Chicago
Sailing Trips & Tours

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Our most recommended Chicago Tours

  • Chicago River: 1.5-Hour Guided Architecture Cruise

    1. Chicago River: 1.5-Hour Guided Architecture Cruise

    Experience more of Chicago than on any other architectural cruise as you travel not only the main Chicago River but also the North Branch of the river (as far as the Old Montgomery Ward Building) and the South Branch of the river (nearly as far as Chinatown). View all of Chicago's architectural highlights during this comprehensive sightseeing tour. Be entertained by the expert and friendly tour guides as they explain the 130 year-long history behind the skyline, while bartenders and staff keep you comfortable with refreshments.  Choose between the fresh air of the open-air decks or enjoy the comfort of the climate-controlled interiors during your cruise. The tour starts at the Michigan Avenue (DuSable) bridge and goes up the main branch of the Chicago River past Wolf Point, and cruises along the north and south branches of the river, before heading back past the Chicago Riverwalk toward...

    The tour was great. The only problem was when my wife and I were checking in and the young man said that my ticket was invalid. The only reason we were able to go on the tour is that there was another gentleman there who knew that I had already purchased two tickets

  • Chicago: 1.5-Hour Lake and River Architecture Cruise

    2. Chicago: 1.5-Hour Lake and River Architecture Cruise

    Experience the architecture cruise that started it all — a Chicago family tradition since 1935. View Chicago’s historic and ever-changing skyline on Chicago's only architecture tour with views from both directly from the Chicago River, and those only possible from Lake Michigan. During this comprehensive sightseeing tour, all of Chicago's architecture highlights will be viewed, discussed, and experienced. Choose between the fresh air of the open-air decks or enjoy the comfort of the climate-controlled interiors during your cruise. The tour starts at the Michigan Avenue (DuSable) bridge and goes up the main branch of the Chicago River to Wolf Point before heading back past the Chicago Riverwalk towards Lake Michigan. On the way, you will learn about ornate, historic early skyscrapers like the Wrigley Building and the Tribune Tower, the imposing art deco Merchandise Mart, mid-century sky...

    The police were chasing drunken boaters, so the locks were closed to all. We spent a long time in Lake Michigan and still continued the tour of the river after the locks opened again. I think it was more like a 3 hour tour and it was great fun.

  • Chicago: 1.5-Hour Romantic Sunset Cruise

    3. Chicago: 1.5-Hour Romantic Sunset Cruise

    Start your sunset cruise on the Chicago River at Michigan Avenue. Make your way along the main branch of the river towards Lake Michigan before entering the Chicago Locks, a modern engineering marvel, that will transfer the vessel onto the great Lake Michigan. The vessel will cruise along Lake Michigan as the sun sets behind the wonderful skyline offering several amazing views. Your local tour guide will give a very brief commentary along the Chicago River and entrance to Lake Michigan, but most of the 1.5-hour cruise is spent without narration, leaving you to watch the sun put on a beautiful display with the City skyline. Admire the many angles of the Chicago skyline from Lake Michigan, one of the largest bodies of fresh water in the world. Capture magical views of Chicago's twin super-skyscrapers, the famous Willis (formerly Sears) Tower and the John Hancock Building. You'll also ge...

    It was the best price for a river tour and I know sometimes if you pay less you get less but this star was outstanding. I would highly recommend

  • Chicago River Architecture Cruise: Skip-the-Ticket-Office

    4. Chicago River Architecture Cruise: Skip-the-Ticket-Office

    Climb aboard a state-of-the-art cruise vessel for a 60- or 75-minute cruise of all three branches of the Chicago River, and marvel at the architecture that has made the city so legendary. Get an insight into the buildings and engineering of a city that gave birth to the skyscraper and is the spiritual home of modern American architecture. Your expert guide will lead you down the Chicago River to uncover hidden gems, as well the city’s most renowned landmarks, such as the John Hancock building, Trump Tower, and more. Relax with a glass of something cold from the cash bar, as you cruise the Windy City’s waterway, and learn its status as a modern metropolis and one of the world’s most beautiful cities.

    we certainly learned a lot on the boat. Our guide was very knowledgeable and personable and the whole crue made us feel welcomed . i will recommend this short boat ride to anyone interested in history and architecture.

  • Chicago Lakefront: Half-Hour Seadog Speedboat Ride

    5. Chicago Lakefront: Half-Hour Seadog Speedboat Ride

    This half-hour Seadog Speedboat ride along Chicago’s lakefront is one of the best ways to view the city’s skyline while learning about the city. Combine an exciting speedboat ride with informative and amusing stories about the world-famous Windy City! As you depart Chicago's Navy Pier, your captain will tell you interesting facts about the pier and the lakefront as he cranks up the music and races to key lakefront landmarks.

    Stop near the picturesque lakefront park of the Chicago Museum campus, where you’ll learn about the architecture and history of Chicago. Admire views of the Magnificent Mile neighborhood, including the Buckingham Fountain, Sears Tower, Grant Park, and Chicago's largest shopping district. Listen to the thrilling sound of the turbo engines as you race around the Lake Michigan waterfront and back to the Navy Pier. Upgrade to the Extreme Thrill Ride Option a...

    Our tour guide was great and the boat ride was fun. The boat was easy to find as well.

  • Chicago River: 45-Minute Family-Friendly Architecture Cruise

    6. Chicago River: 45-Minute Family-Friendly Architecture Cruise

    Admire Chicago’s impressive architecture from a unique perspective aboard a 45-minute cruise sailing down the Chicago River, which features a full-service cash bar and live commentary tailored to entertain the whole family. Experience the best of the Chicago River from Lakeshore Drive to the Willis Tower, navigating along the South branch of the river, before heading back past the Chicago Riverwalk towards Lake Shore Drive and Lake Michigan. Be entertained by the fun and experienced tour guides as they explain the history behind Chicago’s buildings along the river and the exceptional architects who created this ever-changing skyline. Enjoy the most relaxing way to sightsee in Chicago- a perfect way to explore the city free of traffic noise and congestion. Make sure to visit the full-service cash bar featuring authentic Chicago products, including local beer and spirits. Explore the o...

    We had a great time! Shorter ride was perfect for young kids. Boat was clean and staff was friendly.

  • Chicago: Gangsters and Ghosts 2-Hour Walking Tour

    7. Chicago: Gangsters and Ghosts 2-Hour Walking Tour

    See a different side of Chicago on a family-friendly guided tour and hear the tales of the ghosts that haunt the city. Explore the famous Chicago Loop district with interesting stories hidden behind each turn.

    Embark along the Chicago Loop, known as the vice district during the 1920s and 30s. See the places where gangsters such as Al Capone used to party, make deals, and carry out business.

    Visit haunted locations and old crime scenes led by historians. Stop at the Congress Hotel, Death Alley, and the Palmer House. Enjoy a refreshment along with way, with frequent stops and a restroom break.

    We loved this tour, Stephan was very funny and knowledgeable. Will suggest to friends and family:)

  • Chicago: 90-Minute Mob and Crime Bus Tour

    8. Chicago: 90-Minute Mob and Crime Bus Tour

    Experience Chicago’s underworld of criminals and gangsters on a luxury 90-minute bus tour. Find out how some of the world’s most famous criminals, mobsters, and gangsters conned their way through the city. Ride comfortably in luxury, on a climate-controlled bus, as you see famous Chicago crime scenes that range from the 19th century through modern times. Unlike Chicago walking tours, this Mob and Crime Tour isn’t affected by the Windy City weather. Learn about Al Capone, the Untouchables, the Chicago Mob, John Dillinger, Terrible Tommy O'Connor, H. H. Holmes, the Chicago Black Sox, Leopold and Loeb, bank heists, Cap George Streeter, and more. Grab your camera for a drive-by shooting of the historic criminal courthouse, a Chicago architectural landmark where some of Chicago's most notorious cases were tried. Stake out crime scenes like the Biograph Theatre, Holy Name Cathedral, Clark ...

    Our guide was great and very informative. His dad jokes were pretty on point too.

  • Chicago: Lake Michigan Gourmet Brunch/Lunch/Dinner Cruise

    9. Chicago: Lake Michigan Gourmet Brunch/Lunch/Dinner Cruise

    Cruise for 2 or 3 hours on Lake Michigan and see the sights of Chicago from a luxury boat, The Odyssey. Board the boat at Navy Pier and enjoy a personal greeting. Smile for the ship's photographer to capture the memory, then embark on an elegant dining cruise along the Chicago shoreline. After being seated at your private table, tuck into your gourmet brunch buffet or 3-course lunch or dinner consisting of creative meals prepared fresh daily by the on-board executive chef. After your meal, dance to the live music or relax on any of the 3 climate-controlled decks as you watch the skyscrapers of Chicago's distinctive skyline glide by. SAMPLE LUNCH AND DINNER MENU Starters (choice of one): Caesar Salad Lobster Bisque (dinner only) Jumbo Shrimp Cocktail (dinner only, available for additional price) Seafood Tower (dinner only, available fo...

    Thought there would be more dancing and the trip would be 3 hours and not 2 and a half.

  • Chicago Skyline Lake Tour: 40-Minute Sightseeing Cruise

    10. Chicago Skyline Lake Tour: 40-Minute Sightseeing Cruise

    Whether you’re a local or a visitor to the city for the first time, taking in the spectacular views of Chicago's skyline from the lake makes for a perfect outing. This 40-minute Lake Tour takes you on a sightseeing cruise that highlights Chicago's most significant landmarks from beautiful Lake Michigan. You’ll see the city as never before, while listening to informative commentary on Chicago's dramatic history and architectural gems. Sit back, relax, and enjoy the sights as you admire the striking buildings that make up the Chicago skyline that has appeared in so many movies and TV shows.

    The staff on board were very friendly and helpful ! The tour was informative and fun!

Other Sightseeing Options in Chicago

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What people are saying about Chicago

Overall rating

4.5 / 5

based on 436 reviews

Jack, our guide, made the tour! He was extremely knowledgeable and entertaining! It’s probably one of the best guided tours I’ve taken and I’ve traveled around the world. He’s a keeper!

It was a very good experience. I enjoyed the boat ride, the weather and the information about all the buildings and Chicago.

We had a great time! Shorter ride was perfect for young kids. Boat was clean and staff was friendly.

Was an incredible experience!!! I love ❤️ The Windy City

Absolutely loved seeing the architecture of Chicago!