Top Illinois Tours, Sightseeing & Cruises - page 16

Experience Chicago like never before on your all-inclusive small group city tour, led by an expert guide. Discover iconic landmarks, hidden gems, and vibrant neighborhoods with personalized attention and insider knowledge. Enjoy a hassle-free day with transportation, tickets, and lunch included. Explore Millennium Park, Navy Pier, and more, with plenty of photo opportunities and fascinating stories. Book now for an unforgettable Chicago adventure!

Explore the charming towns of Dubuque and Galena on this enriching day trip from Chicago. Begin your journey along the scenic Mississippi River in Dubuque, where you can enjoy free time to stroll, have lunch, or even take a cable car ride for breathtaking views. Continue to Galena, a beautifully preserved historic town where 80% of the buildings are listed on the National Register of Historic Places. Here, you’ll visit the Ulysses S. Grant Home and take in the serene beauty of Grant Park. With a total travel distance of 325 km from Chicago, this tour offers the perfect blend of history, scenery, and relaxation before heading back to the city.

Discover the charm of Milwaukee on a small group day trip from Chicago! Enjoy a guided city tour, explore iconic landmarks, and experience the legendary Miller Brewery with exclusive behind-the-scenes access and tastings. With comfortable transport, expert local insights, and a friendly group atmosphere, this all-inclusive adventure is perfect for curious travelers. Book now for a memorable escape to Milwaukee's culture and flavors!

The route to Lake Geneva follows the incredible coastline of Lake Michigan and eventually into the rolling green hills of Wisconsin. Your group will stop to see landmarks such as the Gold Pyramid House and the stunning Bahāʾī temple. The 85-mile bike ride will bring you right to your boutique inn where your bags will be waiting for you. The following day your guide will take you to the beach where you can kayak or just enjoy some much-deserved lounging. After this you will visit the Apple Barn for a delightful day of seasonal apple or strawberry picking, followed by a stop at their bakery. Don't forget to bring your ID for the wine tasting; they often feature live music and are very family-friendly! Will give you time to explore the shops and ice cream parlors in the charming downtown area before packing the car to drive you back to Chicago.

Celebrate the beauty of spring and the rich history of the National Cherry Blossom Festival, commemorating the 1912 gift of 3,000 cherry trees from Tokyo to Washington, D.C. Visit iconic landmarks like the Lincoln Memorial, Vietnam Veterans Memorial, White House, and U.S. Capitol. Stroll through East Potomac Park, enjoying the blossoms along the scenic 4.4-mile Hains Point Loop Trail, with views of the Martin Luther King, Jr. Memorial, Franklin D. Roosevelt Memorial, and more. Special Note: The 2025 National Cherry Blossom Festival will take place from March 20 to April 13, though bloom timing may vary depending on weather conditions. Immerse yourself in the vibrant beauty of D.C.’s cherry blossoms and explore the city’s rich history on this unforgettable tour!

This private architectural walking tour in Chicago explores residences that reflect the city’s design evolution. You will begin along Lake Shore Drive, where early high-rise living reshaped urban life. What architectural movements defined Chicago’s rise as a global city? Historic homes reveal craftsmanship influenced by leading architects of the modern era. Prestigious streets present a collection of preserved facades that reflect social and cultural history. Landmark residences highlight transitions from classical to modern design principles. This experience offers insight into architectural innovation and the lifestyles that shaped it. Please note: The program and attractions may vary based on booking date/time and crowd conditions, ensuring each visit is a unique experience.

This private historical ghost walking tour in Chicago explores stories rooted in the city’s layered past. You will walk through Lincoln Park, an area shaped by transformation from cemetery grounds to residential district. What traces of earlier history remain beneath modern streets? Architectural landmarks reflect 19th-century development and urban expansion. Historic venues such as theaters and pubs carry narratives passed through generations. These accounts reveal how memory and place intertwine within the city’s cultural fabric. The experience offers a thoughtful perspective on Chicago’s past through legend and documented history. Please note: The program and attractions may vary based on booking date/time and crowd conditions, ensuring each visit is a unique experience.

Experience our Private Excursion tailored exclusively for you! Embark on a serene journey through the picturesque landscapes of USA as you make your way to the heart of the city. Upon your arrival, meet your seasoned tour guide, ready to lead you on an enchanting tour of Art Institute of Chicago. Discover the awe-inspiring allure of Art Institute of Chicago, marvel at the grandeur of Chicago, and capture iconic moments and many more. Leave the details to us as we escort you on an extraordinary adventure, crafting memories that will stand the test of time!

Discover the natural beauty of Lake Geneva and the tranquil Anderson Japanese Gardens on this private 10‑hour getaway from Chicago. Begin your day with convenient pickup and enjoy a scenic drive as your expert guide shares insights about the region. Once at Lake Geneva, you’ll have free time to explore its picturesque lakeside paths, historic estates, and even take an optional cruise. Afterward, immerse yourself in the serene pathways of Anderson Japanese Gardens, where elegant bridges, koi ponds, and peaceful landscapes await. This personalized tour offers a relaxing and enriching experience, perfect for couples, families, and small groups seeking a nature‑filled escape.

Captain Greg and his wife First Mate Cait are world-class sailors. Their resumé includes a 9-month, 6,000 nautical mile voyage from Chicago to the Bahamas and back from October 2020 to July 2021 completing "America's Great Loop". They share their passion for sailing and affinity for Lake Michigan with guests every year. Your meticulously maintained sailing yacht, a 2003 french-built Jeanneau Sun Odyssey 37, offers the flexibility of adventurous sailing with the option to drop anchor & swim or float on the Lake. It is the best private experience in the heart of the city. Your Chicago sailing charters are perfect for summer birthdays, romantic proposals, anniversaries, and more. Take in the sights, sounds and breathtaking scenery of the Chicago Lakefront. From adventurous sailing to relaxing sunset cruises, float parties, Navy Pier fireworks and plenty of special events throughout the year- we have something for everyone!

This tour offers a personalized and stress-free way to experience Chicago, combining comfortable transportation with local insights and flexible stops. Guests enjoy a private ride through iconic neighborhoods and landmarks while learning about the city’s history, culture, and architecture at their own pace. Ideal for airport transfers, short stays, and first-time visitors seeking a relaxed yet memorable city experience

Six days to enjoy the beautiful scenery of the three major lakes in the Great Lakes region of the United States, all of which are located in Lake Michigan in the United States, Lake Superior, the largest freshwater lake in the world, and Lake Huron. Famous cities along the five great lakes: Chicago, Milwaukee and Traverse City along Lake Michigan, Green Bay along Green Bay, and Sault Ste. Mackinac Island, which was once selected as one of the top ten most beautiful islands in the world. Room Details All hotel rooms are based on two Full / Double beds or one King/Queen bed depends on what rooms are availiable at the hotel on the day. The maximum occupancy per room is four travelers. One Room Selection If you are a party of more than four guests or desire to have separate rooms, please create separate bookings. Avoid traveling in a different bus? If you have more than one booking, please provide all confirmation numbers once your bookings are complete.

Step into Chicago’s spirited past as you stroll through the Loop and River North’s most storied taverns on this guided small-group walking tour. Visit four unique pubs—including Chicago’s oldest continuously operated restaurant, classic speakeasies, and media hangouts—each echoing with tales of Prohibition and local legends. Along the way, your expert guide shares colorful anecdotes, local history, and a behind-the-scenes look at architectural gems like the Marquette Building. Perfect for curious adults and pub enthusiasts, this experience takes you off the tourist path for an afternoon of discovery, camaraderie, and the true flavor of the city. *Drinks and food are at your own expense. Must be 21+

Chicago has beautiful skyscrapers, did you know they have ghosts?! This expert-led walking tour reveals the secrets of the city’s skyline and its shadowy history. Led by a passionate local guide, you’ll visit architectural gems and hidden landmarks that boat tours miss bringing Chicago’s rich and eerie past to life.

Shoreline water taxis are the fast and fun way to get to Chicago’s top attractions. Our water taxis aren’t tours, but they are a great way to get around town. Offering multiple docks conveniently located near major attractions including Navy Pier, the Willis (Sears) Tower, Michigan Avenue, Museum Campus, and Union Station.

Looking for something truly local, active, & unforgettable for your kids while you explore Chicago? Bobby’s Chicago Kids Camp is a one-of-a-kind day camp Chicago experience designed with both visiting families and locals in mind. While you enjoy adult time—deep dish at Lou Malnati’s, a stroll through the Art Institute, or an adult-oriented bike tour up to Wrigley—your child is biking the lakefront, kayaking calm waters, & making new friends at the best summer camp in Chicago. Our camp blends active outdoor fun with real Chicago stories. Campers visit landmarks like Millennium Park, the Lincoln Park Zoo, & Buckingham Fountain—learning fun facts & building confidence along the way. We offer flexible booking by the day or week, with half-day & full-day options—perfect for travelers building an itinerary. It’s not just a Chicago kids camp—it’s a chance for your child to experience the city like a local, while you enjoy some grown-up adventure of your own. Book your kids adventure today

Looking for an unforgettable adventure that combines the thrill of paddling with the stunning natural beauty of Illinois? Our Guided Kayak Rentals near Chicago are the perfect way to experience Starved Rock State Park from a whole new perspective.