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 by boat than on any other architectural cruise. See architectural highlights and enjoy an open-air deck or climate-controlled interior as you travel the main River and its north and south branches. 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. It then cruises along the north and south branches of the river, before heading back past the Chicago Riverwalk towards Lake Michigan. On the way, learn about ornate, historic early skyscrapers like the Wrigley Building and the Tribune Tower, the imposing art deco Merchandise Mart, mid-century skyscrapers like the Mies Van der Rohe AMA Building. Don't miss the circular Marina City Towers, the majestic Willis Tower (formerly the Sears Tower and the tallest building in Chicago) the soaring AON Center, and more modernist structures like Aqua, Trump Tower, Nuveen, and the new Vista Tower. During your cruise, have the opportunity to enjoy a full-service cash bar featuring authentic Chicago products, including local beer and spirits, and Garrett’s Popcorn. Don’t forget to take a selfie at the Grand Staircase at the front of the boat or pose for photos at the picturesque stern or bow of this classic vessel.

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Chicago River: 45-Minute Family-Friendly Architecture Cruise

2. 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 open-air decks that allow you to feel the cooling river breeze and see the city from many vantage points that provide perfect photo opportunities.

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

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

Skip the lines at the ticket office and climb aboard a state-of-the-art cruise for a 60- or 75-minute cruise of all 3 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, Marina City, Willis 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. End your tour in the same place where you boarded the boat.

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Chicago Underground Donut Tour

4. Chicago Underground Donut Tour

Take a donut tour of the windy city, and discover the best Chicago has to offer. At each location, you will taste a curated sample of the best donuts. Some of the stops on this downtown tour include Stan's Donuts, Do-Rite Donuts, and Firecakes Donuts, true donut institutions. This two hour walking tour is led by a passionate donut expert who will guide you to some of Chicago's best donut locales. This tour caters to all size groups, both large and small. The donut tour is great for bachelor and bachelorette parties, birthdays, family reunions, weekend getaways, or even corporate events. There are two versions of the Donut Tour: The Classic Downtown Tour, as well as a local neighborhood tour in Wicker Park. Both are great options if you're excited about donuts. It really just depends on what neighborhood you want to explore: if you want to stay downtown or if you want to venture out to the Wicker Park & Bucktown neighborhoods to see how "the locals do it". In either case, don't hesitate to join the tour. Buy your tickets today!

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Chicago: 1.5-Hour Lake and River Architecture Cruise

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

Experience an architecture cruise along the Chicago River and Lake Michigan, a family tradition since 1935. Admire Chicago’s historic and ever-changing skyline with a local expert guide as you cruise through the city. Choose between the open-air decks or the comfort of the climate-controlled interiors during the cruise. Start the cruise at Michigan Avenue (DuSable) bridge and go up the main branch of the Chicago River to Wolf Point before heading back past the Chicago Riverwalk towards Lake Michigan. Learn about historic skyscrapers like the Wrigley Building and the Tribune Tower, the deco Merchandise Mart, mid-century skyscrapers like the Mies Van der Rohe AMA Building, the circular Marina City Towers, the AON Center, and modernist structures like Aqua, Trump Tower, Nuveen, and the Vista Tower. After passing through the Chicago Lock and cruising past Navy Pier, admire the Chicago skyline from Lake Michigan, one of the largest bodies of fresh water in the world. Here you can also see the twin super-skyscrapers, the famous Willis (formerly Sears) Tower, and the John Hancock Building. See the majesty of Grant Park with its famous Buckingham Fountain, and iconic Chicago venues such as Soldier’s Field, Adler Planetarium, and the Shedd Aquarium. Enjoy several vantage points for memorable pictures throughout, and finally arrive back at Du Sable Bridge on Michigan Avenue.

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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.

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Chicago City Mini Bus Tour with Optional Architecture Cruise

7. Chicago City Mini Bus Tour with Optional Architecture Cruise

After your hotel pick-up from most downtown Chicago hotels, board your climate-controlled minibus with a small group of twelve people or less. Enjoy the sightseeing tour which has won Chicago's "Concierge Preferred" award several years running.  Your tour begins in the heart of downtown Chicago, at The Loop.  Here you'll see incredible architecture, including the world's first skyscrapers.  You'll even go inside one that features a beautiful lobby designed by Frank Lloyd Wright.  The stop also includes views of The Chicago Board of Trade and the Willis (Sears) Tower. After The Loop, you'll tour through Grant Park, which is known as the city's front yard. The centerpiece of the park is the Buckingham Fountain (operational May to October).  Museum Campus is up next, with three museums, Soldier Field and the most spectacular skyline views in the city.  After a ten minute photo stop, you'll travel around Millennium Park, featuring The Bean, before heading up north along Wacker Drive, which parallels the Chicago River. You'll arrive in the fancy Gold Coast nightlife area and residential neighbourhood - one particularly interesting sight here is the original Playboy Mansion. Then you'll take a trip through part of Lincoln Park, and end the tour by zipping along Lake Shore Drive, past beaches and old mansions as we get you back to or near your hotel or parking place. For those wanting the ultimate Chicago experience, add on the option of the world-famous architecture cruise of Chicago. After your 2-hour minibus tour and a short break, climb aboard a state-of-the-art cruise vessel for a 75-minute cruise of all three branches of the Chicago River. Marvel at the architecture that has made the city so legendary. Gain insights into the buildings and engineering of a city that gave birth to the skyscraper and is the spiritual home of modern American architecture. An 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 and more.  

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Chicago: 3-Hour Private Speakeasy Cocktail VIP Tour

8. Chicago: 3-Hour Private Speakeasy Cocktail VIP Tour

Spend an evening visiting the Chicago speakeasies that have been open since the Prohibition Era in the 1920s, many preserved in their original conditions. With your own private group, enter by way of secret entrances and enjoy the same cocktails ordered by infamous Chicago gangsters and bank robbers at these venues nearly a century ago. Relive the glamor of the 1920s while listening to stories of the rampant racketeering and bootlegging of the era.   Alcohol is available for purchase at the three to four different speakeasy stops. Your private tour guide will make Prohibition Era drink recommendations and tell you the stories behind them. Travel around with your young, professional guide and be chauffeured in luxury transportation, ranging from a luxury SUV to a full-sized luxury motor coach.

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Chicago: Food, Architecture and History Tour

9. Chicago: Food, Architecture and History Tour

Start your tour under the dazzling marquee of the Chicago Theater (which you might recognize from the movie-musical Chicago). 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. 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, make your way to another delicious destination where you can sample locally made chocolate from a Chicago staple. Next, take a stroll through the beautiful lakefront parks along Michigan Avenue. End up in the picturesque Millennium Park, home to the iconic Bean sculpture. By then, you’ll hopefully have built up an appetite because it’s time to begin your ultimate food experience.  Travel with your guide up to the River North neighborhood, the original Chicago foodie destination. Start your food tour with a well-known Chicago fare: the Chicago-style hot dog. Every Chicagoan has their own preference as to how the dog should be made, and you’ll get a chance to try your guides’ favorite version. Next up is the world-famous Chicago deep-dish pizza, the staple of the Chicago food scene. Visit a pizza place that’s an icon to Chicago natives to try the real deal for yourself. After you’ve filled up on pizza and hot dogs, take a stroll through two more establishments, each one essential to Chicago’s food culture. Then continue your tasting journey with a classic Chicago sandwich: Italian beef.  Sample this sandwich in a real Chicago institution. Your tour ends here, and your guide will be happy to direct you back to your accommodation or share tips for what else to see and do in the city.

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Eastside Chicago: Exploration Game

10. Eastside Chicago: Exploration Game

Start the adventure at The Art Institute of Chicago. It will take you between 1.5 to 2 hours to complete and you can also explore at your own pace. Pause the game and resume anytime from the location where you paused it. You will finish at the Fountain of the Great Lakes. As you solve challenges, the story unfolds and exact directions on your phone will guide you to the next location. So, are you up for an exciting city game? After your booking, you will receive an email on how to download the game to your phone. You can play on your own, in a large group, or in several smaller groups that compete against each other and meet at the final stop of the game. For larger groups, one person can purchase access for the entire group by selecting the number of people in the group. All group members will be able to download and play the city game on their phones. Alternatively, each person can make their own purchase.

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Other Sightseeing Options in Chicago

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What people are saying about Chicago

Overall rating

4.7 / 5

based on 225 reviews

Es un paseo muy bonito, bien explicado, las bebidas a bordo deliciosas, y las fotos que se pueden tomar en el paseo de las 5pm son increíbles, Chicago de noche se ve hermoso.

The tour guide, Jack, was the star of this trip- engaging, knowledgeable, and funny! I would highly recommend a tour with him!

We had beautiful clear skies and really enjoyed the views and listening to the tour guide.

Great tour. Very interesting to learn about Chicago history.

The tour guide for the 2pm sailing was out standing!!