CHI - SXM

$93 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 3/11. 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
Travelers love KAYAK
41 299 237 searches in the past 7 days on KAYAK

Save 23% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
$304
Overall average: $621
Spirit Airlines
Tue 3/10Tue 3/17
ORD - SXM • 1 stop
Cheapest non-stop
$768
United Airlines
Sat 4/11Sat 4/18
ORD - SXM • Non-stop
Nonstop flights
2 days a week
Sat, Sun
You can fly direct with United Airlines and American Airlines. Average duration is 5h 00m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top airlines
Spirit Airlines
Cheapest • from $304 (round-trip)
Delta
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top layover airports
Fort Lauderdale (FLL)
Cheapest • Avg $396 (round-trip)
Charlotte (CLT)
Shortest trip • 6h 47m (one-way)
Insights
Insights
Insights
Insights
Top routes
ORD
-
SXM
Cheapest
ORD
-
SXM
Most popular
Insights
Insights
Insights
Insights
Avoid delays
American Airlines
Most punctual • 86% on-time
Morning flights
Best time • Fewest delays
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 37% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
January
Cheapest • 15% price drop
March
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
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

Tue, Mar 10 - Tue, Mar 17
Spirit Airlines Logo
8:16 pm - 1:15 pm
ORD
-
SXM
15h 59m
1 stop
Spirit Airlines Logo
2:20 pm - 11:17 pm
SXM
-
ORD
9h 57m
1 stop
$304Spirit Airlines
Sat, Apr 25 - Sat, May 9
Spirit Airlines Logo
5:05 am - 1:30 pm
ORD
-
SXM
7h 25m
1 stop
Spirit Airlines Logo
2:35 pm - 12:14 am
SXM
-
ORD
10h 39m
1 stop
$309Spirit Airlines
Sat, Apr 11 - Thu, Apr 16
Spirit Airlines Logo
5:05 am - 1:30 pm
ORD
-
SXM
7h 25m
1 stop
Spirit Airlines Logo
2:35 pm - 12:14 am
SXM
-
ORD
10h 39m
1 stop
$314Spirit Airlines
Mon, Apr 27 - Fri, May 1
Spirit Airlines Logo
5:05 am - 1:30 pm
ORD
-
SXM
7h 25m
1 stop
Spirit Airlines Logo
2:35 pm - 12:14 am
SXM
-
ORD
10h 39m
1 stop
$315Spirit Airlines
Wed, Mar 18 - Tue, Mar 24
Spirit Airlines Logo
5:05 am - 1:15 pm
ORD
-
SXM
7h 10m
1 stop
Spirit Airlines Logo
2:20 pm - 11:17 pm
SXM
-
ORD
9h 57m
1 stop
$317Spirit Airlines
Sat, Mar 7 - Sat, Mar 14
Frontier Logo
6:00 am - 3:20 pm
MDW
-
SXM
7h 20m
1 stop
Frontier Logo
2:35 pm - 10:09 pm
SXM
-
MDW
8h 34m
1 stop
$369Frontier
Tue, Apr 7 - Mon, Apr 13
Southwest Logo
8:50 pm - 1:40 pm
MDW
-
SXM
15h 50m
2 stops
Southwest Logo
2:35 pm - 7:35 am
SXM
-
MDW
18h 00m
2 stops
$596Southwest
Mon, Jul 13 - Wed, Jul 22
Southwest Logo
5:10 am - 2:00 pm
MDW
-
SXM
7h 50m
1 stop
Southwest Logo
3:00 pm - 5:25 am
SXM
-
MDW
15h 25m
2 stops
$610Southwest
Sat, Mar 28 - Tue, Mar 31
Multiple Airlines Logo
9:16 pm - 1:30 pm
MDW
-
SXM
15h 14m
2 stops
Multiple Airlines Logo
3:20 pm - 10:15 am
SXM
-
MDW
19h 55m
1 stop
$619Multiple Airlines
Thu, Mar 26 - Tue, Mar 31
Multiple Airlines Logo
4:55 pm - 1:15 pm
MDW
-
SXM
19h 20m
2 stops
Multiple Airlines Logo
3:20 pm - 10:15 am
SXM
-
MDW
19h 55m
1 stop
$626Multiple Airlines
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.

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 $531 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 January, where tickets cost $584 (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 $782 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 37% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 6 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$93
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly and prices are also 6% 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 $93 for a one-way ticket and $304 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, and Sunday.

  • 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 $672 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 $730 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 $304 or less one-way and $706 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 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 8240 reviews
7.2Food
8.1Boarding
7.9Comfort
8.5Crew
7.8Entertainment
Airline reviews

Flight was delayed by 3-hours and their fix was… complimentary pretzels.

4.0 OkayJahmes, Feb 2026
LAX - MCO
Read more Delta reviews

Flight was delayed by 3-hours and their fix was… complimentary pretzels.

Flight was delayed due to crew being not on time

Flight crew issues delayed my flight by 2 1/2 hours. Causing me to miss my connection.

The staff on board and gate was nice - a welcome change from the usual. We also arrived early, which was a great benefit, given that it takes 30 minutes plus to get bags at SRQ.

The staff was frielndly. The plane was terrible, it was too small and should be decommissioned. There were no back seat screens at all. The only beverages we had a choice from was coffee, tea or water. The only bathroom in the back was behind the flight attendant's jump seat and wasn't working. And I literally felt like I was sitting on top of the guy next to me. It was terribly hot in the plane and we had to sit on the tarmac in Chicago for 1/2 hour due to congestion in Mpls. Wouldn't they have know that before they even boarded us so that we could have sat in comfort in the terminal?

Never got on it. Was re-routed through Detroit and am still in airports 12 hours later waiting for my connecting plane to arrive.

Delta has too many delays now days. It is 1:06 am now. I was supposed to land in Norfolk at 10:30 pm. I got re-booked through Detroit and I’m still in Detroit. I hope to be landed in Norfolk by 3am. I’ve been in airports for 12 hours as of right now. There is a weather delay now but most delays lately have been maintenance.

Very Very late. Subsequent flights left an hour before ours

This is my worse experience with Delta. My colleagues and I were traveling to ICT for work. Usually we connect in Dallas, but this year we decided to book with Delta and connect in Atlanta. We were excited to fly with Delta because we hear great things and Delta is one of my top choices when choosing an airline for travel. On the connecting flights to and from Wichita/Atlanta - it felt hot and uncomfortable on the plane. The plane to ICT was smaller and older and did not have any wi-fi or entertainment. The most terrible experience was at boarding in Atlanta both times traveling to Wichita and then back to Tampa. First on our flight from ATL to ICT - the attendant scanning our boarding pass made us go back to the line when we went up to scan our passes to wait. After a few minutes, she allowed us to come back up to scan but then she asked what boarding zone we were. We told her zone 5, and since we were standing on the wrong side of the small rope partition, she made us go back to stand on the right side. There was another gentleman that came up to board and scan his pass, and she mentioned he was also on the wrong side but she let him go through. Our group had to walk back and forth for no reason, causing an unnecessary delay to board the plane. We have never experienced anything like this, especially when the boarding area was completely empty and everyone already boarded since boarding was earlier than the original boarding time. On our flight from ATL to TPA, the attendants scanning our boarding passes had us scan our passes twice, not explaining to us what was going on. They automatically started tagging our carry on bags and did not explain to us or tell us what was going on and why this was happening. Obviously we knew our bags were being forced to check in but with no reason. There was no announcement or mention and I have never had anyone force me to check in my bag before boarding the plane. We assumed the overhead bins were full but when we boarded the plane, there was a lot of empty bins and a lot of spaces to put our bags. We all were disappointed and frustrated with Delta and will be hesitant to fly Delta again or anytime soon.

Boarding and crew were fantastic, but I paid for a window seat with no window. Seat 11D on a CRJ-900 apparently does not have a window. Lesson learned.

We were delayed for about an hour from taking off due to traffic control procedures at the destination airport. But once in the air, the flight went well. The crew members were great and provided cabin service despite moderate turbulence during much of the flight.

Short flight, but no drink/snack service. The flights both going and coming were delayed.

Not being stranded in Chicago for her airport to 11:30 tomorrow morning the 3rd

I was fully checked in the prior night and i was unchecked and then didn’t have a seat when I boarded. Instead of an aisle seat, I was out in the middle seat of the very last row of the plane.

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

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.

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.

Maintenance took a very long time and then we were in a holding pattern. While a one-off maintenance issue is standard, there were delays on both of my flights for this trip based on maintenance issues with the planes, which delayed both flights over 45 minutes. Thankfully, I didn't have any connections but it wasn't an experience that would make me pick AA if I have other options.

No Snacks or Entertainment. The flight was short, snacks should still be given.

See prior comment about how Kayak mishandled my reservation and delayed my arrival by 6 hours.

Boarding delayed 20 minutes for no reason, no wifi, in flight entertainment, or snacks / waters?

Delayed an hour due to operational issues. Minimal apologies or care for the significant inconvenience caused. Landed at nearly 1am and they still couldn’t find ground staff to get us off the plane promptly.

The aircraft had several problems - from excess fuel to non operational ac. Two hours of delay in Chicago could have been avoided with proper planning and aircraft maintenance.

Crew in Columbia was not prepared for landing. It was a bit of a disaster and getting bags took forever.

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.

We sat on the tarmac for an hour and a half after landing.

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

Flight was delayed due to waiting for crew! Flight attendants did not offer us food or drinks. Did not communicate with them at all other than at boarding and leaving the plane.

Got surprised by passing an additional fee when selecting seats. No snack or drink offered. Will never use spirit again.

The flight was delayed over an hour which got us into DFW at approximately 2:20 am

Went as planned. No wifi included and no screens. No free snacks. Didn't buy food so can't rate that. Unable to charge devices on plane. Staff were friendly and flight was fast, cheap and convenient.

Horrible experience!! In the meantime we were in Philadelphia they didn’t give us some water and the information about the fly on the plane was without empathy!!! Plus the fly started with delay!! So very unhappy moment!!!

Horrible we lost a day at the destination. Flight was canceled at 2am left us scrambling for another airline to get us to destination

The flight was delayed for unknown reasons while other airlines weren’t. It was very frustrating.

Kayak and Spirit could not meaningfully share itinerary data, leading to many hours of remediation.

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

Information on your arrival and departure airports