Chicago
Street Food

Enter your dates to find available activities

Our most recommended Chicago In 1 week

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

    1. 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

    2. 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: Gangsters and Ghosts 2-Hour Walking Tour

    3. 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

    4. 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

    5. 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

    6. 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!

  • 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

Want to discover all there is to do in Chicago? Click here for a full list.

What people are saying about Chicago

Overall rating

4.8 / 5

based on 13 reviews

This was my first time to Chicago this tour was absolutely amazing. Kelly was knowledgeable about everything Chicago..she was able to answer all questions & gave great recommendations. Would highly recommend..

Ravi was a great tour guide. Very knowledgeable. He took us to some great restaurants and Interesting tour around Wicker Park.

Wallach was a terrific tour guide. The tour was really fun and interesting. We saw and learned so much about Chicago!

It was interesting and fun. Our tour guide was considerate and funny. Would absolutely do another tour with you.

Lara was fantastic. We had a bunch of fun and tons of food to try with great information.