, chicago-boat-rentals.com/cruises/fireworks-cruises). 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, tallshipwindy.com). $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 (architecture.org). $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, kayakchicago.com/rentals). $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, seadogcruises.com/chicago; $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, windycitydiving.net). $95 and up.

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