All Illinois Tours & Excursions in 2026 - page 2

Witness Chicago’s stunning skyline from above on this exhilarating helicopter tour. Departing from the Vertiport, the flight offers breathtaking views of the city’s iconic architecture, including Soldier Field and the Shedd Aquarium, as well as the picturesque Lake Michigan shoreline. This unforgettable experience showcases 8 key points of interest along a scenic 10-mile route, perfect for photography enthusiasts and those seeking a unique perspective of the Windy City. - 10-mile scenic helicopter flight over Chicago's skyline - Fly past famous landmarks like Soilder Field and Chinatown - Minimum of 2 passengers required, maximum of 3 per flight - Free parking available at the Vertiport Chicago

Explore the hidden side of Downtown Chicago—and see sights that even many locals miss—on a small-group walking tour of the Pedway (an underground network of tunnels that connects Chicago buildings) and the vibrant Loop. Ideal for architecture fans, this tour includes insider stories and landmarks you wouldn't spot on your own—plus a chance to see Windy City icons like the Picasso Statue and Millennium Park.

Step aboard a boat for a comprehensive cruise that details the history of Chicago's architecture. Enjoy views of the Chicago skyline accompanied by architecture-focused commentary that points out each of the landmark buildings. As you cruise through Lake Michigan, snap photos of you and your party against the stretch of Chicago's 26-mile shoreline.

See Chicago from a different perspective on this evening cruise that explores the city’s darker side. As twilight settles over the skyline, glide along the Chicago River while hearing chilling tales of disasters, infamous criminals, and eerie legends tied to the city’s past. This relaxed river cruise blends atmospheric storytelling with some of the best nighttime views of Chicago’s renowned skyline and landmarks. Grab a drink from the onboard bar, settle in, and let the city’s shadowy history unfold as you cruise through the heart of downtown. By the end of the journey, you’ll have experienced Chicago’s skyline in a whole new way—while uncovering the chilling events, legends, and mysteries that shaped the city. Please arrive 30 minutes in advance!

Discover the hidden gems of Chicago’s Loop area on a walking tour that showcases the best of the neighborhood’s stunning interiors and architectural must-sees. Step behind the facades to explore beautifully designed interiors—from art deco spaces to stained glass mosaics—as you follow a carefully curated route led by a guide. Along the way, learn about the city’s architecture, art, and history, and experience a side of Chicago often missed by travelers, all from a local’s perspective.

Discover one of the Windy City’s most spooky, gruesome destinations when you book advance tickets to the Medieval Torture Museum. Perfect for Halloween—or any other creepy-crawly occasion—this museum includes a wealth of information about medieval torture practices and devices, plus realistic models to add a macabre edge. Book tickets before you travel for a seamless visiting experience, and make use of an audio guide and included ghost-hunting app.

There are lots of ways to take in Chicago’s architectural sights, but most tours don’t mix things up by teaching you about the city’s dark criminal past. On this combination architecture and true crime walking tour, explore with a local guide and listen to intriguing stories as you explore downtown landmarks such as Chase Tower, Palmer House, and much more.

Take in views of the Chicago skyline and its landmarks during this Lake Michigan sightseeing boat cruise. Enjoy a laidback ride, soaking up panoramic views from this unique perspective. Listen to audio commentary to give you fresh insight into the landmarks you see, like Navy Pier and the Willis Tower, and feel free to bring your own lunch or grab a drink at the onboard bar (own expense).

Discover the beauty of Chicago at night during a 1.5-hour cruise on the Chicago River and Lake Michigan. Watch the city sparkle as you pass landmarks such as Museum Campus, Willis Tower, Aon Center and the John Hancock Building, and the illuminated waters of Buckingham Fountain. You'll learn about the history of the city from live commentary by your knowledgeable guide as you glide along the waterfront of Chicago.

Explore a range of interactive exhibits at the Griffin Museum of Science and Industry in Chicago—one of the largest science museums in the country. Rather than simply viewing displays, enjoy hands-on experiences that bring engineering, technology, and natural science to life. Housed in the last remaining building from the 1893 World's Fair, the museum combines historic significance with immersive exhibits, making it an engaging attraction for visitors of all ages.

Get to know the Windy City the easy and comfortable way on a small-group minibus tour. Instead of long walks and navigating public transit, see major landmarks like Museum Campus, Buckingham Fountain, the Magnificent Mile, and Millennium Park from an uncrowded minibus with large picture windows. Your driver and guide knows where to find all the best views, and there are plenty of photo stops along the way.

Explore Chicago's buzzing food scene—and see some of its best-known landmarks on the way—on this two-in-one walking tour. The small group size offers are more intimate experience as you stroll around the vibrant Loop area, spotting highlights from the Willis Tower to the Rookery building. Indulge in a variety of famous Chicago foods, from deep-dish pizza to the world-famous dipped Italian beef sandwiches.

Make the most of your visit to the Art Institute of Chicago with a local, Chicago-based company that knows the museum inside and out. Whether you’re an art aficionado or a beginner, this opportunity lets you learn about the museum and its pieces through the eyes of an art historian guide without the crowds. Enhance your visit by hearing the stories behind major works.

See the Second City from the water with a sightseeing cruise along the Chicago River and the Lake Michigan shoreline, offering a unique perspective of towering skyscrapers and historic architecture. This tour offers stories about the city’s history and culture as you pass by Chicago's landmarks, museums, and buildings. Capture unforgettable images of the city skyline from Lake Michigan, ensuring a unique look at Chicago, perfect for all ages.

Immerse yourself in Chicago’s rich and dynamic African-American heritage during this half-day tour. Enjoy a chronological history of the city, from the "Great Migration" of African-Americans after the Civil War to what the city is like today. Plus, see the former homes of famous Chicagoans, including Barack Obama, Muhammad Ali, Jesse Jackson, and Kanye West.

Souvenirs can be a fantastic way to remember a trip, but ones you’ve made yourself are even more special. In this small-group perfume-making class, craft your ideal fragrance from a range of different scents, from soft floral notes to exotic spices, and when you’re finished, personalize your bottle with a name or initials.

Lovers of history, true crime, and haunted mysteries rejoice—skip the generic sightseeing tours and learn about Chicago’s dark underbelly with this mob history tour. Follow your guide through historic streets and alleys from Grant Park to the “Alley of Death”—also known as West Couch Place—as you learn about the city’s gritty mobsters, doomed ghosts, crime, and vice.

Taste some of Chicago's most iconic foods while walking through one of the Prohibition Era’s most fashionable and notorious neighborhoods. Learn about Chicago's world-famous cuisine and the gangsters who ate it all in one special unique tour! Sample Chicago’s deep dish – as well as prime steak and the world famous “Chicago hot dog" all while treading the streets of Capone’s closest friends and dreaded enemies. Highlights include a visit to an old tunnel used by prohibition gangsters in the basement of one of the establishments; a mansion once used as a brothel for gangsters; the Cathedral where gangsters were gunned down by Capone’s men; and a restaurant owned by the man who brought down what was left of the Chicago mafia in the early 2000’s. Gluten-free/vegan/vegetarian options are available (please reach out prior to the tour to inform us of any dietary requirements.)

Take to the skies and experience Chicago from an entirely new perspective on this extended helicopter tour showcasing the city’s most iconic landmarks, neighborhoods, and waterfront views. The flight begins near the Chicago Fire Practice Facility before heading over Chinatown, where colorful architecture and historic streets create a striking aerial view. From there, you’ll pass McCormick Place, the largest convention center in North America, stretching along the lakefront and highlighting the scale of Chicago’s downtown footprint. Continuing north, you’ll fly over Northerly Island and Soldier Field, followed by the heart of the Museum Campus, where the Field Museum and Adler Planetarium sit against the backdrop of Lake Michigan. Grant Park comes into view next, often called Chicago’s front yard, leading to an aerial look at Millennium Park and the unmistakable curves of The Bean.

Take in the Chicago skyline from a vantage point most travelers miss on this brunch cruise. Gaze up at the Willis Tower, the Old Chicago Post Office, the Tribune Tower, and much more as you drift along the Chicago River while listening to light commentary and enjoying a curated menu of brunch favorites.

See the towers, piers and iconic landmarks along the Chicago River on an architectural cruise 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 the dark side of the Windy City on this nighttime crime history bus tour of Chicago. Through your expert guide's rich storytelling, immerse yourself in tales of notorious mobsters like Al Capone, Frank Nitti, and Bugs Moran as you explore infamous crime scenes including the site of the St. Valentine’s Day Massacre.

Book in advance to take this popular tour that details the mob history of Chicago during the Prohibition Era (1920s-1930s). Learn about the exploits of gangsters like Capone, Dillinger, Moran, and others as you travel by minibus to sites like the Biograph Theater, Holy Name Cathedral, and St. Valentine's Day Massacre. Your guide adopts gangster attire and characteristics that add dramatic flair to the historical commentary.

Swap the standard Chicago itinerary for the chance to experience a whole different side to the city. Walk in the footsteps of Al Capone and John Dillinger while hearing tales of Chicago's haunted past. This walking tour takes you to prohibition-era speakeasies, sites of real life mob shootouts, and provides special access to places tied to historical events that have shaped Chicago.