Chicago
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Our most recommended Chicago Small group

Chicago: Night Tour with Willis Tower Entry & Skyline Cruise

1. Chicago: Night Tour with Willis Tower Entry & Skyline Cruise

Immerse yourself in Chicago’s distinct skyline with bold skyscrapers and incredible views of Lake Michigan illuminated at night on this city tour. Enjoy convenient hotel pickup and drop-off, skip-the-ticket-line entry to Willis Tower, and a scenic Chicago skyline cruise. After getting picked up from your Downtown Chicago hotel, hop in your air-conditioned Mercedes Metris vans and travel to your first stop, Willis Tower, the tallest building in the Western Hemisphere. Take the elevator all the way up to the 103rd floor of the tower, where you can enjoy 360-degree views spanning 50 miles and 4 states. Get your adrenaline pumping at The Ledge – a glass balcony extending 4.3 feet outside the building which provides a thrilling, once-in-a-lifetime experience. Once your feet are back on solid ground, take to the water for a skyline cruise to see the beauty of Chicago's world-famous skyscrapers lit up by the moonlight and bustling city lights. Enjoy a narrated boat tour passing by over 40 Chicago iconic landmarks. End the night by immersing your senses in a spectacular light and music display at Buckingham Fountain – one of the largest fountains in the world. You will also get to see the infamous Chicago Bean (also known as Cloud Gate), Anish Kapoor’s first public outdoor work installed in the United States. At the end of your tour, your guide will take you back to your downtown Chicago hotel.

Chicago: City Minibus Tour with Optional Architecture Cruise

2. Chicago: City Minibus Tour with Optional Architecture Cruise

Start with pickup from your downtown Chicago hotel. Board your climate-controlled minibus and embark on your guided sightseeing tour. Begin in the heart of downtown Chicago, at The Loop. Here you'll see incredible architecture, including the world's first skyscrapers. You'll even go inside one that features a beautiful lobby designed by Frank Lloyd Wright. The stop also includes views of The Chicago Board of Trade and the Willis (Sears) Tower. After The Loop, head through Grant Park, which is known as the city's front yard. The centerpiece of the park is the Buckingham Fountain. Museum Campus is up next, with three museums, Soldier Field, and the most spectacular skyline views in the city. After a ten minute photo stop, travel around Millennium Park, featuring The Bean, before heading up north along Wacker Drive, which parallels the Chicago River. Arrive in the fancy Gold Coast nightlife area and residential neighborhood - one particularly interesting sight here is the original Playboy Mansion. Then you'll take a trip through part of Lincoln Park, and end the tour by zipping along Lake Shore Drive, past beaches, and old mansions, before being dropped off at your hotel. For those wanting the ultimate Chicago experience, add on the option of the world-famous architecture cruise of Chicago. After your minibus tour and a short break, climb aboard a state-of-the-art cruise vessel for a 75-minute cruise of all three branches of the Chicago River. Marvel at the architecture that has made the city so legendary. Gain insights into the buildings and engineering of a city that gave birth to the skyscraper and is the spiritual home of modern American architecture. An expert guide will lead you down the Chicago River to uncover hidden gems, as well the city’s most renowned landmarks, such as the John Hancock building and more.  

Chicago: Downtown Architectural Interiors Tour

3. Chicago: Downtown Architectural Interiors Tour

Jump right into beautiful architectural interiors of the Roaring '20s, taking in the class and elegance of a classic Art Deco masterpiece. Go back 50 years to the 1880s and explore the structure and style of one of the most famous and oldest buildings in downtown Chicago. Next, you'll marvel at a vaulted ceiling from the Postmodern era, surrounded by Moorish details. Finally, you'll end looking up at the world's largest Tiffany stained-glass mosaic, and very close to the world-famous Millennium Park with one of the most famous landmarks of Chicago, "The Bean."

Chicago: Guided City Highlights Tour with Entry Tickets

4. Chicago: Guided City Highlights Tour with Entry Tickets

The day begins with pickup from your downtown Chicago hotel and heads to one of the city’s most iconic landmarks, the Chicago Bean. Learn about this iconic artwork as well as its artist, Anish Kapoor. Next, admire Chicago’s impressive skyline aboard the Shoreline Architecture Cruise. Listen to the onboard narration as you admire over 40 of the city’s landmarks.  Afterwards, head to the tallest building in the Western Hemisphere, Skydeck Chicago. Take the elevator up to the 103rd floor and soak up 360-degree views. There’s also time to walk out onto The Ledge, a special glass balcony which provides a once in a lifetime experience. Later, enjoy a narrated drive through the city and pass by famous sights including the Aqua Tower, Buckingham Fountain, and more. Finally, visit the Adler view point for one last view of the city then enjoy drop-off back to your hotel.

Chicago: City Lights, Lakefront, and Skyline Segway Tour

5. Chicago: City Lights, Lakefront, and Skyline Segway Tour

There's no better way to tour the world-class city of Chicago than on a segway tour! On this tour you will learn about and experience Chicago's top attractions. The seven-mile tour begins at the southern end of Millennium Park. First, glide along the fragrant floral paths and rose gardens of Grant Park. Enjoy the open spaces around famous Buckingham Fountain, and the breathtaking evening display. It is the perfect stop for photos, as this venue has generous views of both Lake Michigan and the majestic skyline. Next, get swept off your feet on this evening segway tour as you glide along the Lakefront, past Monroe Harbor, to the Museum Campus where you can find the most incredible view of the city’s skyline in nighttime splendor. Peek into Chicago's architecture and culture as you learn about the history of the Field Museum, Shedd Aquarium, Soldier Field, and the Adler Planetarium.  Excellent Chicago sightseeing continues as you experience Chicago's illuminated skyline and catch the huge water, music, and lights show at Buckingham Fountain, while heading back through the gorgeous parks and along Michigan Avenue, home of famous outdoor art installations, statues and monuments, and historic hotels, before ending this unique Chicago-style Segway tour.

Other Sightseeing Options in Chicago

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What people are saying about Chicago

Kylie gave an exceptional tour of many of Chicago’s landmark buildings providing excellent architectural and historical analysis in an interesting and easy to understand fashion. She shared interesting information about Chicago’s origins and redevelopment after the Chicago Fire. Throughout the tour she gave us moments to observe, appreciate, and take photos of the various styles of architecture.

Danny really helped me understand and learn how beautiful and fascinating the City is/are, a lot of fun facts too. For someone who likes to travel olone its definetely a safe and fun one. Thank you!

Our tour guide, Muhammad, was fantastic! He was so peppy and knowledgeable! I would highly recommend!

Danny was great, he is very knowledgeable and courteous and knows Chicago’s history .

Rick was a delight and he really knew his history of Chicago!