You never know where a tour of Chicago might take you. You might find yourself sitting in the Chicago Cubs dugout, looking for ghosts in a haunted alleyway, kayaking the Chicago River at sunset, or tasting your way through some of the city’s most iconic bites.
No matter what you’re looking for, these unique Chicago tours guarantee a one-of-a-kind, off-the-beaten-path perspective of the city.
Tours of Chicago
Active and outdoor tours in Chicago
Urban Kayaks
One of the best ways to see the city is from the water. With Urban Kayaks, you can explore the lake or river on a guided kayak tour. Paddle the Chicago River through the heart of the city, surrounded by soaring skyscrapers and some of the city’s most iconic buildings. Or head to Monroe Harbor, where you’ll cruise down the scenic lakefront to the Museum Campus and back. Choose from daytime, evening, or fireworks tours. All skill levels are welcome.
Neon Paddle
Glide along the Chicago River on an electric motorized paddleboard with these one-of-a-kind excursions. Neon Paddle offers glowing paddleboard tours for a neon-lit adventure along Chicago’s iconic waterway, no paddling required. Choose from golden hour and nighttime tours led by expert guides.
City Fit Tours
Get your miles in and your heart racing with a City Fit Tours. Jumpstart your day with some early morning sightseeing with your choice of 5K routes. Led by professional guides, you’ll stop to see the sites, share stories, and snap photos, all while getting in a light workout. They also offer other athletic tours, like the Chicago River Yoga Walk.
Read & Run Chicago
Read & Run Chicago offers literary-inspired running tours, often paired with stops at local bookshops. These easy-paced runs are themed around different fiction and non-fiction books set in Chicago, so you can step inside your favorite books while working up a sweat.
Bike and Roll Chicago
Roll around Chicago’s most scenic spots with Bike and Roll Chicago. Choose from bike or Segway tours covering the Lakefront Trail, Millennium Park, Lincoln Park, and more.
Absolutely Chicago Segway Tours
What’s more unique than cruising around Chicago on a Segway? Absolutely Chicago Segway Tours showcases the best of Chicago on two wheels. Popular tours include the City Lights and Lakefront Museum Campus, along seasonal options that feature summer fireworks or holiday decor.
Bobby’s Bike Hike Chicago
Explore Chicago by bike or by foot with Bobby’s Bike Hike Chicago. These fun, family-friendly tours include activities like biking through scenic lakefront neighborhoods, tasting some of the city’s best bites and brews, and exploring the vibrant Chinatown neighborhood.
Chicago history and architecture tours
Sunset Live Tour
These twilight tours by Big Bus Tours Chicago cruise by the city’s top sites during golden hour. A live guide will narrate as you take in views of the lit-up skyline, Museum Campus, River North, Michigan Avenue, and more. Tours are non-stop and run seasonally. Big Bus Chicago also offers hop-on, hop-off tours and other experiences.
Chicago History Museum tours
Who knows more about Chicago history than the Chicago History Museum? The local museum offers a packed schedule of fascinating tours, covering a range of subjects and time periods. Check out some of their offerings, like Chicago’s on Fire Tour, Devil in the White City Tour, Pilsen Murals Walking Tour, Rosehill Cemetery Tour, and more.
Tours with Mike
These are not your average sightseeing tours. Tours with Mike offers a unique array of experiences that showcase a different side of Chicago. Wander the city’s subterranean passageways with the Underground Chicago (Plus Rats!) tour or join the tongue-in-cheek Ugly Buildings tour.
Chicago Architecture Center tours
Explore the city from a new perspective. The Elevated Architecture: Downtown ‘L’ Train tour from the Chicago Architecture Center showcases Chicago’s amazing architecture from the unique viewpoint of our elevated trains. Learn the history behind this iconic public transit system (like why we call it the ‘L’) and find out how it has helped shape the Loop into what it is today. The Chicago Architecture Center offers a wide range of boat, bus, bike, and walking tours all over the city.
Fly Heli Tours & Charter
Looking for an unforgettable activity for a milestone or special occasion? Fly Heli offers helicopter tours of Chicago, where passengers will enjoy jaw-dropping views as they soar high above some of the city’s most famous landmarks.
Inside Chicago Walking Tours
Step inside iconic Chicago locales with Inside Chicago Walking Tours. These interior-focused architecture tours go beyond the usual and hone in on the hidden details and fascinating stories of significant buildings across Chicago.
Chicago Fireboat Tours
Hop aboard a real retired fireboat and cruise Chicago’s stunning waterfronts with veteran-owned Chicago Fireboat Tours. This historic vessel takes passengers on scenic architecture cruises of the city’s lake and river.
Explore more: Discover our full guide to Chicago boat tours on the river and lakefront.
Chicago ghost and crime tours
American Ghost Walks
Get creeped out on an American Ghost Walks tour. The Original Chicago Hauntings Ghost Tour is a good place to start — you’ll hit some of the most actively supernatural spots in the city, including the sites of Fort Dearborn, the St. Valentine’s Day massacre, the Iroquois Theatre fire, and more. Other Chicago Hauntings Tours include the Lincoln Park Ghost Tour, Devil in the White City Tour, The Resurrection Mary tour (a local urban legend), and more.
Chicago Crime Tours and Experiences
Delve into Chicago’s seedy past with these on-and-off bus tours from Chicago Crime Tours and Experiences. A live guide will cover Chicago’s most infamous true crime stories, including Al Capone, John Dillinger, Leopold & Loeb, H.H. Holmes, and more, with stops at the city’s real-life crime scenes and historic landmarks.
Windy City Ghosts
Explore Chicago’s spookier side during a nighttime tour with Windy City Ghosts. Uncover the city’s most haunted sites on a ghost tour or delve into the city’s seedy past on a mobs and gangsters tour.
Chicago Booze and Boos Tour
This supernatural pub crawl with Nightly Spiritscovers Prohibition-era tales and favorite gangster haunts. Explore one of Chicago’s most historic neighborhoods while hearing tales of murdered gangsters, local lore, and more supernatural secrets.
Explore more: Discover tours of haunted Chicago spots during the spookiest time of year.
Food tours of Chicago
Pizza City USA Tours
Let a James Beard Award-winning food writer be your guide as you dive into the unique world of Chicago-style pizza. During Pizza City USA Tours, you’ll go beyond deep dish (though you’ll definitely try a slice or two of Chicago’s iconic style) with a wide variety of pies, from tavern-style to artisanal Neapolitan.
Underground Donut Tour
Donut lovers, you won’t want to miss this guided tour of some of Chicago’s sweetest spots. Underground Donut Tour takes participants to the city’s top donut shops, from viral hot spots to under-the-radar gems. Choose from tours of downtown or the hip Fulton Market district.
Yes, Chef! Chicago: A Bear-Inspired Food Tour
Visit the real Chicago restaurants behind the hit show during this food crawl based on The Bear, with plenty of bites along the way. Chicago Food & City Tour also offers unique food tours of the city, including spotlights on neighborhood cuisine from Pilsen to Chinatown.
Chicago Foodways Tours
Food and culture collide on these culinary walking tours. Chicago Foodways Tours explore Chicago’s international neighborhoods, where they can sample everything from authentic Vietnamese cuisine to eastern European delicacies.
The Barrel Run
Chicago is one of the nation’s top beer destinations and The Barrel Run whisks you to many of the city’s most popular taprooms. Travel in style on a Prohibition-era styled barrel bus as you cheers to Chicago’s craft brewing scene.
Chicago Pizza Tours
From deep dish to tavern style, Chicago has some strong opinions about pizza. Sample the city’s signature styles with Chicago Pizza Tours. Choose from their popular bus or walking tours, just make sure to come hungry!
Special interest tours of Chicago
Tour Through a Lens
Want to capture the best of your trip to Chicago? Tour Through a Lens helps you tell your travel story during immersive photography tours with a local guide. These urban photography adventures — with options for individuals and public or private groups — are perfect for smartphone users, hobbyists, and pro photographers alike.
Chicago Movie Tours
See the Chicago that’s depicted on the silver screen with Chicago Movie Tours. A local expert will take you to iconic filming locations (from Ferris Bueller to The Dark Knight) and delve into the city’s deep connection to the cinema.
Wrigley Field tours
Go behind the scenes of the second oldest ballpark in the country with a Wrigley Field Tour. The daily tours might take you to the press box, bleachers, visitors clubhouse, Cubs’ dugout, and even out on the field. On game days or days of special events, some access may be restricted, so it’s best to check before purchasing tickets.
On Location Tours
On Location Tours take you to top TV and movie filming locations all around Chicagoland, led by local experts who share behind-the-scenes facts and fun trivia. See iconic settings from Ferris Bueller’s Day Off, The Dark Knight, Blues Brothers, Public Enemies, My Best Friend’s Wedding, While You Were Sleeping, and more.
Chicago neighborhood tours
L Stop Tours
The ‘L’, Chicago’s raised public transit system, is one of the best ways to explore the city. L Stop Tours will take you through different Chicago neighborhoods using the different train lines. Explore Chinatown on the Red Line, discover hidden gems on the Green Line, marvel at street art in Pilsen on the Pink Line, and beyond.
Pilsen Public Art Tours
Chicago’s Pilsen neighborhood is known for its vibrant street art, celebrating the area’s rich Hispanic heritage and history. Pilsen Public Art Tours travels through 50 years of neighborhood history, as told by colorful murals and public artworks.
South Side Tours
The city’s vibrant South Side has been home to literary luminaries, jazz and blues legends, a notable former president, and beyond. Explore the area’s rich history and lasting legacy with South Side Tours, which incorporate personal storytelling from local residents.
Chicago Mahogany Tours
Led by Chicago’s TikTok-famous urban historian, Chicago Mahogany Tours puts a spotlight on lesser known Chicago history on Chicago’s West and South Sides. Join Shermann “Dilla” Thomas for tours of Bronzeville, Englewood, Pullman, and beyond.
Chicago Greeter
See Chicago like you never have before — through the eyes of a friendly local. Chicago Greeter pairs visitors with Chicago residents for free in-depth visit of local neighborhoods based on your interests. Discover everything from hot spots to history to hidden gems.
Please note: some of the above tours are available seasonally and are weather/event dependent. Please check with each tour company for availability.
