Charter Flight to Taste of Chicago

This year's culinary affair set for Sept. 6-8, 2024.

Round Trip One Way Multi-City
qty-minus qty-plus-icon

A Taste of Chicago

Taste of Chicago is the world’s largest food festival. Previously held over five days in July in Grant Park, the city moved the popular event to September last year. 8-10 in 2023. This year’s Taste will takeover Chicago Grant Park Sept. 6-8, 2024, with summer offshoots at Humboldt, Pullmark and Marquette Parks to be announced soon.

This event is basically a smorgasbord of gastronomic treats, as the city’s cooking community comes together in one area. From food trucks to restaurants that set up tents, there are literally hundreds of menu items to choose from, including:

  • Dia de los Tomales
  • Celtic corn on the cob
  • Coconut shrimp
  • S’mores Smush cheesecake

And, of course, there are the traditional Chicago mainstays such as deep-dish pizza, Chicago-style hotdogs and Italian beef. This family-friendly event also happens to be the largest festival in Chicago, and it’s about more than just food. Other attractions include:

  • Live music on multiple stages
  • Pavilions
  • Film showings
A portrait of a happy family eating pizza and laughing.

Start Your Fine Dining Early

When you fly privately with Stratos, you can get a head start on the gourmet fare by requesting in-flight catering.

In addition to delicious eats, the Taste of Chicago attracts a lot of top international talent, as well as up-and-coming local acts. Weezer, Erykah Badu and Robin Thicke have all headlined the festival in past years. If you plan on visiting this extraordinary event, you’re not alone. There can be as many as 1.5 million visitors over the weekend, which means Chicago’s commercial airports will be busier than normal. By booking private charter flights to Chicago with Stratos Jets, you can avoid:

  • Hectic airport terminals
  • Lengthy check-in lineups
  • Lost luggage
  • Cancelled or overbooked flights
A private jet taking off against a backdrop of downtown Chicago.

Recommended private jets for your charter flight to Chicago

When you fly with Stratos, you get access to our nationwide network of aircraft operated by the best air carriers who value safety as much as we do.

8

SEATS

357

MPH

1362

RANGE
$3,120 - $3,822

15

SEATS

548

MPH

7767

RANGE
$16,536 - $19,110

7

SEATS

514

MPH

3337

RANGE
$14,508 - $15,990

9

SEATS

540

MPH

3567

RANGE
$10,296 - $13,260

Private jet airports near Chicago

By arranging charter flights to Chicago, not only do you get to choose when you fly, you can also choose the airport that’s most convenient for your arrival. In the Windy City, there are plenty of options, including Chicago Executive Airport (PWK), Midway International Airport (MDW), Chicago O’Hare International Airport (ORD), Aurora Municipal Airport (ARR), Dupage Airport (DPA), Gary Chicago International Airport (GYY) and Chicago Rockford International Airport (RFD).

Ground Services in Chicago

Flying in late and want to head straight to the hotel, or can’t wait to get to Taste and just need a rental car ready to go at the airport? Whether it’s by pre-arranging a car and driver, rental vehicle or even taking care of hotel reservations, our Trip Support Team is your lifeline to help make your trip to Taste of Chicago memorable.

An airhostess stands behind a limousine as a woman in a black dress exits a private jet on the runway and walks towards the limo.

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)
4.8/5
566 Reviews
4.7/5
25 Reviews
4.5/5
22 Reviews
5/5
4 Reviews
Overall rating (4.88 out of 5) Based on 644 reviews from our trusted Jet Charter reviews
5 1 5 02/20/2021

Smooth, calm, on time and will use it again

5 1 5 01/01/2018

I thought Stratos was professional and easy to work with. We didn't have any problems or communication issues whatsoever. It's really nice when we don't have to deal with 10 different people to coordinate a trip.

5 1 5 09/24/2020

Great rep!

5 1 5 06/20/2017

From pre-trip planning to updates via text message on your way to the airport, Stratos had us covered. We made our way from Emirates @ JFK and the FOB transfer was easy. Joel had already updated Julie (my assistant) before we landed that there were long delays out of JFK due to weather. The transfer to FBO was easy and they were expecting us. The plane was comfortable and modern and the crew could not have been kinder. Thank you guys as always for a great trip. Flight was great and the crew took us right past the storms and my one year old son slept the whole trip; a much needed reprieve for my wife and I.

5 1 5 01/20/2022

Worked with Glenn and he really worked to find the right plane at the right time! Aircraft crew were professional and courteous. Two great cross country flights.

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 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 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 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 04/06/2017

Thanks to Kerry for helping us get to where we need to be ! Very detail oriented company. Pilot's were very professional. See you next time!

5 1 5 02/23/2012

I do not think there is anything else that could have been done to make our flight enjoyable. The crew, Vincent Jordan and Nicholas Gambino, were very professional, extremely courteous and if we were to charter another flight in the future we would love having them as our crew.

5 1 5 08/10/2020

I wanted to thank you for making the arrangements for my trip up north on 7/29/20 & the return flight yesterday with Tyler et all to Orlando. Everyone was very polite, timely, and helpful and we felt completely safe & comfortable traveling with Stratos Jet Charters.

Wishing you well & grateful for a wonderful alternative for traveling.

5 1 5 04/05/2014

You did great. Garett was great, ground transportation was clean, easy and on-time and seamless. It was a good trip and I have already asked for another quote. Don't know if I will use it depending upon cost as this next one is purely personal. But I would like to.

5 1 5 06/12/2017

Everything went perfect. great job. Yes I would recommend your company to my friends.

5 1 5 03/21/2023

I love the team and especially working with Kerry. Always a pleasure

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 03/26/2021

Glenn was great - very responsive. Would have given our experience 5 stars had the airport we intended to land (Ocean Reef) been secured when I paid the monies, instead of 3 days before our scheduled departure from HPN.

5 1 5 11/03/2016

THANK YOU STRATOS!! I have been working with Stratos Jet Charters for almost 3 years now & could not be happier with the services they provide! Working with me on many last minute changes, they are always quick & efficient, extremely professional, genuinely honest & immensely knowledgeable of all products and services they offer. They truly look out for the best interests of their clients. I trust them to always guide me in making the appropriate aircraft choices for our company. I find the ENTIRE team to be THE BEST in the charter aircraft business!!

5 1 5 06/22/2020

Steve made sure we had everything we needed. The travel arrangements were made easily and were efficient. 3 friends and myself had our first experience with flying private with Stratos. The food provided was delicious, the limo and transportation was perfect, and the entire experience was well worth the money. A special thank you to Pilot Dan! He was very helpful and made sure we were comfortable. Definitely a memorable experience. Stratos is my go to place when flying private from this point forward.

5 1 5 10/28/2020

Every thing was smoothly handled from booking to the flight

5 1 5 11/21/2023

Dear Joel  We had an excellent flight, start to finish! Glad you told me how good that choice would be. Pilot quite impressively; flew at 40,000 feet all the way, zero turbulence. Best plane I have charted.  Happy Thanksgiving to you and family, Al

5 1 5 02/15/2021

Stratos was prompt, professional, and competitive. They were also willing to work with me as I was having second thoughts, without being pushy. I had a very enjoyable experience and look forward to using them again.

5 1 5 10/23/2018

From the quoting and booking process to wheels up and down, things could not be better with STRATOS. Joel and his team are amazing and accommodated a last minute return schedule change. They only contract with great companies who have great equipment and outstanding crew. If you are considering Private jet travel I cannot recommend them enough!

5 1 5 05/12/2016

Flight was for an elderly person and the tail number was provided a long time before the flight and I made sure the person flying had all the info written down by someone who could hear and got everything correct. Flyer had that until day before when tail number changed. I had to find someone who could hear me well and right down the correct info for the person traveling so he got it straight in his head and for driver.

5 1 5 09/05/2017

Excellent

5 1 5 08/22/2017

At last minute's notice I needed to find a private plane to get my elderly parents from Bangor, Maine to Atlanta. I googled charter companies and Stratos Charters was first to pop up. I called immediately and Joel (founder and president of company) answered. He could not have been more gracious and helpful. He was the perfect combination of professional and personable. Our charter was arranged and the trip went through seamlessly. Stratos Charter and Joel made a stressful situation into a very pleasant one for us. I highly recommend their services and will definitely use them in the future. Thank you to them!

5 1 5 05/02/2017

Very fast quote ~ excellent pricing, strong safety rating. Trip was excellent.

5 1 5 09/17/2018

I always enjoy working with Stratos Jets. They have a great operation that is seamless.

5 1 5 04/14/2020

Everything was done in super fashion. Anthony the scheduler, Anthony and Terry the pilots were fantastic!

5 1 5 10/05/2012

WE were told to go to First Aviation Services terminal at Teterboro but our plane was at another terminal so we wasted over 45 minutes trying to find our aircraft and our agent was not at all helpful. In fact he told us someone was coming to pick us up and they never came and we had to find someone to help us get to the terminal our plane was located at. The agent asked us for our rental car info but when we landed in Naples the rental car was not at the terminal and we had to find a ride over to the other side of the air field to get our rental car. The flight was great but the handling of the pre and post flight were below normal and not what I am used to when I fly private.

5 1 5 02/12/2014

This was a fantastic trip and our family will remember the rest of their life. Wife says it is the only way to travel via air. Everything was handled perfect

5 1 5 03/13/2015

It was excellent in every respect

5 1 5 10/06/2017

I was frantically looking last minute for a private jet to transport myself and a family member with early onset memory loss from Minneapolis, MN to Keene, NH. I found Stratos Jet Charters online and they caught my eye. From the first phone call to Eric Bold, the broker, to the landing in Keene, NH, I was completely amazed at how easy it was to book the flight and get the details in order. Eric was super sharp and made the entire booking simple and fast in a very professional way. He was also totally available by phone immediately when I needed to talk with him. Sarah, also, helped us with catering and the passenger manifesto and she was just as competent. The pilots, Jeff and Deanna, made us feel very secure and confident about the flight and our comfort. I feel so fortunate to have found this company and will reach out to them for all of my future private jet needs. Thank you, each of you, and thank you, Stratos!!

5 1 5 12/21/2021

As far as I can tell the flight was great. My nephew, his wife and their dog flew from California to Guam for a move. The airport they flew from was changed the day prior to departure due to weather. The catering however didn't make it to the airport so they were on the plane for 15 hours with only the complimentary snacks and the crew shared some of their food with them. When you fly private you expect things to go smoothly...that's why you're willing to pay the extremely high price for. In my opinion there were opportunities missed to make it right. Since they had to refuel in Hawaii there was at least 6 hours to get some kind of catering for them when they landed in Hawaii. I realize that catering needs 24 hours notice but someone couldn't gone above and beyond to make things right and get them fresh fruit and veggie platter with a plain hot pizza or something to give them something other than snacks. I know if the CEO of Stratos was flying this catering issue would've been unacceptable.

Carol - Thank you for bringing this to my attention and you are certainly right.  The ball was dropped.  I have spoken with the private flight advisor regarding the matter and our day of flight process was not followed.  Not having something ready in Hawaii during the fuel-stop is truly a missed opportunity.  I am truly sorry for our misstep and the poor experience this must have been for your nephew and his family.  

Joel A. Thomas 

President and CEO 

5 1 5 01/01/2022

Great customer service!

5 1 5 01/09/2019

This flight was well managed with excellent communication with Joel. We had extreme weather conditions in OAK and Joel was open to correspondence past midnight local time to ensure all was not handled and decided morning of flight. We also appreciate Stratos Jets trust and confidence in following the lead of Axis Jet for moving their clients flight to the next day. We are looking forward to having many more successful flights with Stratos Jets.

5 1 5 03/13/2024

This was probably the 3rd flight that the weather conditions were disregarded and I was told the flight was safe and would be comfortable. While we did land safely, the known turbulence was so intense I left my seat at one point, was thrown from side to side (no vomit bags around) and I was needing to do every breathing technique known to keep myself calm and not hyperventilate. While the crew and all people involved are extremely professional, disregarding weather reports with a strong wind advisory is irresponsible not only for safety but for the customers comfort. I learned upon landing that other flights in that same airport had cancelled so why would mine fly even with the concern I expressed. Will the company lose money to reschedule? I will find it difficult to trust them in the future on any flight with weather advisories.

5 1 5 09/09/2017

Great experience all around. simon was great - awesome customer service mentality and communication throughout.

5 1 5 10/04/2013

Chris was SUPERIOR - great customer service on his behalf. Most certainly will contact him directly for next charter flight. Thank you.

5 1 5 02/23/2018

Thank you for making our jobs easier! Great passengers and your team is always a pleasure to work with! Kind regards, Kim Krum

5 1 5 10/14/2021

As always, Stratos has the best selection of aircraft and crew. Zach is amazing to work with.

5 1 5 05/03/2017

I met Joel, years ago, when he first introduced me to Stratos Jet Charters during its start-up phase.  I was always very impressed on their marketing and honesty, as a broker.  Joel is very genuine and caring when it comes to his customers or the operators that he works with.  I know that Stratos Jets will not sacrifice safety for anything.  I know that he likes to treat everyone like they are part of the Stratos Jet family.  The trip planning process, from quote request to trip planning to  invoice, is seamless – they’ve thought of everything and continue to be ahead of the trend in our industry with the way they do things.  They think of everything!  In my opinion, Stratos Jet Charters set the bar for aircraft brokerage and I will always continue to look forward to working with them.

5 1 5 03/26/2021

Katie was great on very short notice. Here is were the 5th star was lost: No on board bathroom and I was not told about it. I specifically asked about quality of safety and maintenance by operator and got incorrect information initially; although there was no apparent problem .

5 1 5 06/19/2017

Since day one, Joel and his team have been providing us with great customer service and always meet or exceed our needs. They are impeccable in their constant communication, which includes everything from quotes to flight status, and all in between. They are very accommodating to all requests, even the last minute ones. Sarah with trip support has carefully and flawlessly helped with all requested travel arrangements, from car rental to car service. It is hard to find a company these days that is genuine and understands the importance of truly great customer service, and this company and all members of the team, have this! It is very refreshing. I would recommend this company to anyone who has ever thought about trying Jet Charters or has done so for years, it will be a change for the best!

5 1 5 03/23/2020

Glenn was excellent to work with. I spoke with several charter companies before choosing Stratos. Glenn is the reason I chose Stratos Jet to bring my elderly parents home during the initial break of the COVID-19. He was professional, knowledgeable and on top of every detail. This was our first experience with a charter flight and Glenn explained the entire process from start to finish which helped me keep my anxiety in check. My parents flew from Florida to Ohio without any issues. They said the aircraft crew were professional and confident and made them feel safe. The plane was basic, cabin was small so it was a little challenging for older people with limited mobility. My parents are short, 5'4 and 5'1 and both had to duck down to get on and off the plane and while inside the cabin. That being said, we were given the option of a more luxurious cabin but chose not to spend the extra money. Stratos took care of getting my elderly parents home quickly, safely and allowed us to minimize the risks of commercial flying at this time.

5 1 5 02/17/2020

Would definitely recommend Statos Jets. Always know Kerry Hill is doing her best for us.

5 1 5 02/17/2018

Two thumbs up!

5 1 5 01/31/2020

Working together with Stratosjets felt like working with my own team - very friendly and coorperative employees - loyal and trustworthy team - thanks a lot!

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 04/27/2020

Thank You very much. Our experience from the beginning to the end were handled with such care and consideration. Felt very comfortable and am very glad that we chose you.

Frequently Asked Questions

Our friendly, expert air charter agents are here to answer questions or start your quote today. Don`t wait, call right now and we can get you on your way to the destination of your choice! Talk to one of our air chater argents now by calling (888) 593-9066 or by emailing [email protected]

  • How do I choose the right aircraft for my mission?

    dropdown dropdown

    As charter brokers, we do more than simply book your charter flight. At Stratos Jets, our air charter associates are highly trained personnel capable of matching our clients with the appropriate aircraft for their travel needs. Once we determine how many passengers you’re travelling with and how far you’re flying, we can determine which category of aircraft you require. There are many options available. The most common aircrafts hired for private charters include:

    • Cessna’s Citation X
    • Gulfstream’s G650
    • Bombardier’s Global line

    After that, we can help you narrow down the selection of recommended aircraft based on budget, desired cabin amenities, airport requirements, luggage capacity, as well as aircraft age and performance capabilities.

    Staying Safe in the Skies

    At Stratos Jets, air charter safety is our number one concern. One of our key policies is to increase consumer education. This ensures our clients are able to make informed decisions. We also work with our aircraft providers to ensure their safety training programs meet and even exceed our air charter safety requirements. To make this happen, Stratos Jets is an ARGUS Certified Broker. This means that our brokerage firm is:

    • Committed to the best industry practices
    • Adhering to all applicable safety regulations
    • Maintaining the appropriate insurance coverage required
  • Are there additional costs per private jet rental passenger?

    dropdown dropdown

    There are no additional costs per passenger. At Stratos Jet Charters, we base our private jet rental prices per hour, not per guest.

    The Stratos Pricing Estimator

    If you would like to estimate the cost of a private jet charter, use our Stratos pricing estimator page. It lists the most common estimates based on destination and aircraft type. And you can always enter customized data to get an estimate for a specific destination.

    Additional Concierge Charges

    We do charge for some of our additional concierge services, such as in-flight catering and entertainment, hotel bookings and ground transportation. We know our clients’ time is precious, so we offer the value and convenience of “one-stop-shopping” through our Trip Support team. When you book a flight with Stratos Jet Charters, we can take care of all the logistics, including booking hotels, meeting spaces, limousines and tickets to special events. That way you can relax, and enjoy your trip.

    Empty Leg Charters

    Also, since we charge per hour, not per passenger, there are travel bargains to be found with our Empty Leg Flights. Many of our private jet rental flights are one-way, and then we need to move the aircraft to a new destination. To reduce the costs of flying an empty aircraft, we offer discounts to travelers with flexible itineraries. Clever passengers will sometimes split the cost with their fellow travelers, thereby reducing the cost for everyone on the flight.  

  • Can I make last-minute changes to my itinerary?

    dropdown dropdown

    If your plans need to change, we will do everything in our power to accommodate the changes. One of the benefits of hiring Stratos Jet Charters is that we have much more flexibility than commercial airlines and can provide many more air charter services.

    We have two teams that can help you. Here is a brief description of each:

    Charter Sales Agents 

    This is the initial contact team. They evaluate your travel needs to identify the appropriate aircraft type for your travel plan. Pricing is determined by aircraft availability, its position related to the intended departure location and the position of where the aircraft needs to be after performing the customer’s flight.   

    Trip Support Team

    Once the aircraft has been selected, Trip Support works with the customer, the air carrier and all concierge service providers to organize all of the travel details. Trip Support is responsible for coordinating:

    • Departure time
    • Departure and arrival at the Fixed Base departure location
    • Ensuring assigned crew members meet Stratos experience requirements
    • Making sure the insurance is current and everyone is protected
    • Coordinating all concierge services

    In reference to last-minute itinerary changes, any changes would go through the Trip Support Team.

    Our customers often have demanding flight itineraries that can change quickly. They’ve come to appreciate knowing there’s an entire team of people focused on organizing all the details of their trip. Stratos Jet Charters wants to provide our clients with consistently outstanding air charter service and an impeccable safety record.

View all our Frequently Asked Questions >

Are you ready to book your Can I make last-minute changes to my itinerary? charter flight yet?

Our friendly, expert air charter agents are here to answer questions or start your quote today. Don`t wait, call now and we'll get you on your way to your destination!

Call 888-593-9066
Back to top