Chicago Loop Tours & Attractions

Interested in exploring Chicago from the perspective of ghosts and gangsters? Want to really immerse yourself in the history of this great American city, right from the locations that started it all? This tour visits the locations frequented by some of Chicago's most notorious gangsters along with many of the most haunted locations in Chicago!

You can get the best of both worlds with this 2 in 1, history-based guided walking tour of Chicago’s gangsters and ghost stories, right from the famous Chicago Loop Vice District! Upgrade to the bus tour option to experience the same spine-chilling stories by minibus. Includes one stop for an immersive experience.
Duration: 2 hours.

The perfect tour for first timers to Chicago or those who want to explore Chicago's famous foods along with the city's top attractions, all on one tour. Stroll the beautiful streets of downtown Chicago & taste the Windy City’s favorite eats! Bobby’s Bike Hike, whose food tours are ranked Top 10 in America (USA Today) & Top 20 in the world (Tripadvisor), offers this ultimate food & walking tour to explore the hard-working, salt-of-the earth foods Chicago made famous; a slice of deep-dish pizza, a Chicago-style hotdog, Italian beef, popcorn & brownies. Bobby’s expert guides will lead you through downtown Chicago’s most iconic landmarks; Millennium Park, State St, Chicago Theatre, Riverwalk, Michigan Ave, & the Wrigley Building, all the while explaining the tales from Chicago’s rich food-centric history. Enjoy your food tour & receive a bonus 2-hour FREE bike or kayak rental for each ticket bought, adding value to your experience. Bike along the Lakefront Trail or kayak on Lake Michigan.
Duration: 3 hours.

Ready to discover some of the best Chicago has to offer with a local by your side? Join us on an epic tour of some of the city’s greatest hits: incredible architecture both old and new, delicious local treat and iconic Chicago dishes, a uniquely Chicago transit ride, stunning river views and much more!

Duration: 5 hours.

We've always had a passion for donuts, but only recently did we realize just how many others do too. And when looking around, we didn't see anything that truly celebrated donuts in all their glory, hence the Underground Donut Tour was born. This tour is for anyone who truly enjoys donuts. At each location, you'll be able to try a curated sample or samples of that location's best donuts. Many locations offer vegan, gluten or nut free options, however, please make sure to let us know ahead of the tour, so we can make sure to highlight those specifically for you. Our tours include such favorites as Do-Rite Donuts, Firecakes, Stans, and Doughnut Vault.


Duration: 90 to 120 minutes.

Enjoy Chicago’s only bus guided neighborhood pizza tour.  Eat like a local as you travel off the beaten path into Chicago neighborhoods to savor the best pizza.  Your local guide will teach you the science behind ingredient selection and baking as you sample slices from historic pizzerias.  In just a few hours, you’ll leave stuffed, and with an understanding of why pizza is such an important part of Chicago’s culture.
Duration: 3 hours 30 minutes.

Experience the best travel stories for yourself! Join a local expert and uncover hidden gems. Join us for the ultimate foodie adventure in Chicago’s historic River North area alongside a local guide who can show you the best spots for some of the city’s best-loved dishes. From deep-dish pizza to Chicago-style hot dogs, this tour will leave you filled with delicious local foods as well as some insider knowledge into the city’s culinary history and culture.
Duration: 2 hours.

This tour is just a short walk through great Chicago neighborhoods starting near Navy Pier and the Magnificent Mile, and then heading into the Gold Coast & River North. Compare two American pizzas vs. two Italian pizzas to understand how pizza evolved as an immigrant food. Explore Deep Dish, Roman, Neapolitan, and Artisanal pizza in just a couple of hours. Discuss how each of these styles is crafted and the differences in their ingredients, baking techniques, and ovens. Plenty of pizza to eat, come hungry!
Duration: 2 to 3 hours.

Wander through Chicago downtown exploring and gaining new food experience on this walking trip. Dive into the hospitable and authentic atmosphere of the city encountering interesting sights and visiting the principal city landmarks.
Be welcomed by the unique culinary tastes of the Windy City and fall in love with iconic treats, listening to the interesting historical and cultural facts from your guide.

On this walking tour of Chicago, revel in the incredible climate while visiting the most important landmarks of the city following your guide. You will also dive into the diversity of tastes exploring some typical Chicago food and drinks and enjoy a pleasant walk in good company, choosing your path depending on the weather.
Duration: 3 hours.

CHOOSE from our range of discounted tour passes below & save up to $55 per person! Children aged 0-6 are free!

Hassle free booking - no referral to third party operators, we own all of the tours!

5 tour pass - SAVE $55 PER PERSON (redeemable March - Oct)
-Gangster & Food Walking Tour
-Secret Interior Architectural Walking Tour
-Gangsters & Ghosts Minibus Tour
-Luxury Minibus City Sightseeing Tour
-Riverboat Architecture Tour

4 tour pass - SAVE $40 PP (redeemable year-round)
-Gangsters Food Walking Tour
-Secret Interior Architectural Walking Tour
-Gangsters & Ghosts Minibus Tour
-Luxury Minibus City Sightseeing Tour

3 tour pass - SAVE $25 PP (redeemable March - Oct)
-Riverboat Architecture Tour
-Secret Interior Architectural Walking Tour
-Gangsters & Ghosts Walking Tour

2 tour pass - 2 TOURS FOR THE PRICE OF 1 (redeemable year-round)
-Secret Interior Architectural Walking Tour
-Gangsters & Ghosts Walking Tour

All tours are led by an expert tour guide. Book now for the best value!
Duration: 3 to 11 hours.

Chicago and the history of the mob are synonymous when we look back at history. That’s why we provide an in-depth Chicago Gangster Tour that makes all of the infamous stops for our patrons. 

Visit the old stomping grounds of:
• Al Capone
• John Dillinger
• The Untouchables

View crime scenes immortalized in vintage news footage, the theater where the law caught up with Dillinger, the restaurant where the North Side Gang riddled Al Capone’s motorcade with rounds from their Tommy Guns, and the site of the St. Valentine’s Day Massacre.

We bring Chicago’s true crime past to life before your very eyes.
Duration: 3 hours.

Our Prohibition Era Speakeasy Pub Crawl is filled with cocktails and a perfect venue for bachelor or bachelorette parties, corporate events, or just a fun night out on the town to celebrate life and your friends. Hosted by a local historian, the tour makes stops at:
• Al Capone’s neighborhood
• Old Chicago bars
• Prohibition era establishments 

We transport you back in time to the 1920s, entering our venues through secret openings that really shed light on what the city was like 100-years ago. Relive the glamour of this time period while listening to stories of the rampant racketeering and bootlegging. If you’re really feeling up to it, dress the part, too.
Duration: 3 hours.

See Chicago’s most essential landmarks from the comfort of a private vehicle on this 3-hour jaunt around town. Your guide will pick you up directly from your Chicago accommodation, after which you’ll be whisked away to see the sights. From the storied Magnificent Mile to the glamour of the Gold Coast, you’ll encounter the best of the Windy City. This private tour is available in Portuguese, English, or Spanish, and kicks off promptly at 9am.
Duration: 3 hours.

Created by 13-time James Beard Award-winning food journalist Steve Dolinsky, this Sunday-only series of tours is based on his book, "Pizza City, USA" and features four different styles of pizzas in less than three hours. Learn about Chicago's 10 pizza styles, and discover why there's more to The Windy City than just deep-dish. Go back in the kitchens to see how pizzas are made, talk to the owners and taste the differences. Expert "doughcents" will share the history of Chicago pizza as well other interesting tidbits about the neighborhood you're exploring. PLEASE LET US KNOW AT TIME OF BOOKING IF YOU EAT PORK OR PREFER VEGETARIAN.
Duration: 3 hours.

Take your shot at completing this Chicago Scavenger Hunt around the Loop and River North neighborhoods including the Riverwalk.
Complete this solo or build a ScavSquad of up to 5 people and discover the city like never before!
Use clues and hints within the app to complete the objectives (if you get stuck, you can skip and go back later).
Some objectives have prizes so do your best to complete as many objectives correctly.
Once complete, you can view the Leaderboard to see how you did against others.
Duration: 3 hours.