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CHI - SXM

$169 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 6/1. 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
Thu 6/20
Thu 6/27

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 42,596,105 times on KAYAK, and here is why:

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

 
These are the cheapest deals for flights from Chicago to Simpson Bay currently on KAYAK along with options from the most popular airlines KAYAK users selected for this route. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Recent round-trip flight deals from Chicago to Simpson Bay

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Chicago to Simpson Bay.

Recent one-way flight deals from Chicago to Simpson Bay

Only flying one-way? Below are some of the best one-way flight deals from Chicago to Simpson Bay found on KAYAK recently.

Recent last minute flight deals from Chicago to Simpson Bay

Leaving soon but still want a bargain? Check out these latest deals for last minute flights from Chicago to Simpson Bay.

Recent direct flight deals from Chicago to Simpson Bay

The latest deals for direct flights from Chicago to Simpson Bay so you can sit back and relax without the need for a layover.

Cheap bus & train deals from Chicago to Simpson Bay

Find recent round-trip train or bus tickets from Chicago to Simpson Bay.

All round-trip flight deals to Simpson Bay

The cheapest plane tickets to Simpson Bay found on KAYAK recently.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
10:08 am - 3:04 pmMDW-SXM
27h 56m1 stop
4:20 pm - 9:31 amSXM-MDW
18h 11m1 stop
$235Frontier
Find Deal
Sat, Jun 1 - Sat, Jun 8
5:56 pm - 3:04 pmORD-SXM
20h 08m1 stop
4:20 pm - 7:05 pmSXM-ORD
27h 45m1 stop
$265Frontier
Find Deal
Sat, Jun 1 - Sat, Jun 8
5:00 am - 1:44 pmORD-SXM
7h 44m1 stop
2:44 pm - 12:00 amSXM-ORD
10h 16m1 stop
$327Spirit Airlines
Find Deal
Sat, Sep 14 - Sat, Sep 21
6:40 pm - 1:44 pmORD-SXM
18h 04m1 stop
2:44 pm - 9:55 amSXM-ORD
20h 11m1 stop
$344Spirit Airlines
Find Deal
Thu, May 30 - Mon, Jun 3
5:29 am - 4:02 pmORD-SXM
8h 33m2 stops
3:39 pm - 11:57 pmSXM-ORD
10h 18m1 stop
$556American Airlines
Find Deal
Tue, Nov 5 - Tue, Nov 12
6:25 pm - 2:00 pmORD-SXM
17h 35m1 stop
5:00 pm - 7:37 amSXM-ORD
16h 37m2 stops
$558American Airlines
Find Deal
Sat, Nov 9 - Fri, Nov 15
6:00 am - 1:55 pmMDW-SXM
6h 55m1 stop
3:10 pm - 9:46 pmSXM-MDW
7h 36m1 stop
$580Delta
Find Deal
Fri, Jul 5 - Wed, Jul 10
6:55 pm - 1:45 pmMDW-SXM
17h 50m1 stop
3:19 pm - 8:44 amSXM-MDW
18h 25m2 stops
$584Delta
Find Deal
Tue, Jul 23 - Sat, Aug 17
10:43 am - 4:49 pmORD-SXM
5h 06mnonstop
3:55 pm - 11:15 pmSXM-ORD
8h 20m1 stop
$663United Airlines
Find Deal
Sat, Jul 13 - Sat, Jul 27
10:43 am - 4:49 pmORD-SXM
5h 06mnonstop
1:30 pm - 6:14 pmSXM-ORD
5h 44mnonstop
$680United Airlines
Find Deal
Sat, Jul 6 - Sat, Jul 13
7:13 pm - 3:04 pmORD-SXM
18h 51m2 stops
Sat, Jun 1
10:33 am - 2:44 pmORD-SXM
26h 11m1 stop
$181Spirit Airlines
Find Deal
Sun, Nov 3
10:33 am - 2:44 pmORD-SXM
26h 11m1 stop
$182Spirit Airlines
Find Deal
Sun, Nov 3
5:29 am - 4:02 pmORD-SXM
8h 33m2 stops
$336American Airlines
Find Deal
Mon, Nov 4
10:43 am - 4:49 pmORD-SXM
5h 06mnonstop
$433United Airlines
Find Deal
Sat, Jun 1
8:45 am - 2:52 pmORD-SXM
5h 07mnonstop
$526United Airlines
Find Deal
Sat, Nov 2
7:56 am - 11:28 amORD-SXM
26h 32m1 stop
$574Copa Airlines
Find Deal
Sat, Nov 2
6:00 am - 1:55 pmMDW-SXM
6h 55m1 stop
$610Delta
Find Deal
Thu, Jun 27
10:31 am - 4:02 pmORD-SXM
28h 31m2 stops
$666American Airlines
Find Deal
Sat, Nov 2
6:00 am - 1:40 pmMDW-SXM
6h 40m1 stop
$1,070Delta
Find Deal
Thu, May 23
5:56 pm - 3:07 pmORD-SXM
20h 11m1 stop
4:27 pm - 12:58 amSXM-ORD
9h 31m1 stop
$285Frontier
Find Deal
Sat, May 25 - Sat, Jun 1
5:56 pm - 3:07 pmORD-SXM
20h 11m1 stop
2:44 pm - 11:34 amSXM-ORD
21h 50m2 stops
Sat, May 25 - Sat, Jun 1
9:25 pm - 1:44 pmORD-SXM
39h 19m3 stops
2:44 pm - 11:29 pmSXM-ORD
9h 45m1 stop
$694Spirit Airlines
Find Deal
Sat, May 25 - Sat, Jun 1
9:25 pm - 1:44 pmORD-SXM
39h 19m3 stops
2:44 pm - 8:13 amSXM-ORD
18h 29m2 stops
$752Spirit Airlines
Find Deal
Sat, May 25 - Sat, Jun 1
9:25 pm - 1:44 pmORD-SXM
39h 19m3 stops
2:44 pm - 10:14 amSXM-ORD
20h 30m3 stops
$800Spirit Airlines
Find Deal
Sat, May 25 - Sat, Jun 1
10:43 am - 4:49 pmORD-SXM
5h 06mnonstop
1:30 pm - 6:14 pmSXM-ORD
5h 44mnonstop
$950United Airlines
Find Deal
Sat, May 25 - Sat, Jun 1
9:45 pm - 12:35 pmORD-SXM
13h 50m1 stop
1:30 pm - 6:14 pmSXM-ORD
5h 44mnonstop
$955United Airlines
Find Deal
Sat, May 25 - Sat, Jun 1
10:43 am - 4:49 pmORD-SXM
5h 06mnonstop
1:30 pm - 6:14 pmSXM-ORD
5h 44mnonstop
$680United Airlines
Find Deal
Sat, Jul 6 - Sat, Jul 13
10:43 am - 4:49 pmORD-SXM
5h 06mnonstop
1:30 pm - 6:14 pmSXM-ORD
5h 44mnonstop
$725United Airlines
Find Deal
Sat, Jul 13 - Sat, Jul 27
8:45 am - 3:52 pmORD-SXM
5h 07mnonstop
2:55 pm - 6:49 pmSXM-ORD
5h 54mnonstop
$864United Airlines
Find Deal
Sat, Nov 9 - Sat, Nov 16
8:45 am - 3:52 pmORD-SXM
5h 07mnonstop
2:55 pm - 6:49 pmSXM-ORD
5h 54mnonstop
$920United Airlines
Find Deal
Sat, Nov 9 - Sat, Nov 16
10:43 am - 4:49 pmORD-SXM
5h 06mnonstop
1:30 pm - 6:14 pmSXM-ORD
5h 44mnonstop
$983United Airlines
Find Deal
Sat, Jun 29 - Sat, Jul 6
10:43 am - 4:49 pmORD-SXM
5h 06mnonstop
1:30 pm - 6:14 pmSXM-ORD
5h 44mnonstop
$1,068United Airlines
Find Deal
Sat, Jun 22 - Sat, Jun 29
8:45 am - 2:52 pmORD-SXM
5h 07mnonstop
2:55 pm - 6:49 pmSXM-ORD
5h 54mnonstop
$1,261United Airlines
Find Deal
Sat, Nov 2 - Sat, Nov 9
8:45 am - 3:52 pmORD-SXM
5h 07mnonstop
2:55 pm - 6:49 pmSXM-ORD
5h 54mnonstop
$1,694United Airlines
Find Deal
Sat, Nov 9 - Sat, Nov 16
10:43 am - 4:49 pmORD-SXM
5h 06mnonstop
1:30 pm - 6:14 pmSXM-ORD
5h 44mnonstop
$3,395United Airlines
Find Deal
Sat, Jun 8 - Sat, Jun 15
10:43 am - 4:49 pmORD-SXM
5h 06mnonstop
1:30 pm - 6:14 pmSXM-ORD
5h 44mnonstop
$3,400United Airlines
Find Deal
Sat, Jun 1 - Sat, Jun 8

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 $590.

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 October, where the average cost of tickets is $945 and $812 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 $235 on Frontier, followed by Spirit Airlines ($327). One-way flight deals have also been found from as low as $181 on Spirit Airlines and from $336 on American Airlines.

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 $462.

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

$169
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly and prices are also 3% 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 $169 for a one-way ticket and $235 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 Copa Airlines?

    The two airlines most popular with KAYAK users for flights from Chicago to Simpson Bay are Delta and Copa Airlines. With an average price for the route of $706 and an overall rating of 8.0, Delta is the most popular choice. Copa Airlines is also a great choice for the route, with an average price of $713 and an overall rating of 7.8.

  • 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 $332 or less one-way and $663 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 10615 reviews
8.2Boarding
8.6Crew
8.0Entertainment
7.9Comfort
7.4Food
Airline reviews

Rated entertainment as Mediocre as there were major problems with the Infotainment system that took probably a half hour for them to fix.

8.0 Excellentrghinftl, May 2024FLL - BOS
Read more about Delta reviews

Rated entertainment as Mediocre as there were major problems with the Infotainment system that took probably a half hour for them to fix.

Your crew could maybe answer the call bell at least one of the times I pressed it. I pressed it first time with 2.5 hours left in our flight bc my partner was hungry and wanted a sandwich. We finally got the sandwich with 40 mins left in the flight.

Half the bathrooms assigned to economy were out of action

Delta crushed it. Flight attendant in first was attentive and just never stopped. Honestly one of the best domestic flights I’ve been on.

They were an hour late and they didn’t have my wheelchair for me

The Flight crew didn’t serve us until about 1.5 hours into the flight because of turbulence but after it ended it was fine to move around. They served us water only and snacks and then NEVER, NOT ONE TIME came through to collect trash until right before landing about 1.5 hours later. There was absolutely no need for that. They crew was just standing around talking and visiting with each other and really never tried to see if we might want something besides water or even try to come pick up trash. This is VERY unusual for a Delta flight but it was not what I would have expected for a 4 hour flight.

The 1st class male crew member was very pleasant - the short female with round glasses , maybe in 50’s had no personality- never spoke when delivering my food, drink, & never smiled the whole trip! In fact looked annoyed when the boarding proses was happening- I would never hire this woman - unfriendly . Have never dealt with a crew member like her-

5-hour delay due to storms in Tanoa and airspace restricted by Miami traffic controllers.

A regional sized plane was used for a cross country flight with no overhead bin space. I had to "pink check" my laptop and my medications. I was NOT pleased!!!!

Absolutely nothing flight was cancelled and delayed for 2 days. Barely a heads up I want a full refund

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."

Standard flight experience, but there is only power at the seat to row 20 on the aircraft, on my initial check in it did not say that was the case

Energetic crew - flight full of swiftied going to Taylor's opening show in Paris! Long lines for bathroom made out kind of suck though

I’ve had a couple flights this week on United that were delayed by an hour or more

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

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.

It was the worst ever, i will be filing a lawsuit to get a refund. Our flight was delayed 4 hours so we would miss our connecting flight, we were not rebooked to our destination the same day, we were not offered any options to get home on the same day despite being clear that we absolutely cannot get stranded at night due to family, we were forced to book our own flights on a different airline to get home, and spririt is refusing a refund because our flight wasn't cancelled, only delayed. oh yeah, and they lost our luggage on the first part of the trip and you cannot get a hold of customer service when anything goes wrong, on hold for 30+ minutes. and their app breaks so you can't use that either.

This recognisable no-frills airline gets me from point-A to point-B. I was able to get to Chicago without stress. The checked baggage collection and reclaim could be improved.

The crew was the best and very accommodating I know you don't offer any complimentary items but water and coffee will not break the bank !!

My flight was cancelled!!! I had to spend 200.00 on another flight!!

The whole day was a nightmare. Flight extremely late. Boarding was a mess of a nightmare.

When we landed, they kept us on the plane for almost 25 minutes. Could do better.

worst trip ever Spirit lost our Baggs which were never put on the plane in Atlanta. 24 hours ago they are telling me now that the bags are still missing.

Never been on this flight as i had missed it due to delayed connecting flight

Horrible. Delays, no customer support and fake promises and everything. i am suffering to help as due to connecting flight getting missed no support on ground and customer support window is closed and we are sitting o ground without anything

Missed our departing flight due to poor baggage drop staff. At the airport with 2 & 1/2 hours to spare and waited in bag check in until 15 minutes prior to gates closing before baggage staff asked us to move to the front of the line. We weren’t the only passengers that missed the flight. Poor organizational operations by Spirit staff. Otherwise , the return trip was fine.

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.
6/1Sat
2 stops
18h 51mORD-SXM
$169
11/3Sun
1 stopSpirit Airlines
26h 11mORD-SXM
$181
11/3Sun
1 stopSpirit Airlines
26h 11mORD-SXM
$182
11/4Mon
2 stopsAmerican Airlines
8h 33mORD-SXM
$336
6/1Sat
nonstopUnited Airlines
5h 06mORD-SXM
$433
11/2Sat
nonstopUnited Airlines
5h 07mORD-SXM
$526
11/2Sat
1 stopCopa Airlines
26h 32mORD-SXM
$574
6/27Thu
1 stopDelta
6h 55mMDW-SXM
$610
11/2Sat
2 stopsAmerican Airlines
28h 31mORD-SXM
$666
5/23Thu
1 stopDelta
6h 40mMDW-SXM
$1,070

Search by stops

Search by airline

Search by price

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.
5/25Sat
multi-stopFrontier
20h 11mORD-SXM
6/1Sat
multi-stopFrontier
9h 31mSXM-ORD
$285
5/25Sat
multi-stop
20h 11mORD-SXM
6/1Sat
multi-stop
21h 50mSXM-ORD
$402
5/25Sat
multi-stopSpirit Airlines
39h 19mORD-SXM
6/1Sat
multi-stopSpirit Airlines
9h 45mSXM-ORD
$694
5/25Sat
multi-stopSpirit Airlines
39h 19mORD-SXM
6/1Sat
multi-stopSpirit Airlines
18h 29mSXM-ORD
$752
5/25Sat
multi-stopSpirit Airlines
39h 19mORD-SXM
6/1Sat
multi-stopSpirit Airlines
20h 30mSXM-ORD
$800
5/25Sat
nonstopUnited Airlines
5h 06mORD-SXM
6/1Sat
nonstopUnited Airlines
5h 44mSXM-ORD
$950
5/25Sat
multi-stopUnited Airlines
13h 50mORD-SXM
6/1Sat
nonstopUnited Airlines
5h 44mSXM-ORD
$955

Search by stops

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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
$590