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 (4.89 out of 5) Based on 674 reviews from our trusted Jet Charter reviews
5 1 5 12/22/2020

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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 06/15/2023

As usual, Anthony made the entire experience wonderful. He was expeditious in finding options for our trip and maintained continuous communication. The flight and support he provided were excellent.

5 1 5 11/29/2023

Team, We have always enjoyed working with your professional staff. Requests and communication regarding trips are always timely. We hope that we can continue working together to provide a great experience.

5 1 5 06/22/2020

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

5 1 5 06/12/2021

We needed to book a same-day plane for employees and tools to provide urgent assistance to a customer. Zach was effective, proactive and cooperative in providing a solution, precise information and updates. Would recommend Stratos Jet anytime! Thank you!

5 1 5 06/04/2020

I will definitely use Stratos Jets again and will recommend the company without hesitation. It has been several years since I have chartered a jet and this process was very easy and friendly.

5 1 5 07/31/2023

Glenn and Stratos do a great job finding the right aircraft and keeping us up to date.

5 1 5 09/27/2013

None that I can think of

5 1 5 02/18/2019

The crew of Citation very good Cordial and effective Trip punctual all good Thanks

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 07/14/2020

All members of the team communicated extremely well. I worked with Steve to get my flight booked and he checked in with helpful texts and updates along the way. Highly recommend.

5 1 5 03/21/2023

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

5 1 5 12/28/2013

None that I can think of.  Great flight

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

Peace of mind!!! My family and I just completed our first charter on a private jet with Stratos. My wife and I have been on a few of our friend’s charters before and I fly regularly on my company's aircraft but this was the first charter of our own. Stratos and specifically Joel Thomas made my wife and I feel that we were in great hands throughout the planning, selection and ultimately flight process. Family loved it!!! Great experience.

5 1 5 10/17/2018

Heather was an important part of my chose in Stratos.

5 1 5 05/08/2021

Always great to work with the amazing team at Stratos Jets! Kyle was awesome!

5 1 5 03/30/2022

As always, we enjoy working with you all. We all strive to accommodate the clients needs as best as possible, on our end and your end. Looking forward to many more trips with you all in the future.

5 1 5 12/06/2012

I had an exceptional time with outstanding service and crew!

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 01/07/2014

Pricing to be competitive with Marquis etc.

5 1 5 11/22/2016

There is no way to improve on what Garett did for us in our time of personal tragedy. He responded with excellence, compassion, thoroughness etc. He went over and above for an absolute stranger in tremendous need. I can't say enough about the job he did. God bless Garett!!!

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 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 03/20/2020

Absolutely wonderful,....would recommend this to anyone [if they can afford it], real value….worth every penny!! Absolute comfort,.. courteous,... simple booking,...true luxury,.....best possible trip home from Florida !!

5 1 5 04/22/2021

I got quotes from several companies. Glenn at Stratos was the only one who took a personal interest, understood our needs, and kept in regular contact. The jets selected were perfect and were competitively priced.

5 1 5 06/29/2023

Came through for me in the clutch! Sanity saving charter ;-)

5 1 5 01/13/2018

As always, Joel and team delivered. The whole experience was seamless. I would highly recommend Joel and the entire Stratos team!

5 1 5 09/04/2023

We thoroughly enjoyed or experience. The pilot was very experienced and had a great personality as well. Equipment was in great shape. I have to admit, flying with Stratos taking care of the details is the only way to go! Thanks, Joel and the whole trip team.

5 1 5 08/24/2018

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

5 1 5 05/21/2020

Glenn made booking easy and was on top of every detail throughout the process. The flight itself was flawless. Many thanks.

5 1 5 02/15/2021

We appreciate working with you and your team. Thank you.

5 1 5 07/03/2022

Looking forward to our next booking with you! Professionalism at its finest!

5 1 5 10/28/2020

Hassle free travel! Everyone is helpful an kind.

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 12/05/2016

KEEP UP GOOD WORK,WHEN I CALLED WILL HAD MY PAST INFORMATION IN HAND.HE WAS GREAT

5 1 5 11/05/2021

The team and the total Stratos experience consistently impresses me on every trip! The immediate feedback, the technology platform which enables an immediate view of flight and aircraft availability, and of course the wonderful and accommodating communication with the whole team; Stratos is always amazing! They always go the extra mile and are always being preventative and proactive long before wheels up and down. As Stratos clients, we don’t feel any of the industry's current supply crunch. Whatever we have tasked Stratos with they have met and exceeded our needs and we could not ask for more or be happier. The experience, year-over-year is that Stratos has only added more options, more operators and we have only great experiences.

5 1 5 08/12/2020

 
Glenn is great to work with and very professional.
Sincerely, C. D. C.
 
 

5 1 5 07/28/2021

Randy was great. He helped with every aspect of the trip including time changes and catering. Both crews we had were great as well. Explaining, loading and unloading baggage, considerate and very polite. I would definitely use your service again.

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 07/31/2023

Daniel is knowledgeable, responsive and professional. Great job!

5 1 5 04/03/2018

Everything worked out great. Working with Stratos was seamless. When the Trump TFR foiled our plans on both the outbound and inbound legs, Stratos was proactive in finding the best solution for us and minimized the disruption to the timing of our itinerary while also remaining flexible to our schedule as well. Joel could not have been easier to work with, finding us the best options at the best prices.

5 1 5 05/01/2020

I have already recommended Joel to two people and they are both using him!!! I gave Joel only two hours to find us a plane.For medical reasons, we had to go to Houston....In two hours, I had three options...he is wonderful!

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 02/07/2018

Smooth across the board as always. Thanks for the trip.

5 1 5 08/27/2013

It was perfect!

5 1 5 02/12/2020

This service was unmatched and couldn’t have been better!

5 1 5 06/18/2020

Anthony was terrific, good clear quote information, helpful options and overall a very pleasant experience.

5 1 5 12/26/2018

Not sure I could have asked for more. Joel was responsive and delivered exactly what I needed. The two pilots were incredibly accommodating and made the trip very smooth. Thank you Joel

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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