Charter Flight to Taste of Chicago

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

Round Trip One Way Multi-City
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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 (4.9 out of 5) Based on 762 reviews from our trusted Jet Charter reviews
5 1 5 08/14/2017

As always, the folks at Stratos Jet Charters did an outstanding job responding to a short-notice requirement for supplemental lift for our flight department. Their staff is always focused on the customer needs and preferences. Through their proven performance, they have become my "go-to" solution when the need arises.

5 1 5 10/09/2024

I have never met Anthony, but based on his efforts over the years, I would hire him sight unseen. Best customer service. Period. I've gone with other carriers who promised lower price and got stranded. He's always found a way to accommodate even when challenges occur. Top notch.

5 1 5 05/17/2021

We had a great experience, particularly with Steve and the booking process, as well as with flight, which was fantastic. We would highly recommend Stratos. Thanks again!

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 10/24/2023

Although I was not a traveler for this trip, I organized the flight and was the point of contact. The communication and details from our agent made this first time use of Stratos Jet Charters very pleasant. I was able to reach out directly to Steve and he was very patient and helpful with all the questions I had from booking to payment. The memorable moment was with a delay in the departure. Steve sent emails to all but also made a phone call to be sure I was aware. This was so appreciated so I could reach out immediately to the travelers. THANK YOU STEVE AND STRATOS JET CHARTERS.

5 1 5 12/15/2023

Anthony is the best. It's always hectic trying to get the details right and he stays on top of it so I don't have to!

5 1 5 11/25/2018

The whole team is always professional and great to work with. You can tell there's a lot of integrity and experience in the company. Thank you folks!!

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 08/23/2020

It was a treat to fly private again. Everyone at Stratos and Flying Labz were a joy! If I need to fly private again Stratos is the only company I'd reach out to.

5 1 5 07/17/2014

Your company really cares about it's customer and made us feel so comfortable and confident. I would recommend your service to others.

5 1 5 09/15/2017

Would definitely recommend to friends! Joel went above and beyond to get us home after hurricane Irma came through Florida! Joel was in a lot of communication with us due to the high air traffic that day! Can't wait to go through Stratos jets again!

5 1 5 10/07/2020

Just wanted to say that the way you guys relay information is perfect. I've never seen it from any other broker

5 1 5 04/24/2025

We had a critical event to get to and the weather was not great. Glenn did a great job keeping in contact to make sure everything went smoothly.

5 1 5 01/01/2022

Stratos Jets provided excellent customer service! One of the most reliable private jet charters. Glenn was incredibly helpful and professional he made the booking process very easy and kept me updated with trip details daily. Highly recommend Stratos Jet Charters.

5 1 5 01/02/2021

We had a great experience, Anthony our contact was in close contact before the flight keeping us updated and the service was excellent on both sides.

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 05/27/2025

Our experience using Stratos and Joel was phenomenal. From the initial communication to how quickly we got various quotes back for different plane options, to having a discussion with Joel on his recommendation of what fit our needs the best it was five stars across the board. It was so helpful to have someone as knowledgeable as Joel walking us through what to expect each step of the way on our first charter experience. He even took the time to message us letting us know when our planes had hit the ground and were waiting for us and texted us asking how each leg went when we arrived. Overall can’t say enough about what a wonderful experience it was start to finish and we will absolutely be using Stratos and Joel for all of our future chartering needs.

5 1 5 01/18/2024

We had a last minute need for supplemental lift, and were very pleased with the service provided. Glenn did a fantastic job arranging this flight on very short notice and kept me up to date with the details. I would not hesitate to use them again.

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 04/29/2024

Everything went off smoothly and everyone I worked with at Stratos was very patient and helpful. Our small group felt very special! What a treat and yes I’d recommend Stratos to anyone.

5 1 5 09/17/2021

The flight was extremely, even surprisingly, comfortable. The crew was fantastic--professional and courteous. The agent's support was extremely thorough and professional: explanations, details and assistance with car rental was much appreciated. We will highly recommend these services to others.

5 1 5 06/02/2018

Joel, I hope this email find you well. I just wanted to reach out to thank you for the charter service you arranged for us last weekend. It was truly a pleasure to fly with Stratos and we will most certainly book with your charter service again. Thanks again for all of your help this week. It made the trip a breeze! Warm Regards, Matt, Scottie & Harper

5 1 5 12/21/2021

See above.

5 1 5 12/06/2012

I had an exceptional time with outstanding service and crew!

5 1 5 01/29/2026

As has been customary with STRATOS over the past many years, the efficiency and overall ease of traveling couldn't be better ! From booking flights, to the aircraft selection process, to safety concerns, to speed and efficiency in every respect coupled with the knowledge and consistent affability and attention to detail on the part of my agent, Anthony Angelini, my private jet travel experience has been made truly fabulous ! I would highly recommend STRATOS without reservation to anyone interested in private jet travel.

5 1 5 03/31/2019

Glenn,
The trips, one to Iowa & the other back to Dulles, went great. 
Everyone did great jobs & made me & my 94 year old Mom feel comfortable & taken care of. 
Glenn & Rachel were especially helpful. 
I would use your service again and will let Glenn know about my next trip. 
Thanks to you, Glenn, Rachel and the very nice/competent pilots.  Ground staff were great too. 
Thank you.

5 1 5 04/13/2017

We love Joel!

5 1 5 06/27/2017

Simon Crhistian did a great job.

5 1 5 07/31/2023

Ditto!

5 1 5 09/12/2017

Joel was a delight to work with arranging our flight from IRMA. Very professional and accommodating. I would definitely use him and your company again and refer others to you. The flight was fantastic with very nice pilots, James Briggs and Thomas Sommers. We were not the typical passengers as my husband has Alzheimer's and is wheelchair bound. Thanks for everything!!!

5 1 5 11/18/2017

I did have a good experience dealing with the charter staff. The only suggestion I can make would be that when sending revised itineraries or updated information is that somehow you reference what is new or updated info. Either in the email or by highlighting the NEW info. Thank you for using Oak Air.

5 1 5 09/02/2020

Perfect experience.

5 1 5 06/11/2018

KERRY HILL WENT ABOVE AND BEYOND TO HELP ME WITH THIS TRIP FOR MR. SOLLBERGER. SHE IS PATIENT AND KNOWLEDGABLE AND WAS MORE THAN HAPPY TO HELP SEE THAT MR <REDACTED> ARRIVED SAFELY ON THE GROUND AND AT HIS HOTEL . I CANNOT SAY ENOUGH ABOUT KERRY'S EXCELLENCE. THE FLIGHT AND CREW WERE EXCELLENT AS WELL.

5 1 5 01/27/2019

We were so very pleased with the planning, follow up and service. Do not waste your time or money looking anywhere else.

5 1 5 02/21/2022

Great platform, all trip information was readily accessible. Thank you for working with us on this one and keeping the itineraries flexible. No significant feedback otherwise, we look forward to the opportunity to assist with future operations!

5 1 5 07/31/2023

Perfect experience!!!!! The flight was on time, the pilots were great, and Booking with Kyle was easy and exceptional! Stratos is the very BEST option for flying private.

5 1 5 05/27/2014

lower cost flights :)

5 1 5 06/23/2022

The process was easy; plane, limo, pilots and boarding went smoothly

5 1 5 07/09/2021

Always a joy

5 1 5 01/01/2019

Pilots were terrific, polite, and kind.

5 1 5 12/07/2016

The Stratos team has always been highly professional, accommodating and easy to work with to plan and execute our trips. Additionally, their commitment to safety and utilizing experienced crew members puts us at ease to know every trip we book is not only enjoyable but very safe. Couldn't recommend them more!

5 1 5 02/10/2026

Jesse was on the ball throughout the process - made it very easy to arrange our flights. His communication was prompt and clear, and he was always responsive!

5 1 5 10/14/2021

You guys are great to work with!

5 1 5 06/03/2026

My agent did a great job of getting to know about our whole travel party and making the experience especially memorable for our group. She had to be a bit flexible in the planning as our destination changed a bit during the process, but the agent had no problem accommodating us.

5 1 5 02/21/2022

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

5 1 5 12/21/2021

everything went very well in all areas.Thank you .

5 1 5 04/15/2024

Very good communication and timely responses for flight details. We work with alot of brokers and your level of expertise and communication is a breath of fresh air from what we typically see. Thank you again for your business and we hope to continue our relationship with your organization! JR

5 1 5 11/29/2018

I made all of the arrangements for the charter flight for my boss and his family. I worked with Joel Thomas personally, who took the time with me to show the jet options available, all the while considering my boss's medical issues and care requirements. He emailed a jet comparison guide with photographs to view side-by-side so that I could make a wise and informed decision, and walked me through them over the phone. He was determined to provide the best possible experience for everyone. Joel made it all so easy, and it was clear after conversations with him that he has a heart for people and genuinely cares about their needs. I ordered in-flight catering, over the phone, which could not have been any easier. The food was plentiful and exceptional! My boss called me the next day asking that I inquire as to who the local caterer was that supplied the food, as he wants to make sure that we use them in the future. They staged all of the food on beautiful white platters that looked classy and elegant, as though it was all prepared for red carpet guests. And every selection was freshly prepared that day and over the top in flavor! The pilot was very nice and personable and clearly cared about the comfort and safety of his passengers. The plane was extremely comfortable and very luxurious. The seating was perfect for the six of them and their cat, Molly! I received a call the next day from my boss's grown daughter, and all she did was rave about how it was first class all the way! She said I always do such a great job. LOL! It was Joel and the Stratos team that did all the work! My part was easy! Ohhh, and Joel also went out of his way to arrange for ground transportation upon their flight's arrival. I can say from personal experience over the years, that flying does not get any better than going first class with Joel Thomas and his team at Stratos Jet Charters. I want to thank them for making me look like the best assistant ever!!

5 1 5 08/23/2013

Kevin is great to work with. I'll call him again. the aircraft crew were great. Thank you for making this trip so easy for us.

5 1 5 12/02/2025

We love how Joel follows our travels and keeps us alerted to all aspects of the trip, from where the incoming plane is being repositioned from to weather updates and real-time info. We always feel secure and in good hands! Finding Baker Aviation flights for us was lovely as well. Their plane was well-maintained the pilots were excellent. All around, 5 thumbs up!

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?

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    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?

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    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?

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    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
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