Chicago Private Jet Charter

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Chicago is a truly amazing city. Not only is it an architectural giant, but it's also home to some of the best cuisines in the country. It's also home to the latest World Series winners: The Chicago Cubs. If baseball isn't your thing, there are a ton of other reasons why you should arrange a private jet charter to Chicago.

There are more than 700 public artworks scattered around the city, 56 museums, 250 theaters, 225 music venues, nearly 5,200 places to eat, 125 art galleries, 580 parks, and almost 30 beaches. No matter what you're looking for, Chicago has it all. Taking a private plane charter to Chicago is one of the best ways to take in everything the city has to offer, from the arts to the food scene and everything in between.

How Much Does a Private Jet Charter to Chicago Cost?

Want to catch a private air charter to the Windy City? Fares for private jet charter services to Chicago will range from one private aircraft to another, and may depend on your starting destination.

When you fly with Stratos Jet Charters, you can find the perfect private jet charter that lets you skip the nonsense involved with the commercial air experience. Instead, you get to sit back, relax, and embrace the convenience and comfort when you’re 40,000 feet in the air.

Chicago Jet Charter Information

Soar in style in a private jet to Chicago—the third-most populated city in the United States. It's home to more than 2.7 million people and has become known as one of the most important business centers in the world. The city is fun to visit 24 hours a day 7 days a week, with different seasons offering unique experiences.  Visit Chicago in the summer for the best weather and soak up time on the iconic Navy Pier. Fall brings cooler temperatures and plenty of fun. Christmas in the city, while cold, gives you the chance to see Chicago decked out in holiday cheer. And, of course, spring brings bright flowers.

Chicago Nearby Airports

Popular Things to Do in Chicago

Chicago, IL originally started out as a small trading post inhabiting the land at the mouth of the Chicago River. It wasn't until 1837 that Chicago was incorporated as a city and began growing into the Chicago we all know and love today. In 1871 a fire ripped through the emerging city, wiping out nearly 17,000 buildings and 300 citizens. On the heels of this tragic event, Chicago decided to host the World's Fair a few years later. In an effort to rise above tragedy, several iconic buildings were designed and built during this time.

Home to the Chicago Mercantile Exchange, Chicago is an important destination for financial executives and is one of the largest cities in the United States. Visitors from all over the world travel to Chicago to tour its world-class museums, including the:

  • Art Institute of Chicago
  • Chicago Museum of Science and Industry
  • Peggy Notebaert Nature Museum
  • Chicago Children's Museum at Navy Pier
  • Taste of Chicago Food Festival
The city is also home to the Shedd Aquarium, which has been Chicago's premier zoo and aquarium for more than 75 years. This destination is fun for the entire family and shouldn’t be missed. If you’d rather skip the sightseeing and get down to having fun, you’re not alone. You're in luck because Chicago is home to some of the largest cutting-edge sporting venues in the U.S. Wrigley Field and Cellular Field are two of the most well-known and treasured Major League Baseball Stadiums in Chicago. The city has also found favor with football fans. Chicago Bear games are an important part of Chicago's vibrant culture. Soldier Field serves as a memorial to American soldiers who have lost their lives in past wars. Earning a reputation as one of the most iconic NFL stadiums in the country. Whether you’re visiting the city for business or pleasure, charter flights to Chicago are the best way to get to the Windy City on the fly.
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Chicago

For those seeking a reputable broker to arrange a private jet charter to Chicago, Illinois, Stratos Jet Charters' team of knowledgeable aviation charter agents is your go-to source. Stratos handles the planning, scheduling, aircraft sourcing, and every other component of your trip so all you have to worry about is packing your suitcase. Stratos is committed to setting the standard for excellence in private aviation. So, whether you need a private jet charter to Chicago for business or personal travel, our agents will work diligently to provide multiple aircraft options that can accommodate the specific needs of your charter flight, while offering the highest level of safety and convenience. Find airports near any location worldwide to begin planning your next dream destination via a private charter jet. Find airports near any location worldwideRead More

Find airports near any location worldwide

What Our Clients Are Saying

Every charter flight review on this page was submitted by a real Stratos Jets customer. In the interest of transparency, we never change reviews or use incentives to influence these reviews. This way, you can hear directly from our past and current clients about how we handled their private travel experience.

4.5/5 (22)
4.7/5 (25)
4.8/5 (568)
Overall rating (4.89 out of 5) Based on 675 reviews from our trusted Jet Charter reviews
5 1 5 09/17/2021

Other than car rental issue it was great.

5 1 5 03/03/2021

I thought it was very well-organized and information flows were smooth. The broker worked with me to get an excellent option at an attractive pricing point. The flight was smooth and professional. An outstanding experience!

5 1 5 07/31/2023

Daniel is knowledgeable, responsive and professional. Great job!

5 1 5 08/15/2024

Steve always takes care of everything and gets me where I need to be, I do recommend Stratos

5 1 5 08/01/2023

I spent 5 hours waiting for my Delta flight at the Nantucket airport Sunday afternoon. They ended up canceling my flight at 6:30pm. The Delta agent informed me that the earliest flight I could get would be sometime on Tuesday. I had a dinner Monday night and an extremely important meeting on Tuesday in Indianapolis. I could not miss either the dinner or the meeting. I texted Anthony at 6:30pm on Sunday night asking if he could help me get to Indy by 5pm the next day. He and his team went into action and we secured a flight at a decent price that night. Everything went well and I was able to make my dinner and meeting.

5 1 5 05/03/2018

My family has flown with you dozens of times. Everything, from booking, to the flights, to the follow-up shows that you care about your customers. I would definitely recommend Stratos & have already done so.

5 1 5 02/21/2022

Always great to work with you guys!

5 1 5 04/09/2024

Great flight, great plane and great crew! Enjoyed it a lot and highly recommend Stratos Jets.

5 1 5 10/09/2020

All aspects pf the trip were easy and very worthwhile!!

5 1 5 07/31/2023

The lounge in Ft Lauderdale was very professional, comfortable, and accommodating. Pilot was a real gem who charmed my first time flyer guests who started out nervous but hugged him on the way out! Would not hesitate to recommend for charter needs.

5 1 5 08/19/2021

Zach, was phenomenal from beginning to end! What was taking me a half-day to do Zach was able to complete efficiently in a few hours. He periodically made the process as smooth as possible, not to mention giving hourly updates. I would say that Stratos has a customer for life. Zach enjoys and loves what he does and it shows in his work ethic! Thank you!

5 1 5 11/01/2021

Anthony worked hard on our request and came up with a perfect solution. The plane was the right size to hold all our luggage, and the flight on-time, comfortable, and in all respects outstanding. Highly recommended.

5 1 5 03/20/2024

Mostly good. Registration process is painful and there was a little hiccup with confirmed time for departure but we made it work.

5 1 5 02/21/2022

Great pilots, crew, and plane! Helped a lot with Covid stuff.

5 1 5 01/04/2019

I wouldn't recommend this plane that much though. One pilot was nice the other kinda ambivalent. The temp of the plane was either hot or cold and the electrical plugs not functioning. It was transportation only. But we are so happy to all be here with the rest of the family. it was worth the effort.

5 1 5 05/16/2023

I had a great time with the pilots, all of us looking at our route software on our iPads how to get around the rain and stay clear of all the boomers on the way to the field. They did a great job. Fabulous approach to Runway 21 direct. I would fly with these pilots any time anywhere.

5 1 5 10/04/2014

the flight and service was great.

5 1 5 12/03/2024

All Good!!

5 1 5 12/18/2017

Everyone was great

5 1 5 09/17/2020

Smooth and easy

5 1 5 05/09/2012

couldn't get better than this, amazingly efficient and helpful

5 1 5 01/04/2020

As a charter operator, it is hard at times to work with Broker companies to get all of the information we need quick and efficiently back and forth to each other. We had no issues at all in this case when working with Stratos Jets. The team got everything we needed to us in a timely manner and we were able to make the transaction very smooth. I hope your clients enjoyed their flight! Our pilots said they seemed pleased upon arrival. Looking forward to working with you all again!

5 1 5 04/13/2017

I would like to be able to track aircraft on internet.

5 1 5 10/20/2020

Yes

5 1 5 06/14/2017

Great Trip Support Team We love working with Stratos Jets! They are fast to respond, reasonable to work with, and their brokers and trip support team are very detail oriented which leaves little room for error. I would highly recommend them!

5 1 5 06/12/2023

As always, you guys set a great example for what working with a broker should be like. :)

5 1 5 02/26/2025

Victoria and Mark were wonderful definitely made our trip special!

5 1 5 05/22/2021

Zach Rankin is the best jet broker I have ever met! Total first class experience. Super responsive & passionate & customer service oriented. I’m in real estate hospitality....hotels & apartments etc. So I understand how hard it is to execute flawless high-end customer service like Zach.

5 1 5 11/22/2019

Thanks for all your updates. I could get used to this.

5 1 5 04/27/2021

I look forward to booking again..

5 1 5 12/21/2021

See above.

5 1 5 01/12/2014

MY agent did a great job. Due to the immediate nature of the flight, we didn't compare to others but he was very quick to respond.

5 1 5 03/10/2014

The aircraft was fine except for the AC. It either had to be run a full blast (we were wrapped up in blankets) or it had to be off in which case we were very hot.

5 1 5 05/07/2022

After our plane developed mechanical problems and a night of discomfort and doubt, Kyle was able to find a plane and a crew at last minute to save my wife's 60th birthday trip. We arrived a little late but we arrived! You are the best Kyle.

5 1 5 04/05/2022

The family loved the flights wow landings terrific pilots planning to repeat in the future

5 1 5 04/15/2024

Always excellent customer service and flights!

5 1 5 06/12/2022

Excellent Customer Service booking and during the flight!

5 1 5 12/23/2019

Prompt excellent cost saving service. Many choices. Always working to meet my needs.

5 1 5 09/17/2021

The flight was smooth and comfortable The crew was professional and courteous. The agent's support was extremely professional--assisting above and beyond expectations with car shuttling service in Albany. We will highly recommend these services to others.

5 1 5 06/23/2021

Hi Steve and Joel and Sandy,

 

Wanted to say thank you for the quick refund. It’s nice to work with you. Very professional.

 

Bye and best regards to the U.S.,

Claus

5 1 5 10/02/2017

I was thouroughly impressed with the professionalism of the Broker Joel, the flight organizer Sarah and the crew on both legs. The aircraft was clean, in good shape and right on time. The crew was friendly and professional to me and my guests. Two small issues were getting a tail number on less than 12 hours that made getting our rental cars more complex than necessary and more significant was being notified by our bank that you tried to bill my flight a couple times when I paid in full prior to first leg. All in all I would use them again but would encourage one contact who checks in daily a few days prior to flight rather than me having try to figure out who to call when it looked like a couple problems were coming up.

5 1 5 11/13/2022

I have been using Stratos for all of my trips the past 2 years, and they stay on top of all my needs. Thanks to the entire team!

5 1 5 09/17/2020

Kyle was very nice and helpful, he made sure everything was in order and ready to go from beginning to end, really great costumer service. Aircraft was nice, well kept LearJet 40. Pilots Matthew and Jonathan were total sweethearts and very experienced, landing was beyond smooth. Only thing we weren’t so happy about was the fact that you could see some of the wear and tear of the years on the inside of the plane. Overall great experience!

5 1 5 10/28/2015

Stratos continues to exceed my expectations!

5 1 5 09/27/2016

Simon was Great.  There is nothing that cold have been better.

5 1 5 01/09/2021

Very much enjoyed the trip. Glenn was helpful in coordinating every facet of the trip and answering all questions. We greatly appreciated all of the effort.

5 1 5 04/12/2021

Steve and Stratos Jet haven’t once disappointed our family! The service is impeccable, communication is divine and we always feel safe flying with Stratos. Thank you all for constantly humoring me with all of my itinerary changes. I would highly recommend Stratos as well as Steve Stogner to anyone with high level travel needs!

5 1 5 02/26/2018

Pre trip work up seemed very professional. Crew had plane positioned on time and assisted with loading. Just my wife and I and two dogs. It was the dogs first flight so we had some concerns but the crew did a great job in getting them aboard and settled down. flight was uneventful and all worked as planned. No issues at all. Very good

Same on return flight except we arrived a good half hour early but crew jumped to task and loaded us and dogs promptly for return. Only item worth mentioning was during climb out to altitude both my wife and I heard numerous bumping sound on both sides of fuselage up and down the sides and top. We have owned our own planes and owned shares in jets through Flight Options and chartered often over the years and we have never had this type of noise. It almost sounded like rivets coming out or random bird strikes (which I knew it was not). I mentioned it to the co-pilot and he told me to report it so maintenance could be sure to check it out. Said it may be a maintenance issue on an older aircraft but a first for me. After attaining altitude the noise did not reoccur. All else went according to schedule and the pilots were very professional and assisted on and off with dogs and luggage. I would use again this service. Thank

Joel Thomas:  Hi William!  Thanks for the opportunity to serve you and your wife.  We are always grateful when our clients take the time to offer feedback.  We reached out to Chief Pilot of the air carrier you flew with regarding the noise you mentioned and here is what they said:  "Frequently you'll hear noises that sound like that and its just the airplane expanding as altitude, temperature and humidity change.  Its actually very common."  Looking forward to working with you all again soon!  All my best

5 1 5 05/21/2018

Hi All -
I want to give you a stellar report on the plane, crew and service.  The pilots were attentive, friendly, familiar with the aircraft and enthusiastic.
The plane was in good shape, although the back right front facing seat has a little problem locking.  That was not a big deal, and it was the only squawk we could find.
The food service was also excellent.
The price could not be beat.  Kelley and I are looking at dates to do it again if we can get the same price.  I feel the value exceeded the cost.
Thank you all for what you all contributed to this being as fantastic as it was.  I appreciate the concerns that you voiced to me prior to the charter, but am happy to report that the company seems to be running smoothly with reliable aircraft.  I am a picky man, and was thoroughly satisfied and happy about everything involved.
Thank you again, and we look forward to working with you in the future.

5 1 5 07/31/2023

Great communication, everything on time and accurate, highly recommended

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