Tours and Trips in Chicago

Go beyond deep-dish on this 3-hour culinary walking tour of Chicago, which includes five tastings of classic Windy City cuisine. Navigate the endless options of downtown dining with a guide who can provide insight into the best food Chicago has to offer, and skip the lines and the wait with VIP access to popular restaurants.

Don't spend time figuring out what to see in Chicago and how to get there - this hop-on hop-off tour provides a mapped-out itinerary of the city's top sights. With 14 strategically located stops, the tour allows you to explore the Windy City at your own pace. See the world-class Art Institute and landmark skyscrapers, while live commentary on board gives you insight into the city's colorful history. Don't forget to snap a selfie in front of the shiny steel bean in Millennium Park!

See the overlooked highlights of Chicago's Loop district with a 2-hour walking tour that takes in the best of the bustling, vibrant neighborhood's inside spaces. Get behind the façades to explore stunningly designed interiors as you follow a specially-designed route with an experienced guide. Learn about the city's architecture, art and history while visitng a side of Chicago that's beyond the tourist trail, and experience the Windy City with a local perspective.

Start your morning right with 1.5-hour visit to the Willis Tower Skydeck, offering stunning views of Chicago and a delicious breakfast served from 103-stories high. Head to the Skydeck of the Willis Tower, one of the tallest buildings in the Western Hemisphere, for breakfast served 1,353 feet (412m) above the Windy City. Pick from among five morning meal options, such as eggs, pastries, and steak. Enjoy eye-opening views for 1.5 hours before the Skydeck opens to other guests. Finish your morning by checking out the on-site displays of Chicago's culture and history.

Learn the stories behind the skyscrapers on a 2-hour walking tour of Chicago's architectural history and highlights. Follow your knowledgeable guide through the Loop district,  take in the city's most important buildings and get a new perspective on the Second City skyline. Enjoy the bustling streets of this diverse, vibrant neighborhood as you compare buildings across time and contrast works by the same architect. You'll never look at Chicago's iconic building the same way again.

Enjoy two Chicago experiences at one price with this combo bike tour and admission to the Skydeck Chicago at Willis Tower. With a guide, you'll ride through eight neighborhoods and along the Lake Michigan waterfront to take in the city's attractions and scenery, listening to stories and history about Chicago as you go. Then visit the Skydeck for a 360-degree view from 1,353 feet (412 meters) in the air.

Visit the best dessert boutiques along the Magnificent Mile in Chicago on a 2.5-hour cupcake tour led by a guide. Skip-the-line access and all cupcakes are included as you visit up to five bakeries. You'll also see landmarks like the Wrigley Building, Water Tower Place, John Hancock Center, and the Chicago River, and hear commentary about Chicago from your guide.

Explore the outer reaches of the universe with this admission ticket to Chicago's Adler Planetarium, the first planetarium in the United States. Learn about space at the most advanced and oldest planetarium in existence today, with a plethora of shows and exhibits to delight visitors of all ages. Discover must-see shows like Cosmic Wonder, Destination Solar System and Skywatch Live and exhibits like Mission Moon, Our Solar System and the Universe: A Walk Through Space and Time. Admission includes choice of two Sky Shows and tour of historic Atwood Sphere.

You may never have thought of the back alleys of Chicago's North Loop as particularly photogenic. This small group tour will change your perceptions by helping you find the overlooked interesting shots and scenes that make for unforgettable photographs. You don't have to have a fancy camera to participate, just a mind that's open to the art in unexpected places.

This admission ticket for two people gets you and a special someone access to 360 Chicago (John Hancock Observatory) plus a half bottle of Prosecco - a package that's not available for purchase at the tower. After a quick elevator ride to the 94th floor of the Hancock Center, savor panoramic views over Chicago from 1,000 feet (304 meters) above the Magnificent Mile. Lift your glass in a toast to landmarks like Navy Pier, the Willis (Sears) Tower and Lake Michigan. With mobile tickets, simply scan your phone for direct entry into 360 Chicago.

If you can't decide whether you prefer clear daytime or twinkling nighttime city views, this is the ideal activity for you. The Sun and Stars admission ticket to the 360 Chicago Observation Deck allows you to visit twice, so you can come once in the day, once at night. The deck is one of the highest points in Chicago, and this ticket allows you to see the stunning panoramic views in two completely different ways.

Get a front row seat to Chicago's fireworks display during a 25 to 30-minute helicopter ride above the Windy City.  The nighttime tour takes you over Navy Pier, the Loop, and North Side. Listen to in-flight commentary through a provided headset, which also mutes outside noise. Then, fly to Navy Pier and photograph the stunning fireworks from above before returning to the Earth.

Sip your way through Lakeview and Lincoln Park's best beers on a 3-hour walking tour of these iconic Chicago neighborhoods. Follow your guide to a series of bars and breweries for flights of regional craft brews, and raise a glass as you learn how Chicago's immigrant cultures created a proud brewing tradition. Experience the bar scene like a local, try a classic Midwestern pairing at a beer-and-bacon bar, and see what's on draft in the Windy City.

Experience Chicago like never before on this guided, 2.5-hour, small-group Segway tour. Visit popular Grant Park and see famous Buckingham Fountain, with the Windy City skyline as the backdrop. Glide along the lakefront, taking in views of the Field Museum of Natural History, Shedd Aquarium, Soldier Field, Adler Planetarium and Michigan Avenue. Guided Segway training plus the use of a helmet are included. Dress in weather-appropriate clothes with flat, closed-toe shoes.

Explore the Art Institute, Chicago's world-class art museum and the second-largest in the United States, with this Fast Pass Admission ticket. Situated in Grant Park, the museum's incredible range of impressionist, post-impressionist, modern and contemporary works is near the top of the list of Chicago's must-see sights. Among the artists on display are works by Pollack, van Gogh, Renoir, Monet and Picasso plus, plus a striking new Modern Wing and cutting edge graphic and industrial design.With mobile tickets, simply scan your phone for direct entry into the Art Institute.

See the towers, piers and iconic landmarks along the Chicago River on a 90-minute architectural tour through the heart of the city. Enjoy complimentary refreshments on deck as you cruise down the historic waterway, while listening to fun stories and facts throughout the tour. Spot gargoyles that keep watch high above the city, and buildings that range from Neoclassical to Art Deco. Take in over fifty sites from Lake Point Tower to the Navy Pier, and see the Second City from the water.

Discover Chicago from 1,500 feet (457.2 m) above the ground at the 360 Chicago Observation Deck. Open between 9am to 10:30pm, you can visit at a time that fits with your schedule. It's a great experience for adults and children alike. Your ticket also includes admission to TILT, a thrill ride that gives you a hair-raising view over The Magnificent Mile.

Get an overview of Chicago's famous architectural history on this 3.5-hour bus tour. Learn about the city's history through your guide's history, from its founding to the present. Stops include the Loop, Mies van der Rohe's IIT campus, Frank Lloyd Wright's Robie House, and the Museum Campus.

Fly over the sparkling Chicago skyline at night on this helicopter tour. During this 15-minute tour, listen to engaging commentary from your expert pilot as you fly over sights like the Willis Tower (formerly the Sears Tower), Millennium Park, Lincoln Park and the Shedd Aquarium. Comfortable in a state-of-the-art, heated helicopter, enjoy panoramic views of the Lake Michigan shoreline and the city sprawling out below you. Tour route is subject to change.

Ride a bicycle through Chicago's Museum Campus and take in the city sights during a 2.5-hour nighttime ride. View illuminated attractions and pedal along pathways to Buckingham Fountain to see its feast of lights. Finish your guided bike tour at Navy Pier and watch its legendary fireworks display reflected on Lake Michigan and the city skyline. Number of participants is limited to ensure a small-group experience.