• Lou Malnati’s Pizzeria - Lou Malnati’s Pizzeria has been a Chicagoland favorite since 1971, and was voted Best Pizza by Chicago Magazine’s Readers Choice in 2021. Here we’ll enjoy a thick, hearty slice of Chicago-style pizza.

• Billy Goat Tavern (Millennium Park) - 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. Here we’ll sample a Chicago dog with all of the fixins.

• Exchequer Restaurant & Pub - We’ll visit the famous Exchequer, located in the heart of Chicago’s Loop and synonimous with Chicago’s gangster past, specializing in Chicago-centric foods. Here you’ll get a portion of an Italian beef sandwich to sample.

• Palmer House Hilton Historic Lobby - 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.

• Historic Water Tower - 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.

• Millennium Park - 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 - 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 - 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 - 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.

• Crown Fountain - 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.

• Holy Name Cathedral - 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.

• Jay Pritzker Pavilion - 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.

• Chicago Riverwalk - 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.

• Daley Bicentennial Plaza - Daley Plaza, located in the heart of downtown Chicago, is a bustling civic space known for its iconic Picasso sculpture. Surrounded by prominent government buildings, it serves as a hub for public events, farmers’ markets, and features the renowned Christmas tree lighting ceremony during the holiday season.

• The Art Institute of Chicago - The Art Institute of Chicago is one of the oldest and largest art museums in the United States, housing an extensive collection of artworks spanning centuries and diverse cultures. Renowned for its iconic lion statues at the entrance, the museum is a cultural landmark known for its impressive exhibits, including famous masterpieces such as Grant Wood’s “American Gothic” and Vincent van Gogh’s “The Bedroom.”

• Buckingham Fountain - Buckingham Fountain, situated in Grant Park, Chicago, is a majestic landmark and one of the largest fountains in the world. Its intricate design, inspired by the Latona Fountain at the Palace of Versailles, features water displays, light shows, and operates from spring to fall, attracting both locals and tourists alike.

• Chicago Cultural Center - The Chicago Cultural Center, housed in a historic Beaux-Arts building, stands as a cultural hub in the city’s Loop neighborhood. Renowned for its stunning architecture and hosting a diverse array of free public events, the center is a vibrant space where visitors can appreciate art exhibitions, performances, and lectures.

• Harold Washington Library Center - Harold Washington Library Center, located in Chicago’s South Loop, is the largest public library in the city and an architectural gem designed by Hammond, Beeby & Babka, Inc. With its distinctive nine-story glass atrium, the library offers a vast collection of books, multimedia resources, and serves as a cultural and educational hub for the community.

• Bobby’s Bike Hike - Chicago Bike, Walking & Food Tours - FREE 2 HOUR BIKE or KAYAK RENTAL INFO:
  As an additional perk for booking this particular tour, you will get a FREE 2-hour bike or kayak rental (to be used within (+/-) 3 days of your tour booking. 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.

• Local, Expert Guide
• Explore the city’s incredible architecture, a unique blend of old and new
• Stories and insight into Chicago’s history and current events
• Receive insider tips on must-see attractions, activities, and culinary delights for your stay
• Indulge in 5 enticing food stops featuring iconic dishes
• Tantalize your taste buds with the renowned Chicago-style hot dog
• Delight in the famed deep-dish pizza at a Chicago pizza icon
• Savor a classic Italian beef sandwich
• Enjoy classic made-in-Chicago snacks – popcorn and the original brownie
• Lunch
• Water offered at most restaurants (although we encourage you to bring water)
• Enjoy a Free 2-hour Bike Rental or Kayak Rental (weather permitting)

• $15-20 per person (or more) recommended gratuity for guide (Cash, Venmo and PayPal)
• Local craft beer pairings upgrade offered upon arrival (Three 9oz pours) for $19.99/person (Ages21+)

Ready for the ultimate day out in Chicago? We’ll embark on an unforgettable Chicago journey, where iconic flavors like Chicago Pizza, Hot Dogs, Italian Beef, Chicago-mix Popcorn, and the original Brownie await. Opt for the VIP Craft Beer package for a heightened experience. Beyond bites, our expert-guided tour explores Millennium Park, the Chicago Riverwalk, Michigan Avenue, Cloud Gate, Chicago Theater, and more. Enjoy a 5-hour walking tour and receive a bonus 2-hour FREE bike or kayak rental, adding value to your experience. Maximize your day by biking along the scenic Lakefront Trail or kayaking on Lake Michigan. Leave the planning to the local experts. Bobby’s Bike Hike was awarded the following three awards just this year: “Top 10 Food Tours in America” by USA Today, “Top 20 Food Tours in the World” by TripAdvisor, and “Top 15 Vacation Ideas in USA” by Entrepreneur Magazine. Seize the opportunity for the ultimate Chicago fusion of flavors and sights in a single, unforgettable day!

For a full refund, cancel at least 24 hours before the scheduled departure time.