CHI - SXM

$74 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 2/6. 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
1 adult, Economy, 0 bags

KAYAK searches 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, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Simpson Bay, as well as popular online travel agencies
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Everything you should know

Cheapest round-trip
$198
Overall average: $693
Spirit Airlines
Sat 2/7Wed 2/25
ORD - SXM • 1 stop
Cheapest non-stop
$574
United Airlines
Sat 2/7Sat 2/14
ORD - SXM • Non-stop
Top airlines
Spirit Airlines
Cheapest • from $272 (round-trip)
Delta
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top routes
ORD
-
SXM
Cheapest
ORD
-
SXM
Most popular
Insights
Insights
Insights
Insights
When to book
3 weeks
in advance
Our data shows that travelers who book at least 3 weeks in advance save around 35% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
February
Cheapest • 14% price drop
March
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Nonstop flights
2 days a week
There are direct flights from Chicago to Simpson Bay 2 days a week: Sat, Sun.
Direct flights
Direct flights
Direct flights
Direct flights
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Flight Deals
Booking Insights
Flight Deals

Cheap Flights 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 for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Simpson Bay

Sat, Feb 7 - Wed, Feb 25
Spirit Airlines Logo
5:15 am - 2:15 pm
ORD
-
SXM
7h 00m
1 stop
Spirit Airlines Logo
3:20 pm - 11:47 pm
SXM
-
ORD
10h 27m
1 stop
$198Spirit Airlines
Sat, Jan 31 - Sat, Feb 7
Spirit Airlines Logo
5:15 am - 2:10 pm
ORD
-
SXM
6h 55m
1 stop
Spirit Airlines Logo
3:20 pm - 11:47 pm
SXM
-
ORD
10h 27m
1 stop
$200Spirit Airlines
Sat, Jan 31 - Sat, Feb 7
Spirit Airlines Logo
5:15 am - 2:10 pm
ORD
-
SXM
6h 55m
1 stop
Spirit Airlines Logo
3:20 pm - 11:47 pm
SXM
-
ORD
10h 27m
1 stop
$201Spirit Airlines
Sat, Feb 7 - Sat, Feb 14
Spirit Airlines Logo
5:15 am - 2:15 pm
ORD
-
SXM
7h 00m
1 stop
Spirit Airlines Logo
3:20 pm - 11:47 pm
SXM
-
ORD
10h 27m
1 stop
$215Spirit Airlines
Sat, Feb 7 - Wed, Feb 25
Spirit Airlines Logo
5:15 am - 2:15 pm
ORD
-
SXM
7h 00m
1 stop
Spirit Airlines Logo
3:20 pm - 11:47 pm
SXM
-
ORD
10h 27m
1 stop
$216Spirit Airlines
Sat, Feb 7 - Sat, Feb 14
Spirit Airlines Logo
5:15 am - 2:15 pm
ORD
-
SXM
7h 00m
1 stop
Spirit Airlines Logo
3:20 pm - 11:47 pm
SXM
-
ORD
10h 27m
1 stop
$230Spirit Airlines
Sat, Apr 4 - Sat, Apr 11
Frontier Logo
6:00 am - 2:40 pm
MDW
-
SXM
7h 40m
1 stop
Frontier Logo
3:40 pm - 11:42 pm
SXM
-
MDW
9h 02m
1 stop
$477Frontier
Tue, Feb 10 - Fri, Feb 13
Delta Logo
6:00 am - 2:55 pm
MDW
-
SXM
6h 55m
1 stop
Delta Logo
1:38 pm - 10:31 pm
SXM
-
MDW
10h 53m
1 stop
$529Delta
Tue, Feb 10 - Fri, Feb 13
Delta Logo
6:00 am - 2:55 pm
MDW
-
SXM
6h 55m
1 stop
Delta Logo
4:15 pm - 12:46 pm
SXM
-
MDW
22h 31m
2 stops
$534Delta
Wed, May 6 - Sun, May 10
Southwest Logo
6:00 am - 1:40 pm
MDW
-
SXM
6h 40m
1 stop
Southwest Logo
3:20 pm - 11:40 pm
SXM
-
MDW
9h 20m
1 stop
$625Southwest
Booking Insights

KAYAK's insights & trends for Chicago to Simpson Bay flights

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.

How much is a round-trip flight from Chicago to Simpson Bay?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago to Simpson Bay departing in February.

What is the cheapest Chicago to Simpson Bay flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest return flight from Chicago to Simpson Bay costs $546 on the route between Chicago O'Hare Intl Airport (ORD) and Simpson Bay (SXM). It is also the most popular route.

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

The average price of all round-trip flights from Chicago to Simpson Bay clicked on KAYAK for each day over the last 12 months.

When flying from Chicago to Simpson Bay, you should consider leaving on a Sunday and avoid Saturdays if you are looking for the best rates. For your return to Chicago, you’ll find the best rates on Mondays and the most expensive ones on Saturdays.

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 round-trip 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 February, where tickets cost $592 (return) on average. On the other hand, the most expensive months are December and June, where the average cost of round-trip tickets is $797 and $791 respectively.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip 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 week.

To get a below average price on the flight from Chicago to Simpson Bay, you should book around 3 weeks before departure, which saves you about 35% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 8 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$74
Best time to beat the crowds with an average 12% 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 $74 for a one-way ticket and $198 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 airlines offer Wi-Fi service onboard planes from Chicago to Simpson Bay?

    American Airlines, and JetBlue offer inflight Wi-Fi service on the Chicago to Simpson Bay flight route.

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

    The Boeing 737 MAX 8 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?

    SkyTeam, Star Alliance, and oneworld are the airline alliances operating flights between Chicago and Simpson Bay, with SkyTeam being the most commonly used for this route.

  • 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 $706 and an overall rating of 7.9, Delta is the most popular choice. United Airlines is also a great choice for the route, with an average price of $765 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.

KAYAK’s 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 $313 or less one-way and $666 or less round-trip.

Prefer to fly direct from Chicago to Simpson Bay?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Chicago to Simpson Bay Princess Juliana.
Find which airlines fly direct from Chicago to Simpson Bay Princess Juliana Airport, which days they fly and book direct flights.

Direct departures

Chicago to Simpson Bay Princess Juliana

Saturday

American Airlines, United Airlines

American Airlines, United Airlines

Sunday

United Airlines

United Airlines

See more direct flights

Direct returns

Simpson Bay Princess Juliana to Chicago

Saturday

American Airlines, United Airlines

American Airlines, United Airlines

Sunday

United Airlines

United Airlines

See more direct flights

Reviews of the 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.
7.9
DeltaOverall score based on 8052 reviews
7.8Entertainment
7.2Food
8.1Boarding
7.9Comfort
8.5Crew
Airline reviews

Departure was delayed resulting in me missing my connection. Delta did not autimatically find me another flight.

4.0 OkayNeal, Jan 2026
SEA - SLC
Read more Delta reviews

Departure was delayed resulting in me missing my connection. Delta did not autimatically find me another flight.

The seats weren’t reclining even though it wasn’t as exit seat

It was good because we traveled without luggage, carry on only.

I usually get upgraded so my experience is usually amazing. I did not get upgraded this time - which was fine - but the wifi had issues, the monitors were going in & out, & (though not Delta's fault) one of the gentlemen next to me desperately needed a shower.

The entertainment screens were not working and there was no air condition the entire flight. Very uncomfortable.

I have diamond medallion status and usually we are in comfort plus . We were in main this time ( which was fine ) and my husband wanted wine . I have at least 10 vouchers for drinks that are good for this year and next! The attendant would not take the picture of the voucher as proof and never came back to check as She asked me to pull it up on delta Wi-Fi. Instead my husband just used his Amex to buy the wine . Disappointing!!!

Food is basically Sun Chips, cookies or Cheezits. I had an exit row seat so I had plenty of room. The crew was very nice and efficient. Pilot kept us informed. Pretty good flight.

Air travel sucks. It continues to be awful for all airlines. No shame on delta alone.

It was Delta, but the flight attendants were stressful and disrespectful. I am a diamond member a travel weekly. I have not had a negative thing to share in quite some time. But this was noticeable.

Comfort Plus seat 11E seemed smaller than prior flights. The movie selection is good. Watched most of the most recent Tron movie. I'll watch the remaining part later as my movie is saved in the Delta Seatback Experience.

They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!

I understand weather is an issue, but making us chase our plane down at five scheduled gates across three terminals in an airport the size of O'Hare was unfair. They'd have probably been better off to leave gates as TBD until the inbound plane is in final approach instead of running us all over the place. Also, props to the consistently-unprepared ground crew in Richmond for once again leaving my lane parked short of the gate because they couldn't have a crew in place on time with 2 hours notice...

cabin crew was OK, food was OK, the trip from the US to Munich was actually pretty bad comfort wise. Noisy aircraft, lights never dimmed even in Business class (night flight) barely sufficient amenities for the price. I have millions of miles with United but TBH American is gaining ground and Delta has always been marginally better then United although on paper United has more longes and cheaper upgrades.

Essy to get on. The hostess gave very little pop, the plane was late getting in, and we are still waiting for our bags. This sucks. :/

Not United Airlines' fault. It's ORL airport's fault.

Great flight. On time boarding. Smooth flight and on time arrival at EWR. The flight crew was marvelous and there was a great selection of movies on the entertainment system. Our bags were at the carousel before we got there. Another excellent flight from United.

I liked the snacks and the flight attendants were friendly.

The movies offered were great. Staff were very pleasant and very efficient.

After a delay at the gate, C3, at Ohare on Sunday, I left my Blk ski coat on the bench at the gate, lost! Please review my lob claim, thx.

Very nice flight love the small aircraft. We had a wonderful flight attendant. Nice to see someone that really enjoys her job. Don't have her name but had a southern accent.

We were upgraded to First Class and it was a great flight

We experienced gate changes and a long delay. My seat was dirty when I boarded and I had to use wipes to clean it myself. There was an unpleasant and overpowering cleaning product scent on the plane as well that lingered through the flight.

My carry on baggage was damaged. Entire trip, I had to carry the baggage. When complained to the boarding crew, they got mad at me and still asked me to valet check in the cabin baggage. Rude boarding crew!!!

Crew were all friendly and helpful. It was a short flight so just a beverage service with a cookie. After we were boarded the plane took about 45 minutes to leave the gate but it was New Year’s Eve so not shocking there was some delay. Overall good experience and very grateful.

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

The boarding by groups is pointless. The first two groups worked fine, but almost Noone boarded in goups three thru five leaving the vast majority boarding when group six was called. It defeated the purpose of spreading out the crowd.

We loved the steward on the plane. He made the night enjoyable

The plane was late, when we did board the plane was as cold as a freezer. I was freezing the entire flight, no blankets. Lost miserable flight I’ve ever had.

My wife and I love to travel, so we fly a lot. We've already logged 381,075 miles and with practically every major airline. But this flight was very disappointing. It started off well, with no delays and a new plane. But when lunchtime approached, all that good impression was ruined. Instead of white tablecloths, we were offered small, dark placemats, which, as it turned out, were perfectly adequate for the food. All the food offered—and my wife and I only took fish, and the meat—was not just bad, it was downright disgusting and not heated enough. The same applies to the appetizers. This was the first time in many years of traveling that we've been offered such disgusting food.

Lost luggage stuck no clothes and no word after 2 days leaving on cruise no stuff or clothes

Flight was not on time and it was very annoying flight. Keep changing gates.

Liked early boarding for disabled customers. Seat comfort could have been better, would have appreciated an empty seat between my wife and I since I suffer from arthritis, neuropathy, and spinal stenosis. Also aisle seat armrest was immobile and this made it difficult to get into and out of my seat during the flight

The flights were very uncomfortable the seats don't have much leg room at all and they are pretty hard as well.

It was delayed but the landing was the smoothest in a while that I’ve had.

Second time in 3 days I walked off the plane late. This time - almost an hour.

Everything went well. The flight was slightly delayed however we landed on time.

I've flown two Spirit flights recently - boarding for one was somewhat chaotic, with the board listing the wrong flight and causing much confusion; boarding for the other was very smooth and easy. My seat (for which I did not pay extra) was a bit narrow and without great legroom, but it was fine for a NY-Florida trip and was more than worth the low price I paid. The crew was friendly and one flight landed early and the other was only very slightly delayed. All in all a very good experience.

Had to pay for water if wanted it. Seats are close unless you get upgraded. Flight was fine. Will travel again with spirit.

Good! But your flight crews don’t need to ‘eat the mics’ when making announcements. If they held the mics 3 to 4 inches away from their mouths, we could understand them so much better. Otherwise, all is well.

Your flight crew and boarding area crew need to have microphone use training. They all hold the microphone right up to their mouths, way to close making understanding them almost impossible. The microphone should be held about 3 to 4 inches away from their mouths. This would provide for much better clarity through the PA system. ‘Eating the mic’ DOES NOT work.

It was costly and difficult to check in. $85 to take a small suitcase with me, carry on or checked and $75 on the return trip, Plus $25 if I didn't check my self in check in $25, because I couldn't do it on the kiosk. Small very uncomfortable seats, waited on the runway for near an hour each way. It was my worst flight to date.

It was ok. It was expensive to check 2 bags ($75.00 per bag), and then it took a long time to wait for shuttle to take us from one terminal to the terminal where the plane was taking off at LAX. And all of this for a flight where we had to pay for any food or drink that was not water.

It didn’t happen. I booked it and then was told it wasn’t available and then forced to pay far higher prices for a worse option

A 630departure flight Delayed 6hours! They changed my gate, I moved to the new gate. Had our flight on the screen for 12noon departure. I go get above to eat, check screen again and the flight was gone, no notice no announcement, nothing!! They sent my bag on the flight I wasn’t on, got it back to me 3days later. Thank goodness they did refund my money but I will NEVER fly them again.

Due to weather, my flight was delayed, further delayed, then canceled. I eventually got through to a support person who helped me find a different route out of MSP, but to get to DIA, they didn't want to, but eventually did help with the connection ticket purchase. But even this replacement flight was delayed time and time again, and I would have missed my connecting flights and I didn't want to get stuck in a layover city, so after 12 hours at the airport with two young boys who were very tired, we just cancelled our plans and spent the week at home, instead of Nana's.

Plane and crew on board were fine. Everything else was terrible.

The third party booking with cheapflightsfares was awful. Kayak should NOT partner with them. They sold me a bundle including seat selection and carry-on, but did not book the carry-ons with Frontier, so I’m out of pocket for $414 more while I await resolution.

This company socks. It's fraud. They canceled our flight yesterday, and today we were late because of a really long line at the check in bag. At the rebook station, there was ton of people. The workers were all rude. I am gonna make a report to FTC.

One of the worst travel experiences I've had. Had a flight scheduled with CVG to RSW on VLSWQX this morning departing at 5:30. Two individuals at the gate and one was in training. Not her fault but she didn't have the ability to check people in resulting in at least 15 families that didn't make it on the plane because they weren't checked into the system in time. When arriving at the airport to drop off our prepaid checked bags, the bag drop off agent asked if we could check our bags at the gate because of the long line. We said no problem so arrived at the gate by 5:00. They told those people that had previously paid for checked bags to stand off to the side while they let others that either didn't have a checked bag or their bag was already on the plan through. Realizing the gate workers had an issue, they either called for help or this lady showed up late for work as she didn't arrive until 5:15. The worker who had been there training the other individual and working diligently to make sure all passengers got on board. He even said that at one point all people that are currently in line are fine but asked the person in training to stand outside the ticketing area around 5:15 to notify any late travels that the flight was in boarding process and they arrrived too late. At that point, we're sill standing off to the side with our pre-paid checked bags patiently waiting. When the new lady arrived she couldn't have been more rude. It was an awful seen. Essentially they had asked for those without an assigned seat to board last, those with pre-paid checked bag stand off to the site and any traveling with a larger items that needed to be checked at the gate (such as a stroller), wait on the side. They realized that the flight needed to leave on time so the gate attendant shut the gate. So anyone without a seat assignment, those that had pre-checked bags, and the worst one I saw was a mother with two infant children was in line with use because she was asked to stand to the side because her stroller. When they shut the door to the plan they told her she could no longer get on. Her checked bags were already on the plane with her car keys in them, and the lady told her we couldn't accept anyone else on because the door was shut. She didn't even have a way to get home from the airport. Truely evil behavior. I've flown Frontier enough to know customer service is not a top priority in the company's mission, but this was an all-time low. I'm sending this after an 18 hour drive that our family just completed to Bonita Springs . I felt really bad for the lady being trained and the other individual trying to help, but when the new lady came to the gate she was truly one of the rudest individuals I've ever met. One lady had been there since 4am but because she didn't have an assigned seat they wouldn't let her on the plan.

I loved the staff on the plane. So friendly and helpful! However, there was an argument and misunderstanding by the staff and a customer at the gate, and the staff member was being unprofessional. When we arrived in Atlanta, we waited 1.5 hrs for our luggage to arrive. When I asked the airport attendant, they said Frontier had the longest wait for luggage out of any airlines, and that they could not be held responsible for the delay.

Everything you need to know for your flight from Chicago to Simpson Bay

Information on your arrival and departure airports