Things to do in
Trump Tower, Chicago

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Trump Tower, Chicago: Our most recommended tours and activities

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: Hop-on Hop-off Open Top Bus Tour

3. Chicago: Hop-on Hop-off Open Top Bus Tour

From your vantage point on the double-decker sightseeing bus you'll enjoy panoramic views of Chicago’s finest skyscrapers, including the 875 N Michigan, the Willis Tower and the Wrigley Building. Take in the city's impressive landmarks as your tour guide provides entertaining commentary and insight into Chicago's history. Enjoy exploring this dynamic city with the freedom to hop-on and hop-off as many times as you wish to visit attractions such as the Shedd Aquarium and the Field Museum. You’ll travel down the famous Magnificent Mile, considered one of the great avenues of the world, and continue across the Michigan Avenue Bridge over the Chicago River. The bridge connects the north and south sides of the city. This hop-on, hop-off bus tour of Chicago makes it easy for you to explore the city's sights at your own pace. There are 13 stops, where you can hop-off to visit attractions and explore places of interest. The stops are conveniently located to make navigating your way around the city easy, and with a choice of Classic, Premium or Deluxe tickets, you can take your time discovering Chicago. Be sure to take advantage of admission to the Chicago Architecture Center, included with the Premium and Deluxe tickets, to dive deeper into the city that invented the skyscraper. So don't wait, just hop-on an exciting journey through Chicago.

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

4. 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 City Mini Bus Tour with Optional Architecture Cruise

5. 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: Must See Chicago 90 minute Walking Tour

6. Chicago: Must See Chicago 90 minute Walking Tour

Starting at the Chicago Architecture Center (CAC), this tour gives you an overview of many of the must see buildings and landmarks in the City of Chicago. Led by an expert guide who has been rigorously trained by the CAC to be equal parts storyteller and educator, you will get a fantastic introduction to the city’s wide variety of architectural styles, construction methods, and materials. There is so much to see downtown, and this tour makes it easy and fun to learn about some of the buildings that make Chicago’s architecture world-class. There are lots of photo opportunities along the way, so be sure to bring your camera! The tour covers three of the main focal points of Downtown Chicago – the Chicago Loop, the heart of historic Chicago; the Chicago River, the lifeblood of the city; and Millennium Park, where the iconic “The Bean” sculpture is located. Landmark buildings covered on this tour include soaring modernist skyscrapers (Willis Tower, John Hancock Center, and AON Building), buildings paying homage to classical styles (Wrigley Building, Tribune Building, the Chicago Theatre, and the Art Institute of Chicago), Art Deco edifices (Carbide & Carbon Building and the Chicago Board of Trade Building), and recently completed skyscrapers (Aqua & Trump Tower). Finally, admission to the Chicago Architecture Center (CAC) is also included with your walking tour ticket. CAC exhibits focus on Chicago’s diverse neighborhoods, housing types, leading architects and future projects, and include the largest scale model of the city, with more than 4,250 miniature buildings and a cinematic backdrop animating key moments in its history. The stories of the city begin at the CAC.

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Other Sightseeing Options in Trump Tower, Chicago

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What people are saying about Trump Tower, Chicago

Overall rating

4.8 / 5

based on 4,650 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!

A great way to figure out where you want to spend additional time. Canopy on the roof keeps you warm, even when chilly.

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

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