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Trump Tower, Chicago

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.

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

2. 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.

Chicago: 45-Minute Family-Friendly Architecture River Cruise

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

Admire Chicago’s impressive architecture from a unique perspective aboard a cruise sailing down the Chicago River, which features an indoor and outdoor deck, along with live commentary tailored to entertain the whole family. Treat yourself to a full-service cash bar at your own expense. 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, exploring 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.

Chicago: 90-Minute River and Lakefront Cruise at Night

4. 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 and the uses of the lock from your guide. You’ll also feel the boat rise as you enter Lake Michigan and lower as you return to the river, a unique experience for any boat lover.

Chicago: Big Bus Hop-on Hop-off Sightseeing Tour

5. Chicago: Big Bus Hop-on Hop-off Sightseeing Tour

From your vantage point on the double-decker sightseeing bus, you'll enjoy panoramic views of Chicago’s finest skyscrapers, including the John Hancock Center, the Willis Tower, and the Wrigley Building. Take in the city's most impressive landmarks while listening to entertaining commentary and insight into Chicago's history. Explore 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 Natural History Museum. You’ll travel along the famous Magnificent Mile, considered one of the great avenues of the world, and continue across the Michigan Avenue Bridge over the Chicago River. This hop-on, hop-off bus tour of Chicago makes it easy for you to explore the city's sights at your own pace. All stops are conveniently located to make navigating your way around the city easy, and with a choice of 24- or 48-hour tickets, you can take your time discovering Chicago. With the 48-hour ticket, enjoy a non-stop Panoramic Night Tour of the city included with your ticket! Admire the illuminated skyline from the Museum Campus and see River North's vibrant nightlife scene.

Chicago: Family Fun Urban Adventure River and Lake Cruise

6. 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 River.

Chicago: City Minibus Tour with Optional Architecture Cruise

7. Chicago: City Minibus Tour with Optional Architecture Cruise

Start with a pickup from your downtown Chicago hotel. Board your climate-controlled minibus and embark on your guided sightseeing tour. Begin 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, head through Grant Park, which is known as the city's front yard. The centerpiece of the park is the Buckingham Fountain. Museum Campus is up next, with three museums, Soldier Field, and the most spectacular skyline views in the city. After a 10-minute photo stop, travel around Millennium Park, featuring The Bean, before heading up north along Wacker Drive, which parallels the Chicago River. Arrive in the fancy Gold Coast nightlife area and residential neighborhood - one particularly interesting sight here is the original Playboy Mansion.  Then, take a trip through part of Lincoln Park, and end the tour by zipping along Lake Shore Drive, past beaches, and old mansions, before being dropped off at your hotel. For those wanting the ultimate Chicago experience, add on the option of the world-famous architecture cruise of Chicago. After your 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 as the city’s most renowned landmarks, such as the John Hancock building and more.

Chicago: Must See Chicago 90 minute Walking Tour

8. 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.

Chicago: Elevated Architecture Walking Tour

9. Chicago: Elevated Architecture Walking Tour

Join a walking tour to explore Chicago’s memorable architecture from the unique perspective of elevated trains and station platforms. Learn the history behind the "L" system and hear how it has shaped the development of buildings within the Loop. Experience riding the “L” for yourself. The city's first elevated train started making trips in 1892. Now considered one of Chicago’s most defining features, the "L" offers one-of-a-kind views of downtown. By being more than 20 feet off the ground, you'll see architectural details that are missed by most pedestrians at street level. With this tour, you’re in for one of the most comprehensive tours in the Loop, passing hundreds of buildings and Chicago highlights. As you make your way around the city, listen to narration by your guide about Chicago’s transit system and architectural significance.

  • Guided tours
  • Water activities
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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 5,783 reviews

Enjoyed the entire experience & certainly worth the time & money. Sat top deck even through the River's mist. Tour guide, Dave, was the highlight of the trip. Very knowledgeable about the artitecture of the buildings and history of the city along with some witty comedy.

We took the 18:45 and it was an excellent choice. We could see the buildings under dusk and with beautiful lights. The guide was very active and passionate with her description.

I think everyone should experience this just ONCE in their life. It was an amazing experience!.

Very enjoyable excursion and knowledgeable cruise host.

Really enjoyed it and the guide was very friendly.