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Our most recommended Chicago Rentals

  • 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 Lakefront: Half-Hour Seadog Speedboat Ride

    4. 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

    5. 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: Lake Michigan Gourmet Brunch/Lunch/Dinner Cruise

    6. 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: 90-Minute River and Lakefront Cruise at Night

    7. Chicago: 90-Minute River and Lakefront Cruise at Night

    Experience the magic of Chicago at nighttime and watch the city's glorious skyscrapers, historic buildings and modern marvels come to life with millions of twinkling lights. Relax and unwind at the end of the day on a cruise which not only lets you enjoy the scenic Chicago River, but also takes you through the Chicago Harbor Lock and out onto Lake Michigan where you can admire epic views of the sparkling Chicago skyline and shoreline. Throughout the ride, listen to lively narration about Chicago's rich history as the onboard guides point out the many sights of the city including Buckingham Fountain, Willis Tower, Aon Center, John Hancock Building, Museum Campus, Marina City, Wrigley Building, Chicago Tribune Building, Navy Pier, the Lighthouse and more. This tour also gives you the unique experience of passing through the Chicago River Lock System, while learning about the operation an...

    Great activity and perfect timing on the fireworks. The only improvement I would suggest is an expanded food menu.

  • Chicago: Lake Michigan Buffet Brunch, Lunch or Dinner Cruise

    8. Chicago: Lake Michigan Buffet Brunch, Lunch or Dinner Cruise

    See the sights of Chicago from onboard the Spirit of Chicago with a 2-hour (brunch and lunch) or 3-hour (dinner) cruise on Lake Michigan. Enjoy a buffet dining experience as you sail through the Windy City, and delight in panoramic views of the city's famous skyline. Board your vessel at Navy Pier and receive a personal greeting. Have your photo taken by the ship's photographer to capture the memory before being seated at your private table. Once there, gorge on your brunch, lunch, or dinner buffet consisting of creative prepared fresh daily, and listen to the onboard DJ's tunes. After your meal, play games like giant Jenga and shuffleboard, or bust out some moves on the dance floor. Don't forget to visit any of the 3 climate-controlled decks to watch the skyscrapers of Chicago's distinctive skyline glide by. SAMPLE BRUNCH BUFFET MENU Early Risers Se...

    We left a bit late, so didn’t get the full time on the cruise. It would be nice if we could view the food that will be offered when we make the reservation. The food could have been better.

  • Chicago: Family Fun Urban Adventure River and Lake Cruise

    9. Chicago: Family Fun Urban Adventure River and Lake Cruise

    Discover Chicago’s stunning skyscrapers, historic buildings, and modern marvels on this fun, family friendly boat cruise. Relax and unwind as you admire scenic views from the Chicago River and the Chicago Harbor Lock. Then move out onto Lake Michigan where you can gaze upon the entire city skyline and shoreline. During the boat ride, enjoy lively narration and stories about Chicago’s rich history as your knowledgeable guides point out the many sights of the city including Willis Tower, Aon Center, John Hancock Building, Museum Campus, Marina City, Wrigley Building, Chicago Tribune Building, Navy Pier, the Lighthouse and more. The tour also gives you the opportunity to experience passing through the Chicago River Lock System. Listen to your guide explain the full workings of the lock and feel the boat rise as you enter Lake Michigan, and then lower again when returning to the Chicago Ri...

    Relaxing and informative, a view and perspective from the river that most don’t get to see.

  • Chicago River: Brunch, Lunch, or Dinner City Cruise

    10. Chicago River: Brunch, Lunch, or Dinner City Cruise

    Admire the unparalleled riverfront views as you enjoy a fine dining experience on the Chicago River. Arrive early for your 2-hour cruise, dressed to impress. Explore the beautiful Chicago Riverwalk when boarding the boat. The crew will welcome you aboard, and the ship's photographer will record the moment. You'll be escorted to your table in the dining area. With its gorgeous glass-enclosed design, you can enjoy Chicago's incredible architecture from your seat. Savor a delicious meal prepared freshly onboard, and choose to buy a cocktail from the bar.   To add to your enjoyment, the dinner cruise includes music provided by an onboard DJ. During the lunch and brunch cruises, occasional onboard narration will be provided about some of the architectural highlights along the river. On Wednesday and Saturday evenings throughout the summer, you'll have amazing views of the Navy Pier firewor...

    Beautiful time and wonderful staff. Well worth the money spent, will definitely book again soon!

Other Sightseeing Options in Chicago

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What people are saying about Chicago

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!