Buy Now, Book Later
Free Returns & Exchanges
No Expiration Dates
Instant E-Vouchers

Unique Gifts for Him in Chicago

Looking for a great gift in Chicago for a special man in your life? Look no more - our Chicago experience gifts for him are the perfect, unforgettable, gift for any occasion to let him know how special he is.
97 Results
  • Location:
  • Experience Type:
  • Price:

All Experiences on this page have been loaded.

How it Works

Instant gifts. Lasting memories.
Your step-by-step guide to giving the ultimate gift.


Choose from 2,000+ experiences nationwide

Pick the perfect experience gift or buy an egift card and let your recipient choose their own adventure.


E-Voucher Delivered Instantly

After checking out, you can easily print or email your Experience Voucher. While delivery is instant, the memories will last a lifetime.


Easy to redeem or exchange

Your recipient can book their experience at their convenience either online or by calling us. And if they'd prefer to do another one, they can easily exchange it.


Create unforgettable memories

Our trusted vendors and passionate team will ensure that your recipient will be treated to the experience of a lifetime—making memories that will last for years to come.

Hassle-free Gifting

Our experienced team takes the risk out of gift-giving with handpicked experiences that are guaranteed to delight. We only work with top-rated experience providers and offer flexible policies to make giving a great gift a no-brainer—no matter who you're shopping for.

Learn More

Created with Sketch. Easy Returns & Exchanges

We offer 30-day returns or your recipient can easily exchange their gift for anything else in our marketplace, anytime—free of charge.

Created with Sketch. No Expiration Date

Our vouchers never expire, so your recipient can redeem them at their convenience.

Created with Sketch. Price guarantee

No markups, no added fees. You'll pay the same price as buying directly from our experience providers, but with the flexibility of easy returns and exchanges.

  • As one of America's favorite big cities, Chicago comes with plenty of experience gifts for men that are sure to bring memories!

    From bold bucket list wishes to finding the coolest things to do in Chicago, Cloud 9 Living has the best way to celebrate a special occasion with a special guy in unbelievable (and unforgettable) style.

    The Windy City comes with loads of ways to play in the air up there, if air-venturous gifts for guys in Chicago are what a lucky lad you know might be after. Tempt him to spread wings of his own in unfathomable ways that are sure to take his breath away — literally! Give him a glider lesson or hang gliding excursion that has him telling tall tales of exploring new heights for years to come. Or send him skydiving either indoors or straight out of a plane! Does he dream of being in the pilot's seat? Make it happen with one of the best Chicago gifts for him to go sky-high: the chance to fly an airplane for himself, under the superb guidance of an FAA certified flight instructor. And helicopter lessons are available, too — which certainly deserves a woohoo!  Speaking of helicopters, don't miss out on thrilling Chicago experiences men really like, such as city tours by air! He can sit in the comfort of a historic Hughes OH-6A, admiring impeccable views of either downtown Chicago or the northwest ‘burbs. Or drift merrily over rolling Illinois landscapes aboard one of aviation's oldest and most impressive modes of transportation: a hot air balloon ride.

    While there truly are lots of incredible options to choose from, don't be too quick to think that flying is the only way for a fella to enjoy the rush of a grand adventure in Chicago! With hot race tracks like Chicagoland Speedway and Autobahn Country Club ever so close to the Windy City, you're sure to find gifts he'll love — especially if he's a "car guy!" From rugged to sleek, but both kinds rarin' to go, you can get a favorite fella grinning from ear to ear when he unwraps a race car driving experience from Cloud 9 Living. With options like ride along and drives, as well as features like driving gear and professional instruction included, these gifts for him near Chicago that come with four wheels are tough to beat! Get him gunnin' for the finish line, making miles of memories with events like racing at the Autobahn Country Club in a Lamborghini, Ferrari, Audi or Porsche. Or rev a horsepower-hungry engine on the Chicagoland Speedway with rides and drives in stock and Indy cars — just like the pros do on Sundays!

    Want more ways for him to satisfy a need for speed? Get him headed to the H2O with gifts for him in Chicago that make a seriously fun splash! A high-speed boat ride over the waves of Lake Michigan will have him hollering for joy in no time! This wild excursion on the water departs from Navy Pier, where passengers board the Seadog Extreme  to brave spins, turns and impressive 45 MPH speeds on open water. And for a slightly calmer outing, but with smiles and wind in the hair all the same, check out sailing charters on Lake Michigan!

    With great gifts for men in Chicago like these, laced with just enough adrenaline, it's never been easier to wrap up a solid rush and a lifetime of memories!