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Chicago

Good for groups

Our most recommended Chicago Good for Groups

Chicago: Big Bus Open-Top Panoramic Night Tour

1. Chicago: Big Bus Open-Top Panoramic Night Tour

From the top deck of a double-decker bus, experience Chicago at night. Enjoy a 75-minute, panoramic tour and take in unique views of the Chicago skyline, comprised of world-famous skyscrapers and revolutionary architecture. Take a photo overlooking downtown from the Museum Campus in front of the Adler Planetarium. Be amazed by the beautiful water and light display of The Buckingham Fountain as you discover the bustling nightlife of Chicago. Marvel at the magical light show of the one-of-a-kind Art on the Mart, displayed on the facade of the Merchandise Mart. See the city reflect off The Bean (Cloud Gate) at the famous Millennium Park. Experience the city that built the skyscraper, and see architectural marvels like the John Hancock Center, the Wrigley Building, the Chicago Tribune Building, and the Willis Tower. Finish your tour at the Chicago Riverwalk, with the knowledge that you can continue exploring the city with confidence. From the pioneering skyscrapers to the Great Chicago Fire, this night tour will take you on a journey you won't soon forget. Be sure to soak up the exciting atmosphere that makes the Windy City such a fascinating and dynamic place.

Chicago: Bikes, Bites, and Brews Biking Tour

2. Chicago: Bikes, Bites, and Brews Biking Tour

Working up an appetite won’t be a problem on this signature bike tour combing city sightseeing with the best foods and brews in Chicago.Sample Chicago’s 4 favorite food groups – pizza, hot dogs, brownies, and beer. You’ll learn the history behind the iconic foods and also get a taste of some of Chicago’s most popular neighborhoods. On the daytime version of the tour, cruise through Wrigleyville, Gold Coast, Old Town, Lakeview, and Lincoln Park. On the nighttime version of the tour, bike through the skyscrapers and bars of downtown Chicago and see Millennium Park and Buckingham Fountain at night. On either route, enjoy the beautiful lakefront trail as well. This tour is 13 miles with perfect breaks along the way for sampling. Your experienced guide will keep you safe, in-the-know, and well-fed. Bikes provided.

Chicago Food Tasting: 2.5-Hour Guided Walking Tour

3. Chicago Food Tasting: 2.5-Hour Guided Walking Tour

Combine an enjoyable walk around Chicago's downtown to see some of the city’s top sites with stops to sample some of the city’s famous tastes. On this 2.5-hour guided walk, you'll get to taste the foods Chicago is best known for doing right. Enjoy deep-dish pizza, the original Italian pastries, Chicago-style hot dog, and a classic Italian beef sandwich. Enjoy a VIP craft beer sample for an additional fee. Along the way, you’ll see some of Chicago's most iconic spots including Millennium Park, the Chicago Riverwalk, the Art Institute, and the famous Bean. By the end of the tour, your stomach will be full of delicious food and your head will be full of fascinating knowledge about Chicago. During the colder months, the tour makes use of the unique underground Pedway system that connects much of downtown and keeps you warm and cozy. On warmer days, you’ll walk at street level to enjoy the large promenades of the loop. The leisurely walking pace is suitable for people of all fitness levels.

Chicago: 3-Hour Private Speakeasy Cocktail VIP Tour

4. Chicago: 3-Hour Private Speakeasy Cocktail VIP Tour

Spend an evening visiting the Chicago speakeasies that have been open since the Prohibition Era in the 1920s, many preserved in their original conditions. With your own private group, enter by way of secret entrances and enjoy the same cocktails ordered by infamous Chicago gangsters and bank robbers at these venues nearly a century ago. Relive the glamor of the 1920s while listening to stories of the rampant racketeering and bootlegging of the era.   Alcohol is available for purchase at the three to four different speakeasy stops. Your private tour guide will make Prohibition Era drink recommendations and tell you the stories behind them. Travel around with your young, professional guide and be chauffeured in luxury transportation, ranging from a luxury SUV to a full-sized luxury motor coach.

Chicago: Night Tour with Willis Tower Entry & Skyline Cruise

5. 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: 1-Hour Escape Room Adventure

6. Chicago: 1-Hour Escape Room Adventure

The concept is simple, but the game is anything but — enter a series of elaborately designed rooms, you and your group must work together to find clues and crack codes to complete your mission. Escaping will require teamwork, communication, wits, and a sense of adventure. With five thrilling adventures to choose from, you may find yourself as a spy sent to recover a stolen painting or a falsely-accused prisoner determined to break out of jail. Once you arrive, a dedicated game guide will take you to your adventure and help you as needed. You will have exactly 60 minutes to complete the mission in your adventure and escape. No matter your choice of game, keep your wits about you and focus: you’ve only got one hour. After you and your group have emerged victorious, you’ll be conveniently located in River North, so you can easily celebrate with a bite to eat.

Chicago: City Minibus Tour with Optional Architecture Cruise

7. Chicago: City Minibus Tour with Optional Architecture Cruise

Start with a 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 10-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, 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 as the city’s most renowned landmarks, such as the John Hancock building and more.

Chicago: Guided City Highlights Tour with Entry Tickets

8. 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: Downtown Architectural Interiors Tour

9. 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: Private Architecture Tour - 3 or 6 Hours

10. Chicago: Private Architecture Tour - 3 or 6 Hours

Start with pickup from your hotel and meet your local tour guide, an expert on the architecture of Chicago. Travel through the city in luxury private transportation to discover its rich architectural history. See famous buildings such as the Sears Tower, The John Hancock Building, and the Wrigley Building Discover Gothic gems along the Magnificent Mile, historic brownstones, and the Frank Lloyd Wright homes of Oak Park. Enjoy a unique added value opportunity to view not only the outside but the amazing hidden interior of many of the buildings on the tour. At your discretion, make numerous stops along the tour to go to the top of the sky decks of famous skyscrapers. Walk along the Chicago River and enter the inside of buildings designed by many famous architects. This tour has several different options. Enjoy the sites of the downtown Chicago area with its many skyscrapers, amazing interiors and great photo opportunities. You may also choose the Oak Park Frank Lloyd Wright Homes and Studio option in lieu of the downtown tour where you will have the opportunity to view the interior of his very first home and studio along with over two dozen of his original structures lining Forest Street in Oak Park anchored by Unity Temple, considered to be the world's first building of the modern architectural style. Each of the above separate options are 3 hours long. If you are to choose both options for a full 6-hour touring experience, enjoy a lunch stop at one of Chicago's many famous hot dog stands or deep-dish pizza joints.

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What people are saying about Chicago

We had a really nice tour guide: Jason who took us to some great places. The late afternoon/early evening cruise was well worth it, going to Ellis tower at night was great as well. Seeing the “Bean”, the Fountain lights and show at the Buckingham Fountain was great too. We got some good facts and knowledge shared with us. All is all, great night and a great start to our short stay in Chicago. Got some recommendations as well from Jason on some things we could do.

We are visiting from Scotland and one of our party had tried escape rooms in Glasgow. This has to be so much better. The fact u get out the cell to then have to get out not one but another 3 rooms is awesome. The last code was extremely difficult and unless the guy hadn’t pointed it out at the end we would never have guessed that lol. We enjoyed it that much that we have now booked to go do a different room later tonight.

AMAZING! Dylan our tour guide made the day so much fun! The food was amazing and I was so full by the end of the tour but completely satisfied. As a solo traveler I couldn’t rate it anymore.

Absolutely amazing! The guide was awesome! Super knowledgeable and humourous.

Very informative, interesting and very entertaining.