Chicago has sightseeing tours galore, but these tours offer a different twist to the typical introduction to Chicago. Give these unique offerings a try — you might find yourself sitting in the Chicago Cubs dugout or sneaking into a hotel kitchen for a brownie tasting.

If you've done the classic architecture river boat 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 much to share: courageous labor activists, crafty tavern owners, pioneering architects, wealthy mansion dwellers and more. 

Look further into the intersection of Chicago's architecture, history and culture with Chicago Detours, which uncovers secret tidbits and reveals places even the locals don't know exist. 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 their Interior Architectural Tour that 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 of eating, drinking and exploring Chicago's entertainment history.

For the chance to cover more of the city by foot, get your miles in and get your heart racing with a City Running Tours. Jump start your day with some early morning sightseeing with your choice of 5K routes. Led by professional guides, you'll see stop to see the sites, share stories and snap photos all while getting a light workout in.

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.

For the adventure seeker, navigate through architectural canyons on Chicago's waters 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.

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.

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.

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.

For the budding photographer in you, go on a Chicago Photo Safari. You'll tour top Chicago attractions with a skilled professional photographer who offers tips on composition, lighting, and exposure to make sure you capture terrific images of city sites. Consider making this one of your first activities so you can practice your skills for the rest of your trip.

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.

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.

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.


Related Listings

Chicago History Museum
1601 N. Clark St.
Chicago, IL 60614
(312) 642-4600

The Chicago Theatre
175 N. State St.
Chicago, IL 60601
(312) 462-6300

Free Tours by Foot
1400 N. State Pkwy.
Chicago, IL 60610
(312) 612-0826

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Chicago Detours
Various Locations
Chicago, IL 60603
(312) 350-1131

Chicago Architecture Foundation
224 S. Michigan Ave.
Chicago, IL 60604
(312) 922-3432

Inside Chicago Walking Tours
Chicago, IL 60625
(312) 799-0164

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