Chicago City Private Driving Tour

  • 4 - 10 Hours
  • Driving Tour
  • Group price up to 6Groups 7+ Please call to book
  • Private Tour
  • Daily

Highlights Tour

A driving 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!

Community Impact

Travel exposes us to new cultures, customs, and experiences, and a private WeVenture tour highlights some of the less-visited Chicago neighborhoods and supports these communities in a way that other tours are unable to when limited to the city’s usual tourist destinations.

Local businesses are at the heart of our community, and our support of such places on tour can help build a sense of connection in the neighborhoods. Our tours build in opportunities to patronize small and family-owned businesses that keep Chicago authentic.

Taking a ride with WeVenture opens up possibilities to sample a variety of cuisines and include the stories of the different cultures who integrated them into Chicago’s food scene. In turn, we’re able to contribute to the economic growth of these underrepresented communities.

This driving tour opens up the potential to not only support more areas of the city and help us play a bigger role in the diversification of experiences Chicago has to offer but also allows our guests to see how and where everyday residents of Chicago live and work.


Chicago Theatre

This is where your tour begins – underneath the iconic neon sign made famous in both movies and musicals! Here, you’ll meet your guide and then set off through bustling downtown Chicago.

Chicago Riverwalk

If the weather is good, we’ll be able to take a wander down to this iconic river and soak in the views it has to offer. Sights include Marina Towers, the Britannica Building, and the Sears Tower (now known as the Willis Tower).

Wrigley Building

You can’t think of Chicago without thinking of the Wrigley Company. This skyscraper with its central clock tower, first built in the early 1900s, no longer houses the Wrigley Company, but is home to several other significant businesses and consulates.

Millenium Park

This is where the iconic “Bean” sculpture (actually called The Cloud Gate) lives. You’ll have plenty of time to soak in Chicago’s most famous piece of art before your tour concludes. You’ll be in the perfect central location to continue exploring Chicago – with plenty of restaurant, bar, and attraction recommendations from your guide.

Cloud Gate

Also known as The Bean, this sculpture is located in Millennium Park, where you’ll have plenty of time to soak in Chicago’s most famous piece of art before your tour concludes. You’ll be in the perfect central location to continue exploring Chicago – with plenty of restaurant, bar, and attraction recommendations from your guide.

The Loop (Chicago)

Your tour takes place in this lively neighborhood of shopping, nightlife, performing arts scenes, and, of course, restaurants with the best food Chicago has to offer!

Price Includes

Price Excludes

  • Local English-speaking guide
  • Private Transportation
  • Additional food and drink
  • Souvenirs
  • Souvenir and guide gratuity

Pickup Information

Start times: We offer pick up anytime between 9am-2pm

Pickup: This tour offers custom pick up and drop off (hotel,airports,etc)


Driving Tour

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