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 (4.88 out of 5) Based on 634 reviews from our trusted Jet Charter reviews
5 1 5 05/16/2023

The whole process was easy and went BETTER than planned. Glenn was my agent and he made sure everything was handled completely and we had no worries. The plane left exactly on time and was an upgrade from the originally chosen plane. The car was waiting when we landed at the hanger and only had a few steps from the plan to the car. We made our appointment as planned and my family was so happy. I recommend Stratos highly.

5 1 5 05/01/2018

Yes i will recommend it

5 1 5 02/26/2020

A big thanks to Joel and his team as always. The trips were both excellent and every detail was handled from adverse weather upon arrival to a last minute departure day change, Stratos always is so responsive and communicates everything clearly. We love our trip support team and they ensure that travel with our two young children is always planned for and enjoyable. The value that Stratos brings breaks down as follows: 1. It starts with their online marketplace 2.market and equipment knowledge to assist you in your trip planning to the best possible plane and choices of airports to best serve your needs and schedule 3.Aviation marketplace knowledge which ensures the best operator for your needs (always fully insured and Argus Gold or Plat) with great planes 4. trip support and seamless process from ground transport and catering to wheels up/ down This is the best, easiest and turnkey as you can get in the Private Jet marketplace.

5 1 5 11/10/2017

Great experience

5 1 5 06/28/2021

From the first quote and phone call to departing the plane and follow up, service was outstanding! Frank (our point of contact) saw to every question and requirement we had with professionalism, courteousness, and speed. I am very used to hiccups and miscommunications when traveling, but with this trip there were absolutely none. The flight crew was friendly, accommodating, and very good at what they do. The flight was probably the smoothest I've ever had. I know that depends on a lot of factors, but it definitely added to the experience. I wouldn't hesitate to recommend and use Stratos Jets in the future.

5 1 5 06/27/2023

We did have a slight issue when the plane came in there was a mechanical concern that delayed my parent's trip but Kyle lined up aother plane for us so they could get to their destination with the least amount of inconvenience. The catering was delicious and the flight back went off without a hitch.

5 1 5 10/14/2021

This was our 6th trip with Stratos/Simon Christian. We will do this again w/ you next summer. I've sold you to friends i believe who also will be booking with you/Simon Christian. thank you for everything..

5 1 5 03/22/2020

Stratos responded to our request for a flight to leave Anguilla before the flights in and out were stopped. We called Thursday night for a flight on Friday (borders closed at midnight Friday). Response was great ! All aspects ...the agent (Glen) kept in constant contact making sure of all the details with constant updates. The pilots ...Brian and Richard were great...real pros and very friendly. Made sure our flight was comfortable and safe.

5 1 5 07/09/2021

Easy to book with and were very accommodating with a last minute booking.

5 1 5 09/19/2018

My boss recently travelled to Europe for the entire month of August. During that time his jet had mechanical issues and could no longer fly where he wanted. He had about 12 flights left in his trip around Europe and Stratos Jet Charters, especially Heather Latch, saved our lives. They were able to accommodate 90% of the trips he wanted at the time he wanted. She really was a life saver for myself and my boss. I will definitely use Stratos Jets again and work with Heather any day of the week! They are magnificent!!

5 1 5 09/13/2017

Recently booked a jet for 11 people from my organization to continue operations during hurricane Irma. As business owners know, operations do not cease during a disaster and customers must continue to be served. Stratos Jet Charters booked the aircraft we needed within an hour of reaching out. Our team was able to continue business operations in NYC seamlessly. Much appreciation to Joel and his team for fast action!

5 1 5 11/05/2021

Outstanding service throughout entire process. Able to meet requirements quickly Professional service provided while maintaining a personal touch

5 1 5 09/02/2012

Everyone involved was courteous and helpful in getting a last minute emergency trip arranged. However, the premise for using your services was to be GUARANTEED ARRIVAL by a SPECIFIC TIME. Neither the departure nor arrival was anywhere close to what was promised. Hence, our reasons for hiring Stratos to take us became unnecessary and a wasted expense

5 1 5 08/24/2018

Everything great but itineraries always change last minute (tail #, terminal) which has caused problems.

5 1 5 02/07/2018

This was a last minute medical request. Joel, who I have worked with in the past took time away from his vacation to assist me with a fight that met my needs exactly. He’s friendly and professional and a credit to any organization!

5 1 5 12/06/2012

I had an exceptional time with outstanding service and crew!

5 1 5 06/25/2018

Stratos offers the best overall value you can get for private air charter PERIOD. I have done tons of research and cost models and there is no better value. Joel and his team do all of the hard work for you. My family tried Wheels Up, local charter companies and App Based Deadhead charter and they were all really disappointing. All of these option look good but when you compare cost per hour, schedule flexibility and booking Stratos is always a better cost and value proposition. The equipment is always great (this trip was a Citation X with a beautiful brand new interior and every feature possible) and Stratos works around your schedule and exact needs. We have made all types of requests due to my young family and the Stratos staff and cabin crews are always so helpful and accommodating. They never have over sold us and always are sensitive to every need. Most importantly Joel only will put us with great operators. We were in and out of Aspen and safety was the number one concern and he always covers all aspects of the trip but safety first. Again, I can’t say enough about the Stratos experience and team.

5 1 5 10/31/2022

Good communication between Stratos and me regarding the jet being on site on ready for departure. Plenty of advance notice with the updates. This made my planning much easier.

5 1 5 09/22/2020

Joel Thomas is knowledgeable and attentive. We always feel that we are getting the attention we need. The charters he has put together for us have been exactly how we wanted them to be. We have no hesitation in giving him our highest rating.

5 1 5 09/22/2021

Especially impressed that you were able to find us a rental car when there were none available in the entire area. You guys are wizards. The flight was comfortable and the pilots competent and professional. Thank you for helping us make this trip happen.

5 1 5 02/02/2017

Kerry absolutely gets an A+ in customer service. Very well run jet service company.

5 1 5 07/22/2019

Amazing customer service and overall experience from my first contact with Kimberly. Stratos truly delivers what they promise!

5 1 5 05/03/2021

Your whole operation is responsive and attentive, always good to deal with them

5 1 5 12/03/2019

Hey Wanted to let you know that your pilots were so thoughtful and attentive to my daughters needs yesterday.  They removed all unnecessary obstacles for her.  Thank you so much

5 1 5 01/01/2022

All was just fine

5 1 5 01/06/2018

As the operator, this client showed great brokerskills. Precise emails and everything was provided shortly after requested. Would love to work with StratosJets again soon.

5 1 5 05/07/2022

All Good......................and easy!

5 1 5 02/21/2022

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

5 1 5 04/07/2021

The Team at Stratos arranged another great flight for our family. We had a great Lear 45 with a brand new interior! The pilots could not have been kinder and sweeter with our boys and the entire journey was totally seamless. If you are considering Charter you are missing out if you are not using Stratos- THE BEST SAFETY, SERVICE & PRICE value combination- period! Thank you Stratos Team again.

5 1 5 05/04/2020

We were very disappointed in the catering service. The lobster was undercooked and the sevruga caviar we ordered turned out to be lumpfish. Which we did not eat. We intended to take all the food to our home with the lobster, which we were going to cook to make it suitable to eat, but when we arrived home discovered that our food had not been unloaded from the plane. The only thing we ate on the plane was a small piece of the lobster.

5 1 5 10/14/2019

Stratos Jets has always been a great company to work with, very friendly staff.

5 1 5 12/21/2021

From the ease of booking the flights and actual flights, it was effortless. I would definitely recommend Stratos to friends and use you again. Kyle was wonderful to work with, very helpful, and communicative. Both our flights were lovely. Staff was professional and courteous. All in all a great experience.

5 1 5 07/31/2023

Eastern Air Services (crew and plane) were wonderful. Stratos micro obsession with baggage and weights was beyond logical and anything that I had ever experienced in prior charters. Turned out there was PLENTY of room in cargo for additional baggage and that my guests were no where near any weight limitation. The only reason I tolerated the craziness was the price differential. Next time, if they are not the best price I am going back to my regular charter companies. ------------------------------------------------------------------------------------------

Good Morning Gail,
Thank you for taking the time to raise the issue of our team's insistence on passenger and baggage weight.  I share in the blame as I am a pilot (I fly a Pilatus PC12 and Beechcraft Bonanza for my family).  Understanding the performance limitations of an older King Air, the relatively short runway of 5000' at Wildwood and warm summer temperatures, we like to air on the side of caution.  Please know that I have developed processes at Stratos to ensure that every flight we organize is arranged exactly as I would for my own family's travels.  Safety First.
I hope that while these requests were a bit cumbersome, you see that it was done with the best intentions for the safety of your flight and I certainly hope that going forward, Stratos can earn the opportunity to serve you based on our commitment to excellence rather than a cost comparison.
Sincerely,
   
Joel A. Thomas - Get to know Joel
President and CEO

5 1 5 02/19/2014

on the way down, the pilot was nervous, which made a couple of my guests worry...

5 1 5 04/20/2023

This trip was to return home from our 5.5 month winter sojourn in Florida. We had planned everything around this return date. Our cars had been shipped home that day. We had run down all the food. The cancellation occurred when we were out for dinner the night before the planned trip. We therefore did not find out about it until about 10pm. Anthony did a good job of helping with the recovery over the next hour. He responded instantly to almost every email. Unfortunately, because everything for ourselves and our fellow passengers had been planned around leaving on that particular day, we were very limited in our selection of recovery flights. As a result we paid an extra $7k+. Once that was settled and I had figured out how to get the extra money to you quickly enough, things went smoothly. When the flight was first booked (months ago) I had expressed some discomfort with the fact that the plane operator was so small and seemed to be focused on another business model. Anthony said that he had great experience with them and their reliability. It was unfortunate that my concerns turned out to be correct. As things have turned out, it now seems to me that I should be booking my flights right at the last minute, not rely on leaving on a certain date and, perhaps, even trying to catch an empty leg.

5 1 5 05/23/2021

Thanks for the great service again Kyle!

5 1 5 01/01/2018

Once again, Stratos Jets provided perfect travel service with competitive prices! We needed to move a family member with memory loss and agitation from Boston to Houston on very short notice. Joel set everything up within 24 hours- a beautiful private jet, cars and drivers at both ends of the trip, a security detail plus catering. I am completely impressed with this company and will use them whenever I need private jet service. Thank you, Joel!

5 1 5 12/15/2020

Anthony was amazing! He was compassionate, detailed, attentive, proactive and so many other things that I could not begin to put into words for our complicated travel situation. The flight crew was amazing for the journey and ground crew and the ops crew saved my family. I can never put into words how much I appreciate Anthony and the Stratos Team. We will never think of using another charter company for any of our needs! Thank you so much!

5 1 5 11/01/2023

Probably to save on hotels for crew (Wisconsin would be cheaper than Toronto). Weather did not cooperate so cost us half an hour. Not the end of the world, but still an annoyance that could have been avoided.

5 1 5 06/20/2021

Probably the best charter experience I have ever had. Zach really came through for me when I was in a bind. Thanks Zach and keep up the good work.

5 1 5 03/20/2014

We had a great experience. Our normal broker is equally as professional and good. So we would be happy to try you again as we would our previous broker. 

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 07/03/2019

As always, Kerry did a great job for us. Very happy with aircraft interior, performance and crew.

5 1 5 12/27/2016

We have been using Stratos for a couple of years now and appreciate their dedication to using only the safest charter operators. Just completed the front end of a back to back for the Christmas Holiday.

5 1 5 01/20/2014

I do not know what more anyone could have done. The service was nothing short of amazing from everyone involved. The trip was for my ailing mother to attend my brothers wedding. If it had not been for all of you this would not have been possible, and for that we are truly greatful!

5 1 5 08/03/2022

Daniel was very responsive late into the night and early morning and was able to arrange our flight in hours. Time from first contact to wheels up was less than 12 hours. The FBO's and crew provides were very accommodating and helpful. 5 stars!

5 1 5 06/22/2020

Nice, easy and prompt communication. Pleasure working with your team

5 1 5 11/08/2018

Excellent communication with Glenn. I would definitely recommend Stratos. Our aircraft was a newer model and very clean. Crew provided a nice experience.

5 1 5 01/01/2019

Stratos is very professional, great communication, easy to work with

5 1 5 05/09/2017

Having used many charter companies before with mixed experiences, I can say with confidence that Stratos has the best service and highest level of professionalism of any of the charter services I have encountered. Most recently, we had an unfortunate last minute cancellation of a charter booked through another service, and Stratos came through at the last minute to find the right plane at the right price for us with under 24 hour notice. I cannot thank them enough for their professionalism as well as their willingness and ability to go above and beyond to find the right charter for us - even as a first time customer.

Are you ready to book your Chicago charter flight yet?

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