Chicago’s best tours cut straight to the city’s essentials. For architecture buffs, nothing beats the 90-minute river cruise, offering unmatched views of downtown’s soaring skyline. The guided Segway tours provide an efficient two-hour overview of major attractions, while neighborhood food tours showcase authentic local eats, from proper deep-dish pizza to classic Chicago dogs.
The evening ghost tours through River North are surprisingly informative, mixing true crime history with Chicago’s notorious gangster era. For active travelers, bike tours connect the downtown highlights with local neighborhoods, and the Michigan Avenue scavenger hunts make sightseeing interactive and fun.
Let’s explore the standout tours worth your time and money.
Key Points
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Chicago offers a diverse range of culinary tours, showcasing the city’s renowned pizza, hot dogs, and other signature dishes.
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Segway and walking tours provide an immersive way to explore Chicago’s landmarks, architecture, and neighborhoods.
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Historical, architectural, and crime-themed tours offer insights into the city’s rich past, from gangsters to haunted locations.
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Unique and themed tours, such as LGBTQ+ neighborhood exploration and evening crime tours, cater to specialized interests.
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Comprehensive city exploration and architecture tours combine sightseeing, river cruises, and detailed insights into Chicago’s iconic buildings and landmarks.
2-Hour Guided Segway Tour of Chicago
A 2-hour guided Segway tour provides visitors a unique opportunity to explore the highlights of Chicago. The tour takes participants through Millennium Park, Buckingham Fountain, and the Museum Campus, offering a balanced mix of flat and sloped segments.
Led by knowledgeable guides, the small group of up to 8 participants learns city history and insider facts during the tour.
Segway training and safety gear are provided, ensuring a safe and enjoyable experience. The meeting point is conveniently located near public transportation, making it accessible for most travelers.
However, the tour isn’t recommended for pregnant individuals and isn’t wheelchair accessible.
With an overall rating of 4.8/5 stars based on 422 reviews, the Segway Experience of Chicago tour is a highly recommended activity.
Positive feedback highlights the professionalism, knowledge, and humor of the guides. While some suggestions for improvement include office cleanliness and communication clarity, the tour remains a popular choice for those seeking a unique way to discover the city.
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Michigan Avenue Rendezvous Walking Tour With Smartphone App
The Michigan Avenue Rendezvous Walking Tour with Smartphone App offers a unique and interactive experience for exploring Chicago’s renowned Michigan Avenue. This 2-hour walking tour, priced at $15.63 per person, allows participants to discover hidden gems and iconic landmarks along the Magnificent Mile and Cultural Mile using a location-based mobile app.
The tour features a scavenger hunt-style experience with trivia and challenges that bring the city’s history and culture to life. Participants can join anytime after booking and are provided instructions for downloading the Leplace World app, which guides them through each step of the journey.
While the tour isn’t suitable for individuals with mobility impairments, visually impaired, or those over 80 years old, it promises an engaging and informative way to explore Chicago’s vibrant urban landscape.
With free cancellation up to 24 hours in advance and a pay-later option, the Michigan Avenue Rendezvous Walking Tour is a convenient and flexible way to discover the city.
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Bikes, Bites, and Brews: Chicagos Signature Dishes Bike Tour
What better way to experience the iconic flavors of Chicago than on the Bikes, Bites, and Brews: Chicago’s Signature Dishes Bike Tour? This half-day outing covers approximately 13 miles, guiding participants through Wrigleyville, Old Town, Lincoln Park, and the Gold Coast.
Rated 4.9 stars from 616 reviews, the tour is a hit with 99% of travelers. Led by expert local guides, the tour offers generous samples of Chicago’s famous foods, including deep-dish pizza, Chicago-style hot dogs, and decadent brownies.
Between bites, cyclists will visit two local breweries to sip on craft beer specialties. Key sights along the way include the Lincoln Park Zoo, Navy Pier, and Buckingham Fountain.
Suitable for ages 16 and up, the tour has a manageable pace and requires a moderate fitness level. At $89 per person, the Bikes, Bites, and Brews tour provides an engaging and delicious way to explore the Windy City’s culinary and cultural highlights.
With rave reviews and a high recommendation rate, it’s an excellent choice for groups, families, and first-time visitors to Chicago.
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Chicago Downtown Tour
Exploring the heart of Chicago, the Downtown Tour offers visitors a comprehensive introduction to the city’s iconic landmarks and hidden gems.
This 1.5-2 hour excursion showcases the architectural marvels that have made Chicago a global leader in design, from the soaring Willis Tower to the striking Art Institute of Chicago.
Along the way, guests can admire the neo-gothic façade of the Chicago Theatre, the striking bridges that span the Chicago River, and the lively energy of Navy Pier.
For those seeking a more immersive experience, the tour also includes a 45-minute family-friendly architecture river cruise, providing a unique perspective of the city’s skyline.
With a range of ticket options, including the CityPASS that grants access to five top attractions, the Downtown Tour caters to a variety of budgets and interests, making it an essential part of any Chicago itinerary.
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Chicago: Gangsters and Ghosts Walking Tour
Offering a captivating glimpse into Chicago’s notorious past, the Chicago Gangsters and Ghosts Walking Tour takes visitors on a journey through the city’s shadowy underworld.
With an impressive 7,132 reviews and a 95% recommendation rate, this two-hour walking tour is a must-do for anyone interested in Chicago’s rich history.
Led by knowledgeable historians, the tour explores the city’s Roaring Twenties era, delving into tales of bootleggers, speakeasies, and infamous gangsters like Al Capone.
Guests will visit iconic sites such as the Palmer House, Congress Hotel, Millennium Park, and the Chicago Riverwalk, all while seeing ghost stories and captivating narratives.
The tour’s engaging storytelling and enthusiastic guides have earned praise from travelers, who highlight the clarity, enthusiasm, and ability to keep the group engaged despite the city’s noise.
While the tour isn’t wheelchair accessible, it’s suitable for those with moderate physical fitness.
With prices starting at €34.28 per person and free cancellation up to 24 hours before the event, the Chicago Gangsters and Ghosts Walking Tour is a compelling and accessible way to explore the city’s dark history.
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Chicago: Oktoberfest Walking Brewery Tour in Logan Square
Though the Chicago Gangsters and Ghosts Walking Tour provides a captivating glimpse into the city’s notorious past, the Chicago: Oktoberfest Walking Brewery Tour in Logan Square offers a unique opportunity to explore the city’s vibrant craft beer scene.
This 2.5-hour tour takes guests on a journey through the Logan Square neighborhood, known for its thriving craft beer culture. Visitors will enjoy tastings at three local breweries, getting an inside look at the brewing process and sampling some of the best beers the city has to offer.
The tour also includes a stop at a traditional German restaurant, where participants can indulge in authentic Oktoberfest fare. With knowledgeable guides, this experience provides an immersive and educational look at the burgeoning craft beer scene in Chicago’s Logan Square.
Whether you’re a beer enthusiast or simply looking to try something new, the Chicago: Oktoberfest Walking Brewery Tour is a must-do activity for visitors to the Windy City.
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Chicago River 90-Minute History and Architecture Tour
The Chicago River 90-Minute History and Architecture Tour provides an immersive journey through the city’s architectural legacy. Covering over 130 years of history, this highly-rated tour (92% recommended) takes travelers on a narrated exploration of iconic structures, including the Willis Tower, Merchandise Mart, and Wrigley Building.
Accommodating up to 300 people, the tour features indoor and outdoor seating options, allowing visitors to enjoy the sights in climate-controlled comfort or take in the fresh air. Along the way, the professionally-trained guides highlight the architectural significance of each landmark, enhancing the educational value of the experience.
With positive reviews praising the informative guides and breathtaking views, the Chicago River 90-Minute History and Architecture Tour stands out as a must-do activity for anyone seeking to enjoy the city’s rich architectural heritage.
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Tour Chicago LGBTQ+ Style
Enjoy Chicago’s vibrant LGBTQ+ heritage through the captivating Tour Chicago LGBTQ+ Style. This 2-hour guided adventure explores the city’s historic LGBTQ+ neighborhoods, including Downtown Chicago, Boystown, and Andersonville.
Along the way, you’ll learn about the LGBTQ+ rights movement and discover iconic landmarks that shaped the community’s history. The tour combines walking and bus transportation, allowing you to experience the city’s diverse LGBTQ+ culture.
Highlights include the Jane Addams Hull-House Museum and the First Ward Ball, where you’ll gain insights into the community’s rich past. At the end of the tour, you can unwind with two complimentary mimosas at a local pub.
Suitable for participants aged 13 and older, the tour is designed to exceed guest expectations. Chicago Be Free Tours™ is dedicated to showcasing the city as the best Gay City in the world.
With free cancellation and the option to reserve now and pay later, this tour is a must-do for anyone interested in exploring Chicago’s LGBTQ+ history and culture.
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Chicago Evening Crime Tour by Bus
Although Chicago is renowned for its vibrant cultural attractions, the city also boasts a captivating criminal past that continues to intrigue visitors. The Chicago Evening Crime Tour by Bus offers a unique opportunity to explore the lives of notorious mobsters, visit infamous crime scenes, and explore the city’s colorful history of lawlessness.
Lasting 2.5 hours, the tour departs at 7:30 PM from a meeting point in downtown Chicago. Traveling by luxury coach, guests can expect live narration from knowledgeable guides, as well as access to Prohibition-era tunnels, a mini mob museum, and other immersive experiences.
With a maximum capacity of 39 travelers, the tour provides an intimate and engaging exploration of Chicago’s underworld, from the St. Valentine’s Day Massacre to the haunts of Al Capone and Bugs Moran.
Highly recommended by past participants, the Chicago Evening Crime Tour offers a captivating blend of education and entertainment, catering to those fascinated by the city’s shadowy history.
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Chicago: Magnificent Mile Walking Tour
Spanning 1.5 hours, the Chicago: Magnificent Mile Walking Tour offers visitors an in-depth exploration of the city’s premier shopping district and its architectural wonders.
With a live English-speaking guide, the tour takes participants on a journey through the transformation of Pine Street into the iconic Magnificent Mile. Along the way, you’ll marvel at architectural icons like the Tribune Tower, Wrigley Building, and 875 N. Michigan Ave. (formerly Hancock Tower), each showcasing diverse styles from Parisian to Art Deco.
Inside the Medinah Athletic Club, you’ll admire the stunning Egyptian and Renaissance-inspired decor, as well as the bas relief sculptural panels in an Art Deco office building.
The tour’s $30 per person price tag includes admission to the Galleries of the Chicago Architecture Center, supporting the organization’s education initiatives.
While the tour is wheelchair accessible, it’s not suitable for those with mobility impairments.
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Chicago City Tour With Architecture River Cruise Option
The Chicago City Tour with Architecture River Cruise Option provides visitors a comprehensive exploration of the city’s renowned landmarks and architectural wonders.
This small-group tour, limited to just 10 passengers, offers a personalized experience aboard a climate-controlled, air-conditioned minibus. The tour showcases key attractions, including the Museum Campus, Buckingham Fountain, and the iconic Rookery Building, along with panoramic views of Lake Michigan and Chicago’s notable neighborhoods.
Guests can choose to upgrade their experience with an open-top boat tour on the Chicago River, focusing on the city’s impressive architecture and historical significance.
With four designated photo stops, the tour allows visitors to capture memorable moments. The expert guide provides insightful historical and cultural commentary throughout the excursion.
Highly praised for its knowledgeable guides, efficient organization, and intimate group size, this tour is an excellent choice for those seeking to efficiently explore Chicago’s highlights.
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Chicago River: 90-Min Architecture Boat Tour
For those seeking a deeper dive into Chicago’s renowned architectural heritage, the Chicago River: 90-Min Architecture Boat Tour offers an immersive experience. Rated 4.8 out of 5 stars by over 5,900 reviews on GetYourGuide, this guided cruise along the Chicago River provides a unique perspective on the city’s iconic buildings.
The 90-minute tour skips the line, allowing guests to maximize their time admiring the stunning architecture. From the comfort of a boat, participants gain insights into the design and history of landmarks such as the Willis Tower, the Merchandise Mart, and the Lyric Opera House.
The knowledgeable guide shares fascinating stories, bringing the city’s rich architectural legacy to life.
At $45 per person, the Chicago River: 90-Min Architecture Boat Tour is an affordable and convenient way to explore Chicago’s architectural wonders. Whether you’re a first-time visitor or a local seeking a new perspective, this cruise provides an engaging and immersive experience that isn’t to be missed.
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Chicago Lake and River Architecture Tour
This comprehensive 45-minute Chicago Lake and River Architecture Tour allows visitors to discover the city’s iconic landmarks from a unique vantage point.
Cruising along Lake Michigan’s 26-mile shoreline, the tour provides stunning views of the Chicago skyline and its landmark buildings. With 2,012 reviews and a 93% recommendation from travelers, this architectural tour is a must-see activity in Chicago.
Accompanied by a knowledgeable local guide, the tour offers live commentary on the city’s rich architectural history.
Passengers can enjoy the experience from the indoor and outdoor climate-controlled seating, with the option to purchase snacks and drinks. The tour is stroller-accessible, and service animals are allowed, making it suitable for families and all ages.
With a badge of excellence and a lowest price guarantee, this tour is an excellent value for visitors looking to explore Chicago’s breathtaking landscape from the water.
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Lincoln Park Haunted History Walking Ghost Tour
Nestled within the historic Lincoln Park, the Lincoln Park Haunted History Walking Ghost Tour takes visitors on a captivating journey through the district’s eerie past. Lasting 2.5 hours and priced from €37.40 per person, this guided tour offers a unique opportunity to explore the haunted sites and uncover the spooky secrets of the area.
Participants will start their adventure at the Chicago History Museum, where they’ll learn about the rumored hauntings surrounding Abraham Lincoln’s deathbed. The tour then leads them to the last marked grave of the Chicago Cemetery, the Couch Tomb, and the Lincoln Park Zoo, which was built upon the ashes of the Great Fire.
Visitors will also hear chilling tales about Café Brauer’s history as a Prohibition-era speakeasy and the notorious St. Valentine’s Day Massacre site.
Throughout the tour, guests will become ghost hunters, using paranormal equipment and engaging with spectral evidence. With photo stops at various haunted locations, this immersive experience combines history, mystery, and the paranormal, making it a must-try for anyone seeking a truly unique adventure in Chicago.
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Chicago Walking Food Tour With Secret Food Tours
Offering a delightful blend of culinary exploration and sightseeing, the Chicago Walking Food Tour with Secret Food Tours invites participants to discover the city’s vibrant food scene and iconic landmarks.
With a near-perfect 98% recommendation rate from previous travelers, this two-in-one walking tour is a must-do experience in Chicago.
Over the course of the tour, guests will savor classic Chicago fare, including deep-dish pizza, Chicago-style hot dogs, and a secret dish revealed on the day.
Along the way, they’ll also visit landmarks like the Willis Tower and the Rookery Building, gaining insights from a knowledgeable local guide.
The tour, which accommodates a maximum of 12 travelers, includes hotel pickup and drop-off, and offers the flexibility of free cancellation up to 24 hours in advance.
Whether you’re a foodie or a sightseer, the Chicago Walking Food Tour promises an unforgettable adventure through the heart of the Windy City.
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The Best of Chicago in 2H Walking Tour
Travelers seeking a comprehensive exploration of downtown Chicago’s iconic landmarks and architecture can embark on the two-hour “The Best of Chicago in 2H Walking Tour.”
This guided walking excursion takes participants on an immersive journey through the heart of the city, showcasing its renowned skyscrapers, historic theaters, and picturesque public spaces.
Priced from $40 per person, the tour offers free cancellation and a “reserve now, pay later” option, making it accessible and flexible.
Highlights include visiting Cloud Gate, the famous sculpture in Millennium Park, and Garrett’s Popcorn, a beloved local institution since 1949. Participants will also marvel at the grand Chicago Theatre and potentially conclude their tour along the scenic Riverwalk.
Led by knowledgeable guides, the experience promises an engaging and informative exploration of Chicago’s rich cultural and architectural heritage.
This tour is recommended for active travelers, as it involves walking and isn’t suitable for those with mobility challenges.
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Chicago Favorites Ultimate Food and Walking Tour
The “Chicago Favorites Ultimate Food and Walking Tour” offers an immersive exploration of the city’s renowned culinary and cultural landscape. Boasting 1,413 reviews and a 96% traveler recommendation, this 3-hour, 1.5-mile walking tour takes visitors on a delicious journey through iconic Chicago landmarks and neighborhoods.
Participants can indulge in 4-5 food tastings, including deep-dish pizza, Chicago-style hot dogs, and the original brownie recipe. Local craft beer samples are available for an additional fee. The tour is wheelchair accessible and stroller-friendly, with dietary restrictions accommodated.
Guided by local experts, the experience provides historical insights and architectural highlights, with alternative routes available in colder months. Reviewers praise the knowledgeable guides and enjoyable food experiences, making this tour a fantastic way to discover the best of Chicago’s food scene and cultural heritage.
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Walkin With Colin: Chicago Tour Du Jour
Walkin with Colin: Chicago Tour du Jour offers a two-hour immersive exploration of the city’s rich history, art, and architecture. Priced at $44 per person, this limited-group tour (up to 10 participants) is led by a top-rated professional guide and showcases iconic cultural landmarks and hidden gems.
Highlights include the Chagall’s Four Seasons, the Marquette Building, and the Chicago Picasso Statue, among others.
The tour’s focus on engaging storytelling and extraordinary buildings and art installations makes it an ideal choice for curious minds and those interested in cultural experiences.
With a 5-star overall rating and 100% recommendation from travelers, this tour provides an exceptional value. Participants can conveniently reserve and pay later, and cancellations up to 24 hours in advance are eligible for a full refund.
Whether you’re a local or a visitor, the Walkin with Colin: Chicago Tour du Jour is a must-try for anyone seeking a captivating glimpse into the city’s vibrant cultural heritage.
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Chicago Crime and Mob Bus Tour
Offering a captivating alternative to the cultural heritage exploration of the Walkin with Colin tour, the Chicago Crime and Mob Bus Tour invites visitors on a thrilling journey through the city’s notorious gangster past.
Boasting a 90% recommendation from travelers and a Badge of Excellence, the tour provides an immersive experience aboard a luxury air-conditioned coach. Guests will discover the stories of infamous criminals like Al Capone and John Dillinger, with stops at key locations such as the Biograph Theatre and the site of the St. Valentine’s Day Massacre.
The live interactive guide shares fascinating insights, while photo opportunities at crime scenes and access to Prohibition Era tunnels enhance the tour. Complementing the engaging content, the inclusion of a mini mob museum and historic video footage ensures a comprehensive and memorable exploration of Chicago’s underworld history.
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Chicago: Small-Group History and Architecture Walking Tour
Immersing visitors in Chicago’s captivating history and architectural marvels, the Chicago: Small-Group History and Architecture Walking Tour offers an engaging and informative exploration of the city’s iconic landmarks.
Priced at €46.98 per person and lasting 2.5 hours, this small-group tour (limited to 10 participants) guides travelers through the city’s highlights, including the renowned Cloud Gate (“The Bean”), the scenic Chicago Riverwalk, and the unique Chicago Pedway.
Along the way, knowledgeable guides share insights into the city’s resilience and the evolution of its architecture, from the Tribune Tower to the Magnificent Mile.
Offering optional add-ons like a street food experience and a visit to the Starbucks Reserve Roastery, the tour provides a comprehensive and flexible experience.
Highly praised by past participants for its informative nature and engaging format, this walking tour is an excellent choice for anyone seeking to uncover the rich history and design of Chicago.
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Chicago in a Day: Food, History and Architecture Walking Tour
This comprehensive Chicago in a Day: Food, History and Architecture Walking Tour provides visitors with a captivating exploration of the city’s iconic landmarks, rich culinary scene, and storied past.
Spanning approximately 5 hours and covering 3-4 miles, the tour immerses guests in Chicago’s diverse heritage through carefully curated food stops, guided narration, and up-close encounters with architectural masterpieces.
Participants can expect to sample deep-dish pizza, Italian beef sandwiches, Chicago-style hot dogs, and classic popcorn, equating to a full meal’s worth of generous tastings.
Along the way, the knowledgeable local guides regale travelers with insights into the city’s Prohibition Era legacy and other fascinating historical anecdotes.
With a maximum group size of 12, the tour offers personalized attention and ample opportunities for questions and discussion.
Wheelchair-accessible and suitable for all ages and fitness levels, this highly-rated experience earns a 98% recommendation rate from previous visitors.
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Chicago: West Town Walking Tour
The West Town Walking Tour takes visitors on an immersive exploration of one of Chicago’s most vibrant and culturally diverse neighborhoods. Located just west of the downtown area, West Town boasts a rich history and a thriving arts, music, and culinary scene.
Priced at $29.00 and lasting 2 hours, this highly rated tour (4.9 out of 5 from 170 reviews) offers an insider’s perspective on the neighborhood’s architecture, hidden gems, and community spirit.
Guests can expect to discover the area’s eclectic mix of modern and historic buildings, including the iconic Ukrainian Village and Wicker Park districts.
Along the way, the knowledgeable guides share stories about the neighborhood’s evolution and its influential role in shaping Chicago’s cultural identity.
Whether you’re a first-time visitor or a local seeking to uncover new layers of the city, the West Town Walking Tour provides an engaging and insightful experience.
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Chicago River 45-Minute Architecture Tour From Magnificent Mile
Visitors can embark on a captivating 45-minute architecture tour along the Chicago River, departing from the Magnificent Mile. This family-friendly excursion is suitable for all ages and offers live commentary on the city’s rich history and architectural heritage.
The tour showcases key landmarks, including the iconic Chicago Riverwalk, Michigan Avenue Bridge, Wrigley Building, and Willis Tower. Travelers can enjoy the indoor and outdoor seating on a first-come, first-served basis, with a climate-controlled lounge for comfort.
Onboard amenities include restrooms, snacks, drinks, and souvenirs. While the tour isn’t wheelchair accessible, it’s stroller-friendly and near public transportation.
With an impressive 92% recommendation rate and a 4.7 rating from 1,948 reviews, this architectural river cruise is a must-do experience for visitors looking to explore Chicago’s stunning cityscape.
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Chicago: Ghost Bus Tour of Haunted Locations
Offering a spooky adventure through Chicago’s haunted hotspots, the Ghost Bus Tour led by renowned paranormal researcher Ursula Bielski takes visitors on a 3-hour journey to uncover the city’s supernatural side.
Departing from the Congress Plaza Hotel, the tour visits several locations with eerie pasts, including the Lincoln Park Zoo, Jane Addams Hull-House Museum, and the Nederlander Theatre. Along the way, participants have the chance to capture evidence of the paranormal with cameras and recorders.
The tour also highlights key sites of interest, such as the Eastland Disaster site, where a tragic accident took 844 lives, and the infamous “Death Alley,” the location of a major theater fire.
Travelers ride in a luxury bus equipped with a bathroom, ensuring a comfortable experience. While not suitable for young children, the Ghost Bus Tour offers an engaging and educational exploration of Chicago’s haunted history for those brave enough to uncover the city’s supernatural secrets.
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Chicago Pizza Tour
Touted as one of the top food tours in Chicago, the Chicago Pizza Tour takes guests on a delectable journey through the city’s renowned pizza scene.
With over 400 glowing reviews and a 97% recommendation rate, this small-group guided tour showcases a variety of pizza styles, from deep dish to tavern-style and coal-fired.
Lasting a few hours and beginning at 11:00 am, the tour explores four different neighborhoods, stopping at significant pizzerias to sample four slices of pizza while learning about Chicago’s rich pizza culture.
The tour includes transportation by air-conditioned mini-coach, local guide commentary, and gratuities, all for a starting price of $89 per person.
While not wheelchair accessible, the tour operates in all weather conditions, making it a suitable option for both travelers and locals.
Reviewers consistently praise the knowledgeable and entertaining guides, particularly highlighting the “James” guide, and the overall fun and informative nature of the experience.
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Sum Up
Chicago offers a diverse array of tours showcasing the city’s rich history, architecture, and culinary delights. From guided Segway tours to walking tours highlighting gangsters and ghosts, there’s something for every visitor’s interest. With options ranging from bike tours to river cruises, travelers can explore Chicago’s iconic landmarks and discover its unique neighborhoods. These tours provide an engaging and informative way to experience the city’s vibrant culture and sights.