Looking for the perfect experience gift in Chicago, Illinois? Whether it's a birthday, anniversary, or just-because moment, nothing beats giving someone a real experience. We've curated the best local activities and adventures in Chicago — from adrenaline-pumping track days to relaxing food tours and everything in between. Every experience listed here can be booked directly through the original operator, so you're always getting the real deal.
Things to Do in Chicago
- Supercar Track Xperience at Autobahn Country Club - Drive an exotic supercar at Autobahn Country Club near Chicago. Pro coaching included, safety gear provided, and lap packages for real track thrills. (from $249.00)
- Routes POR Route 66 with Audio Guide - Route 66, known as "The Main Street of America", runs through eight states from Chicago to Santa Monica. EN route to Illinois, POR Missouri, Kansas, Oklahoma, Texas, New Mexico, Arizona and California (from $0.00)
- Paint Night and Cocktails at Trendy Venues Across Chicago - Ready for a night that’s equal parts laughter, creativity and cocktails? Join this hands-on paint and sip class in Chicago hosted through!, and rediscover how fun it feels to just make something. Your (from $0.00)
- Downtown Chicago City Tour In a Lamborghini[60 Minute Experience] - Experience Chicago in unparalleled style with a 10-mile cruise through the city in a luxury or exotic vehicle. Glide through iconic streets, turning heads at every stop, while taking in the captivatin (from $0.00)
- Chicago Cubs Baseball Game at Wrigley Field - One of the oldest and most iconic franchises in Major League Baseball and a founding member of the National League, the Chicago Cubs’ legacy dates all the way back to 1876. The tradition and heritage (from $0.00)
- Chicago Blackhawks Ice Hockey Game at United Center - One of the “original six”, dating way back to 1926, the Chicago Blackhawks are the epitomise NHL history. For an experience filled with tradition and history, look no further than attending a Blackhaw (from $0.00)
- Neon Paint Therapy Experience - Paint ""Therapy"" is allowed for individuals aged 18 and over. In the case of a group, all participants must be 18 or older Engage in a vibrant explosion of creativity with the Neon Paint Therapy Exp (from $0.00)
- Bike Tour in Chicago - Take a spin through the Windy City on a bike tour and discover the most remarkable and world-famous sights. Hit the streets like a local with your guide, dive into the bustling life of the business di (from $0.00)
- Downtown Chicago History Walking Tour with Expert Guide - Discover the rich history and culture of downtown Chicago on this guided walking tour with local expert Dave Lineal. Stroll the city's streets and enter historic buildings while gaining insight with f (from $0.00)
- Awesome Scavenger Hunt at Lincoln Park Zoo - "Dive into adventure with Let’s Roam, your go-to for the ultimate app-led adventure hunts! Step into a world where every landmark and hidden gem is waiting to be discovered. Challenge yourself with tr (from $0.00)
- Chicago Airport Transfer: Chicago to O'Hare Airport ORD in Business Car - Your safety is our crew’s biggest priority. Before your journey even begins, your chauffeur completely disinfects the vehicle and places free hand sanitizer in the back seat. One of our professionally (from $0.00)
- Astounding Scavenger Hunt in Chicago - Dive into adventure with your go-to for the ultimate app-led adventure hunts! Step into a world where every landmark and hidden gem is waiting to be discovered. Challenge yourself with trivia, tackle (from $0.00)
- Arrival Private Transfer: O'Hare Airport ORD to Chicago in Luxury Car - Your safety is our crew’s biggest priority. Before your journey even begins, your driver completely disinfects the vehicle and places free hand sanitizer in the back seat. One of our professionally-tr (from $0.00)
- Guided Audio Road Trip Route 66 - Live the mythical Route 66 as it should be: at your own pace, with freedom and with the feeling of being walking a living history. This audio guide accompanies you from Chicago to Los Angeles, transfo (from $0.00)
- Private Acrylic Painting Class in Chicago - Our "Fluid Art" experience is truly unique. It offers a mesmerizing journey into the world of art unlike any other. Participants are guided through an exciting process using acrylic paints, silicone, (from $0.00)
- Private Art Splash: Chicago Group Painting Experience - Discover a truly unique experience at Shot of Art! Immerse yourself in creative art sessions tailored for all occasions, from bachelor parties to corporate events. Our private rooms offer the perfect (from $0.00)
- Amazing Scavenger Hunt: Time For a Go in Chicago - Let’s Roam leads the way as the top app-led adventure hunt company! Explore the city’s top landmarks and uncover hidden gems while tackling trivia questions and overcoming challenges. Whether you're c (from $0.00)
- Discover Chicago: A Self-Guided Walking Tour - Discover Chicago's soaring ambition and neighborhood soul with your self-guided audio tour, allowing you to explore America's most architecturally significant city at your own pace. Begin at Millenniu (from $0.00)
- Seamless Chicago Airport Transfers with Deenil Experiences - Arriving at your destination is effortless with Deenil Experiences’ airport transfer service. Enjoy a smooth ride in a clean, luxurious vehicle, where comfort meets safety. Your professional chauffeur (from $0.00)
- Astounding Chicago Bar Crawl: Chi-Town Showdown - "Dive into adventure with Let’s Roam, your go-to for the ultimate app-led adventure hunts! Step into a world where every landmark and hidden gem is waiting to be discovered. Challenge yourself with tr (from $0.00)
- A Spectacular Audio Tour : Wonders of Chicago - "Dive into adventure with us, your go-to for the ultimate app-led adventure hunts! Step into a world where every landmark and hidden gem is waiting to be discovered. Challenge yourself with trivia, ta (from $0.00)
- Departure Private Transfer: Chicago to O'Hare Airport ORD in Luxury Car - Your safety is our crew’s biggest priority. Before your journey even begins, your chauffeur completely disinfects the vehicle and places free hand sanitizer in the back seat. One of our professionally (from $0.00)
- Historic Pullman Private Half-Day Walking Tour - Step into Chicago’s past and explore the story of America’s first model industrial town on this guided walking tour through the Pullman Historic District. Once the heart of George Pullman’s luxury rai (from $0.00)
- Balloon Museum Chicago Exhibition Ticket - Explore the fascinating connection between art and emotions at the EmotionAir exhibition. This unique showcase features inflatable art that serves as a mirror to our deepest feelings, allowing visitor (from $0.00)
- Chicago River Yoga Walk Tour - This is truly an experience like none other. It is combination of a historical walking tour of the Chicago Riverwalk and Yoga. It is a very non-traditional Yoga experience as we incorporate flows alon (from $0.00)
- Big Bus Chicago: 48-Hour Hop-on Hop-off Tour & 360 CHICAGO Deck - Explore Chicago at your own pace with a 48-hour hop-on hop-off bus tour, providing unlimited access to the city's iconic neighborhoods and landmarks. Relax on open-top buses while enjoying engaging au (from $0.00)
- A Spectacular Scavenger Hunts Chicago Adventure - Dive into adventure with Let’s Roam, your go-to for the ultimate app-led adventure hunts! Step into a world where every landmark and hidden gem is waiting to be discovered. Challenge yourself with tri (from $0.00)
- Departure Private Transfer: Chicago to O'Hare Airport ORD in Business Car - Your safety is our crew’s biggest priority. Before your journey even begins, your chauffeur completely disinfects the vehicle and places free hand sanitizer in the back seat. One of our professionally (from $0.00)
- Airport Transfer: O'Hare Airport ORD to Chicago by Luxury SUV - Your safety is our crew’s biggest priority. Before your journey even begins, your driver completely disinfects the vehicle and places free hand sanitizer in the back seat. One of our professionally-tr (from $0.00)
- Art Boom 3 in 1 : Adults-Only Private Art Experience in Chicago - Here's what you can expect during your 1.5-hour private room experience: Shooting/Spinning Art Experience: Collaborate with your group to create a masterpiece on a large canvas (24x36 inches) using o (from $0.00)
- Private Transfer: Midway Airport MDW to Chicago by Luxury SUV - Reliable ground transportation from the airport The modern traveler will appreciate the importance of a hassle-free journey from the airport. If you travel several times a year to distant destinations (from $0.00)
- Luxury Limousine Transfers in Chicago - Elevate your travel experience in Chicago with luxurious limousine transfers that redefine comfort and sophistication. Whether it’s a corporate event, wedding, or a night out, each ride offers plush i (from $0.00)
- Chicago Architecture, Art and History Tour - Off The Beaten Path - This short but sweet and unique adventure will take you on a 2-hour walking tour by the interiors of the most iconic buildings of Chicago downtown. Dive into the extravaganza of splendid hidden gems (from $0.00)
- Private Chicago Suburbs Movie Sites Tour - Discover Hollywood magic in the heart of the Midwest on the Chicago Suburbs Movie Sites Tour. Visit real filming locations from classics like Ferris Bueller’s Day Off and Home Alone to modern hits lik (from $0.00)
- Chicago: Luggage Storage Close to Millennium Park - Experience the freedom of exploring without the extra weighting in Chicago. Our luggage storage service ensures your belongings are secure, allowing you to enjoy the wonders of your destination with p (from $0.00)
- Romantic Chicago Date Night: A Creative Art Experience - SHOOTING&SPINNING IS ALLOWED FROM 18 YEARS OF AGE. In case it is a group, everyone must be 18+ What sets our Date Night Art Experience apart is the perfect blend of excitement, creativity, and connec (from $0.00)
- Arrival Transfer: O'Hare Airport ORD to Chicago by Luxury SUV - Your safety is our crew’s biggest priority. Before your journey even begins, your driver completely disinfects the vehicle and places free hand sanitizer in the back seat. One of our professionally-tr (from $0.00)
- Resilience and Revolution: Audio Tour of Chicago’s Black History - Chicago is inseparable from its Black history, where local pioneers helped shape the city’s story. On this self-guided audio tour through downtown Chicago, you’ll hear untold stories of Black excellen (from $0.00)
- Wind City Wanderlust: A Private Chicago Family Odyssey - Skip the crowds this is a private tour for your group only! Embark on a family adventure starting at the iconic metal horse sculpture at 425 S. Financial Place, a symbol of strength in the city's bust (from $0.00)
- Romantic Chicago Walking Tour: Love Stories & Landmarks - Skip the crowds this is a private tour for your group only! How about an unforgettable time in Chicago with your beloved? If you're looking to have the most romantic time while visiting famous attract (from $0.00)
- Private Walking Tour of Chicago’s Artsy Cultural Landmarks - Skip the crowds this is a private tour for your group only! Dive into "Chicago's Artsy Cultural Landmarks – Walking Tour," a vibrant exploration of the city's iconic artistic and architectural gems. S (from $0.00)
- Echoes of Elegance Private Tour Chicago’s Architectural Splendors - Skip the crowds this is a private tour for your group only! Embark on a captivating journey through Chicago’s most illustrious addresses, where each step tells a story of architectural brilliance, his (from $0.00)
- Wheelchair Accessible Airport Transfer Chicago to O’Hare, Midway - Travel in Comfort & Accessibility with Chicago’s Premier Private WAV Service. Your professional, fully licensed driver will meet you curbside at O’Hare (ORD) or Midway (MDW) and assist with boarding (from $0.00)
- Exclusive Downtown Chicago Guided Walking Tour 12ppl Max - What do the artists Picasso, Chagall, Miro, and Kapoor all have in common? Incredible public art hiding in plain sight amidst world famous architecture. Tour Chicago in a small group perfect for busy (from $0.00)
- Lincoln Park Spirits Ghost Private Walking Tour - Skip the crowds this is a private tour for your group only! “Lincoln Park Spirits: A Ghostly Walk Through Chicago’s Past” takes you on an eerie exploration of the Lincoln Park neighborhood. Begin at J (from $0.00)
- Happy Hour Fireboat Cruise - Take part in a unique evening Happy Hour Cruise, featuring fresh craft beers while cruising the stunning Chicago skyline. Every Thursday and Friday evening, this 2-hour experience begins on Lake Michi (from $0.00)
- Chicago Private Boat Day - Sunset, Skyline & Celebration - Experience the beauty and excitement of Chicago from the water aboard Misunderstood, a premier charter boat perfect for parties, events, or a relaxing day on Lake Michigan. Cruise past iconic landmark (from $0.00)
- Chicago Downtown Walking Tour & Lake Michigan Cruise Tickets - Walk beneath Chicago’s soaring skyline, hear its hidden stories, then see it shimmer from the water on a lake cruise. From the iconic Bean to the legendary theatre district, this tour brings the city’ (from $0.00)
- Curbside Sedan Transfer from ORD & MDW to Downtown Chicago - Experience a seamless and stylish journey from O'Hare (ORD) or Midway (MDW) airports to downtown Chicago with our premier Sedan transfer service. Our luxury sedans offer ample space for up to 3 passen (from $0.00)
- Chicago Midway Airport (MDW) to Chicago City - Round-Trip Private Transfer - Book your Private Round-Trip Transfer from Chicago Midway Airport (MDW) to Chicago or address and return. Don't go through all the hassle of waiting in a long taxi or shared shuttles queues and use o (from $0.00)