30 Chic & Charming Chicago Experience Gifts

Whether it’s deep dish pizza, a Prohibition city tour or some spectacular jazz music, the Windy City has so much great stuff to do. It’s hard for a person to decide how to spend his time.

If your friend’s a first-time visitor to the city, it can be especially difficult to choose between one exciting adventure and another. Even long-time residents of the city are constantly discovering new and exciting things to do there. Here are 30 of the best Chicago experiences.

Chicago Experience Gift Ideas

exotic dinner for the connoisseur

For Your Foodie Friend: Exotic Dinner for the Connoisseur, Chicago, IL

If you have a friend who absolutely loves exotic, unique food, this is the gift for her. You can choose to host this dinner yourself in your own home and invite your friend over, or you can buy the experience for her and allow her to host the dinner in her home.

Either way, executive chef Christopher Tong will come into the chosen home and fix a delicious, delectable meal featuring imported caviar, exotic wild game, seasonal seafood and other specialty items right there in the kitchen.

His staff will set the table and serve your friend and all her guests for a night that none of you will soon forget.

old town comedy and craft beer tour

A Gallon of Laughs: Old Town Comedy & Craft Beer Tour, Chicago, IL

For the friend who loves beer and laughter, you can’t beat the Old Town Comedy and Craft Beer Tour. Your friend will visit several different improv comedy clubs, including the world-famous Second City and Zanies Comedy Club.

At each stop, he’ll get to taste the house brews, drinking in the same spots as many of the cast members from SNL, Wayne’s World and more. He’ll experience Old Town like it was meant to be experienced, and he’ll get a great history lesson on the traditions and cultures of the city, including learning about what went down during Prohibition.

Plus, he won’t be able to get enough of all the delicious beer.

NASCAR ride along

For the Friend with a Need for Speed: NASCAR Ride Along, Joliet, IL

Send your friend off to the Chicagoland Speedway, established in 2001 as one of the first motor sports facilities in all of Chicago. There he’ll get to ride shotgun with an actual NASCAR driver in a real NASCAR stock car cruising around the track at about 155 miles per hour.

It’s truly the ride of a lifetime, and if your friend is an adrenaline junkie, he’ll want to go again as soon as he’s done.

ZIP LINE adventure course

For the Kid at Heart: Ultimate Zip Line Adventure Course, Western Springs, IL

This adventure is almost as gorgeous as it is exciting. Get your friend out of the hustle and bustle of the Chicago city, and send her into Bemis Woods, where she’ll get to experience what USA Today called one of the “10 Best Zip Line Courses in the US!” She’ll get to fly through the trees like Tarzan for the next two to three hours.

There are 39 different crossings and five zip lines, all guaranteed to get your friend’s blood pumping. She’ll also love getting to see Bemis Woods from an entirely new angle – the tops of the tree canopy.

kayak tour for Chicago

An Evening on the Water: Sunset Kayak Tour, Chicago, IL

This is another exciting, beautiful adventure for any friend who loves the great outdoors. Instead of the woods, though, this experience will find your friend kayaking down the Chicago River as the sun sets on the horizon behind the gorgeous Chicago skyline.

In total, it’s a three-hour tour down the river, and he’ll see some of the most beautiful and inspiring architectural landmarks in Chicago. There’s a lesson before the kayaking starts, as well, so even if your friend has never sat in a kayak in his life, he should do just fine on this leisurely row down the river.

Fireworks bike tour

Light up the Night: Fireworks Bike Tour, Chicago, IL

If your loved one enjoys biking, this eight-mile tour is the perfect gift for her. She’ll start her ride at Ohio Street Beach with a gorgeous view of Olive Park and Navy Pier. Her guide will tell her a little about the history of the sights, and she’ll get to see the giant Ferris wheel lit up in all its glory.

There she’ll also get to sit back and enjoy the Navy Pier fireworks show. Next up, she’ll bike to Oak Street Beach and then alongside the gorgeous Chicago River. The tour continues through other famous Chicago landmarks, such as Millennium Park, Buckingham Fountain, Soldier Field and more.

sunrise hot air balloon ride

Send Them Drifting through the Clouds: Sunset Hot Air Balloon Ride, Hampshire, IL

This one takes place a little outside of Chicago actually. Your friend will lift off from a city called Hampshire, which is only about an hour and ten minutes away from Chicago proper. If she has the time and inclination to make the drive, the experience will be entirely worth it as she floats through the Illinois countryside, enjoying the scenic flyover in a hot air balloon.

She’ll be able to experience the world’s oldest form of flying, and she can even help with setup if she chooses. She’ll fly for about 45 minutes before landing and joining in a celebratory champagne toast.

private art lessons

For the Budding Artist: Private Art Lessons, Skokie, IL

If you have a friend in your life who’s into art or who’s always wanted to be able to paint but never quite learned how, this is the perfect gift. Because your friend will be paired with his own, private art instructor, he can be at any stage of his artistic journey and still do just fine in the class.

He’ll be taught many of the technical aspects of painting and drawing, including how to use the different types of media such as pencils, oil paints, watercolors and more. He can choose to focus his efforts on drawing human figures, portraits, still life drawings or landscapes.

If he’d prefer to learn a little more about applied and decorative arts, his private art instructor can assist with that as well.

host and wine tasting party

For the Sommelier: Host Private Wine Tasting Party, Crown Point, IN

Don’t let the location of this experience scare you off. Even though the company that hosts these parties is based out of Crown Point, Indiana – which is only about an hour outside Chicago anyway – the party would actually take place in the comfort of your or your friend’s own home, meaning there’s no need for her to drive anywhere if she doesn’t want to do so.

The party is a private affair, and your friend can invite her own guests. A professional sommelier will be there to guide all the party members through the tasting of six different, delicious wines.

He’ll also teach the guests to taste wine like a professional, going over the basics of how to distinguish between different varieties of wine. There are two different packages: a mid-range package, which focuses on wines ranging from $20-$25 each, and a high-end package, which provides guests with wines in the $40-$45 range.

If the party guests are already familiar with the basics of wine-tasting, the sommelier will teach a more advanced course.

west loop food tour

Pizza, Burgers and Donuts… Yum Yum: West Loop Food Tour, Chicago, IL

If there’s one thing Chicago is known for, it’s the delicious food. Help your friend experience all the best food Chicago has to offer by buying him a ticket to the West Loop Food Tour, where he’ll experience dishes from the West Loop’s most renowned and enticing restaurants.

Whether he’s a lover of pizza, donuts or traditional Italian fare, there’s something on this tour to suit his palate. There’s even a stop that’ll let him taste some delicious Poblano food as well.

drive a Dragster

For the Adrenaline Junkie: Drive a Dragster, Elwood, IL

For the friend who loves speed but doesn’t just want to ride along with someone else, this experience could be just the thing she needs. Send her to the Route 66 Raceway, where she can actually drive a dragster on the track.

She’ll start off receiving classroom and safety instruction from World Champion driver Frank Hawley and his team. Then she’ll get to drive on a 1/8-mile warm-up. Afterwards, she gets to go all out, driving the dragster two full quarter-mile runs, going from 0-60 in less than three seconds.

golf lessons with a PGA Pro

For the Friend Who Loves to Golf: Private Golf Lesson with a PGA Pro, Chicago, IL

Pair your friend up with PGA Class A member, John McCartin, and help him bring his golf game up to a whole new level. He’ll get a one-hour, private lesson with McCartin that’ll teach him to play golf like a pro.

Together, the two of them will work on adding distance to his drive, choosing the perfect grip and ball position, hitting straight irons, improving his short game and so much more. Other topics that may be covered include swing mechanics, proper alignment and proper posture.

He’ll feel more confident in his golf game after this lesson than he ever has.

cocktail tour

A Blast from the Past: Prohibition Cocktail Tour, Chicago, IL

This is probably one of the most popular experiences in the entire Chicago area. In addition to getting to drink some of the most authentic, Prohibition-era cocktails in Chicago, your friend will also enjoy a killer history lesson about Prohibition and old-school Chicago on this tour, which lasts over three hours.

She’ll visit some of Chicago’s most famous bars and former speakeasies, including the Wicker Park lounge, Friendly Neighborhood Bar in Old Town, the Down Tavern and more. The history is enlightening, the crime stories are intriguing and the cocktails are superb.

It doesn’t get much better than that.

chicago lunch Cruise

Lunch by the Pier: Chicago Lunch Cruise, Chicago, IL

This is another one for the foodies. The Chicago lunch cruise boasts “good company, delicious food, festive entertainment and stunning views,” and it delivers on those promises. Your friend will board the beautiful Spirit of Chicago, where he’ll be able to order drinks and explore the ship as it sets off, and he’ll enjoy a totally new view of Chicago from the open-air rooftop of the ship.

For lunch, he’ll be able to visit the grand buffet, where he’ll choose from a wide variety of food options including assorted salads and sides, numerous casserole and pasta dishes, a wide variety of different meat dishes and a devilishly delightful dessert bar.

indian food and cultural walking tour

Spice Things Up a Little: Indian Food & Cultural Walking Tour, Chicago, IL

Although not the only food tour on the list, this is the only one that features a walking tour through Little India. It’s also the only one that’ll provide your friend with four different tastings of the traditional foods of India, Pakistan and Bangladesh.

This is the most authentic South Asian culture tour in Chicago, and your friend will enjoy such delicacies as Mughlai cuisine, traditional South Indian vegetarian dishes, Pakistani barbecue, delicious South Asian sweets and North and West Indian juice, tea and snacks.

Additionally, he’ll have the chance to view Indian-style architecture, visit a Sikh temple and browse local Indian boutiques.

city lights bike tour

For the Biking Enthusiasts: City Lights Bike Tour, Chicago, IL

This is another one for the friend who loves biking. It’s a beautiful, eight-mile tour of the city by night. It’s very similar to the fireworks bike tour, but your friend will get to see different sights and attractions on this one.

In addition to seeing the gorgeous Navy Pier by night, she’ll also see the lit-up Chicago skyline, Millenium Park, the Shedd Aquarium, the Field Museum, the Adler Planetarium and more. In total, it’s about a three-hour bike tour, and your friend will love every second of it.

snow tubing and brewery adventure

Let it Snow: Snow Tubing and Brewery Adventure, Chicago, IL

If your buddy has been wanting to get out of the city proper and back in touch with nature, this is the perfect experience for him. He’ll head up to Wilmot Mountain and have an evening adventure that includes lots of great food and some snowtubing fun.

From the departure spot, it’s about a two-hour drive to the mountain, but it’s a beautiful, scenic bus ride your friend isn’t likely to mind too much. Once he’s there, he’ll start at the top of the mountain and spend the next two hours flying over the snow-covered hills.

He’ll finish off the night in a local brewery, where he’ll have dinner and the option to purchase some of the best local beers in all of Illinois.

walking Chicago pizza tour

Pizza, Pizza!: Walking Chicago Pizza Tour, Chicago, IL

It doesn’t get much more Chicago than pizza, which is probably why this walking Chicago pizza tour is one of the most popular Chicago experiences on the whole list. The tour takes about two and half hours and is designed and led by a native Chicagoan who also happens to be a pizza expert.

Your friend will visit four different popular pizzerias and get to experience stuffed crust pizza, deep dish pizza and more. Tell her to bring her appetite!

virtual homebrew lessons

For the Master Brewer: Virtual Homebrew Lesson, Various Locations (Remote)

This is a memorable experience your friend can do from the comfort of his own home. He’ll have the kit, called “the home brew essentials kit,” delivered to his door, and he can choose to login and take advantage of his three-hour virtual lesson any time he wants.

In addition to learning how to brew delicious suds, he’ll also enjoy the comedic entertainment of his teachers. This is a lesson he won’t soon forget, and before you know it, the two of you’ll be enjoying his home brews together.

malt row beer tour

For the Master Lover of Brews: Malt Row Beer Tour, Chicago, IL

If your friend’s the type who loves beer but doesn’t necessarily want to make her own, send her on the Malt Row Beer Tour instead. Chicago is home to over 150 breweries, which can make it hard to choose between them.

With this tour, she’ll be taken to five of the very best stops in Chicago, where she can enjoy the delicious brews while learning quite a bit about the history of beer, breweries and Prohibition in Chicago.

Additionally, she’ll be able to enjoy some of the newest beers and breweries in the area, so it’s perfect for taste-makers all over Chicago.

tandem skydiving

For the Adventurous Soul: Tandem Skydiving, Rochelle, IL

This is another one that’s going to take your friend a little over an hour to get to because it’s outside of Chicago proper, but if you have a friend who would love to do something wild that would give her a rush, she’s not going to mind the drive for this experience.

This skydiving adventure pairs her up with one of the most experienced companies in the country, and all the instructors are certified by the U.S. Parachute Association. She’ll board the plane with 22 other jumpers and get matched with her own personal jump buddy.

She’ll fly somewhere between 9,000 and 14,000 feet above the ground before the two of them jump out the door into a 30-second (or 60-second) free fall (depending on which height she jumps from). Once she breaks through the beautiful cloud canopy, she’ll deploy her parachute and glide down to the ground.

indoor skydiving

A Safer Way to Skydive: Indoor Skydiving, Chicago, IL

If you have a friend who wants to skydive but isn’t sure he wants to jump out of any planes, this indoor skydiving adventure might be the perfect compromise. He’ll jump inside a 100% safe, indoor wind tunnel, and whether he’s an experienced jumper or someone who’s never jumped before in his life, he’ll do just fine.

The wind tunnel is clear, so you can even go along and watch as he floats weightlessly in the air. He can hover in the air, spin in the breeze, touch down on the ground and then start the flying process all over again.

It’s the closest thing to true flight a human being is likely to ever experience.

scape room

For the Wannabe Sherlocks: Escape Room, Chicago, IL

With this package, your friend will have the ability to choose between four different escape room packages. Whether he decides to go with the Heist, the Prison Break, the Gold Rush or Special Ops, he’ll have 60 minutes to get acquainted with his teammates and find the clues, solve the puzzles and make it out of the Escape Room before the timer runs out.

This is a great experience for the two of you to share together, along with several of your other friends and loved ones. It’s a great way to improve your teamwork and critical thinking skills, and everyone is sure to have a blast.

architectural kayak tour

For the Friend Who Loves Architecture: Architectural Kayak Tour, Chicago, IL

Your friend can experience the beauty of the gorgeous Chicago River while kayaking down it with an instructor with 20+ years of experience. She’ll get to see some of Chicago’s most famous architecture including buildings made by Frank Lloyd Wright, Mies van der Rohe, Louis Sullivan and more.

The kayaking tour lasts about three hours and doesn’t require your friend to have any prior experience with kayaking. She can take some snacks and a camera and can snap some stunning photos along the way.

navy pier food tour

A Chicago Staple: Signature Food Tour at Navy Pier, Chicago, IL

This is another experience for the food-lover in your friend circle. Send your friend out to Navy Pier for the Navy Pier food tour, where he’ll not only enjoy the gorgeous sights and festivities of the pier but will also get to taste five of Chicago’s most famous foods including pizza, hot dogs, cupcakes, cheese curds and more.

Some of the stops along the tour could include Garrett Popcorn, Tiny Tavern, Brown Sugar Bakery, America’s Dog and Giordano’s Pizzeria. In total, the tour takes about two hours, and his guide will also give him some great history about the food and drink scene in Chicago and how it has evolved over the years.

helicopter tour

Soar through the Clouds: Helicopter Tour for 3, Schaumberg, IL

When you purchase this package for your friend, you can choose from either the Downtown Tour or the Northwest Tour. The Downtown Tour will fly him over downtown Chicago, also known as “the Loop,” where he’ll see such sights as the John Hancock Building, Navy Pier, the United Center, Willis Tower, Wrigley Field and more.

If you purchase him a ticket on the Northwest Tour, he’ll fly over the Northwestern suburbs of Chicago, catching glimpses of the Fox River, the Grand Victoria Casino, Barrington Hills, the Woodfield Mall and more.

Either way, he’ll be riding on an OH-6A helicopter flown by an FAA-Certified pilot. It’s a great way for even the locals to experience Chicago in a whole new way.

lake Michigan sailing charter

Experience the Wind in the Windy City: Lake Michigan Sailing Charter, Chicago, IL

If you have a friend that’s always said how much she’d love to sail around on her own private sailboat, this is the gift for her. With this gift, she’ll board her own private charter with up to five of her closest friends and spend the day sailing around Lake Michigan with a USCG-licensed captain.

The sailboat is a 39-foot luxury sailboat specifically designed for comfort and performance. She’ll get to experience the Chicago skyline in an all new way. The ship is equipped with hot and cold running water, a swim platform and swim shower, a large, retractable canopy and cockpit seat cushions.

There’s also an on-board bathroom and a kitchenette for keeping all of her favorite foods fresh and ready to eat.

Chinatown food tour

A Taste of Culture: Chinatown Food Tour, Chicago, IL

For the friend who loves food, culture and history, this gift experience is pretty unbeatable. He’ll take a walking tour through Chinatown with a guide who’ll tell him a lot about the history and traditions of that part of the city.

He’ll get to experience the flavors of various regions in China, including the Canton, Szechuan and Mandarin regions. He’ll enjoy sit-down tastings in five different, popular restaurants in the neighborhood and learn a lot about Chinese folklore and traditions.

Some of the delicious food options include dim sum, Shanghai-French pastries, Hong Kong-style barbecue, roasted duck, etc.

bikes bites tour north route

A Little Bit of Everything: Bikes, Bites and Brews Tour – North Side Route, Chicago, IL

For the friend who loves biking, beer and lots of food, this Bikes, Bites and Brews Tour is the perfect gift. He’ll get to experience four things that Chicago’s best known for – pizza, cupcakes, hot dogs and beer.

He’ll also get to see a lot of Chicago’s famous architecture and spend some time biking through such neighborhoods as Lakeview, Lincoln Park, Old Town, Wrigleyville and the Gold Coast. The whole trip covers about 13 miles, and all the biking will certainly have him work up an appetite.

Chicago fireworks dinner cruise

Dinner and a Show: Fireworks Dinner Cruise, Chicago, IL

Give your friend the opportunity to enjoy a night of gorgeous fireworks while drifting on the waves with this unique experience. She’ll board her cruise ship to the sounds of a live DJ and people laughing, dancing and having a good time.

If the beautiful Chicago skyline and the shining stars overhead aren’t enough, she’ll also be treated to a stunning view of the Navy Pier fireworks display. She can enjoy a few drinks while dancing or exploring the ship.

Dinner is a delicious, gourmet meal, and afterwards, she can relax on the largest outdoor patio deck in the whole city while the fireworks boom overhead.

Finding the Best Chicago Experiences

Ask anyone, and s/he’s sure to tell you that finding gifts for people is a whole lot easier when those gifts are experiences as opposed to materialistic things. Finding some kind of exciting experience for your friends to have in Chicago is even easier because there’s simply so much from which you can choose. Chicago is consistently lauded as one of the United States’ best and most exciting cities, and there is always something going on.

As long as you don’t get your friend or couple an experience gift that’s completely out of left field – such as a beauty makeover and pedicure for your brother the lumberjack or an all-day beer cruise for your best friend who doesn’t drink – you’re probably going to be alright. Just choose an experience you think would be enriching and entertaining for that special person in your life. It doesn’t have to be the flashiest, most exciting or most expensive experience on the list. Just make sure it’s something your friend would enjoy and would give her/him happy memories to look back on fondly.


What is the best experience you’ve ever had in Chicago?

Is there something fun and exciting to do there that everyone should experience that we left off our list? Have you ever done any of the things on our list, or have you given any of things on our list as a gift for someone else? Let us know all about it in the comments.

Also be sure to like and share our article so that all your friends can learn about some of the most happening things going on in the Windy City.

Come back again soon for more great gift-giving ideas!

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