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CHI - SXM

$132 Find cheap flights from Chicago to Simpson Bay

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Simpson Bay departing on 6/8. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
Wed 6/5
Wed 6/12

Search hundreds of travel sites at once for deals on flights to Simpson Bay

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Simpson Bay.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Simpson Bay.
In the last 7 days travelers have searched 42,573,820 times on KAYAK, and here is why:

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Cheap flight deals from Chicago to Simpson Bay (CHI-SXM)

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Simpson Bay that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
5:56 pm - 3:07 pmORD-SXM
20h 11m1 stop
4:14 pm - 12:58 amSXM-ORD
9h 44m1 stop
$205Frontier
Find Deal
Sat, May 18 - Sat, May 25
5:56 pm - 3:07 pmORD-SXM
20h 11m1 stop
4:14 pm - 12:58 amSXM-ORD
9h 44m1 stop
$244Frontier
Find Deal
Sat, May 18 - Sat, May 25
5:05 am - 1:48 pmORD-SXM
7h 43m1 stop
2:44 pm - 10:53 pmSXM-ORD
9h 09m1 stop
$263Spirit Airlines
Find Deal
Wed, Jun 5 - Wed, Jun 12
6:40 pm - 1:48 pmORD-SXM
18h 08m1 stop
2:44 pm - 10:53 pmSXM-ORD
9h 09m1 stop
$271Spirit Airlines
Find Deal
Tue, Jun 4 - Wed, Jun 12
5:56 pm - 3:07 pmORD-SXM
20h 11m1 stop
2:44 pm - 11:29 pmSXM-ORD
9h 45m1 stop
Sat, May 25 - Wed, May 29
5:00 am - 1:44 pmORD-SXM
7h 44m1 stop
4:20 pm - 7:05 pmSXM-ORD
27h 45m1 stop
Sat, Jun 1 - Sat, Jun 8
8:20 pm - 1:00 pmORD-SXM
15h 40m1 stop
5:00 pm - 9:03 amSXM-ORD
18h 03m1 stop
$553American Airlines
Find Deal
Sat, Oct 26 - Fri, Nov 8
5:40 am - 1:40 pmORD-SXM
7h 00m1 stop
3:20 pm - 11:56 pmSXM-ORD
9h 36m1 stop
$555Delta
Find Deal
Mon, Jun 3 - Thu, Jun 13
8:20 pm - 1:22 pmORD-SXM
16h 02m2 stops
4:00 pm - 9:02 amSXM-ORD
18h 02m1 stop
$558American Airlines
Find Deal
Tue, Oct 15 - Tue, Oct 22
6:00 am - 1:40 pmMDW-SXM
6h 40m1 stop
3:20 pm - 2:55 pmSXM-MDW
24h 35m1 stop
$564Delta
Find Deal
Mon, Jun 3 - Wed, Jun 12

Flights from Chicago to Simpson Bay - Travel Insights & Trends

Get data-powered insights and trends into flights from Chicago to Simpson Bay to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Chicago to Simpson Bay flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for one-way flights from Chicago to Simpson Bay.
Our data shows that the cheapest route for a one-way flight from Chicago to Simpson Bay cost $297 and was between Chicago O'Hare Intl Airport and Simpson Bay. On average, the best prices are found if you fly this route. The average price for a return flight for this route is $583.

What’s the cheapest day of the week to fly from Chicago to Simpson Bay?

The average price of all flights from Chicago to Simpson Bay clicked on KAYAK for each day over the last 12 months.
If your flying dates are flexible, you should consider flying to Simpson Bay on a Wednesday, as we generally find the cheapest rates on that day for this route. On the other hand, Saturday is the most expensive day to fly from Chicago to Simpson Bay. For your return ticket, we recommend flying on a Monday and avoiding Sundays for the best deals.

What is the cheapest month to fly from Chicago to Simpson Bay?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Chicago to Simpson Bay, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.
The cheapest month for flights from Chicago to Simpson Bay is September, where tickets cost $644 on average. On the other hand, the most expensive months are July and November, where the average cost of tickets is $945 and $847 respectively.

How far in advance should I book a flight from Chicago to Simpson Bay?

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from Chicago to Simpson Bay, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price on the flight from Chicago to Simpson Bay, you should book around 5 days before departure. For the absolute cheapest price, our data suggests you should book 54 days before departure.

Which airlines provide the cheapest flights from Chicago to Simpson Bay?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
The cheapest return flight ticket from Chicago to Simpson Bay found by KAYAK users in the last 72 hours was for $205 on Frontier, followed by Spirit Airlines ($263). One-way flight deals have also been found from as low as $132 on Spirit Airlines and from $313 on Delta.

Which airlines fly non-stop between Chicago and Simpson Bay?

Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for flights from Chicago to Simpson Bay.
There is just one airline that flies from Chicago to Simpson Bay direct and that is United Airlines. The best one-way deal found from United Airlines for the route is $441.

How many flights are there between Chicago and Simpson Bay per day?

There is a maximum of 1 nonstop flight a day that takes off from Chicago and lands in Simpson Bay, with an average flight time of 5h 06m. The most common departure time is 10:00 am and most flights take off in the morning. Each week, there are 1 flights.

Which cabin class options are there for flights between Chicago and Simpson Bay?

The average price of flights for each cabin class for the route found by users searching on KAYAK over the last 2 weeks.
There are 3 cabin class options for the route. These are Business, Economy and Prem Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

How long does a flight from Chicago to Simpson Bay take?

Nonstop flights from Chicago generally make it to Simpson Bay in 5h 06m. The flying distance between the two cities is 2,188 miles.

What’s the earliest departure time from Chicago to Simpson Bay?

Early birds can take the earliest flight from Chicago at 10:43 am and will be landing in Simpson Bay at 4:49 pm.

What’s the latest departure time from Chicago to Simpson Bay?

If you prefer to fly at night, the latest flight from Chicago to Simpson Bay jets off at 10:43 am and lands at 4:49 pm.

Good to know

Low season

September

High season

February

Cheapest flight

$132
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly and prices are also 4% lower on average.
Flight from Chicago O'Hare Airport to Simpson Bay

When to book flights from Chicago to Simpson Bay

Are your dates flexible? Find out the best times to travel from Chicago to Simpson Bay based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Chicago to Simpson Bay

  • What is the cheapest flight from Chicago to Simpson Bay?

    In the last 3 days, the lowest price for a flight from Chicago to Simpson Bay was $132 for a one-way ticket and $205 for a round-trip.

  • Do I need a passport to fly between Chicago and Simpson Bay?

    Yes, you’ll need a passport to travel to Simpson Bay from Chicago.

  • Which airports will I be using when flying from Chicago to Simpson Bay?

    On your way to Simpson Bay, you’ll fly out from one of these Chicago airports: Chicago Midway or Chicago O'Hare Intl. You’ll be landing at Simpson Bay Princess Juliana.

  • Which aircraft models fly most regularly from Chicago to Simpson Bay?

    The Boeing 737-700 is the aircraft model that flies most regularly on the Chicago to Simpson Bay flight route.

  • Which airline alliances offer flights from Chicago to Simpson Bay?

    Star Alliance is the only airline alliance operating flights between Chicago and Simpson Bay.

  • On which days can I fly direct from Chicago to Simpson Bay?

    You can catch a nonstop flight from Chicago to Simpson Bay on on Saturday.

  • Which is the best airline for flights from Chicago to Simpson Bay, Delta or United Airlines?

    The two airlines most popular with KAYAK users for flights from Chicago to Simpson Bay are Delta and United Airlines. With an average price for the route of $711 and an overall rating of 8.0, Delta is the most popular choice. United Airlines is also a great choice for the route, with an average price of $913 and an overall rating of 7.4.

  • How does KAYAK find such low prices on flights from Chicago to Simpson Bay?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Simpson Bay.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Simpson Bay?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Simpson Bay from Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Simpson Bay?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Simpson Bay with an airline and back to Chicago with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Simpson Bay?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Simpson Bay from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top tips for finding a cheap flight from Chicago to Simpson Bay

  • Looking for a cheap flight? 25% of our users found flights on this route for $487 or less one-way and $590 or less round-trip.

Prefer to fly non-stop from Chicago to Simpson Bay?

Find which airlines fly direct from Chicago to Princess Juliana, which days they fly and book direct flights.

Nonstop departures

Chicago to Simpson Bay Princess Juliana

Saturday

United Airlines

United Airlines

See more direct flights

Nonstop returns

Simpson Bay Princess Juliana to Chicago

Saturday

United Airlines

United Airlines

See more direct flights
See more direct flights

Top 5 airlines serving from Chicago to Simpson Bay

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Simpson Bay. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Chicago to Simpson Bay? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
DeltaOverall score based on 10818 reviews
8.2Boarding
7.9Comfort
8.0Entertainment
8.6Crew
7.4Food
Airline reviews

Very frustrated with boarding gate crew. She announced the plane was small and they would be limiting us to one item to carry on. Not a problem for me as I understand the tiny planes have limited space!! Not the case here! It was a rather large plane and had plenty of room for bags! So because I don’t want to be one of “those people” who ignores the request to check a carry on I did so asking if I would be able to pick it up at the bottom of the ramp on arrival in Knoxville to which she responded “yes”! Then I watched as every other passenger held onto their 2 items and boarded!! Then when we arrived in Knoxville our 2 carry ons had been put with all the other luggage and we had to go to baggage pick up and wait for all the big checked bags to come off the carousel! So she lied!! Frustrating. Next time I won’t be so nice!

8.0 ExcellentCynthia, May 2024ATL - TYS
Read more about Delta reviews

Very frustrated with boarding gate crew. She announced the plane was small and they would be limiting us to one item to carry on. Not a problem for me as I understand the tiny planes have limited space!! Not the case here! It was a rather large plane and had plenty of room for bags! So because I don’t want to be one of “those people” who ignores the request to check a carry on I did so asking if I would be able to pick it up at the bottom of the ramp on arrival in Knoxville to which she responded “yes”! Then I watched as every other passenger held onto their 2 items and boarded!! Then when we arrived in Knoxville our 2 carry ons had been put with all the other luggage and we had to go to baggage pick up and wait for all the big checked bags to come off the carousel! So she lied!! Frustrating. Next time I won’t be so nice!

It was a good experience except when boarding a female flight attendant did not go out of her way to assist my teenage daughters in finding space for their carry-ons after their compartments were full.

On time departure, smooth trip, flight attendant told through passengers the gate we would arrive at and the gate our outbound flight was departing from. Early arrival

Checking in at the airport the agent only booked the first keg of my trip and had my checked luggage going to the airport with a layover! Never was issued a boarding pass for the second leg or received sticker fir my checked bag. All was well in the end! Delta agents helped to resolve the situation!!!

Delayed due to an ill passenger after loading. Not preventable on Delta's part. Was in first class. The seats are becoming worn and detaching from their velcro attachments. Only got snacks on flight. The attendant was not the friendliest.

I would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

Big plane, long flight, absolutely no leg room and basically non existent air! I am 5”4’ and always travel Main Cabin, I was miserable on this plane and could barely move when we arrived in Cabo due to the cramped leg area!

From Atlanta to Cabo I would have hoped on a plane that size I would have been able to breathe and wiggle my feet a little! The leg room in that plane is non existent and I am only 5”4’. And the air vent either wasn’t working very well or just could not blow air from the ceiling to the seat area as I was suffocating through the entire flight! And please don’t say I would have been more comfortable in first class because I cannot afford those rates and have always travelled Main Cabin without issues !

The pilots were good. Disappointing when planes don't have electrical ports

I liked the piloting of the aircraft. Very disappointed about lack of electrical ports. Also, although a short flight. there was enough time to hand out snacks to comfort + seats as was done for first class.

Copa performed as expected for the amount of money I was willing to spend for the flight; it wasn’t exceptional but it was not bad in any way either. The crew was good; friendly and straightforward. The food was airplane food, so no expectations there and the entertainment was lacking but that was my fault for owning an IPhone with a charging port that’s not compatible with the rest of the world. I’d fly Copa again.

Left my bags in origin city on a business class ticket , spent about 2-3 days in the same clothes plus the flight .

the planes are not modern there are no phone chargers

As usual, the flight with normal legroom was not very comfortable, but the second flight was much better because we had paid for extra legroom. It was very nice to check our bags without an extra fee.

LOCKED MY BAG WITHOUT CONSENT. Had to have my zippers cut upon arrival in Costa Rica.

Pros: "The seats in economy were confortable. The best thing was Copa gave us seats in the second line and my family traveled together."
Cons: "Coffe service could better the experience"
Pros: "The crew was very interested on help and attentive with the passengers. But the seat wasn't comfortable. The design of the cushion is not the best to be seating"
Pros: "You were on time, that is the most important thing in a fly"
Cons: "You could improve your entertainment, you are not a cheap company"
Pros: "That there was seltzer"
Cons: "The management of preparing the flight and plane so that it was ready for the trip!!"
Pros: "Copa was convenient and easy. Very easy boarding process and I appreciated the day flight."
Cons: "This is a business class that is equivalent to a US carrier domestic first class. Good seats, not lay flat but wide on my 737-800. The food and service emulated say American Airlines Domestic 1C as well. Everything was just good enough, and much cheaper that international business on the majors."

Great! The plane was decently sized and comfortable. The staff was nice and there was great in flight entertainment

Last minute gate change nearly caused us to miss our flight. Change was not announced or displayed in the main board at the old gate. Terrible communication. When we landed we had to wait 20 minutes because there was another plane at the assigned gate. Not the crew’s fault, but adding 20 minutes to a 45 minute flight sucked.

Nothing beats ANA customer service on my opinion. Maybe because of their Japanese culture (and food). Arigatō

delay several times and wait extra long to board. no entertainment service because there are problem for some rows. always encounter some delays for the last flight of the day.

Flight delayed for 2 hours due to a part. The plane sat waiting for boarding for a long time and during final preflight inspection the issue was found. Why not do the preflight inspection sooner if you know the plane is being used?

The flight experience was very good! Especially the United Club!

I was not able to buy food in the flight. They refer to include your Credit card in the APP, and if you are not from USA (i have a credit card form Canada) it is not possible

Aircraft has better leg room than any of United's larger planes. We had requested mobility assistance for this and related flights. United's response to all was superb.

The flight from Ottawa to Chicago took a lot longer due to DC in Ottawa. We got to Chicago and went to our gate to catch our flight. We only had nine minutes I found that very stressful.

Good boarding. Crew started quick with drinks and food. They came around several times for trash which I really liked. Other than turbulence due to storms in the area, flight was great.

It was spectacular. I had basic Economy and was given so much space and their seats lean back so far. Staff was superb, food was superb, everything was superb, Finnair is Fantastic.

Good flights. Departure and arrivals were on time. DFW was a little problematic in that the Skytrain without prior notice bypassed the Echo terminal so that delayed my arrival at my connecting flight.

Because I can’t stand very long in one place, I was allowed to reword.

We were delayed bc ground crew gave the flight crew the wrong paperwork. We taxiied to the runway then back to the gate to get the correct paperwork that no one bothered reviewing the first time we pushed back. Boarding was rude and stressful like it always is. Gate agents and flight attendants are all over 55 years of age, embittered by years of underpayment From AA leading to their passive agressive bitchiness for no reason.

Boarding time was easy & quick. Crew was excellent. In-flight entertainment was great/easy. Seats are too small and not enough room between rows: felt like a sardine/very cramped.

5 hour flight - full flight - not enough room to use my computer - slightly delayed - Admirals club was excellent quality food, drink made up for flight seating. No food offerred on flight, you ahd to prebook.

Excellent- plan was barely populated. I cannot remember a flight where I was able/encouraged to stretch out!

Great flight. Boarding was efficient and quick. On time departure and smooth flight. Flight arrived early at destination. Good experience.

Baggage claim took too long and priority bags were not delivered first.

Had technical issue which delayed the flight period. Flight crew knew there was 5 passengers that the connecting flight was within 15 minutes once at the gate. Rather than identify the 5 passengers to assure they got first. The flight attended mentioned it but didn't assist to assure passengers with connecting flights off first. This caused a hardship and our party of 3 missed the connecting flight.

Terrible… missed our flight due to ridiculously long time to go thru baggage check-in!

The crew was not great or professional. It seemed like they didn't really want to be there. A true lack of effort for accommodating customers.

Everything was really good but the seats are not very comfortable.

I paid for WiFi, but it (WiFi) was very very slow, will never take again! Impossible open Utube 😤😤😤

I had no legroom, although I paid for extra legroom. I could barely put my bag in front of my feet and under the seat. The Wi-Fi was horrible. In fact the flight attendant said that they had to reboot it and see if it was going to work and never did.

The guy with severe body odor sat next to me. For the whole duration of the flight it was a torture. The airline should have better policy on limiting people with bad body odor to board the flight. Passengers should not be the ones to endure bad odor for the whole duration of the flight. The airline should be e the one to ensure decent air quality for ever passenger.

Overall it was a miserable experience... I will never fly spirit for more than a 3 hour flight or overnight.

The boarding attendant was slightly rude when I asked about checking our stroller. Made me feel like I was bothering her.

My wife and I are both handicapped and at boarding they upgraded us to a seat closer to the front rather than all the way towards the back. Much appreciated.

Not much seat room, but that was unexpected. But the seat headrest was very uncomfortable.

Book cheap flights from Chicago to Simpson Bay

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Chicago to Simpson Bay found on KAYAK in the last 72 hours.
6/8Sat
1 stopSpirit Airlines
7h 43mORD-SXM
$132
8/24Sat
1 stopSpirit Airlines
7h 44mORD-SXM
$150
6/8Sat
2 stops
45h 09mORD-SXM
$178
8/22Thu
2 stops
18h 48mORD-SXM
$209
8/24Sat
2 stops
27h 16mORD-SXM
$230
6/8Sat
3 stopsSpirit Airlines
41h 42mORD-SXM
$242
8/24Sat
2 stops
22h 17mMDW-SXM
$281
8/22Thu
1 stopDelta
26h 38mMDW-SXM
$313
6/8Sat
nonstopUnited Airlines
5h 06mORD-SXM
$343
5/30Thu
1 stopDelta
6h 40mMDW-SXM
$347

Search by stops

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Last minute flights from Chicago to Simpson Bay

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Chicago to Simpson Bay that are departing in the next 10 days.
5/11Sat
multi-stopSpirit Airlines
7h 44mORD-SXM
5/15Wed
multi-stopSpirit Airlines
9h 45mSXM-ORD
$495
5/11Sat
multi-stopSpirit Airlines
7h 44mORD-SXM
5/15Wed
multi-stopSpirit Airlines
9h 45mSXM-ORD
$552
5/7Tue
multi-stopSpirit Airlines
15h 19mORD-SXM
5/11Sat
multi-stopSpirit Airlines
9h 45mSXM-ORD
$625
5/7Tue
multi-stopSpirit Airlines
14h 44mORD-SXM
5/11Sat
multi-stopSpirit Airlines
9h 45mSXM-ORD
$703
5/11Sat
multi-stopDelta
7h 00mORD-SXM
5/15Wed
multi-stopDelta
17h 30mSXM-ORD
$854
5/9Thu
multi-stopDelta
6h 40mMDW-SXM
5/14Tue
multi-stopDelta
17h 45mSXM-MDW
$940
5/9Thu
multi-stopDelta
7h 00mORD-SXM
5/14Tue
multi-stopDelta
9h 45mSXM-ORD
$940
5/11Sat
multi-stopAmerican Airlines
16h 08mORD-SXM
5/15Wed
multi-stopAmerican Airlines
12h 24mSXM-ORD
$946
5/9Thu
multi-stopAmerican Airlines
8h 50mORD-SXM
5/14Tue
multi-stopAmerican Airlines
12h 24mSXM-ORD
$986
5/7Tue
multi-stopAmerican Airlines
8h 50mORD-SXM
5/11Sat
multi-stopAmerican Airlines
12h 24mSXM-ORD
$1,091

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Flights to Simpson Bay

Destination:

Simpson Bay (SXM)St. Maarten

Return flight deals:

Simpson Bay - Chicago

Cabin classes:

$1,444
$2,013
$583