Welcome to Chicago: Private Half-Day Tour with 360 Observation Deck

Travel CuriousCrown Fountain, 201 E Randolph St.Chicago, IL 60611
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Total Price: $348.84 (USD)
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See Chicago from the ground up and from way up high on this private Chicago walking tour! Discover more about The Windy City while taking advantage of all the city has to offer– including the expansive trails of Millennium Park, the opulent stores on Magnificent Mile, unique art and architecture that defines the city, and a stunning view of the Chicago skyline.

up to 3 hrs up to 1 people

Good To Know

from Ashley, one of our Chicago Travel Experts
  • See Chicago from the street view and from way up high!
  • Explore Millennium Park and the Loop community, and stroll across the DuSable Bridge.
  • Visit the Cloud Gate sculpture, Magnificent Mile, Daley Plaza, and more.
  • Includes tickets to the 360 Observation Deck.
  • Tour duration is approximately 3 hours.
  • Suitable for culture vultures of all ages.
  • This is an exclusive tour with just you, your group and your guide.
  • Bring your camera!


from Welcome to Chicago: Private Half-Day Tour with 360 Observation Deck
Located in America’s Midwest along the Great Lakes shoreline, Chicago - known colloquially as the Windy City - occupies America’s third-largest metropolitan area: a huge, vibrant expanse packed with incredible history and architecture and fine public art. Discover the compelling character of America’s third-largest city, renowned for its jazz-and-blues heritage, striking architecture, historic streets and a fine array of public art.

On your private half-day tour, you will:
  • Meet your guide at the Crown Fountain that although is off during the winter months, it showcases an interactive work of art which projects video images of Chicago citizens
  • Explore Millennium Park, a gathering green space in the heart of the city that has won awards for its accessibility and design
  • See the Chicago Athletic Association hotel, an 1893 architectural icon on historic Michigan Avenue
  • Discover the Cloud Gate sculpture, also known as ‘The Bean’, reflecting the city's famous skyline in the center of Millennium Park
  • Walk into the Loop community area and spot The Picasso, an unnamed sculpture by the famous artist Pablo Picasso in Daley Plaza
  • Walk across DuSable Bridge over the Chicago River, an iconic movable bridge with two levels of vehicular and pedestrian traffic
  • Visit The Chicago Roastery - Starbucks Reserve, a 5-story building dedicated to the art and craft of coffee
  • Take a stroll down the Magnificent Mile, a vibrant area for shopping and dining
  • See the Medinah Athletic Club, now the InterContinental hotel, built in 1929 and born as a luxury men’s club
  • Pass by the Chicago Water Tower, the current home of Chicago's tourism office and one of the few surviving buildings to the Great Chicago Fire
  • End your tour with fascinating views of Chicago’s skyline from atop the Hancock Tower Observation Deck

When it was founded in 1837, Chicago’s early buildings were clustered around the mouth of the Chicago River. On your Private Chicago Half Day Highlights tour, explore the city famed for its bold architecture, past and present, incredible museums, and innovations in a wide variety of fields, from natural history and buildings to food and science.

On your Private Chicago Half Day Highlights tour, visit all the city’s major sites, including favorites such as the Magnificent Mile, Millennium Park and Hancock Tower. Your guide is a local who has plenty of tales about Chicago life together with an in-depth knowledge of its character.

As you journey down the Magnificent Mile, you will learn how Chicago has earned each of its nicknames, including the City of Broad Shoulders, the Second City, and of course, the Windy City. Lastly, your guide will escort you to the Hancock Tower to bid on your adieus.

You will then travel to the top of the Hancock Tower’s Observation Deck, where you can enjoy 360-degree views of the entire city at your own leisure.

  • A friendly, professional English-speaking tour guide for your own private group
  • Plenty of time to take photos of your favorite places
  • Hancock Tower Observation Deck admission tickets

  • Hotel pick up and drop off
  • Food and drinks
  • Gratuities
  • Transportation

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Frequently Asked Questions about Welcome to Chicago: Private Half-Day Tour with 360 Observation Deck

Where is the meeting point for this Travel Curious tour?

Your guide will meet you at the Crown Fountain, located at 201 E Randolph St, Chicago, IL 60601. Please be at the location 10-15 minutes prior to your tour.

How long is this tour?

Tour duration is approximately 3 hours.

What does the tour include?

This tour includes tickets to the Hancock Tower Observation Deck, a local English-speaking guide, and an expertly guided walking tour.

Is transportation included?

Transportation is not included.

Is parking provided?

No, but there are multiple parking garages and street parking available near the departure point. One of which is the Prudential Plaza Garage. Fees vary according to length of stay, time of the day, and day of the week.

Are there any restrictions for this tour?

This tour is suitable for all ages. All guests must be at moderate physical fitness as the majority of the tour will be spent walking. Accommodations can be made according to need of the guests.

What should I bring?

Bring your camera and cash on hand for any other purchases or gratuities (optional).

What should I wear?

Casual clothing and comfortable shoes are recommended.

Will there be other people on the tour?

This is a private walking tour, which means that it will just be you, your group and your guide on the tour.

How does Travel Curious ensure the quality of their guides?

All tour guides currently active go through a vetting process in which they carry out interviews, check previous reviews and employers references if applicable. More importantly, they make sure that these guides provide an excellent experience for the guests.