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 (4.88 out of 5) Based on 655 reviews from our trusted Jet Charter reviews
5 1 5 12/21/2021

Transparant, smooth, easy working with the entire team

5 1 5 05/08/2020

After our flight, I sent an email to Joel Thomas (CEO) telling him about our experience. Joel called me last night to thank me for email. In part, my email to Joel said: Ernest Hemingway once said: "The best way to find out if you can trust somebody is to trust them". We trusted Stratos Jet Charters with our first charter flight, and the actions of all of your employees and contractors sustained our trust in Stratos. I told my wife when we were flying down: "Kyle (Jones) must sleep with his phone or computer on his pillow". It didn't matter when I called, texted, or emailed. Kyle always responded on a near immediate basis. Wow! Since this was our first charter, Kyle professionally and patiently walked us through the entire charter process with accurate, complete, and well-documented information. He seemed to always be a step ahead and in many, many cases, anticipated our questions and preemptively answered them. In a world where you hesitate to call a service provider or financial institution because you know you will be stuck on hold or in voicemail hell, it is indeed a breath of fresh air to find a company who communicates so very, very well and truly appears to care about their customers and the customer's experience with them. Most of my interaction was with Kyle Jones but I also had communications with Sandy Milam and she exhibited the same responsiveness as Kyle. The ground crews at Signature Flight Services at TEB and PBI were equally adept at continuing that service of excellence. Last but certainly not least, pilots Ernie Guido and Don Poskitt were the icing on the cake. As a former CEO of a professional services business, I know how important the client experience is and how communication is one of the very key components. I just wanted to be sure you heard about our experience from a very satisfied customer. Kudos to you and your staff.

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 03/12/2014

Outstanding service.  Appreciate all the aircraft options

5 1 5 02/28/2024

Anthony is great to work with and always extremely responsive which is key when we have an AOG and need a charter quickly!

5 1 5 03/23/2020

Kyle from Stratos Jet was great to deal with... quick responses....great service....great prices....A+ experience

5 1 5 05/03/2018

Stratos arranged a private jet to Toronto for me last minute. Everything went well and the Challenger 300 was very nice. Thank you

5 1 5 02/21/2022

Always great to work with you guys!

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 10/24/2023

Everything was as expected.

5 1 5 12/17/2018

With only a 15 hour window from my 1st request to Joel to wheels up, Stratos provided me with a great plane, rate and service. I texted from overseas and within 30 minutes had a quotations. With 2 hours Joel and his team came back with even better rates and we locked in the Flight! I am always amazed at the service and how they track every detail of the flight and my progress. Even though I am in a second tier city I get amazing flight options with Joel and his team. The equipment was a light jet with brand new soft goods and fantastic pilots. Everyone was super friendly and when you book through Stratos you are treated as an Aircraft owner. Thank you again guys! MAG Pittsburgh, PA

5 1 5 10/14/2021

Class act from beginning to end!

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 05/09/2012

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

5 1 5 03/08/2020

Joel and his team did a great job as always!!

5 1 5 04/15/2020

yes!

5 1 5 05/18/2020

It's so easy to book and Anthony is amazing. No hiccups and always informative.

5 1 5 12/19/2023

Great equipment, a competent/courteous crew and a smooth flight make for a terrific trip!!

5 1 5 05/05/2021

Your team was easy to work with and the clients were great. We look forward to working with you again. our trip # was Z0HQZZ

5 1 5 02/05/2021

Great trip all round. Glenn and the team were terrific. The crew on the day were amazing.

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 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 09/21/2013

It's all good !

5 1 5 07/12/2013

We had quite a number of issues booking this trip, which resulted in add'l work and follow up for me. As broker these issues should have been handled / caught prior to making a proposal. I believe I had to sign 4 different revised quote sheets for this trip! Also the final signed sheet stated we would land in LFMD on the return leg. Hence we booked transportation for pick up at LFMD. However flight landed in LFMN. This caused add'l stress and expense for no reason. I have only now seen that the last itinerary link showed an arrival at LFMN - but I never opened this one since all previous ones, including the contract reconfirmation showed LFMD. As for the aircraft itself: it was one of the oldest ones I have ever flown. The door / separation to the toilet / luggage area was broken (not the lock but the entire frame!) and the toilet was not accessible due to a lot of "stuff" (amenities, water bottles, etc.) being thrown in / stored in the area. Overall cleanliness was not superb either. Finally, the catering we requested was not available / not complete. Breakfast (eggwhite and sausage!!) was cold and wet and the fruitplatter had molded grapes; no ice bucket, nor champagne glasses were present. On the return leg, fruitplatter was nice but again no ice bucket nor champagne glasses were present. As a matter of fact, the soft drink container was not even replenished w new ice!! So overall - yes, we flew from A to B but the service experience was disappointing.

5 1 5 08/21/2022

Kyle immediately answered the phone when I called, after normal work hours, needing a plane the next morning. He worked with me for hours to find the right plane. I flew out the next morning at 9am. Kyle followed along with both that flight as well as the return the next day to make sure everything was fine. I feel comfortable knowing that Stratos carefully chooses their planes with the highest safety ratings. Thank you to Kyle and his team for their attention to detail and care that their customers have an excellent and safe travel experience. I highly recommend Stratos Jet Charters

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 10/28/2020

Experience with Stratos was fine. Flight crew was both professional and personable. Aircraft was in top shape.

5 1 5 02/12/2020

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

5 1 5 03/27/2024

I've had 3 round trips with Stratos and except for a little fog on one leg everything was always great! The pilots were all awesome! StratosJets is a very dedicated company to make sure everything is safe and sound.

5 1 5 01/08/2023

My agent was wonderful. However, my scheduled flight time was changed due to the owner wanting to use their plane. This change resulted in my missing an engagement. No discount was given to me for my inconvenience. The lack of observance of a signed contract was shocking and frankly showed a lack of integrity. I expect monetary compensation.

5 1 5 09/14/2017

I have worked with quite a few different charter companies over the years and Stratos Jets has been the easiest to work with. I always work with Kerry Hill because she very professional, friendly, and is just down right awesome at her job. I often need last minute trips for my boss and she always gets back to me quickly regardless of what time of day it is. I truely feel she goes above and beyond to make sure every aspect of the trip runs smoothly and everyone is happy. I can't say enough about how much stress is taken out of booking these flights because I know Stratos and Kerry have everything I need covered.

5 1 5 06/08/2022

The pilots were very kind and understanding. We had enough luggage capacity but the jet itself I thought was a little less luxurious than what I had imagined. All in all it was a good trip.

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 01/24/2018

As the assistant who actually booked the trip and made the plans for my employer and her family, I must say that the experience was a new one for me. That said, the unfamiliar process was made much simpler thanks to the knowledge, expertise and patience of my rep, Christina Nesbit. She was extremely informative and helped thru each step of the process, reassuring me that the passengers were getting the most appropriate plane for their needs. I will double check to be sure there isn't any additional feedback I am missing, but to date I was told that the flight was a pleasurable one and they were appreciative and impressed that the President came to greet them pre flight as well. Thank you, Shari

5 1 5 06/22/2017

Always a pleasure to work with the Stratos Jet crew. You all have great communication with us which makes our life as an operator easier. Great job from Kerry, Sarah, and Trip Support as always.

5 1 5 10/30/2017

Joel and Stratos are amazing! He made sure our flight was tailored perfectly and was very responsive and always available for contact. They catered specifically to our needs with late notice. The pilots were fantastic and patient, especially considering we had three animals and arrived 10 minutes before take-off. They provided the smoothest flight in the Hawker we’ve ever taken. Stratos offered transportation to and from; the boarding process was welcoming and convenient. We will only fly privately with Stratos Jets through Joel and his team. Thank you guys for everything!

5 1 5 07/21/2019

I worked with Kimberly from Stratos Jet Charters. She was very enthusiastic and helpful. In fact because of her enthusiasm and helpfulness, I chose Stratos over a another company that gave me a slightly lower quote. She answered all my questions and did her best to meet all my requests. The flight was excellent, plane was comfortable and the pilots were very helpful and professional. There was a bit of miscommunication about the hours of customs at my home airport .. and lead to a bit of confusion about the return departure time. Ice for beverages had melted on the first leg, and not all the drinks were stocked according to what was promised. My requests were fulfilled however for the return flight. I'm a coffee drinker, coffee was well stocked, but very little cream available, kinda curdled!!. These are tiny details but better supply of online refreshments would have made the flight perfect!! Beautiful views, no delays, smooth landings, and comfortable seats and lav. Beautiful shiny, clean plane. . the CJ3. Had a great time!

5 1 5 12/13/2016

Garret has provided excellent service and is attentive and easy to work with. The pilots on this trip were EXCEPTIONAL at dealing with our needs and providing service with the passengers needs and schedule. Very high compliments to the whole team for this flight.

5 1 5 02/21/2022

Great partnership and always a pleasure working with your team! We are all looking forward to many more.

5 1 5 04/19/2017

Top notch customer service from the initial contact through the end of trip, incredibly quick turn-around-time for a quote, very detail oriented itinerary. I highly recommend Stratos for any of your charter needs!

5 1 5 08/12/2020

Let me just add K___ and my thanks for a perfect flight.  Great crew, great plane and and wonderful flight. Doesn't get any better.

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 09/17/2021

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

5 1 5 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 03/30/2022

I feel very confident that Kerry Hill and her team will take excellent care of the trip that we plan. It was a great experience everyone was pleased with the outcome. I would recommend Stratos to anyone looking for Charter service

5 1 5 04/14/2020

Always a pleasure working with Stratos Jets. Never have had a bad experience.

5 1 5 11/26/2018

Everything about our experience was great. The quoting process was painless - several options were presented. Once the decisions were made there was great follow up from Rachel and her colleagues to handle every administrative matter with our trip. Everything went as planned and we were very happy. I would highly recommend considering Stratos for your next charter.

5 1 5 10/20/2022

Anthony made the booking easy and kept us fully informed. Flight itself was definitely 5 start. Good plane, good crew, good weather. What more can one ask?

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 12/21/2021

The level of service provided by Stratos is very high. Glenn and team continue to listen and understand our needs and organize excellent service. The latest provider was the best so far. Thank you team.

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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