Chicago
Urban Exploration

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Our most recommended Chicago Urban Exploration

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

    3. 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 River: 45-Minute Family-Friendly Architecture Cruise

    4. 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 Buffet Brunch, Lunch or Dinner Cruise

    5. 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: Ghosts of Lincoln Park Walking Tour

    6. Chicago: Ghosts of Lincoln Park Walking Tour

    Meet your guide at the meeting point then set off on an unforgettable walking tour through Northside Chicago. Travel back in time as you visit some of the city’s most haunted locations in the mysterious Lincoln Park neighborhood. Learn about the forgotten burial ground that forms the foundation of this bustling district. Check out the bathroom mirrors at Lincoln Park Zoo, home to the ghost of a Victorian woman in white. And, hear about the spirit that haunted Al Capone in his final days.  Throughout the tour, you’ll listen to the strange and disturbing tales of each location. On the standard tour, visit eight historic sites, or opt for the extended tour which includes 12 ghoulish locations. By the end of the tour you’ll have learned about and experienced firsthand the alternative side of Chicago.

    Tammie was an excellent guide, engaging and full of interesting stories. Other people on the tour squealed with delight as she told them tales of ghosts. Also some great history thrown in!!

  • Chicago: 360 Observation Deck and TILT with Mob Bus Tour

    7. Chicago: 360 Observation Deck and TILT with Mob Bus Tour

    Head to 360 Chicago, one of the city’s most impressive landmarks. Ride up to the 94th floor and soak up panoramic views of the city from the observation deck. See the city’s famous skyline as well as the lakefront and 4 neighboring states.  Next, experience Chicago’s most thrilling attraction, TILT. The first of its kind in the world, TILT lets you see the city from a totally new angle, offering downward facing views from over 1000 feet up. Later, discover the underground world of criminals and gangsters on a 1.5 hour mob-themed bus tour. See the places where infamous mobsters conned their way to riches as you listen to tales of their criminal activities. Learn about Al Capone, the Untouchables, the Chicago Mob, John Dillinger, and more.

    The observation deck was great but the mob bus tour sucked however the tour guy was funny. We only made 2 stops and they weren’t that interesting. A stop in front of a theater, the alley where Dillinger was killed mural , and a stop is see a safe. We didn’t get off the bus to see the safe. I would advise people to skip the mob bus tour

  • Chicago: 1.5-Hour Open-Top Double-Decker Night Tour

    8. Chicago: 1.5-Hour Open-Top Double-Decker Night Tour

    From the top deck of a double-decker bus, experience Chicago at night. Enjoy a 75-minute, live-guided panoramic tour and take in unique views of the Chicago Skyline, comprised of world-famous skyscrapers and revolutionary architecture. Take a photo overlooking downtown from the Museum Campus in front of the Adler Planetarium. Be amazed by the beautiful water and light display of The Buckingham Fountain as you discover the bustling nightlife of Chicago. Marvel at the magical light show of the one-of-a-kind Art on the Mart, displayed on the facade of the Merchandise Mart. See the city reflect off of The Bean (Cloud Gate) at the famous Millennium Park. Experience the city that built the skyscraper and see architectural marvels like 875 N Michigan Ave (formally the John Hancock Building), the Wrigley Building, the Chicago Tribune Building, and the Willis Tower. End the tour at the Chicago ...

    It was awesome, although we didn't get the complimentary popcorn? People were saving sets for others that were LATE causing others to not get sets up top.

  • Chicago: History, Culture and Architecture Walking Tour

    9. Chicago: History, Culture and Architecture Walking Tour

    Start your tour under the dazzling marquee of the Chicago Theater (which you might recognize from the movie-musical Chicago) before heading off into the bustling city. Your first stop is inside one of the best-preserved spaces built for shopping in Chicago, featuring an unforgettable atrium at its core. Then head towards the Chicago Pedway, a uniquely Chicago feature used by locals and commuters daily to move about the city in a network of underground tunnels. Afterward, head back above-ground near City Hall and head inside to see the classic interior design and architecture. Next, enjoy a sweet treat, and local tradition: Chicago-style popcorn. Weather permitting, take a stroll along the Chicago Riverwalk while taking in views of several soaring buildings, including Marina Towers, the Britannica Building, and the Willis Tower. From there, either hop on the ‘L’ train or a water taxi o...

    I had an amazing time on this tour! In my opinion, the walking tour allowed me to see so much more of the city, up close and from my own personal viewpoint. The tour guides were very friendly, funny, and knowledgeable. We were even given "Garrett's Popcorn" and "Fannie May Chocolate" as some sweet treats. I highly recommend this tour, and I'm so glad that I did it!!

  • Chicago: Bikes, Bites, and Brews Biking Tour

    10. Chicago: Bikes, Bites, and Brews Biking Tour

    Working up an appetite won’t be a problem on this signature bike tour combing city sightseeing with the best foods and brews in Chicago.Sample Chicago’s 4 favorite food groups – pizza, hot dogs, brownies, and beer. You’ll learn the history behind the iconic foods and also get a taste of some of Chicago’s most popular neighborhoods. On the daytime version of the tour, cruise through Wrigleyville, Gold Coast, Old Town, Lakeview, and Lincoln Park. On the nighttime version of the tour, bike through the skyscrapers and bars of downtown Chicago and see Millennium Park and Buckingham Fountain at night. On either route, enjoy the beautiful lakefront trail as well. This tour is 13 miles with perfect breaks along the way for sampling. Your experienced guide will keep you safe, in-the-know, and well-fed. Bikes provided.

    Our tour guide was Thomas. The tour was very fun and the food was delicious. First stop was the deep dish pizza and craft beer. Very light to my surprise . Next the Chicago Hotdog and last the gelato. Lastly a beer. It was a great start to my first time in Chicago.

Other Sightseeing Options in Chicago

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What people are saying about Chicago

Overall rating

4.7 / 5

based on 225 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!

I've been on a few different boat tours and this one was amongst the best. Very engaging and informative guide.

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

The overall experience was excellent. The guide was absolutely knowledgeable.

Absolutely loved seeing the architecture of Chicago!