10 Bus Tours in Chicago That You Shouldn't Miss

September 24, 2021 Rebbecca Marino

The windy city is a cornucopia of modern art, fine dining, cutting edge comedy, and die-hard sports fans. Snap a photo of your reflection in the silver Cloud Gate sculpture at Millennium Park before heading to Grant Park to get hit with the refreshing spray of Buckingham Fountain. There are dozens of museums and theater companies in Chicago, so a cultural experience is never hard to find. You’re sure to laugh your head off at the Second City Theater, the professional launch pad of many famous comedians.
Restaurants in Chicago

1. Private Chicago Highlights Driving Tour

Chicago Travel & Tours
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5.0 based on 12 reviews

See Chicago’s most essential landmarks from the comfort of a private vehicle on this 3-hour jaunt around town. Your guide will pick you up directly from your Chicago accommodation, after which you’ll be whisked away to see the sights. From the storied Magnificent Mile to the glamour of the Gold Coast, you’ll encounter the best of the Windy City. This private tour is available in Portuguese, English, or Spanish, and kicks off promptly at 9am.

Inclusions: Hotel/port pickup and drop-off, Driver/Guide, Private transportation, Private tour

Exclusions: Food and drinks, unless specified, Gratuities

Reviewed By KedarS88

A day is not enough to explore all the potentials!! that is best I can describe this outlet mall. One gets spoiled with choices and you can shop till you drop.

2. Private Al Capone Gangster Tour in Chicago

Chicago Private Tours and Productions
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5.0 based on 2 reviews

Chicago and the history of the mob are synonymous when we look back at history. That’s why we provide an in-depth Chicago Gangster Tour that makes all of the infamous stops for our patrons.  Visit the old stomping grounds of: • Al Capone • John Dillinger • The Untouchables View crime scenes immortalized in vintage news footage, the theater where the law caught up with Dillinger, the restaurant where the North Side Gang riddled Al Capone’s motorcade with rounds from their Tommy Guns, and the site of the St. Valentine’s Day Massacre. We bring Chicago’s true crime past to life before your very eyes.

Inclusions: Hotel pickup and drop-off, Transport by private vehicle

Exclusions: Gratuities

Reviewed By 768marthah

We took the private architecture tour of Chicago Private Tours and Productions on 11/22/19. Stevie did not disappoint. His depth of knowledge and storytelling ability made us feel like Al Capone himself was in the Empire room with us. We learned about the history and saw the interiors of the most amazing buildings while being driven to the curb by chauffeur Carmela. Learned about the history of skyscrapers, Union Stock Yard, the World’s Fair in 1893 and it was so interesting that I bought “The Devil and the White City” for the plane ride home. Stevie even added a quick stop at Harry Carey’s so we could see the secret underground tunnel to the courthouse - used at a time when corruption reigned in the city. This tour was my favorite part of the weekend in Chicago and I highly recommend.

3. Private Chicago Architecture Tour

Chicago Private Tours and Productions
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5.0 based on 4 reviews

Despite the Great Fire that once ravaged the city of Chicago over a century ago, the city is credited as the birthplace of the modern skyscraper. Chicago is so renowned for architecture that it’s the most vertical metropolis from here to Hong Kong. On our Chicago Architecture Tour, we’ll stop at and discuss: • Sears “Willis” Tower • The John Hancock Building • Gothic gems • Magnificent Mile notable locations • Historic brownstones • The Frank Lloyd Wright homes of Oak Park We offer a uniquely added value opportunity to view not only the outside, but also explore the inside of many of these infamous buildings. Our tour will satisfy the architecture style and structural tastes of the most discerning traveling.

Inclusions: All taxes, fees and handling charges, Professional guide, Hotel pickup and drop-off, Private tour

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Reviewed By 768marthah

We took the private architecture tour of Chicago Private Tours and Productions on 11/22/19. Stevie did not disappoint. His depth of knowledge and storytelling ability made us feel like Al Capone himself was in the Empire room with us. We learned about the history and saw the interiors of the most amazing buildings while being driven to the curb by chauffeur Carmela. Learned about the history of skyscrapers, Union Stock Yard, the World’s Fair in 1893 and it was so interesting that I bought “The Devil and the White City” for the plane ride home. Stevie even added a quick stop at Harry Carey’s so we could see the secret underground tunnel to the courthouse - used at a time when corruption reigned in the city. This tour was my favorite part of the weekend in Chicago and I highly recommend.

4. Original Chicago Haunting Ghost Bus Tour

1601 N Clark St, Chicago, IL 60614, USA Chicago Hauntings
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5.0 based on 1 reviews

Our classic Chicago Hauntings Chicago Ghost tour is a 2.5 to 3-hour fully-narrated tour by coach bus, with numerous stops along the tour route at some of the most actively haunted sites in Chicago, including the site of the Eastland Disaster, where 844 souls perished on the Chicago River; Death Alley, where more than six hundred children and their chaperones lost their lives in the worst single building fire in American history; the site of the infamous St. Valentine’s Day Massacre in storied Lincoln Park, the original and the now abandoned City Cemetery, where an estimated 13,000 unmarked graves remain. Some of our most common stops include murder sites, disaster sites, cursed skyscrapers, gangland sites, Chicago’s most haunted house, and others. You are welcome to take photos at all of our stops — sometimes your camera may capture more than just spooky scenery.

Inclusions: Restroom on board, Air-conditioned vehicle

Exclusions: Alcoholic Beverages, Snacks

Reviewed By jodi916

Lara was an excellent & engaging guide. We learned a lot of Chicago history along the way. We toured in October - would highly recommend bringing a warm coat, gloves & a hat. Breezy and chilly near the water.

5. Chicago City Minibus Tour

DoubleTree by Hilton Hotel Chicago - Magnificent Mile, 300 E Ohio St, Chicago, IL 60611, USA See it All Chicago Tours
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5.0 based on 21 reviews

Enjoy Chicago’s famous sights and fabulous skyline views on this award-winning small-group sightseeing tour of the city. Travel through Chicago with an expert guide on a comfortable minibus, stopping at iconic locations like early skyscraper "The Rookery" (Frank Lloyd Wright architecture), Museum Campus (for the BEST skyline view in town), Millennium Park (The Bean), Buckingham Fountain, The Magnificent Mile, Lincoln Park, Chicago River, The Gold Coast, Lake Shore Drive and more! Along the way, your guide will provide historical and informational commentary about the area and its many attractions. The small-group atmosphere with maximum of 10 people ensures a more personal experience. 

Inclusions: Hotel pickup and drop-off to most downtown Chicago hotels, Vehicles sanitized after each tour. , Transport by 12-passenger, air-conditioned minibus, Three photo stops, Face masks must be worn at all times when inside the vehicle

Exclusions: Food and drinks, Gratuities

Reviewed By W5101KSlesliea

Great tour , guide very knowledgeable and funny. Bus was clean ,I really enjoy the tour . Try it today

6. Chicago Private Tours

Chicago Private Tours
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4.9 based on 133 reviews

PRICE IS PER VEHICLE AND YOU MAY BRING UP TO 4 PASSENGERS TOTAL.  Thank you for contacting Chicago Private Tours! We would love to help your group discover Chicago.  Our services include pick up from your downtown Chicago hotel, a 3-4 hour private City Tour in a chauffeured vehicle, and the services of one of our knowledgeable guides. This means you will have two people working with you the entire time, allowing you to get out of the vehicle with your guide at several stops. These stops include, but are not limited to Millennium Park, Lincoln Park Conservatory, Museum Campus, and more.  The tour will be interactive and entertaining, covering history, architecture and culture.  We share stories to bring Chicago's rich history to life. Once the tour concludes, we will drop your group off at your preferred, downtown Chicago location.

Inclusions: Driver/guide, Local guide, Professional guide, Private transportation, Pick up at your Downtown Hotel

Exclusions: Gratuities

Reviewed By nchurik

These guys were great! They were very knowledgeable, adjusted on the fly and kept our day entertaining. I'll use them again!

7. Chicago City Minibus Tour with Optional Architecture River Cruise

DoubleTree by Hilton Hotel Chicago - Magnificent Mile, 300 E Ohio St, Chicago, IL 60611, USA See it All Chicago Tours
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4.7 based on 370 reviews

Enjoy Chicago’s famous sights and fabulous views on this award-winning small-group sightseeing tour of the city. Travel through Chicago with an expert guide on a comfortable minibus, enjoy world renowned architecture including the world's first skyscrapers, Museum Campus (for the BEST skyline view in town), Millennium Park (The Bean), Buckingham Fountain, The Magnificent Mile, Lincoln Park, Chicago River, The Gold Coast, Lake Shore Drive and more! Along the way, your guide will provide historical and informational commentary about the area and its many attractions. The small-group atmosphere with maximum of 10 people ensures a more personal experience.  You also have the option to upgrade to include a 75-minute Architecture Cruise down the Chicago River! This popular open-top boat tour offers the perfect vantage point to admire the city’s renowned buildings.

Inclusions: Local guide, Three photo stops, Transport by 12-passenger, air-conditioned minibus, Hotel pickup and drop-off to most downtown Chicago hotels, Chicago River Architecture Boat Tour (if option selected)

Exclusions: Gratuities, Food and drinks

Reviewed By philyfriar1234

Be prepared to learn much about Chicago's past as you tour many famous areas of this amazing city! Rick will keep you highly entertained with his narration of the tour and stories about the history of Chicago. I was suprised that he has only lived here about 15 years as his knowledge of the city would make you think he was a life long resident. You cant go wrong with this tour!! Ken & Joyce Lexington, KY

8. Chicago Night Crimes Bus Tour

163 E Pearson St, Chicago, IL 60611, USA Chicago Crime Tours and Experiences
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4.7 based on 57 reviews

Join us for a fun night of exploring Chicago's crime history on this 2-2.5-hour bus tour that includes: * World famous crime scenes like the St Valentine's Day massacre * Stops on-and-off the bus at famous crime sites * True Crime history * Historic video footage * Interactive live commentary * Crime quiz * Souvenir pamphlet with photos * Luxury climate-controlled bus * So much more! Some of the world’s most notorious criminals, mobsters & gangsters bamboozled their way through Chicago. Escape into the city’s criminal underworld as you investigate stories about Al Capone, The Untouchables, the Chicago Mob and more. From a luxury coach, see the sites of storied crime scenes including Biograph Theatre, Holy Name Cathedral, and the St Valentine's Day Massacre, one of Chicago's most notorious murders. Snap photos of the historic criminal courthouse, and hop on-and-off the coach to walk the path that Chicago gangsters John Dillinger and Hymie Weiss followed just before their deaths.

Inclusions: Luxury temperature controlled coach bus, Professional tour guide and chauffeur, Live commentary on board, Photo opportunities off the bus at infamous crime scenes, Test your knowledge with the Crime Quiz, Historic video footage, Keepsake brochure with special offers

Exclusions: Gratuity

Reviewed By ElayneG159

We had an amazing tour guide Michael who entertained us with history. The time on the tour flew by. My 11 year old granddaughter was interested the entire tour

9. Chicago Craft Brewery Barrel Bus Tour

600 N Clark St, Chicago, IL 60654, USA The Barrel Run
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4.6 based on 25 reviews

There’s never been a better time to be a beer drinker — and Chicago, with its thriving brewery scene and many destination-worthy beer bars, is the perfect city for suds lovers. Visit four of its craft breweries on this all-inclusive, 3.5-hour tour, where you’ll get to tour brewery production facilities and enjoy copious samples of local brews. To keep things interesting, you’ll travel in a barrel-shaped bus. Morning and evening departure times are both available.

Inclusions: 45-55 ounces of craft beer, Professional guide, Live commentary on board, Transport by climate-controlled barrel bus

Exclusions: Gratuities, Hotel pickup and drop-off

Reviewed By DAO1959

We have a great day with Barrel Run team. They were in good spirtis and the tour was top notch. I would recommend it to my friends. The team I was with loved it.

10. Go Chicago Explorer Pass with SkyDeck and 360 Chicago

Chicago, IL, USA Go Chicago
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4.3 based on 199 reviews

Create your own sightseeing itinerary with the Chicago Explorer Pass, saving up to 45% on ticket prices. This multi-attraction pass, valid for 60 days after your first use, provides admission to your choice of up to five attractions, tours or activities. Select from more than 30 top sites and things to do, including SkyDeck Chicago, Navy Pier and a Shoreline Architecture River Cruise. It's the easiest and most affordable way to explore the Windy City at your own pace. Simply save your pass on your mobile device (available as your 'ticket' after purchase) and go – no voucher redemption required! The pass also provides discounts at restaurants and retailers around the city.

Inclusions: Access to 2, 3, 4 or 5 attractions, activities or tours, FREE Digital guidebook with attraction information, Discounts and special offers at select restaurants and retailers

Exclusions: Transportation to/from attractions, Food & Drink unless stated, Gratuities

Reviewed By Travelbuglifer

Bought a 3 day go pass for St Patrick's Day weekend in Chicago. We went on the architecture river cruise and rode the Navy Pier ferris wheel on day 1. All other activities including museums, planetarium, and aquarium closed that night due to the pandemic. Go Pass refused to refund any part of the 3 day pass. So it cost $179 for each of us for 2 activities. This is corporate greed at its finest.

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