Best of 14 Road trips in Chicago
Discover our curated list of top-ranked Road trips in Chicago, compiled from extensive research across reputable websites and blogs. Explore outstanding options like Tours & Boats Architecture Tours, Wendella Tours & Cruises, Bobby's Bike Hike - Chicago Bike, Walking & Food Tours, Chicago Crime Tours and Experiences - Gangsters, Mobsters and Criminals, Chicago Detours. Let's explore together!
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- 1. Tours & Boats Architecture Tours
- 2. Wendella Tours & Cruises
- 3. Bobby's Bike Hike - Chicago Bike, Walking & Food Tours
- 4. Chicago Crime Tours and Experiences - Gangsters, Mobsters and Criminals
- 5. Chicago Detours
- 6. Rek Travel - travel agency - biuro podróży
- 7. Choose Chicago
- 8. Chicago Travel & Tours
- 9. The Road Less Traveled
- 10. Two Lane America
- 11. Sidewalk Food Tours of Chicago
- 12. Drive the US
- 13. Oasis Travel
- 14. Trans Adventure Tours
1. Tours & Boats Architecture Tours
Historic river tour with expert guides
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The architectural boat tour in Chicago was an informative and enjoyable experience for a family revisiting the city. A knowledgeable guide provided interesting insights about the buildings, making the tour valuable for anyone.
Visiting Chicago after living there, the family wanted to show their teenage children the city's unique architectural landscape and history. The boat tour proved to be an excellent introduction, leaving them with a positive impression of the city's architectural heritage.
The architectural boat tour in Chicago was an informative and enjoyable experience for a family revisiting the city. A knowledgeable guide provided interesting insights about the buildings, making the tour valuable for anyone.
Visiting Chicago after living there, the family wanted to show their teenage children the city's unique architectural landscape and history. The boat tour proved to be an excellent introduction, leaving them with a positive impression of the city's architectural heritage.
2. Wendella Tours & Cruises
Historic boat tours since 1935
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A road trip to Chicago led to an exciting discovery - Wendella Tours & Cruises. The highlight of the tour was the architecture cruise on the river, providing a unique and fascinating view of the city. It is highly recommended for anyone visiting Chicago.
During our road trip, we stumbled upon Wendella Tours & Cruises and decided to give it a try. The boat tour offered a different perspective of the city and was a great addition to our trip. The experience was enjoyable and informative, making it a recommended activity for tourists.
A road trip to Chicago led to an exciting discovery - Wendella Tours & Cruises. The highlight of the tour was the architecture cruise on the river, providing a unique and fascinating view of the city. It is highly recommended for anyone visiting Chicago.
During our road trip, we stumbled upon Wendella Tours & Cruises and decided to give it a try. The boat tour offered a different perspective of the city and was a great addition to our trip. The experience was enjoyable and informative, making it a recommended activity for tourists.
3. Bobby's Bike Hike - Chicago Bike, Walking & Food Tours
Eco-friendly, Local Guides
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Bobby's Bike Hike offered an amazing tour of Chicago. The tour was well-supported by knowledgeable guides, with Lizzie assisting during the ride and Ian providing insights into the city's history and sights. The route was designed to include unique locations that were otherwise hard to find.
Initially, I felt nervous about riding a bike after such a long time, but the tour was designed to accommodate all levels. The stops featured delicious treats like pizza, cupcakes, and hotdogs, which filled us up and kept our energy levels high. Overall, the bike tour was a standout experience in Chicago, and I look forward to joining more tours with Bobby's Bike Hike in the future.
Bobby's Bike Hike offered an amazing tour of Chicago. The tour was well-supported by knowledgeable guides, with Lizzie assisting during the ride and Ian providing insights into the city's history and sights. The route was designed to include unique locations that were otherwise hard to find.
Initially, I felt nervous about riding a bike after such a long time, but the tour was designed to accommodate all levels. The stops featured delicious treats like pizza, cupcakes, and hotdogs, which filled us up and kept our energy levels high. Overall, the bike tour was a standout experience in Chicago, and I look forward to joining more tours with Bobby's Bike Hike in the future.
4. Chicago Crime Tours and Experiences - Gangsters, Mobsters and Criminals
Interactive and informative crime tour
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The guided tour was a standout experience during our road trip. Our guide's expertise brought the history and stories of the area to life, making it a memorable visit for anyone exploring Chicago. It is highly recommended as a must-do activity for any traveler.
The tour offered a perfect blend of education and entertainment. With numerous stops for photo opportunities and exploration, it provided a fun and engaging experience. Its combination of informative content and chances to explore made it an ideal addition to our road trip itinerary.
The guided tour was a standout experience during our road trip. Our guide's expertise brought the history and stories of the area to life, making it a memorable visit for anyone exploring Chicago. It is highly recommended as a must-do activity for any traveler.
The tour offered a perfect blend of education and entertainment. With numerous stops for photo opportunities and exploration, it provided a fun and engaging experience. Its combination of informative content and chances to explore made it an ideal addition to our road trip itinerary.
5. Chicago Detours
Unique, off-the-beaten-path tours
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Chicago Detours offers unique and engaging road trips for tourists and long-term residents alike. Their tours provide a deep dive into the history and culture of Chicago, offering a fresh perspective on the city. The company prides itself on delivering well-organized and informative experiences that are far from the typical bus tour.
Whether you're a history buff, an architecture enthusiast, or just love exploring new places, Chicago Detours has a tour for you. From uncovering hidden gems to learning about Chicago's notorious gangsters, their tours are designed to educate and entertain. With a team of knowledgeable and passionate guides, you'll come away with a newfound appreciation for the Windy City.
Chicago Detours offers unique and engaging road trips for tourists and long-term residents alike. Their tours provide a deep dive into the history and culture of Chicago, offering a fresh perspective on the city. The company prides itself on delivering well-organized and informative experiences that are far from the typical bus tour.
Whether you're a history buff, an architecture enthusiast, or just love exploring new places, Chicago Detours has a tour for you. From uncovering hidden gems to learning about Chicago's notorious gangsters, their tours are designed to educate and entertain. With a team of knowledgeable and passionate guides, you'll come away with a newfound appreciation for the Windy City.
6. Rek Travel - travel agency - biuro podróży
Customized travel packages
Seeking an unforgettable vacation? Look no further than REK Travel, where my mom embarked on a sensational Hawaii getaway. Every detail was expertly arranged for a relaxing and enjoyable trip, from beach frolics to volcano explorations. Without a doubt, one of my most cherished travel experiences, all thanks to the exceptional job done by REK Travel agency. The tour guides, Izabela and Rafał, were not only supremely organized but also imparted a wealth of fascinating insights, making the journey truly remarkable.
7. Choose Chicago
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Chicago is an excellent starting point for road trips, with a range of destinations offering diverse experiences. To the east lies the pristine coastline of Lake Michigan, a scenic drive with various stops and activities to enjoy. Head southwest, and you'll reach Memphis, a city steeped in music history and soulful tunes.
The Midwest has much to offer, with historical cities, stunning national parks, and great brews all within driving distance from Chicago. To the north, you can explore the wild landscapes of the Great Smoky Mountains, while to the west, you'll find the great breweries that line the way to Minneapolis. Each route offers its unique charm and highlights, making road trips from Chicago an unforgettable adventure.
Chicago is an excellent starting point for road trips, with a range of destinations offering diverse experiences. To the east lies the pristine coastline of Lake Michigan, a scenic drive with various stops and activities to enjoy. Head southwest, and you'll reach Memphis, a city steeped in music history and soulful tunes.
The Midwest has much to offer, with historical cities, stunning national parks, and great brews all within driving distance from Chicago. To the north, you can explore the wild landscapes of the Great Smoky Mountains, while to the west, you'll find the great breweries that line the way to Minneapolis. Each route offers its unique charm and highlights, making road trips from Chicago an unforgettable adventure.
8. Chicago Travel & Tours
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A must-visit location for any American road trip is the iconic Route 66, which begins in the city of Chicago. Travelers can take a picture at the official Route 66 sign located between East Adams and South Michigan Avenue, and make stops at notable sites such as the Gemini Giant, Pontiac murals, and the Lincoln Presidential Library.
Chicago is not only a great starting point for Route 66 but also for various other exciting Chicago road trips. The city's central location in the Midwest provides easy access to numerous historical cities, scenic state parks, and stress-relieving breweries.
A must-visit location for any American road trip is the iconic Route 66, which begins in the city of Chicago. Travelers can take a picture at the official Route 66 sign located between East Adams and South Michigan Avenue, and make stops at notable sites such as the Gemini Giant, Pontiac murals, and the Lincoln Presidential Library.
Chicago is not only a great starting point for Route 66 but also for various other exciting Chicago road trips. The city's central location in the Midwest provides easy access to numerous historical cities, scenic state parks, and stress-relieving breweries.
9. The Road Less Traveled
10. Two Lane America
11. Sidewalk Food Tours of Chicago
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Exploring Wicker Park in Chicago was a delightful way to experience the city. By viewing it from a tourist's perspective, Chicago residents were able to discover local gems that contribute to the city's rich diversity.
Taking the River North tour with Jake was an excellent decision. This tour allowed us to see different parts of the city while sampling a variety of foods in both sit-down restaurants and casual, stand-and-eat establishments. We particularly enjoyed the pizza and were thrilled to have the opportunity to try food from Rick Bayless' restaurant. The tour provided a great balance of learning about the city's history and culture while satisfying our taste buds.
Exploring Wicker Park in Chicago was a delightful way to experience the city. By viewing it from a tourist's perspective, Chicago residents were able to discover local gems that contribute to the city's rich diversity.
Taking the River North tour with Jake was an excellent decision. This tour allowed us to see different parts of the city while sampling a variety of foods in both sit-down restaurants and casual, stand-and-eat establishments. We particularly enjoyed the pizza and were thrilled to have the opportunity to try food from Rick Bayless' restaurant. The tour provided a great balance of learning about the city's history and culture while satisfying our taste buds.
12. Drive the US
13. Oasis Travel
14. Trans Adventure Tours
