Heading out to the coast, even if that coast happens to be on Lake Michigan, is about as good a cure for the Monday blues as you’re ever gonna find.
Most folks figure you gotta head way down south to key out, wiggle your toes in the sand, and sip on something cold. But if you blow out a flip-flop in the Windy City, don’t panic. Right at the foot of Chicago’s high-rises sits Oak Street Beach, a sweet little slice of freshwater paradise on America’s "Third Coast."
No saltwater sting, no sharks—just warm sand, a cool breeze off the lake, and those towering steel palm trees they call skyscrapers.
Wastin' Time on the Sands
Whether your idea of paradise is working on your tan or kickin' up some sand on the court, Oak Street is built for easy livin':
Cast Off on Two Wheels: Grab a cruiser and roll down the Lakefront Trail. Just keep it low and slow, there are plenty of fellow wanderers out taking in the view.
Jump on In: When the late-summer weather gets warm, the water temperature hits a cozy 70°F. Lifeguards keep watch from 11:00 AM to 7:00 PM, so you can drift without a care. Leave the paddleboards at home, though.
Kick Back in Style: Shade is hard to come by, but the local Beach Chairs Concierge will set you up with a chair and an umbrella starting at $15. No reservations needed, just show up early, kick off your shoes, and let the clock run out.
Cheeseburgers & Cold Drinks on the Water
You can’t have a proper beach day without a cold drink and a bite to eat.
Whispers at Oak Street Beach: Right on the sand, this open-air spot is the only place in town where you can eat with the freshwater washin' past your toes. Grab a Polish dog and a cold beverage at the concession bar, or sit down for a burger and seafood. The service moves at its own lazy pace, but who's rushin'? The view alone is worth the price of admission.
Drifting Down the Trail: If you feel like wanderin', take a stroll north to Shore Club for a fish bowl and some lobster tacos, or head down to Navy Pier to grab a classic Chicago dog.
Keep the Island Vibes Rollin' Around Town
Once you've rinsed the lake sand off your feet, Chicago keeps the beach-town energy alive all across the city:
Castaways at North Avenue Beach: Just a short cruise up the Lakefront Trail, you'll spot a full-sized boathouse shaped like a giant ocean liner stranded right on the sand. The rooftop deck serves up ice-cold drinks, burgers, and live music with unbeatable lake views.
Tiki Boats on the Chicago River: Hop aboard a floating tiki bar with Island Party Boat or one of the local river charters. You can sip a rum cocktail under a thatched umbrella while drifting past famous skyscrapers.
Margaritaville at Navy Pier: Head down to the pier for a little familiar magic. Soak up the sights of Lake Michigan from their weather-protected outdoor deck, grab a frozen concoction, and order up a proper "Cheeseburger in Paradise."
Ready to Change Your Latitude?
If you're ready to trade the rat race for a freshwater breeze, contact Come Monday Travel today. We'll handle all the details, booking, and planning for your ultimate Chicago beach getaway—so all you have to do is pack your favorite Hawaiian shirt and enjoy the ride.
