Tours and Trips in Chicago

See more of the Windy City with this money-saving, 2.5-hour, hop-on, hop-off sightseeing bus ticket. Enjoy informative on-board narration as you cruise by 13 Chicago landmarks including the Art Institute, Field Museum, John Hancock Building, and much more. A range of ticket validation periods, ranging from 24 to 72 hours, also help ensure maximum flexibility.

Spend a morning or afternoon observing Chicago's iconic urban landscape as you work with a local artist to create your own urban sketch of the city. Learn professional techniques working with pencil, pen, and watercolor, and let your inner artist out onto the page. Explore the city, working inside or outside depending on the season, and go home with photo documentation of your work including photos you sketching in the city and with your final work of art. This tour is Ideal for budding or experienced artists interested in seeing Chicago in a different light and connecting with the urban world in an artistic way.

On a Chicago hop-on hop-off tour, you can enjoy easy transportation around the city to see the sights that interest you most at your own pace. Select the pass you want when booking, and create your own itinerary in Chicago to check out attractions such as the Michigan Avenue, Navy Pier and Millennium Park. Hop off and on the double-decker bus whenever you wish, and listen to narration about the city on board.

Visit the Skydeck, located on the 103rd floor of the Willis Tower (formerly the Sears Tower) with this pre-paid admission ticket. From the highest point in the city, look out on Chicago's skyline for panoramic views of the sprawling Windy City. Peruse the interactive displays and exhibits showcasing Chicago's history, which are geared toward curious learners of all ages. Then walk out on to the Ledge, a glass balcony that allows views of Navy Pier and Wrigley Field from one of the world's tallest buildings, standing 1,353 feet (412.4 meters) tall.

Enjoy an unforgettable sky-high meal during this 2-hour Willis Tower dining experience at the Skydeck, an observation room situated high above Chicago's magnificent urban landscape. This 1,353-foot (412m) viewing area provides the magical setting for your evening, accompanied by a delicious Chicago-style, deep-dish pizza. Best of all, this special excursion offers VIP after-hours access to the Skydeck, ensuring the ultimate setting for that special occasion.

Tower above the Windy City's world-famous skyline with admission to 360 Chicago (John Hancock Observatory). Ascend 94 stories to the observation deck of one of the tallest buildings in North America aboard its lightning-fast elevator. Then check out bird's-eye views of landmarks like the famous Willis (Sears) Tower and the lakefront shoreline, and enjoy a variety of interactive touch screens and educational exhibits on site. Upgrade to the Sun and Stars package for two visits to the observation deck within 48 hours. With mobile tickets, simply scan your phone for direct entry into 360 Chicago.

Experience Chicago from the air and the water on this two-part tour that features a river cruise and a helicopter ride above the city. First, take a cruise down the Chicago River to learn about the architectural history of the town. Then, board a state-of-the-art helicopter and fly above the skyline. Both tours are fully narrated and you will see Navy Pier, Wrigley Field, Soldier Field, the John Hancock Center, Willis Tower, and more.

Set your paddle into the Chicago River on a leisurely 2.5-hour kayak tour past the skyscrapers of downtown Chicago. Both novice and experienced kayakers will be at ease on this excursion past sights such as the Civic Opera Building and the Marina City Towers. Hear fascinating tales of the Windy City as you gaze at a stunning architectural landscape from the water, just how the original Chicago natives originally navigated the area!

Enjoy a special day out in Chicago with this tour that combines a helicopter tour and dinner for two at the Duck Inn. Fly high above the Windy City for epic aerial views and photo ops, accompanied by guided commentary. Upon landing, head to the Duck Inn, a pre-Prohibition era tavern, for an intimate dinner.

Explore Chicago's iconic landmarks on this 2-hour sightseeing tour led by an expert guide. Board a comfortable, large-windowed minibus with a small group of twelve people or less. This ensures an intimate touring experience as you enjoy downtown and some North side neighborhoods. You will have a chance to get out and visit several locations such as the 1888 skyscraper called The Rookery, with its Frank Lloyd Wright designed lobby and the unparalleled skyline views from Museum Campus. Listen as your guide talks about the historical and cultural factors that make Chicago unique. The city tour ends at Millennium Park, home of the famous Cloud Gate sculpture, commonly referred to as "the bean." Opt to upgrade your tour with a popular 75-minute open-top boat tour on the Chicago River that focuses on the city's renowned architecture. Pick-ups from most downtown Chicago hotels are included.

Taste five classic Chicago dishes during a 2.5-hour walking tour that visits several renowned restaurants in downtown Chicago. Your guide takes you to favorite eateries around River North and Streeterville, and provides skip-the-line access at popular places. Sample foods such as deep dish pizza, Italian beef sandwiches, hot dogs, sweet and savory popcorn, and other delicious bites. You'll also hear from your guide about Windy City history, and see Magnificent Mile landmarks such as the Wrigley Building, Tribune Tower, and Chicago Water Tower.

Travelers who like to get to know a city by seeing it from above will love this tour. View Chicago's long coastline from the seat of a helicopter, then take your time spotting each individual landmark from the observation deck at 360 Chicago. There will be opportunities to take lots of impressive photos. Choose between a daytime or nighttime tours, for unforgettable views at any time of day.

Enjoy lunch above the clouds at the Willis Tower, where authentic Chicago-style pizza is paired with unforgettable views of the Chicago skyline. Customize your own perfect pizza from a list of gourmet ingredients, then select a salad and a traditional Italian dessert. Capture unforgettable images from the dining room on the 99th floor, then continue to The Ledge, a glass floored balcony perched near the top of America's tallest building.

See Chicago from several angles, including the 103rd floor of Willis (Sears) Tower, where you have early access to the Skydeck. This Viator VIP package "” available nowhere else "” provides a crowd-free morning overlooking city landmarks from glass-enclosed balconies. Follow up your vista with a 2-hour narrated trolley tour past Grant Park, the John Hancock Center, the Wrigley Building and more. Finish with an afternoon cruise on the Chicago River and enjoy a complimentary drink as you discover the city's distinctive skyscrapers from an architecture-savvy guide.

Cruise down the Chicago River to see the city's famous architecture on this 60-minute tour. With commentary from your onboard guide, watch the spectacular skyline glide by, including more than 40 notable buildings like the Aon Center, the Wrigley Building and the John Hancock Building. Cover all three branches of the Chicago River, passing the East Bank Club, the old Post Office Building and the Willis Tower (formerly known as the Sears Tower).

Cruise through Chicago on this family-friendly bicycle tour catered to kids. Perfect for kids age 10 and under, this tour mixes fun games and contests in with educational stops at some of Chicago's iconic sights. Parents can ride along with their children on cruiser-style bikes during this safe, enjoyable 2-hour tour that covers an easy 4.5 miles (7 km).

Travel back in time to the original 1893 World's Fair in Chicago for this guided, 3.5-hour food tour. Led by Chicago's 'Gold Coast Queen,' Bertha Palmer, hear her favorite memories from the great 1893 Columbian Exposition and enjoy five different food tastings from around the Windy City.

Step off the tourists' path to visit Lincoln Park, a neighborhood beloved by Chicagoans for its stately homes, historic zoo, and stunning green areas. Your tour begins at the charming Children's Fountain and continues to unexpected sites like the shrine of the first American saint. As your local guide leads you through the city's largest park, you'll marvel at the wild feel of this neighborhood just north of downtown Chicago.

Welcome to Chicago River Boat Architecture Tours! We're proud to present you with an in-depth, expert architectural-based river boat tour that delves into one of the most remarkable American cities today. Known for unique, daring, and historical architectural pursuits, it's hard to cover all of the design and building treasures that make up the Windy City today. If you're ready to learning more about the designs, people, and innovations behind these creations, throw on your captains hat and get ready to cruise along the Chicago River and see what architects from around the world travel to see in Chicago.

This is the easiest and most affordable way to explore some of Chicago's top attractions at your own pace. The Chicago Explorer Pass, valid for 30 days after first use, provides admission to your choice of three, four or five attractions, tours or activities that will save you up to 42 percent on regular ticket prices. Create your own sightseeing itinerary by choosing from among over 25 top sites and things to do, including Lincoln Park Zoo, Navy Pier and and LEGOLAND Discovery Center.