Chicago Highlights & Attractions Walking Tour

  • 2 Hours9am Daily
  • Ages from 1+
  • Level: An easy stroll
  • Length: 1.5 miles
Ages Pricing (Mon-Thurs) Pricing (Fri-Sun)
Adult (12+) $42.99 $44.99
Youth (4-11) $37.99 $39.99
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 the Highlights of Downtown Chicago

Visit Chicago’s top attractions on a single walking tour

Walk your way through Chicago’s most popular attractions and locations as our guides share amazing stories of Chicago’s unique history, colorful characters, and the attractions that define its landscape.  We’ll explore Millennium Park, with its hidden gardens, fountains made up of faces that spit water at each other, and Chicago’s most iconic symbol, Cloud Gate, often dubbed ‘the bean’.

We’ll also visit Chicago’s Riverwalk where you’ll see the most Instagrammable viewing points of our skyline, as well as Michigan Avenue (aka the Magnificent Mile) and the Chicago Theater with its iconic marquee.  You won’t want to miss this tour.  If you’re hungry, we offer the same tour combined with Chicago’s most notable homegrown foods, including Chicago-style pizza, hot dogs, Italian beef, and brownies.  It’s called the Chicago Favorites Food and Walking Tour.

What’s Included

  • Informative walking tour of Chicago’s top downtown attractions.

What to Bring

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

Important Info

  • 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

The adventure begins along Michigan Avenue, dubbed the Magnificent Mile, for its amazing shopping and attraction experience. We’ll explore the Historic Water Tower, the only building to survive the Great Chicago Fire of 1871.  Then we’ll walk by Holy Name Cathedral, home to Chicago’s Catholic Cardinal who still gives regular sermons.  The structure also holds a more sinister past, as it has bullet holes from Al Capone’s days in Chicago.  

Then it’s on to the Wrigley Building, one of Chicago’s most iconic architectural wonders.  Meet your guide and all of the other fun people on your tour.  Your guide will lead you down the beautiful, wide sidewalks to Chicago’s Riverwalk, where you’ll witness some of the best architectural views this amazing City has to offer.  Bring a camera!  Then it’s off to Millennium Park. At this stop you’ll catch a peek of some of our favorite (and most-heavily Instagrammed) works of public art such as Cloud Gate, the Pritzker Pavilion, and the Crown Fountain. You’ll learn about Chicago’s front lawn, Grant Park, where you’ll hear why it’s always ‘Forever Free and Clear’. Ample photo opportunities guaranteed! 

After the fun of Millennium Park, we’ll head back over to State Street for a stop at the iconic Chicago Theatre, with its famous ‘Chicago’ marquee that even Chicagoans can’t help gawking over. Then it’s down State Street, ‘that Great Street’ as dubbed by the late great Frank Sinatra, with its notable shops, center of commerce, and home to the theater district.  The last stop will be a visit to the Daley Plaza, which is right outside of City Hall and home to many street festivals and activities.

This tour is sure to take you to all of Chicago’s most loved attractions. 



Extra Information

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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