CHI - SXM

$115 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 5/2. 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
$300
Typical prices: $790-$587
Spirit Airlines
Sat 5/9Sat 5/16
ORD - SXM • 1 stop
Cheapest one-way
$79
Typical prices: $229-$260
Spirit Airlines
Sat 5/2
ORD - SXM • 1 stop
Top airlines
Cheapest • from $300 (round-trip)
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
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Airline reviews
Airline reviews
+1
Nonstop flights
Not available
There are currently no direct flights between Chicago and Simpson Bay. You'll need at least 1 connection.
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Top layover airports
Cheapest • Avg $384 (round-trip)
Shortest trip • 6h 44m (one-way)
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Top routes
Cheapest
Most popular
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Avoid delays
Most punctual • 80% on-time
Best time • Fewest delays
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When to book
in advance
Our data shows that travelers who book at least 4 weeks in advance save around 31% compared to booking last minute.
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When to travel
Cheapest • 33% price drop
Most popular
Good to know
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+1
+1
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Simpson Bay!
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, May 9 - Sat, May 16
Spirit Airlines Logo
5:05 am - 1:30 pm
ORD
-
SXM
7h 25m
1 stop
Spirit Airlines Logo
2:35 pm - 11:15 pm
SXM
-
ORD
9h 40m
1 stop
$300Spirit Airlines
Sun, May 3 - Thu, May 7
Multiple Airlines Logo
5:05 am - 1:37 pm
ORD
-
SXM
7h 32m
1 stop
Multiple Airlines Logo
2:35 pm - 11:38 pm
SXM
-
ORD
10h 03m
1 stop
$305Multiple Airlines
Sun, May 3 - Thu, May 7
Multiple Airlines Logo
5:05 am - 1:37 pm
ORD
-
SXM
7h 32m
1 stop
Multiple Airlines Logo
2:35 pm - 11:38 pm
SXM
-
ORD
10h 03m
1 stop
$306Multiple Airlines
Fri, Jun 5 - Thu, Jun 11
Air Canada Logo
8:20 pm - 5:00 pm
ORD
-
SXM
19h 40m
1 stop
Air Canada Logo
6:00 pm - 2:55 pm
SXM
-
ORD
21h 55m
1 stop
$315Air Canada
Thu, May 7 - Sun, May 10
Spirit Airlines Logo
5:05 am - 1:30 pm
ORD
-
SXM
7h 25m
1 stop
Spirit Airlines Logo
2:35 pm - 8:22 am
SXM
-
ORD
18h 47m
1 stop
$329Spirit Airlines
Sun, May 3 - Thu, May 7
Spirit Airlines Logo
5:05 am - 1:37 pm
ORD
-
SXM
7h 32m
1 stop
Spirit Airlines Logo
2:35 pm - 11:15 pm
SXM
-
ORD
9h 40m
1 stop
$330Spirit Airlines
Fri, Jun 5 - Thu, Jun 11
Air Canada Logo
6:22 pm - 5:00 pm
ORD
-
SXM
21h 38m
2 stops
Air Canada Logo
6:00 pm - 8:00 am
SXM
-
ORD
15h 00m
1 stop
$356Air Canada
Wed, Jun 3 - Wed, Jun 10
Southwest Logo
8:50 pm - 1:25 pm
MDW
-
SXM
15h 35m
2 stops
Southwest Logo
3:00 pm - 10:00 pm
SXM
-
MDW
8h 00m
1 stop
$630Southwest
Tue, Jul 14 - Sun, Jul 19
Southwest Logo
5:10 am - 2:00 pm
MDW
-
SXM
7h 50m
1 stop
Southwest Logo
1:55 pm - 11:45 pm
SXM
-
MDW
10h 50m
1 stop
$660Southwest
Wed, Oct 14 - Fri, Oct 23
Delta Logo
6:00 am - 1:49 pm
MDW
-
SXM
6h 49m
1 stop
Delta Logo
3:14 pm - 12:33 pm
SXM
-
MDW
22h 19m
2 stops
$670Delta
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 May.

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 $737 on the route between Chicago O'Hare Intl Airport (ORD) and Simpson Bay (SXM). It is also the most popular route.

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 September, where tickets cost $427 (return) on average. On the other hand, the most expensive months are December and April, where the average cost of round-trip tickets is $797 and $787 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 4 weeks before departure, which saves you about 31% 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$79
Best time to beat the crowds with an average 33% drop in price.
Most popular time to fly and prices are also 8% 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 $79 for a one-way ticket and $300 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.

  • 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 $612 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 $660 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.

Reviews of the top 4 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 8438 reviews
8.5Crew
7.9Comfort
7.2Food
7.8Entertainment
8.1Boarding
Airline reviews

Everything was great. The only issue is unfixable. Seats are too small. 😁🤪

10.0 ExcellentAnonymous, Apr 2026
ATL - AMS
Read more Delta reviews

Everything was great. The only issue is unfixable. Seats are too small. 😁🤪

This wasn't my experience with Delta. It was just the Pegasus flight. Seats were very hard. Staff was kinda rough. Not very nice. Charged me for snacks. For a 4 hour flight I would've expected more.

Crew was nice, meal was good. Entertainment had to be rebooted 3 times and still did not work. Turns out there was residue on screen, it needed to be cleaned to prevent the touchscreen buttons from continuously activating. I had entertainment for the last 45 minutes of a 5 hour 45 minute flight. Really unacceptable for first class. Flight attendent indicated your cleaning solution creates this problem. Seems as if this is widely known, you should be using a different product or cleaning better. Really really disappointing which simply added to the wi fi on your planes with reliably never ever works.

The baggage belt was not updated on the Delta App and was displayed on the wrong belt board. Was not expecting this to happen.

The plan was delayed and left DC 90 minutes late. However, it showed a 20 minute delay on the delta app, then a 12 min delay. It turned out to be an hour delay. I found out where the plane was with flightaware. Stop keeping customers in the dark about what is going on.

Everything went smoothly, although the usual gripes about airline travel were still present: the boarding process is inefficient, the snack selection is limited, and so on. Since there was extra space on the flight, the gate agent rearranged many people's seats to put people on the aisles and windows, leaving the middle seats empty, as much as possible, which was pretty great.

Landed without a gate ready. Plane is extremely old and dirty.

All the amenities was wonderful, if they could keep their prices that low. I'd fly with them all the time.

Very old plane with no inflight entertainment. I purchased the internet pass and it was nearly unusable.

My tray was broken so i had no place to work or eat except my lap. Flight attendant said I would get an email with some credit or miles, it was a complete waste of time as I could only function at about 20% of normal. I have not received anything yet.

The crew was great. Very friendly and responsive. The plane was old, small and tight. We ran out of overhead space and I had to check. Middle seat was particularly tight.

Several missed and almost missed connections. It felt like everything was being patched together last minute without enough resources and it ended up being an extremely stressful experience that basically ruined our weekend on the west coast. What a waste.

Crew was friendly. Seats are too narrow, particularly when a big person is in the adjacent seat, but I understand this is due to smaller planes usually flight into Lincoln. I have experienced several flight delays going out and coming into Lincoln airport, I say maybe 50% or higher of the flights I've taken out of this airport have been delayed.

Great flight. Boarded efficiently. Arrived early at CLT. There was no in flight entertainment on this aircraft. Great crew.

The seat was comfortable. There was a lot of turbulence. If it weren't for that,it would have been okay.

Poor communication, flight was delayed for preventable reasons. I missed my connection.

The boarding timing needs to be improved. The flight was delayed again because it took way too long to board. I was already exhausted from sleeping at the airport and spending all day there due to delay from my previous flight that connected in Chicago.

Great until we got to FRA. The next trip leg we were put in Business Class where seats had minimal padding!!!! They were awful and United Airlines needs to have their Lufthansa partner up their game or I won’t fly with them again!!

No meal service to the back of the plane as it started late or was too slow to get it out before it was time to land.

Terrible, if possible won't be flying again anytime soon!

Original flight was on time, then late, then changed gates...4 times. Once our newest plane came in, it was fine.

I almost missed my flight and they helped me out enormously

Delays experienced in boarding/take off due to incoming plane delayed. However, the boarding time/depart time in the app was significantly delayed in providing these updates. Usually not updated until an hour after we should have already boarded. Poorly managed.

Moved to earlier flight which unexpectedly had maintenance issues initially indicated as quick fix to ultimately plane changes. Moved back to original flight, also delayed. In all cases customer updates and communication very unclear, no updates on drivers for delays.

Typical AA - late by 90+ mn. Gate changed twice... Changed the departure time 6 times No explanation, no communication on reasons for delay I travel with AA twice a year... and it is consistently very poor.. I will continue to use AA only when i have to.

The gate got changed several times and the flight was delayed over an hour. Awful experience

American continues to decline in their customer service and its beyond disappointing.

It was an older plane. First Class was not especially roomy or comfortable. It was a short flight so there were no meal but they did offer mixed nuts which used to be normal but now is rare. Crew member was very polite and professional.

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

As previously stated the delay I experienced flying from Wichita to Chicago caused a host of issues. When I finally was able to be booked on the last remaining American flight from Chicago to Cincinnati, the gate changed four times with the last change occurring very near the scheduled boarding time. While I didn't have a problem moving from gate to gate, I did notice and make note of others that had mobility issues and had to move each time for the gate change.

They canceled my flight and never told me. There was no follow up email. I had to buy another ticket the day of.

Easy to get our TSA pre check #added. Flight crew was great and entertaining and we landed early!

Flight was delayed 6plus hours Did not take flight Customer service was terrible Will never fly again and will spread how terrible you are You stink

I didnt have a flight. Kayak must be on drugs because I confirmed with spirit that I had no booked flight.

They cancelled our flight. 2 hours before we were supposed to take off and offered us nothing! We got our money back and that was it. No other flight to get to our cruise no working with another airline or with us to get there. Terrible customer service, no apology.

We get stuck in the plane when landed during 45min and no communication from the crew People were listening to their phone and music out loud and nobody told them anything I definitely want stop booking spirit flight it is a disaster

Good: It was cheap and they got us to our destination safely. Not so Good: Gates experience with many, many nauseatingly (almost) threatening announcements about bags size and how much they were going to charge us if our bag was too big, even to the point of having a gate agent roaming around through the passengers eyeballing bags size and making people go check their bags in the sizers.

Terrible. The flight was randomly delayed in Chicago causing us to miss our connection and they offered us a flight the next day at 6 am and it would have taken till 345 to get to Pensacola. They didn’t cover any fees. Our bags also supposedly were on the flight to Pensacola and we tried to get them yesterday after driving 6 hours and nobody was available. Worst company ever and will never use them again. Had to pay for a rental. Spirit is claiming in climate weather for the delay but there wasn’t any weather issuesz it’s a bunch of bullshit and I am not happy

Checking in at desk in Chicago was horrible. Person was not friendly never smiled and said my flight was not paid for so I had to give another credit card. Then it ended up that I was charged twice. Then after arriving at my destination had to wait on the phone a long time to speak to a person to fix the double charge! Thank goodness the flight was perfect.

Flight was delayed for 12 h. They should stop overlooking flights.

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

Information on your arrival and departure airports