The 14 Best Chicago 2024 Tours

There are plenty of Chicago tours to choose from that will appeal to those who love food, architecture, and history. These tours offer a great way to experience the city’s vibrant culture and to get to know its rich history. Plus, you’ll get to sample local cuisine and explore the stunning architecture that the city is known for. We have listed below The 14 Best Chicago 2024 Tours that you can always make your most preferable choice from.

The experience of exploring a new city is more enjoyable when you have a local guide along. Because of this, Enigma Guides has put together a list of 14 top-notch guided Chicago Tours. These experiences will give you a deeper appreciation of Chicago’s culture and history, whether you’re sightseeing along the river to see the Willis Tower or sampling the city’s famous deep-dish pizza.

1. Chicago Pizza Tours – Original Chicago Pizza Tour:

This tour offers a delicious exploration of Chicago’s renowned pizza scene. Participants get to taste various styles of pizza while learning about the history and culture of Chicago’s pizza-making tradition. Reviewers may praise the tour for its delicious pizza selections, knowledgeable guides who offer insights into the city’s pizza culture, and the overall fun and enjoyable experience. Criticisms might include issues with pacing or crowded tour groups.

• Description: Experience Chicago’s renowned pizza scene on this guided tour, tasting various styles of pizza and learning about its history.
• Ticket Fee: Around $50-$70 per person.

2. Chicago Crime Tours:

Delve into the darker side of Chicago’s history with this tour, which takes visitors to infamous crime scenes and provides insight into the city’s mobster past and notorious criminals. Reviewers might appreciate the tour’s fascinating stories about Chicago’s criminal history, engaging guides, and the opportunity to visit notable crime scenes. However, some reviewers may find the content too dark or sensationalized.

• Description: Explore Chicago’s darker history of crime and corruption, visiting historic crime scenes and landmarks with knowledgeable guides.
• Ticket Fee: Approximately $40-$60 per person.

3. Inside Chicago Walking Tours – Dazzling Interiors of the Loop:

This tour takes participants inside some of Chicago’s most architecturally stunning buildings, offering a behind-the-scenes look at their interiors and the stories behind their design. Positive reviews may highlight the tour’s unique access to stunning architectural interiors, informative guides, and the chance to learn about the hidden gems of Chicago’s Loop area. Criticisms might include limited availability or high ticket prices.

• Description: Delve into the architectural wonders of Chicago’s Loop district, discovering hidden interiors and learning about the city’s rich history.
• Ticket Fee: Typically $25-$40 per person.

4. City Cruises by Hornblower – Seadog Lakefront Speedboat Tour:

Experience the thrill of speeding along Lake Michigan’s shoreline on a Seadog speedboat tour. Enjoy exhilarating views of Chicago’s skyline while learning about the city’s landmarks from the water. Reviewers may commend the tour for its thrilling speedboat ride, spectacular views of the skyline, and knowledgeable narration. However, some reviewers might mention concerns about rough waters or motion sickness.

• Description: Experience the thrill of a speedboat tour along Chicago’s lakefront, with spins and views of landmarks accompanied by historical narration.
• Ticket Fee: Around $30-$50 per person.

5. Chicago Food Planet – Gateway to the West Loop Food Tour:

Food enthusiasts can indulge in this tour, which explores the culinary delights of Chicago’s West Loop neighborhood. Sample a variety of dishes while discovering the area’s vibrant food scene. Positive feedback might focus on the delicious food samplings, knowledgeable guides who share insights into the local culinary scene, and the variety of eateries visited. Criticisms could include small portion sizes or high prices.

• Description: Chicago Food Planet offers a guided culinary tour through the vibrant West Loop neighborhood, known for its diverse food scene and trendy eateries.
• Ticket Fee: Approximately $60-$80 per person.

6. Chicago Prohibition Tour – Original:

Step back in time to the era of Prohibition with this tour, which immerses participants in the sights and sounds of 1920s Chicago. Learn about the city’s speakeasies, gangsters, and the prohibition era’s impact on Chicago’s culture. Reviewers might enjoy the immersive experience of stepping back into Chicago’s Prohibition era, engaging guides, and the opportunity to visit historic speakeasies. However, some reviewers might find the tour too focused on the past or lacking in interactive elements.

• Description: Step back in time to the Prohibition era, exploring Chicago’s history of crime and speakeasies with expert guides.
• Ticket Fee: Typically $30-$50 per person.

7. Absolutely Chicago Segway Tours – Chicago Lakefront/Museum Campus:

Glide along Chicago’s picturesque lakefront and explore its iconic museum campus on a Segway tour. Enjoy panoramic views of the city’s skyline and learn about its history and landmarks along the way. Positive reviews may highlight the fun and ease of riding a Segway, beautiful lakefront views, and informative commentary from guides. Criticisms might include safety concerns or issues with equipment maintenance.

• Description: Explore Chicago’s picturesque lakefront and Museum Campus on a Segway, while indulging in a variety of local cuisines.
• Ticket Fee: Around $70-$90 per person.

8. Chicago Architecture Foundation River Cruise:

Discover the architectural wonders of Chicago from the comfort of a boat on the Chicago River. Learn about the city’s famous buildings and skyscrapers while cruising past them on this informative tour. Reviewers might praise the tour for its breathtaking views of Chicago’s skyline, informative architectural commentary, and comfortable boat accommodations. However, some reviewers may find the tour too long or repetitive.

• Description: Cruise along the Chicago River while learning about the city’s architecture from expert guides, offering unique perspectives on the skyline.
• Ticket Fee: Around $40-$50 per person.

9. Big Bus Chicago Hop-On Hop-Off Tour:

Explore Chicago at your own pace with this hop-on hop-off bus tour. Visit top attractions and landmarks while enjoying informative commentary and the flexibility to disembark and rejoin the tour at your leisure. Positive feedback might focus on the convenience of exploring Chicago’s attractions at one’s own pace, informative commentary provided during the tour, and the accessibility of the hop-on hop-off system. Criticisms could include crowded buses or long wait times.

• Description: Enjoy a flexible sightseeing experience aboard a double-decker bus, with stops at major landmarks and attractions throughout Chicago.
• Ticket Fee: Typically $40-$50 per person for a day pass.

10. Urban Kayak Chicago Riverwalk – Historic Chicago Tour:

Paddle along the Chicago River and soak in the city’s history on this kayak tour. Glide past iconic landmarks and learn about Chicago’s past from knowledgeable guides. Reviewers may appreciate the unique perspective of exploring Chicago’s history from the water, knowledgeable guides, and the peacefulness of kayaking along the river. However, some reviewers might mention concerns about safety or physical exertion.

• Description: Paddle along the Chicago Riverwalk, taking in the city’s skyline and historical landmarks while learning about its heritage.
• Ticket Fee: Approximately $40-$60 per person.

11. Bobby’s Bike Hike Chicago – Bikes, Bites & Brews Tour – Signature Dishes:

Combine biking, eating, and drinking on this tour that explores Chicago’s culinary scene. Sample signature dishes and local brews while pedaling through the city’s neighborhoods. Positive reviews might highlight the enjoyable combination of biking, eating, and drinking, delicious food samples, and engaging guides. Criticisms could include difficulties keeping up with the group or issues with bike maintenance.

• Description: Pedal through Chicago’s neighborhoods, sampling signature dishes and craft brews while learning about the city’s culture.
• Ticket Fee: Approximately $60-$80 per person.

12. Tall Ship Windy – Chicago Skyline Sail:

Sail along Lake Michigan aboard the Tall Ship Windy and admire Chicago’s skyline from the water. Enjoy breathtaking views and learn about the city’s architecture and history from the crew. Reviewers might commend the tour for its scenic sail along Lake Michigan, friendly crew, and educational commentary about Chicago’s architecture. However, some reviewers might mention discomfort due to motion sickness or limited seating options.

• Description: Sail on Lake Michigan aboard a tall ship, enjoying panoramic views of Chicago’s skyline and learning about its maritime history.
• Ticket Fee: Typically $30-$50 per person.

13. Tastebud Tours – Taste of Chicago:

Indulge in a culinary adventure through Chicago’s diverse neighborhoods with this tasting tour. Sample a variety of dishes representing the city’s rich food culture. Positive feedback may focus on the diverse selection of food tastings, knowledgeable guides who share insights into Chicago’s culinary scene, and the overall value of the tour. Criticisms might include long walking distances or crowded tour groups.

• Description: Immerse yourself in Chicago’s culinary delights with this guided tasting tour, sampling a variety of dishes from top eateries.
• Ticket Fee: Approximately $60-$80 per person.

14. Shoreline Sightseeing – Skyline Lake Tours:

Relax on a leisurely cruise along Lake Michigan with Shoreline Sightseeing. Enjoy panoramic views of Chicago’s skyline and landmarks while learning about the city’s history and architecture. Reviewers might appreciate the tour for its stunning views of Chicago’s skyline, comfortable boat accommodations, and informative narration about the city’s landmarks. However, some reviewers might mention concerns about weather-dependent cancellations or overcrowded boats.

• Description: Cruise along Lake Michigan for stunning views of Chicago’s skyline, with narration highlighting the city’s history and architecture.
• Ticket Fee: Around $25-$35 per person.

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