Chicago’s best 2-hour tours cut right to the city’s core experiences. The guided Segway tours are a smart choice, efficiently covering major landmarks while avoiding tired feet. I particularly love the river architecture cruises – they’re informative and offer unbeatable photo angles of the city’s famous buildings. Evening wine and cheese cruises combine great views with local flavors, making them a terrific value. The Loop interior walking tours reveal hidden architectural gems most visitors miss, and they run rain or shine. Skip the gimmicky ghost tours and stick with these proven winners. Check out our tested favorites below.
Key Points
- Segway tours offer a 2-hour guided experience highlighting iconic Chicago landmarks like Millennium Park and the Lakefront with high traveler recommendation.
- Customized private walking tours provide a personalized 2-hour experience focused on specific interests such as history or architecture, led by licensed guides.
- Private Chicago River cruises offer a 2-hour scenic exploration of the city’s waterways, including transportation and optional alcoholic beverages.
- The 2-hour wine and cheese cruise showcases views of the Chicago skyline while pairing local wines and cheeses for a unique experience.
- Private architectural walking tours provide exclusive interior access to notable Chicago buildings, covering a range of historic and modern styles in 2 hours.
2-Hour Guided Segway Tour of Chicago
Discover the vibrant heart of Chicago on a thrilling 2-hour Segway tour.
This small-group experience caps at 8 participants, ensuring personalized attention from your knowledgeable guide, Mike aka Captain Segway.
Glide past iconic landmarks like Millennium Park, Buckingham Fountain, and the Museum Campus, while learning captivating city history and insider facts.
The scenic route features a mix of flat and sloped segments, allowing you to master the Segway with the provided training and safety gear.
With over 420 reviews and a 95% traveler recommendation, this tour offers an efficient and enjoyable way to explore Chicago’s top sights.
Free cancellation up to 24 hours prior and a lowest price guarantee make this tour a must-book for your Chicago itinerary.
Read our full review: 2-Hour Guided Segway Tour of Chicago Review
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2-Hour Chicago Lakefront and Museum Campus Segway Tour
This 2-hour Segway tour takes riders on an exhilarating journey through Chicago’s picturesque lakefront and renowned Museum Campus.
Covering 7-8 miles, the scenic route showcases the city’s iconic landmarks, including Grant Park, Buckingham Fountain, Shedd Aquarium, and Soldier Field.
With 99% traveler recommendation and a Badge of Excellence, this small-group tour offers an engaging, informative experience led by knowledgeable guides.
Suitable for adults and children 12+, the tour includes a Segway lesson, helmet, and live commentary.
Guests consistently praise the tour’s unique perspective and the professionalism of the guides.
Whether you’re a first-time visitor or a Chicago local, this Segway adventure is a must-try for a fun and memorable exploration of the city.
Read our full review: 2-Hour Chicago Lakefront and Museum Campus Segway Tour Review
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Your Way or the Highway: 2-hour Customized Private Walking Tour in Chicago
Stepping beyond the exhilarating Segway tour, visitors seeking a more personalized exploration of Chicago can embark on a 2-hour customized private walking tour.
Rated 5.0 and recommended by 100% of travelers, this tour allows you to focus on your specific interests, whether that’s history, architecture, street art, or the local food scene.
Led by CTPA licensed guides, the tour accommodates private groups of up to 6 participants and offers pickup options at your hotel or a selected location.
Wheelchair and stroller accessible, the tour is also near public transportation, making it accessible to most travelers.
With free cancellation up to 24 hours before and a reserve now, pay later option, this tour provides a flexible and tailored experience in the Windy City.
Read our full review: Your Way or the Highway: 2-hour Customized Private Walking Tour in Chicago Review
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2-Hour Haunted Segway Tour of Chicago
Set out on a thrilling Haunted Segway Tour of Chicago, where participants uncover the city’s dark past. This highly-rated 2-hour tour showcases the city’s gruesome history, from infamous gangsters to deadly disasters.
Led by certified guides, guests explore significant sites like the Iroquois Theatre fire and the Chicago River maritime disaster, all while riding Segways. With a maximum of 8 travelers, the tour offers a personalized experience.
Suitable for ages 12 and up, the tour runs in all weather conditions. Priced from $78.48 per person, the tour includes Segway orientation, safety gear, and gratuities.
Advance booking is recommended, as these tours sell out quickly during the summer months.
Read our full review: 2-Hour Haunted Segway Tour of Chicago Review
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Chicago River 2-Hour Private Cruise for 6 People With Captain
Visitors can take a relaxing 2-hour private cruise along the iconic Chicago River with a dedicated captain. The cruise departs from the Chicago Riverwalk entrance at the corner of Wacker Drive and Columbus Drive.
Private transportation is included, and alcoholic beverages are available for purchase. The tour is suitable for up to 6 people and concludes back at the meeting point.
However, the cruise isn’t wheelchair accessible. While the tour generally receives positive feedback, one recent review noted issues with changes to the itinerary and lack of communication from the company.
Potential customers should be aware of these customer service concerns before booking.
Read our full review: Chicago River 2-Hour Private Cruise for 6 People With Captain Review
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2-Hour Chicago Wine and Cheese Cruise
Why not take in the breathtaking sights of Chicago’s skyline from the unique vantage point of a 2-hour wine and cheese cruise along the city’s iconic waterways?
The 2-Hour Chicago Wine and Cheese Cruise offers an intimate setting for travelers to savor delicious wine and cheese pairings while admiring the stunning views of the city.
With a maximum capacity of 150 passengers, the cruise departs from Wendella’s Dock 4 between the Wrigley Building and Trump International Hotel & Tower.
While the cruise receives mixed reviews, it seems to offer a memorable experience for those seeking a relaxing way to enjoy Chicago’s famous skyline at sunset.
Read our full review: 2-Hour Chicago Wine and Cheese Cruise Review
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Private 2-Hour Walking Tour: Chicago Loop Interior Architecture
For travelers seeking an in-depth look at the architectural marvels that define Chicago’s iconic Loop district, the Private 2-Hour Walking Tour: Chicago Loop Interior Architecture offers an immersive experience.
This private, guided tour provides exclusive access to the interiors of some of the city’s most renowned buildings, showcasing the ingenuity and artistry that have shaped the Chicago skyline.
Led by a licensed local guide, the tour covers a range of styles, from the historic grandeur of the Chicago Cultural Center to the modern elegance of the James R. Thompson Center.
With transportation and all entrance fees included, this tour delivers a comprehensive and enriching exploration of Chicago’s architectural heritage.
Read our full review: Private 2-Hour Walking Tour: Chicago Loop Interior Architecture Review
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The Best of Chicago in 2H Walking Tour
During this immersive 2-hour walking tour, travelers can explore the best of Chicago’s iconic sights and hidden gems.
Led by a knowledgeable local guide, the tour covers major attractions like Garrett Popcorn and the 47th Street Red Line station.
Along the way, you will enjoy food and drink samples, including the renowned Garrett Popcorn.
With a maximum group size of 30, the tour provides an intimate and personalized experience.
Though not wheelchair accessible, the tour is stroller-friendly and located near public transportation.
Travelers should have a moderate fitness level, as the tour involves walking.
Confirmation is provided upon booking, and hotel pickup and drop-off are included.
Read our full review: The Best of Chicago in 2H Walking Tour Review
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The Sum Up
Chicago offers a range of captivating 2-hour tours and experiences, from gliding through the city on a Segway to cruising the river and exploring architectural wonders. Whether you’re seeking a haunted adventure, a wine and cheese excursion, or a customized walking tour, there’s something to suit every traveler’s interests and preferences. With so many options, visitors can make the most of their time in the Windy City.