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Best of Chicago: Architecture & Highlights City Private Tour

Quick Details

2 hour Private Walking Tour
3 hour Private Walking Tour
4 hour Private Walking Tour
5 hour Private Walking Tour
6 hour Private Walking Tour
7 hour Private Walking Tour
8 hour Private Walking Tour
9 hour Private Walking Tour
10 hour Private Walking Tour

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Highlights Tour

A 2-3–hour walking tour can certainly cover the absolutely iconic sites of Chicago. We’ll be happy to take some photos for memories at Millennium Park, home to visitors’ favorite sculpture affectionately known as The Bean, as well as the prestigious Art Institute of Chicago. For any architecture and engineering fans in the group, we’ll have plenty of time to take in the soaring skyline of The Loop and explore its subterranean walkways beneath the beautifully restored historic buildings among downtown’s glassy skyscrapers. The Chicago Riverwalk is a nice addition to your whirlwind tour of the city’s most significant spots, as this is where the locals recreate and enjoy the spectacular views of the city along the Chicago River.

Half-Day Tour

A half-day tour (4-6 hours) can cover a lot more ground and even give us a chance to include a fun ride on the “L”, Chicago’s rapid-transit system, to the River North neighborhood. Here, we can arrange for admission to the acclaimed Museum of Contemporary Art or – for our adrenaline seekers – an elevator ride up to the 94th floor of the 360 Chicago Observation Deck! If the view out over the city and Lake Michigan isn’t enough, opt for the TILT experience, providing downward facing views from 1,030 feet!

If you want to keep your feet on the ground, we can stroll along the Magnificent Mile below. This lively area is perfect for shopping, dining, and exploring more of Chicago’s modern and historic architecture, from the second-oldest water tower in the United States to the terracotta Wrigley Building skyscraper.

Full-Day Tour

Enjoy everything our Highlights and Half-Day tours offer and more on this all-day (6-10 hours) Chicago experience! No visit to the city is complete without a stop for some deep dish pizza or a classic hot dog, so we’ll take you to our favorite haunts to get the very best. Another must-see in the city is our magnificent Union Station, a historic neoclassical architectural wonder and busy intercity and commuter rail terminal. Speaking of transportation, we love showing off our city by water taxi – let us arrange tickets in advance so you can enjoy the sights from the Chicago River!

With our extra time, we’ll have more of an opportunity to really explore Chicago’s waterfront, visiting Navy Pier and its small amusement rides as well as the Chicago Children’s Museum.

A venture up to Old Town will allow us to enjoy a stroll through the handsome Lincoln Park. Our team can also arrange for admission to Lincoln Park Zoo or the nearby Chicago History Museum. Comedy fans will definitely want to make a pass by the venerable comedy club where many comics and actors made their mark, The Second City. No matter your request, we can build out a tour itinerary with something for everyone in your party to enjoy!


  • Local English-speaking guide

Not Included

  • Additional food and drink
  • Souvenirs
  • Tips/gratuities for your guide


Request a Custom Private Tour

Want to customize your own tour? Fill out the form below to create your own private tour, and we will be in touch.

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