Charter a sailboat from Belmont Harbor
Outfitter Chicago Sailing
Details Choose from a fleet of 23 sailboats that can accommodate up to 12 passengers.
What you get Wind in your hair, an iconic skyline, and a professional captain to keep you in line (and onboard)
Wallet damage $525 to $735 for a three-hour daytime sail depending on boat size; $90 a person or $150 a couple for a fireworks sail on Wednesdays or Saturdays
Tip Don’t be that guy with black sneakers and a bottle of red. White soles and white wine only. chicagosailing.com
Standup paddleboard at Kathy Osterman (Hollywood) Beach
Outfitter Chicago Paddle Co.
Details: Rentals (including board, paddle, leash, and life preserver) are first come, first served. If you’re more of a pack person, you can reserve a spot in a group trip, like Rise & Grind, the popular sunrise paddle followed by coffee on the beach.
What you get: A serene trip and a killer tan
Wallet damage $30 an hour
Tip Roll with it. Literally. The less you fight for control of a wave, the less likely you are to demonstrate your best belly flop. chicagopaddlecompany.com
Kayak or canoe the Skokie Lagoons
Outfitter: Chicago River Canoe and Kayak
Details: The Winnetka boat launch is on the south side of Tower Road, just west of Forestway Drive.
What you get: A self-guided escape (boat, paddle, and life vest included) from the city, with wetland wildlife galore
Wallet damage: $15 an hour for a single kayak; $20 an hour for a canoe or tandem kayak
Tip: Keep an eye out for a pair of bald eagles nesting across the river from the launch site. chicagoriverpaddle.com
Reel in a big one on Lake Michigan
Outfitter: Endorfins Charter
Details: The 53-foot Diazepam holds six passengers and departs from Montrose Harbor daily.
What you get: Captain John Oberman’s boat is bigger, faster, and decked out with more swanky marine electronics than other local charters. Or so he says.
Wallet damage: $1,000 for six hours. Those state-of-the-art fish-finding radars don’t come cheap.
Tip: Captain John will tell you to take motion sickness prevention pills the night before the trip. Do everyone a favor and listen to him. endorfinscharter.com
Scuba dive at a shipwreck
Outfitter: Windy City Diving
Details: A 34-foot catamaran for up to six certified divers leaves from Burnham Harbor for half-day weekend trips 10 miles offshore.
What you get: Titanic vibes, thanks to more than a dozen wrecks, including the Buccaneer, a 1925 merchant ship 72 feet down
Wallet damage: $130 a person for a two-tank dive
Tip: Don’t go expecting to see pretty fish. They aren’t the main attraction here. windycitydiving.net
Jet Ski at 31st Street Harbor
Outfitter: Chicago Water Sport Rentals
Details: Before jetting off, you’ll receive an orientation, a life vest, and—by request only—a wetsuit.
What you get: A view you won’t forget—perfect for a #humblebrag selfie
Wallet damage: $99 to $125 an hour
Tip Look for the LED billboard truck parked on a barge floating in the harbor that broadcasts Cubs or Sox games. chicagowatersportrentals.com
Party on a yacht out of Belmont Harbor
Outfitter: Chicago Party Yacht
Details: The 60-foot Martini (up to 35 guests) runs daily private trips.
What you get: Basically anything you want. This is a choose-your-own-adventure cruise helmed by a licensed captain.
Wallet damage: BYO and a three-hour minimum for $2,600. Catering packages and holidays are extra.
Tip: You can live out your spring break fantasies at the booze-soaked spread of docked boats (i.e., the Playpen), where you get a front-row seat to the best parade of butts in town. chicagopartyyacht.com