Chicago
Architecture

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Our most recommended Chicago Architecture

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: Willis Tower Skydeck and The Ledge Ticket

2. Chicago: Willis Tower Skydeck and The Ledge Ticket

Enjoy an unrivaled view over the city of Chicago on a trip up the city's Willis Tower. This famous building, once known as the Sears Tower, is not only home to a Skydeck on the 103rd floor, but it also features The Ledge, a series of 4 glass-paneled boxes that extend out from the building's facade to give visitors a view straight down. As you wind through the ground levels of the Willis Tower, you will be surrounded by museum-quality exhibits highlighting the iconic tower. Learn about Chicago's rich history and culture through these informative visuals. Watch a video presentation, "Reaching for the Sky," where you will be briefed on the history of the building and of architecture in Chicago. Then step into your elevator and you will be amazed at how quickly it ascends. As you travel, your multimedia-equipped elevator will inform you about your vertical progress. Upon reaching the 103rd floor, step out onto the Skydeck, which offers views spanning over 50 miles and across 4 states. Then summon your courage to step out onto The Ledge, a glass balcony that hangs over the edge, for vertigo-inducing views 1,353 feet (about 412 meters) straight down to the city below! Download the Skydeck Mobile App for a free viewfinder which points out many of Chicago’s notable landmarks. Learn more about sights like Navy Pier, Wrigley Field, Grant Park, Art Institute of Chicago, Shedd Aquarium, and Field Museum of Natural History.

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Chicago River: 45-Minute Family-Friendly Architecture Cruise

3. 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: 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 from a local expert tour guide giving interactive live commentary 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. You'll also view historic video footage, receive an informative pamphlet with photos, and can even take part in a crime quiz. Stake out crime scenes like the Biograph Theatre, Holy Name Cathedral, Clark Street Bridge, and other Chicago landmarks. See the site of the St. Valentine's Day Massacre, one of Chicago's most notorious murder scenes. Get off the bus and walk the path that notorious Chicago gangsters John Dillinger and Hymie Weiss followed just before their deaths. Travel into the criminal past of Chicago's River North, Gold Coast, Lincoln Park, Old Town, Loop, and Magnificent Mile neighborhoods.

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

5. 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: Brunch, Lunch, or Dinner City Cruise

6. 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 fireworks display. Sample dinner menu Choice of starter: Caesar salad Lobster soup Choice of main course: Jumbo lump crab cakes Maple and mustard glazed chicken breast Braised beef short rib Jumbo forest mushroom ravioli Choice of dessert:  Eli’s original cheesecake Duo seasonal sorbet Chocolate decadent cake Odyssey signature warm butter cake Sample Brunch Menu Choice of starter: Caesar salad Scottish smoked salmon toast Greek yogurt and granola parfait Fresh blueberries and strawberries Choice of main course: Cannellini bean shakshuka Maple and mustard glazed chicken breast Scrambled eggs  Raisin and cinnamon french toast Choice of dessert: Eli's New York style cheesecake Tres con leche flan Triple chocolate mud pie Freshly cut fruit and fresh strawberries Sample Lunch Menu Starter: Caesar Salad Choice of main course: Jumbo forest mushroom ravioli Maple and mustard glazed chicken breast Oven baked Atlantic salmon fillet Braised beef short rib Choice of dessert: Eli's New York style cheesecake Freshly cut fruit and fresh strawberries Duo of Sorbet

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Chicago: 45-Minute Private Helicopter Flight for 1-3 People

7. Chicago: 45-Minute Private Helicopter Flight for 1-3 People

Enjoy spectacular views of Chicago from an MD500 helicopter. This 45-minute helicopter flight over Chicago covers all the important highlights of the city from McCormick Place and Soldiers Field in the South to Wrigley Field in the North. Depart from Schaumburg Regional Airport and see some of Chicago's highlights including the Willis Tower, the John Hancock Building, Navy Pier, and Lake Michigan with its beaches and picturesque shoreline. Also see the Chicago River, Grant Park, Millennium Park, Buckingham Fountain, and Museum Campus. Make sure you also look out for Wrigley Field, home to the Chicago Cubs, and the United Center, where the Chicago Bulls and Blackhawks both play. This is a private helicopter experience for 1 to 3 passengers. Travel in complete safety with a professional pilot who will provide you with live commentary through noise-canceling headphones. In the summertime, have the added thrill of the doors being able to be off during the flight.

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

8. 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: Go City All-Inclusive Pass with 25+ Attractions

9. Chicago: Go City All-Inclusive Pass with 25+ Attractions

The Chicago All-Inclusive Pass by Go City provides free admission to the city’s top activities, attractions, and tours, offering the ultimate in convenience, savings, and flexibility. Choose durations of 1, 2, 3 or 5 days at a low, pre-paid price. Save up to 45 percent compared to buying individual attraction tickets. The more you see, the more you save! Take a trip up to SkyDeck Chicago, visit the Field Museum, have fun at Navy Pier, and enjoy a cruise. All these and more are included in the cost of your Chicago All-Inclusive Pass. See the complete list below. The Chicago All-Inclusive Pass comes with a digital guide including useful attraction information. Use it to help you decide what to do, where to go and how to get there. Activities, attractions, and tours included with the Chicago All-Inclusive Pass: • Shedd Aquarium • SkyDeck Chicago • Hop-On Hop-Off Big Bus Chicago: 1-Day Classic Tour • 360 CHICAGO • Adler Planetarium • Museum of Science and Industry • Field Museum • Navy Pier Centennial Wheel and Rides • Shoreline Architecture River Cruise • Shoreline Classic Lake Tour • Chicago Children's Museum • LEGOLAND Discovery Center • Bike Chicago: 4 Hour Bike Rental • Tall Ship WINDY • Chicago History Museum • Lincoln Park Zoo Rides • Museum of Contemporary Art • The Escape Game Chicago • Robie House • Frank Lloyd Wright Home and Studio Tour • Panoramic and Scenic North Side Tour • Historic Chicago South Shore Tour • Grand Tour • Chicago Theatre Tour • Ernest Hemingway Birthplace Home • 10pin Bowling Lounge • American Writers Museum

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Chicago: Art Institute Tour Before Opening Hours with Guide

10. Chicago: Art Institute Tour Before Opening Hours with Guide

Experience a guided tour around some of the world’s greatest and most iconic art pieces at the Art Institute of Chicago. Avoid the crowds and lines, meeting your expert guide at the Institute before opening times and explore the expansive collection, learning more about both contemporary and classic pieces. Although the museum usually hosts 1.79 million people per year, you will be able to stroll among the pieces at leisure, getting up close and personal with works by famous and infamous artists like Edward Hopper, Pablo Picasso, Salvador Dali and Andy Warhol. The Art Institute of Chicago is home to the greatest collection of Impressionist artwork in the world. Your guide will provide expert information on the collection and the museum’s history and hidden gems.

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Other Sightseeing Options in Chicago

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What people are saying about Chicago

Overall rating

4.5 / 5

based on 1,499 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!!