Menu

UNIQUE CHICAGO TOURS 

What should you expect from a Chicago tour? The unexpected!

You might find yourself sitting in the Chicago Cubs dugout or sneaking into a hotel kitchen for a brownie tasting, or walking in the footsteps of gangsters. It's up to you which adventure you choose.

Inside Chicago Walking Tours

If you've done the classic architecture riverboat tour already, or maybe the Chicago weather is keeping you on land, then delve deeper and see beyond building exteriors with Inside Chicago Walking Tours. Rather than a basic 101 on architectural styles or a laundry list of engineering facts, tour guide/founder Hillary will sweep you up in the great stories of Chicago history. Storytelling is the foundation of these guided walks, and there's so much to share: courageous labor activists, crafty tavern owners, pioneering architects, wealthy mansion dwellers, and more. 

Chicago Trolley & Double Decker Co.

Chicago Detours

Look further into the intersection of Chicago's architecture, history and culture with Chicago Detours, which uncover secret tidbits and reveal places even the locals don't know about. Tours feature interactive, visual elements to enhance the experience, including photos and videos on iPads (for walking tours) or screens (for bus tours). Focus on Chicago's most unique spaces and concepts, with outings like the Interior Architectural Tour, which includes the underground Pedway system, the Jazz, Blues & Beyond Tour, which includes a harmonica lesson with a live blues musician, and the Historic Bar Tour, where you can eat, drink and explore your way through Chicago's entertainment history. 

City Running Tours

For the chance to cover more of the city by foot, get your miles in and get your heart racing with a City Running Tour. 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.

Free Tours by Foot 

Looking for a budget-friendly way to see the city? How about a walking tour where you name your own price! No upfront costs means the value is up to YOU. This unique twist makes exploring Chicago's downtown and neighborhoods an economical excursion. From literary legends to blues clubs, your 2-hour Free Tours by Foot outing covers the city, with professional tour guides leading the way. And in the end, you always feel like you get what you paid for... whether that's a competitive price you decide on or nothing at all.

Urban Adventure Quest

Imagine Chicago as a giant game board! Urban Adventure Quest. Get a team together for this city scavenger hunt, solve clues that lead to hidden gems, and complete challenges while learning about the local history of Chicago. This three-hour experience is lead by smart phones beginning within the loop on a course among historic buildings, into the beautiful parks, and down the various cultured streets.  

Wateriders: Chicago Kayak Tours and Rentals 

Chicago River Kayaking

For the adventure seeker, navigate through architectural canyons on Chicago's waterways from the cockpit of a kayak. Even beginners can quickly pick up the skills to maneuver their own boat, though 2-person kayaks are available for the less intrepid. Take a guided tour of the Chicago River through the heart of downtown with Wateriders: Chicago Kayak Tours and Rentals for some memorable views and a truly Chicago experience.

Gangster History with Untouchable Tours

Experience Chicago as it was during the 1920s and 1930s, and learn all about the old gangster hot spots and hit spots while you're at it. You'll hear historically accurate accounts of the exploits of Capone, Moran, Dillinger and the rest of those less than moral boys. It's an exciting ride on a new custom-built Untouchable Tours Gangster Bus: climate controlled, great air conditioning, comfortable seats!

History Pub Crawls 

Prohibition — this aspect of US history is enmeshed in Chicago's own history. Get a true "taste" of the bygone speakeasy life through Booze, Bars, and Bootlegging! Prohibition Era Chicago, just one of the many History Pub Crawls offered by the Chicago History Museum. Go back in time to uncover some of the infamous watering holes that even the law could not stop during the 13-year period when alcohol was banned.

Chicago Architecture Foundation

You may know about the World's Columbian Exposition of 1893, a milestone event that put the international spotlight on Chicago, but were you aware of its dark side? During this time when the burgeoning metropolis was shining, a serial murderer masqueraded as a charming doctor and used the fairgrounds to lure his female victims. The Chicago Architecture Foundation tour Devil in the White City (named after the best-selling novel by Erik Larson), explores the horrid, yet true, tale. On the bus tour, historic stops bring the era to life and lend insight into the lives of two famous men: Chicago architect Daniel Burnham and serial killer H. H. Holmes.

The Second City 

Keeping it on the lighter side, comedy powerhouse The Second City finds the funny in all things Chicago, specifically in their home neighborhood of Old Town. Stroll the streets that surround the theater while you laugh and learn about famous alumni haunts nearby and the historic community's architecture and development over the years. The Second City Walking Tour (offered May through October) ends inside The Second City so you can check out the lobby photo display that documents over 50 years of comedy here: famous faces that include John Belushi, Bill Murray, Mike Myers, Steve Carell and Tina Fey.

Dining Tours

Chicago Dine Around

At Chicago Dine-Around, experience the best of Chicago dining in one unforgettable culinary adventure to Chicago’s best restaurants aboard the Progressive Dining Tour. You’re picked up in a stylish coach bus, before traveling to the first restaurant for hors d'oeuvres, the second restaurant for the main course, and the third restaurant for dessert (minimum group of 12). Alternatively, embark on an Architectural Dining Tour. Chicago Dine-Around conveniently picks you up in a stylish coach bus and escorts you on a narrated architectural tour and to dinner. Capture magnificent views of Chicago’s renowned skyline as you cruise along the Chicago River and/or Lake Michigan (minimum group of 15). Ideal for team-building, networking and all types of corporate events, Chicago Dine-Around offers several packages, menu options and event themes, allowing you to tailor the program around your group's needs.

Theater Tours

Auditorium Theatre Chicago

Step behind the scenes on a Marquee Tour of The Chicago Theatre, where you will discover the glorious French-Baroque architecture of this majestic venue and stand on the famous stage, plus uncover renowned performers' autographs and colorful murals on dressing room walls. Broadway In Chicago also offers tours of some of its theaters on Saturdays, so you can take a tour and then see a show later that night.A museum in a hotel? Chicago has it.

History is Hott Lunch & Tour

Take a walk through history — and enjoy an exquisite meal while doing it — with The Palmer House Hilton's History is Hott Lunch & Tour. Start out by dining inside Lockwood, the property's modern American fare restaurant. Then follow that up with a tour of the historic hotel's art-deco lobby, grand ballrooms and guestrooms  all the while with a glass of wine in hand. The biggest eye-opener may be the museum, a modest room on the mezzanine level teeming with vintage artifacts, each one with a story to tell. This exclusive look into the Palmer House and its archives is led by the property's resident historian, a passionate storyteller who recounts much of the Chicago history that is intertwined with the hotel, from the Great Chicago Fire to Potter and Bertha Palmer.

Wrigley Field Tour 

Wrigley Field Tours

So maybe you're not a pro athlete but did you know that you can sit in the Cubs dugout? Take a Wrigley Field Tour for your chance to look out onto the bricks and ivy like Ernie Banks, Billy Wiliams, Sammy Sosa and other greats have. Stroll through the legendary ballpark (built in 1914, it's the second oldest in Major League Baseball) that is 's home to the beloved Chicago Cubs. Kids, history buffs and baseball fans alike — though maybe not White Sox supporters! — will love getting behind the scenes of the Friendly Confines. Daily Wrigley Field Tours may include visits to bring you into the clubhouses, press box, locker rooms and/or infield dugouts, and possibly even a step out onto the field to see the bricks and ivy from the players' perspective. On game days or days of special events, some access may be restricted, so it's best to ask when purchasing tickets.

Please note: Some of the above tours are available seasonally and are weather dependent. Please check with each tour company for availability.

Featured Partners