The nation’s third-largest city is one of the most popular jet charter destinations. Here you’ll find endless recreational activities, exciting nightlife, and cultural-rich experiences. When you begin your descent in your private jet from Denver to Chicago, the steely skyscrapers will likely be the first thing to catch your eye. Then, the sprawling blue waters of Lake Michigan are sure to catch your gaze as you find yourself dropping into the Windy City.

When you soar into the Windy City on a private jet from Denver to Chicago, you’ll arrive in comfort and style, ready to tackle everything the city has to offer. Here are all the reasons why you should book a private jet charter to the Windy City.

Things to Do After the Private Jet Charter to Chicago Touches Down

It’s hard to imagine squeezing in so many things to see and do when staying in Chicago for a short time; however, we’ve put together a few of our top sights and activities so you can make the most out of your stay—brief or otherwise—in Chicago.

See the Mile High Sights

From the stratospheric, glass-floored Willis Tower to the stained-glass Robie House, the architecture in Chicago is worth a second glance. Some of the most iconic sights to enjoy when you book a private jet from Denver to Chicago include:

Willis Tower Skydeck – As the highest observation deck in the United States, the views from Skydeck are absolutely unrivaled, and for a glimpse into the history of this iconic city, the lower deck features a museum with interactive exhibits, like the fly-through video tour of the city, along with snippets of history.

The Bean in Chicago

Cloud Gate, aka “The Bean” – It’s been featured in many movies and TV series but seeing it in person is nothing like catching it on screen. Located in the lakefront Millennium Park, this stunning piece of public art is one of the largest permanent outdoor art installations in the state, and it’s been one of the most iconic sights since it was unveiled in 2004.

Adler Planetarium – As the first planetarium in the Western Hemisphere, the Adler Planetarium was built in the 1930s along the shores of Lake Michigan. Since then, it’s become home to two dome theaters, which provide a variety of shows, and several exhibits that cover topics ranging from the accomplishments of marginalized groups to life on other worlds.

Buckingham Fountain in Chicago

Buckingham Fountain – Built in 1927, the Clarence Buckingham Memorial Fountain is one of the largest water features in the world. Between 8am and 11pm, the fountain sporadically comes alive, shooting 15,000 gallons of water through roughly 200 nozzles each minute, creating eye-catching and breathtaking displays.

360 Chicago – Like its name implies, this observation deck provides visitors with 360-degree views of the Chicago skyline and surrounding area. For the thrill seekers in your group, the deck’s newest feature tilts visitors at an outward angle so they can look straight down from the glass enclosure.

Michigan Avenue in Chicago

Michigan Avenue and the Magnificent Mile – No visit to Chicago is complete without a visit to Michigan Avenue. Here you’ll find numerous galleries, theaters, boutiques and luxury shops among some of the most popular attractions in the city, including John Hancock Center, the Wrigley Building, and the Tribune Tower.

Wrigley Field in Chicago

Wrigley Field – For the sport enthusiasts among your group, Wrigley Field is the perfect place to catch a Cubs game. As the second-oldest Major League Baseball park in the US, it’s also a great place to visit for history buffs with an interest in historic venues.

Experience World Class Fare

Best Steakhouse: Bavette’s Bar and Boeuf – This restaurant is a popular choice for diners looking for an amazing meal and an intimate dining experience. Be forewarned, reservations are highly encouraged as early as possible!

Best Italian: Monteverde – The meals at this top-choice restaurant are prepared by a Top Chef alum and boast large portions and absolutely amazing flavour profiles. Every pasta on the menu is worth ordering at least once.

Best BBQ: Lem’s BBQ House – Since 1951, Lem’s has been serving up some of the best BBQ meals in the state. The ribs are aquarium-smoked, a method that’s unique to the South Side of Chicago, and worth experiencing at least once in your lifetime.

Best Deep Dish Pizza: Pequod’s Pizzeria – Chicago is well known for its deep dish pizza, and you’d be remiss to not try a slice during your stay in Chicago. Pequod’s has mastered the art of the “caramelized” crust, so if you’re looking for the best in the city, you can’t go wrong here.

Book a private jet from Denver to Chicago

How much does it cost to book a private jet from Denver to Chicago?

When it comes to pricing out the travel cost of your trip to Chicago, there are a few things to consider. The location you depart from will have a big impact on the cost of a charter as will the size of aircraft you prefer to hire.

What is the cheapest way to fly private?

Aside from waiting around for an empty leg private jet charter from Denver to Chicago to pop up around the time you hope to travel, you may want to consider the membership option. At Stratos, we offer two membership tiers: Soar and Soar Higher.

Soar Membership Highlights

  • $8,500 initial investment for 6 months
  • Guaranteed flight availability (outside of 72-hour notice)
  • Penalty-free flight cancellations
  • Unlimited flight bookings
  • No additional fees

Soar Higher Membership Highlights

  • $14,500 initial investment for 12 months
  • Guaranteed flight availability (outside of 72-hour notice)
  • Penalty-free flight cancellations
  • Unlimited flight bookings
  • No additional fees

The charter rates for members are:

Super-light Private Jet $8,798/hr
Light Private Jet $9,768/hr
Midsize Private Jet $9,887/hr
Super-midsize Private Jet $11,985/hr
Heavy Private Jet $14,988/hr


Learn More About Memberships



Ready to book a private jet charter from Denver to Chicago? Trust the jet charter professionals at Stratos. Our private flight advisors are heavily skilled in all things aviation. From helping you select the aircraft best suited to your travel needs to booking additional concierge services, we’ve got you covered. Request a free quote today! (888) 593-9066