Great Outdoor Date Ideas for the Chicago Adventurer
Bright lights, big city, plenty of adventure. The third largest metropolitan area in the U S of A is home to a variety of beautiful natural sights just waiting to be explored by a couple of adventurers like yourselves. Here are our top adventure date ideas in Chicago to mix things up.

Rent a couple of scooters and zip through Chicago


You always imagined you'd rent a scooter when you visit Venice, Italy or something, but life's too short and Chicago is too beautiful not to. Before you're on your way, you'll get the hang of the basics thanks to scooter experts (who also happen to be very experienced and helpful). No more waiting for the "L" - race your better half down Chicago's grid streets and you'll have a blast. Obviously. Scooters are designed for blasts.

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26.2 miles of marathon fun


Runners and running couples will appreciate this one. You and your date can combine four feature tours from Chicago Running Tours & More into one fun 26.2-mile marathon or split it up into multiple sessions. Brag about it to your friends or just mellow outdoors while getting in a good workout. Warning: this activity is best for couples who are both in good shape.

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Kayaking through Chinatown

water adventures
city life

Want to brush up on your kayaking skills so you don't capsize? Want to spend time with your bae so your relationship doesn't capsize? Well, great because this four-mile kayaking adventure guides you from Chinatown to Wolf Point and back again to work on your technique and bring out your competitive side.

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Sail the waters of Lake Michigan like a pirate

water sports

You be the captain, your partner the first mate. Or vice versa. Either way, both of you should adventure out on the windy waters of Lake Michigan for an afternoon of sailing and sun. You'll each get your own single-person sailing kayak, which can be alternately powered using a MirageDrive pedaling system. Where you're going, you won't need roads.

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Tandem hang gliding for the adventurous people


No experience is necessary to board a microlight trike and learn what it's like to glide approximately 2,000 feet above the ground with your partner in flight by your side. Take in the breathless views as your breath becomes more shallow and thank/curse your gf/bf for making you go. It's time to conquer your fear of heights (and commitment). Test your ability to survive a "vacation". Coupledom is fun in Chicago, but the real test comes with a road trip close by. True adventurers are up for a bit of traveling and it's a great date to see where you're at in your relationship. Stock up on Cheetos, pop, car tunes and hit the road jack (but come back). You could make it a day trip to Milwaukee or Galena or go overnight to a Michigan winery (highly recommended).

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Skydive without jumping out of a plane(?)


This technically doesn't count as being "outdoors" but that's because it's a simulated skydiving adventure, minus the part where you jump out of a plane. The adrenaline rush is just as real, though, as you and your date float inside iFLY's 1,000 horsepower vertical wind tunnel with absolutely NOTHING tethering you to planet earth. All from the comfort of iFLY's facility.

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Parkour for the hard core... couples


Are you Chicago's next American Ninja Warrior? Well, you or your date could be after you learn the art of parkour. With an emphasis on developing strength and body fitness, this course's intensity adjusts to your skill level. If you've ever wanted to leap between buildings, now you can at least learn how to do it safely (ya crazy kids).

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Experience Chicago

chicago tour
chicago walking tour
chicago loop tour
loop tour
affordable walking tour

Mother nature is a fickle parent and she's inflicted a lot of damage upon Chicago over the years; almost as much as Chicago's inflicted damage upon itself. Does the Great Chicago Fire of 1871 ring a bell? This walking tour is the perfect way to get out of the house, enjoy the outdoors and forget that the tour is taking you to Chicago's worst disaster spots, including allegedly haunted sites and creepy alleys.

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Probably many things, but if you and your date want to play dress up and play incognito to see the sites of Chicago in a new light, this tour is for you. It gets the two of you outdoors where you'll encounter the secret details and overlooked spots of Second City from a knowledgeable tour guide. It's a great reminder of why you live in this amazing town - as if you needed one.

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