Chicago Loop
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Our most recommended Chicago Loop Wheelchair Accessible

Chicago: Gangsters and Ghosts 2-Hour Walking Tour

1. Chicago: Gangsters and Ghosts 2-Hour Walking Tour

See a different side of Chicago on a family-friendly guided tour and hear the tales of the ghosts that haunt the city. Explore the famous Chicago Loop district with interesting stories hidden behind each turn. Embark along the Chicago Loop, known as the vice district during the 1920s and 30s. See the places where gangsters such as Al Capone used to party, make deals, and carry out business. Visit haunted locations and old crime scenes led by historians. Stop at the Congress Hotel, Death Alley, and the Palmer House. Enjoy a refreshment along with way, with frequent stops and a restroom break.

Chicago: Museum of Illusions Timed Entrance Ticket

2. Chicago: Museum of Illusions Timed Entrance Ticket

Experience the impossible with an entry ticket to the Museum of Illusions Chicago. Immerse yourself in a world where your eyes will be in a constant battle with your brain. Located in the heart of the Chicago Loop, this brain-boggling museum is a one-of-a-kind destination all about optical illusions. Illusions challenge you to see things differently and reveal a lot about how your brain interprets reality. Experience more than 60 visual and educational exhibits featuring holograms, stereograms, optical illusions, and immersive rooms that are designed to tease the senses and trick the mind. Illusions include: defying gravity in the Tilted Room; growing and shrinking in the Ames Room; walking on walls in the Rotated Room; experiencing infinite space in the Infinity Room; confusing your mind in the Vortex Tunnel; posing in the Beuchet Chair; meeting your doppelgangers at the Clone Table. Then spend some time in the Smart Playroom with games that will stimulate and challenge your mind. Enjoy some friendly competition with friends and family while simultaneously improving your cognition, problem-solving skills, and memory. Overall, the museum is designed to encourage you to have fun while learning the mechanics behind each and every illusion you experience. And don't forget your camera or smartphone when you visit as there are eye-fooling photo-ops around every corner.

Chicago Food Tasting: 2.5-Hour Guided Walking Tour

3. Chicago Food Tasting: 2.5-Hour Guided Walking Tour

Combine an enjoyable walk around Chicago's downtown to see some of the city’s top sites with stops to sample some of the city’s famous tastes. On this 2.5-hour guided walk, you'll get to taste the foods Chicago is best known for doing right. Enjoy deep-dish pizza, the original Italian pastries, Chicago-style hot dog, and a classic Italian beef sandwich. Enjoy a VIP craft beer sample for an additional fee. Along the way, you’ll see some of Chicago's most iconic spots including Millennium Park, the Chicago Riverwalk, the Art Institute, and the famous Bean. By the end of the tour, your stomach will be full of delicious food and your head will be full of fascinating knowledge about Chicago. During the colder months, the tour makes use of the unique underground Pedway system that connects much of downtown and keeps you warm and cozy. On warmer days, you’ll walk at street level to enjoy the large promenades of the loop. The leisurely walking pace is suitable for people of all fitness levels.

Chicago: Treasures of the Golden Age Walking Tour

4. Chicago: Treasures of the Golden Age Walking Tour

This Historic Treasures of Chicago tour covers the most significant historic architectural landmarks in Chicago’s Loop. Your expert guide, trained by the Chicago Architecture Center, will focus on great cultural buildings from the late 19th and early 20th centuries, which harkened back to earlier time periods and were designed in revival styles such as Beaux Arts, neo-Georgian and neo-Gothic. Marvel at exteriors and interiors of dazzling beauty and startling originality, and get a glimpse inside some of the city's most beloved buildings.    The highlights of this walking tour will include the Chicago Cultural Center, home to the world's largest Tiffany dome; the iconic Marshall Field's department store, now Macy's on State; and the Palmer House, a beautifully restored hotel from the 1920s. 

Chicago: Art Deco Skyscrapers Walking Tour

5. Chicago: Art Deco Skyscrapers Walking Tour

Tour the lobbies of five opulent Art Deco skyscrapers built near the banks of the Chicago River during the business boom of the Roaring '20s. Art Deco abounds in Chicago. The style made its way to the city in the 1920s, after it was showcased at an international art exposition in Paris. It was widely seen at the 1933-1934 Century of Progress Exposition in Chicago as well. Influenced by Cubism and the art and architecture of the ancient Middle East, Art Deco can be found in popular motifs like zigzags, octagons, sunbursts and flowers. Art Deco reflects the era’s fun-loving optimism with lavish materials and geometric ornaments. Discover the origins of Art Deco while admiring buildings like the Carbide and Carbon Building (now the St. Jane Hotel), the Chicago Motor Club Building (now the Hampton Inn), the colorful, but often overlooked, Trustees System Service Building (now the Century Tower) and the Engineering Building—all of which are designated Chicago landmarks. This tour ends at the Merchandise Mart.

The Chicago Theatre Marquee Tour

6. The Chicago Theatre Marquee Tour

Explore the grandeur of The Chicago Theatre, which opened in 1921, on a 1-hour guided tour. Your guide will accompany you through the elegant lobby, sweeping staircase and the majestic auditorium, which is complete with murals above the stage and on the ceiling. During your visit, you will get access to various sections of the seven-story, 3,600-seat auditorium and an intimate view of the 29-rank Wurlitzer theatre pipe organ, the first musical instrument having attained a city landmark status.  Next, view artist signatures on the dressing room walls, including Frank Sinatra, Dean Martin, Dolly Parton and many more. You will finish your tour on a high and feeling like a star as you get the chance to stand on the famous Chicago Theatre stage. Once called “the Wonder Theatre of the World”, the Chicago Theatre hosts over 175 events a year, bringing together the world’s brightest stars and greatest productions.

Chicago: Private 3-Hour Al Capone Gangster Tour

7. Chicago: Private 3-Hour Al Capone Gangster Tour

Experience amazing stories of true crime coming to life on this three-hour private tour. Visit many of the old venues where gangsters used to operate, including old speakeasies and historic hotels. Your expert historian guide will accompany you and your private group in luxury accommodation to historically significant locations in the city. View crime scenes immortalized in vintage news footage, the theater where the law caught up with Dillinger, and the restaurant where the North Side Gang riddled Al Capone’s motorcade with rounds from their Tommy guns. See the site of the infamous St. Valentine’s Day Massacre, and sit in Al Capone’s booth at the Green Mill. Finally, visit the location where Public Enemy #1 John Dillinger was assassinated by the FBI.

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What people are saying about Chicago Loop

Overall rating

4.1 / 5

based on 269 reviews

We had a great tour with Lizzie. She was great fun and had great enthusiasm. Learned a lot and thoroughly enjoyed it

Lots for fun and learned a lot about this history of Chicago- tour quide was awesome. Highly recommend it!

Sarah was an awesome guide! Very funny and knowledgeable! We really enjoyed our tour with her!

Andrea did an amazing job to make it entertaining yet informative.

Great tour about the history of gangsters and ghosts in Chicago!