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Chicago Loop Tours

Our most recommended Chicago Loop Tours

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: Big Bus Hop-on Hop-off Sightseeing Tour

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

From your vantage point on the double-decker sightseeing bus, you'll enjoy towering 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 unique and exciting 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. With a choice of 24 or 48-hour tickets, you can take your time discovering Chicago.

Chicago: Mob and Crime Bus Tour

3. 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 an enclosed, 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: 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 Food Tasting: 2.5-Hour Guided Walking Tour

5. 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: Secret Food Tour

6. 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.

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What people are saying about Chicago Loop

Overall rating

4.5 / 5

based on 740 reviews

This was a wonderful hour and a half guide down the river. I had already walked Chicago for five days with an architectural book in my pocket, and I still thoroughly enjoyed this tour. The sights from the river open up views to buildings you don’t normally see walking. 90% of the tour guide information was not in my tour book. We went on a cold December day, roughly 17° with 15 mile an hour wind down the river. I had a long sleeve shirt, vest, a windproof suit, mittens, and I was just warm enough to be comfortable, except for my feet. I wish I would have worn by snow boots. However, they sell handwarmers down in the lower level of the theory, so I bought a pair and put them in my shoes; solved the problem:)

Beautiful boat ride! The views and the architecture are amazing! Tour guide was a lot of fun, many jokes and interesting information. If you do it during the wintertime wear warm clothes, it’s pretty cold.

Great tour. Although it was super cold. We went inside and purchased their delicious hot chocolate and it kept us warm to go back up and the tour. The staffs were very professional and friendly.

Worth every penny, even braving extreme cold! Had excellent indoor (warm) options too; I liked being on deck to get a full view of all the wonderful structures!

It was a very fun tour and we learned a lot about the city that we didn't know before. Lizzie was an excellent guide!