One Day in Chicago Food & Highlights Walking Tour

  • 5 Hours10:30am Daily
  • Ages from 1+
  • Level: An easy stroll
  • Length: 2.5 miles
Ages Pricing (Mon-Thurs) Pricing (Fri-Sun)
Adult (12+) $95.99 $99.99
Youth (4-11) $75.99 $79.99
Infant (0-3) $9.99 $9.99

FREE 2 Hour Bike or Kayak Rental (included with this tour purchase)Terms Below:

  • To be used within +/- 3 days of your tour booking.  

  • Bike rentals take place at Bobby’s Bike Hike World Headquarters, 540 N. Lake Shore Drive, Chicago, IL60611.  Bike shop is open year-round (excluding Thanksgiving & Christmas).

  • Kayak rentals take place at Ohio Street Beach, Bobby’s Kayak, 550 E. Grand Avenue, Chicago, IL 60611.  Kayak shop open mid-May to mid-October, weather dependent.

  • Offer excludes Saturday Bike/Kayak rentals between Memorial Day (end of May) Weekend to Labor Day (early September).  Kayaking only available from June-September)

  • No discounts for not using this activity or issues due to weather restrictions.

  • Option NOT Available for Private or Custom Group Tours

See and Eat the Highlights of Downtown Chicago

This tour will give you a unique look at the city from a local expert’s perspective. Have you always dreamed of eating your way through Chi-town while bouncing from one eye-popping attraction to another? Then our Chicago walking and food tours are for you.

Leave the planning to us, our tours have been awarded the following:

Top 10 Food Tours in America – USA TODAY
Top 20 Food Tour in World – TripAdvisor
Top 15 Vacation Experiences in America – Entrepreneur Magazine

Embark on an unforgettable expedition through the culinary and cultural tapestry of Chicago, where every flavor and landmark tells a tale of the city’s vibrant soul. Our immersive journey takes you to the heart of Chicago’s gastronomic treasures, featuring iconic delights such as the world-famous Chicago Pizza, a symphony of flavors in the classic Hot Dogs, the savory indulgence of Italian Beef, the irresistible crunch of Garrett Popcorn, and the decadent original recipe Brownie. Elevate your experience by opting for the VIP Craft Beer package, allowing you to savor three exquisite local craft beers in generous 9oz pours. It’s not just a food tour; it’s a celebration of Chicago’s culinary prowess.

But this adventure is not just about savoring delectable bites. Our expertly guided tour will lead you through the pulsating energy of Millennium Park, where art and nature converge in a breathtaking dance. Meander along the enchanting Chicago Riverwalk, where the city’s architectural marvels reflect on the tranquil waters. Stroll the glamorous expanse of Michigan Avenue, the legendary Magnificent Mile, marvel at Cloud Gate (affectionately known as ‘the Bean’), bask in the grandeur of the Chicago Theater, wander down State Street (that great street), visit the Chicago Water Tower (the only downtown building to survive the Great Chicago Fire of 1871), visit the World’s largest Tiffany glass dome, and much more.  Not only will you get a wonderful 5 hour touring experience, but we’ll give you an additional free 2 hour bike or kayak rental as an additional value.  This way you can maximize your entire experience through visiting more neighborhoods via biking the 20 mile Lakefront Bike Trail.  Or if biking isn’t your thing, you can do a 2 hour kayak rental on the calm, clear waters of Lake Michigan (inside the break wall off Ohio Street Beach, arguably the most photo-worthy beach in Chicago)

Seize the opportunity to have the ultimate Chicago experience – a fusion of flavors and sights that defines the spirit of the city in a single, unforgettable day!

What’s Included

  • Tour prices include all five food samples. Beer samples can be added for an additional fee.
  • Three craft beers with the VIP Craft Beer Package.
  • Storied history of Chicago’s classic dishes and the establishments that created them.
  • Informative walking tour of the Windy City’s most beloved landmarks.
  • Either 2 hour bike rental or 2 hour kayak rental (to be used within three days of your tour, weather permitting.)*excludes Saturdays between Memorial Day Weekend to Labor Day. Kayaking only available from June-September

What to Bring

  • Please bring an ID.
  • Please bring a bottle of water.
  • Wear comfortable clothing/shoes.

Important Info

  • Additional Costs might be incurred for restricted diets or changes to menu items.
  • Please arrive 15 minutes before scheduled tour time!
  • Tours run snow, rain, or shine!

Departure Locations

  • Stan's Donuts & Coffee, 750 N. Rush Street, Chicago, IL 60611

Locations Visited Include:

  • Millennium Park
  • Chicago Theatre
  • Michigan Avenue and Shopping District (Magnificent Mile)
  • Cloud Gate (the Bean)
  • Pritzker Pavilion
  • Crown Fountain
  • Daley Plaza

What to Expect

Let’s start our epic day long experience!

Meet your group and guide as you check in for this epic, 5 hour experience through Chicago’s top highlights, food and attractions.  Embark on an enchanting journey through the heart of Chicago, where the magic begins at the Historic Water Tower on North Michigan Avenue.  This building is one of the few still standing after the Great Chicago Fire of 1871.  We’ll then stroll down to one of our renowned deep-dish pizza havens. As you step into the pizza paradise, you’ll be greeted by our lively and charismatic guide, a storyteller of Chicago’s epic history. Settle in for a tantalizing experience as you dive into a bubbling, cheesy, and stuffed Chicago pizza pie, paired perfectly with a locally crafted beer for those indulging in the VIP Craft Beer Package. Discover the secrets behind the creation of the Goliath pizza and understand why locals cherish it and visitors journey from every corner of the globe for a slice of this culinary masterpiece.

Explore Chicago’s top attractions

Continue your adventure with a leisurely stroll down the bustling Michigan Avenue, passing underneath the iconic Wrigley Building, a jewel that has adorned the Magnificent Mile since time immemorial. The walking tour then meanders along the picturesque Chicago Riverwalk, providing a mesmerizing backdrop of the downtown skyline and architectural wonders. Pause at a family-run Italian gem along the Riverwalk for a taste of their acclaimed Italian beef sandwich, a tradition that has stood the test of time and remains a local favorite.

Approach the grandeur of the Chicago Theatre, with its iconic ‘CHICAGO’ marquee, while your guide weaves informative commentary throughout the tour. Next, embrace the history and charm of the Billy Goat Tavern, an institution immortalized during the Belushi-era of SNL. Here, savor the unique Chicago-style hot dog, a Windy City culinary masterpiece, and delve into the fascinating story behind this one-of-a-kind creation.

Millennium Park….Go Beyond

Venture into Millennium Park, the cultural heartbeat of Chicago, featuring the renowned Cloud Gate, affectionately known as ‘the Bean.’ Marvel at this stainless-steel masterpiece amidst other public art delights, including the LED-faces of The Crown Fountain and the Frank Gehry-designed Pritzker Pavilion.

Chicago invented the brownie?

Conclude your culinary odyssey at the Palmer House hotel, a haven of elegance and history. Relax in the lavishly decorated lobby as you savor a delectable Chicago brownie, the hotel’s legendary creation. As the longest continually-operating hotel in North America, Palmer House adds a touch of historical splendor to your epicurean journey, not to mention the home of the world’s first ever brownie.  We’ll sample the original recipe brownie.

Extra…Extra…Learn all about it

The walking food tour concludes with expert suggestions for the remainder of your visit, guiding you to more delightful dining experiences in the vibrant downtown Chicago area. Immerse yourself in the flavors and stories that make Chicago an unparalleled destination for culinary and cultural exploration.  And don’t forget, your ticket gets you a free 2 hour bike or kayak rental so you can explore not just Chicago’s downtown area, but many of the connected lakefront neighborhoods by bike.  Or, if biking isn’t your thing you can kayak on Lake Michigan inside the calm, clean waters of the breakwall at Ohio Street Beach, arguably the most photo-worthy beach in all of Chicago.



Extra Information

The best way to see Chicago is from the streets. Whether you are visiting the Windy City for the first time or you have lived here your entire life, there are places on our city tour you would probably never find on your own.

This tour will give you a unique look at the city from a local expert’s perspective. Have you always dreamed of eating your way through Chi-town while bouncing from one eye-popping attraction to another? Then our Chicago walking and food tours are for you. Leave the planning to us, our tours have been awarded the following:


2023 Awards

Top 10 Food Tours in America – USA TODAY
Top 20 Food Tour in World – TripAdvisor
Top 15 Vacation Experiences in America – Entrepreneur Magazine


Chefs often give our guests off-menu samples and specials that restaurant diners don’t get to order. Plus, when you embark on our Chicago Classics Food Tour, you know you’ll be burning calories as you stroll through town — so feel free to load up your plate!

·         Expert guides who keep you engaged and amused while on the tour

·         Outstanding stories about and insights into Chicago culture

·         A chance to stimulate all five senses as you walk around town

·         Accessible to people of any fitness level

·         Perfect for all ages

·         Please arrive 15 minutes before scheduled tour time!

·         Tours run snow, rain, or shine!

·         Free 2 hour bike or kayak rental to use within 3 days of your tour date
(excludes Saturdays between Memorial Day Weekend to Labor Day)



Lou Malnati’s Pizzeria has been a Chicagoland favorite since 1971, and was voted Best Pizza by Chicago Magazine’s Readers Choice in 2021.

Gino’s East Pizzeria (alternative pizza stop) has been a Chicagoland favorite since 1966, owes it’s quality to slowing down the entire pizza-making process.

Located right next to the world-famous Millennium Park, the famous Billy Goat Tavern serves delicious Chicago-style hot dogs to Chicago locals and Millennium Park visitors every day of the week.

Specializing in Italian Beef and thin-crust pizzas, Bongiorno’s is a family-run business and takes pride in providing you with the best home-cooked Italian food and service in Chicago. They have won many awards from the Hungry Hound, Chicago Magazine, and TripAdvisor speak well for their work. We’ll visit Exchequer, located in the heart of Chicago’s Loop, specializing in Chicago-centric foods. Here you’ll get a portion of an Italian beef sandwich to sample.

Palmer House, home of the original Chicago brownie invented by Bertha Palmer. Part of the Palmer House Hotel, their brownie is a must try and we’re lucky enough to sample one on the tour.

We’ll be sampling beer along the way at each destination with the VIP Beer Upgrade.


Millennium Park, nestled in the heart of Chicago, is a dynamic urban oasis that seamlessly blends art, architecture, and nature. Home to iconic landmarks such as the Cloud Gate sculpture and the Crown Fountain, the park offers a vibrant cultural experience against the backdrop of the city’s skyline.

The Magnificent Mile, a bustling stretch of Michigan Avenue in Chicago, is a shopper’s paradise and architectural marvel. Lined with upscale boutiques, flagship stores, and luxury hotels, its glittering lights and grandeur make it a captivating destination for both locals and visitors.

Cloud Gate, known affectionately as “The Bean” debuted in Millennium Park in 2006. Designed by famed Indian artist, Anish Kapoor, this giant, stainless steel masterpiece has become one of the most famous symbols of Chicago arts and culture.

The Chicago Theatre was added to the National Register of Historic Places June 6, 1979, and was listed as a Chicago Landmark January 28, 1983. The distinctive Chicago Theatre marquee, “an unofficial emblem of the city”, appears frequently in film, television, artwork, and photography.

The Crown Fountain, a striking feature within Chicago’s Millennium Park, is an interactive work of public art designed by Jaume Plensa. Comprising two towering glass block towers that display changing digital faces and spout water from their mouths, the fountain creates a unique and engaging experience for visitors, combining artistry with water elements.

The Historic Water Tower, located on Michigan Avenue, is a surviving symbol of the city’s resilience, having withstood the Great Chicago Fire of 1871. Built in 1869, the limestone tower features a Gothic Revival design and stands as one of the few structures that survived the devastating fire. 

Holy Name Cathedral in Chicago, completed in 1875, is another stunning example of Gothic Revival architecture, with its intricate spires and intricate detailing. As the seat of the Archdiocese of Chicago, the cathedral holds historical significance and is renowned for its beautiful stained glass windows and majestic interior. 

The Pritzker Pavilion, situated in Millennium Park, Chicago, is an architecturally stunning outdoor amphitheater designed by Frank Gehry. Characterized by its distinctive steel ribbons and open-air structure, the pavilion hosts a variety of cultural events and performances, providing a harmonious blend of art, nature, and innovative design.

The Chicago Riverwalk is a picturesque waterfront promenade that winds along the Chicago River, offering breathtaking views of the city’s renowned architecture. Dotted with charming cafes, public art installations, and lively events, the Riverwalk serves as a dynamic hub where locals and visitors alike can soak in the scenic beauty of the city.

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