Things to do in
Chicago Loop

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Our most recommended things to do in Chicago Loop

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: Mob and Crime Bus Tour

2. Chicago: Mob and Crime Bus Tour

Experience Chicago’s underworld of criminals and gangsters on a luxury 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.

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 12 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 24- or 48-hour tickets, you can take your time discovering Chicago. With the 48-hour ticket, enjoy a non-stop panoramic sightseeing bus tour through Chicago at night too. Admire the illuminated skyline from the Museum Campus and see River North's vibrant nightlife scene. Take one loop from Michigan Avenue to the Magnificent Mile and the Cultural Mile. In addition, be sure to take advantage of admission to the Chicago Architecture Center, included if an appropriate option is selected, to dive deeper into the city that invented the skyscraper. So don't wait, just hop on an exciting journey through Chicago.

Chicago: Gangsters and Ghosts 2-Hour Walking Tour

4. 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

5. 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

6. 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: City Minibus Tour with Optional Architecture Cruise

7. Chicago: City Minibus Tour with Optional Architecture Cruise

Start with 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 ten 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 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, 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 the city’s most renowned landmarks, such as the John Hancock building and more.  

Chicago Crimes Night Tour

8. Chicago Crimes Night Tour

Uncover how some of the world’s most famous criminals, mobsters, and gangsters conned their way through the Windy City. Ride in luxury on a climate-controlled bus, as you explore famous Chicago crime scenes ranging from the 19th century through to modern times. Learn about Al Capone, the Untouchables, the Chicago Mob, John Dillinger, The Lady in Red, Captain George Streeter, Frank "The Enforcer" Nitti, Bugs Moran, Johnny Torrio and more. Grab your camera for a drive-by shooting of historic and architectural landmarks, and stake out crime scenes like the Biograph Theatre, Holy Name Cathedral and St. Valentine's Day Massacre, one of Chicago's most notorious murder sites. 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.

Chicago: Secret Food Tour

9. Chicago: Secret Food Tour

Sample the culinary delights of Chicago with the help of a fun and enthusiastic foodie guide. Be amazed by the city's eclectic mix of architecture and public art along the way. Taste delicious bites as you explore the city's central Loop district for 3 hours. Get better acquainted with what sets this friendly Midwest metropolis apart from other destinations and get a great insight into the art, architecture and everyday life in the city. Benefit from your guide's local knowledge and get tips to help you sightsee and explore the food and dining scene some more in your own time.

Chicago: Treasures of the Golden Age Walking Tour

10. 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. 

Other Sightseeing Options in Chicago Loop

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What people are saying about Chicago Loop

Overall rating

4.6 / 5

based on 2,517 reviews

We had an extremely knowledgeable and personable guide on our cruise, the boat was clean and comfortable, overall a great way to learn about Chicago architecture and history at the same time.

Once you have your pass, you can make the day your own. A nice variety of places to learn and explore.

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

It was a great time. The narration was very informative. Awesome tour

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