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 2/22. 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
$219
Overall average: $690
Spirit Airlines
Mon 2/9Wed 2/18
ORD - SXM • 1 stop
Cheapest non-stop
$570
American Airlines
Sat 2/7Sat 2/14
ORD - SXM • Non-stop
Top airlines
Spirit Airlines
Cheapest • from $219 (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
January
Cheapest • 15% 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

Mon, Feb 9 - Wed, Feb 18
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
$219Spirit Airlines
Mon, Feb 9 - Wed, Feb 18
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
$224Spirit Airlines
Wed, Feb 18 - 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
$227Spirit 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
$235Spirit Airlines
Mon, Feb 23 - Sat, Feb 28
Multiple Airlines Logo
8:16 pm - 2:15 pm
ORD
-
SXM
15h 59m
1 stop
Multiple Airlines Logo
3:20 pm - 10:39 pm
SXM
-
ORD
9h 19m
1 stop
$250Multiple 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
$252Spirit Airlines
Sat, Apr 4 - Sat, Apr 11
Frontier Logo
6:00 am - 2:20 pm
MDW
-
SXM
7h 20m
1 stop
Frontier Logo
3:25 pm - 8:07 pm
SXM
-
MDW
29h 42m
1 stop
$482Frontier
Wed, Feb 18 - Wed, Feb 25
Delta Logo
6:00 am - 2:50 pm
MDW
-
SXM
6h 50m
1 stop
Delta Logo
1:38 pm - 10:31 pm
SXM
-
MDW
10h 53m
1 stop
$529Delta
Sat, Feb 21 - Wed, Feb 25
Delta Logo
6:00 am - 2:50 pm
MDW
-
SXM
6h 50m
1 stop
Delta Logo
1:38 pm - 10:31 pm
SXM
-
MDW
10h 53m
1 stop
$559Delta
Sat, Apr 4 - Sat, Apr 11
Frontier Logo
6:00 am - 2:20 pm
MDW
-
SXM
7h 20m
1 stop
Frontier Logo
6:51 pm - 4:09 pm
SXM
-
MDW
22h 18m
2 stops
$586Frontier
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 January, where tickets cost $586 (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 $219 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 $697 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 $677 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 8096 reviews
7.9Comfort
8.5Crew
7.8Entertainment
8.1Boarding
7.2Food
Airline reviews

No WiFi. Comfort plus should have alcohol provided, crew only offered water or tea. Who the heck wants tea?

2.0 MediocreKyle, Jan 2026
GNV - ATL
Read more Delta reviews

No WiFi. Comfort plus should have alcohol provided, crew only offered water or tea. Who the heck wants tea?

The flight was delayed and oversold. I volunteered to give up my seat for compensation. Thinking I could get a good night's sleep instead of arriving home at 2 am. It took over an hour to get the new reservation confirmed, three different gate attendants, and two red coats. It took even longer to confirm the overnight hotel, and when I arrived, the line was 45 minutes long, with two people checking in, and at least 15 people slowly, very slowly—no food except frozen convenience food, no coupon for food from airlines. Slept, headed back to the airport, and that flight had an equipment change and a gate change just as they were about to board. It took an additional hour to board as they cleaned the plane from storage.

There was no wifi available on this flight. And there were no screens, no onboard entertainment, no entertainment options at all. It was like travelling in the 1990s again, except without even a main screen for options. Seats, as usual, were tight and uncomfortable.

Good seat comfort ORF to ATL. Bad seat ATL to SEA (terrible lumbar support, hard, ouch)..

Because I was moved to an exit row, the snacks in economy comfort, the selection of snacks was better.

I upgraded to first. Quick and easy boarding. Comfortable seat with power and a nice IPA.

Probably not the fault of Delta but there was delay after delay after delay and I ended up getting home 4 hours later then I should have at 1:30 in the morning

Easiest airport experience ever in my life at MSP with Delta check-in and flight attendant gave us a bottle of champagne in celebration of our 10-year wedding anniversary, so overall amazing!

No in flight service, no explanation - FC got service, C+ did not, unsure about Economy. No turbulence to speak of, so I guess another way to cut cost, or promote health and well being of Delta employees? Also, boarding in MEM combined zones, and with overhead space already full on both flights after Zone 2/ Diamond, presents a huge challenge to find a space for a bag. Delta, other than point A to B, is no longer reasonable to fly - very poor experiences, not even taking into account the chastising at the gate and rude crews, across the board.

It would have been better if the flight wasn't delayed by 2.5 hours

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.

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.

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.

Horribly late because they had no crew!!! And then jet bridge didn’t work!! Then we arrived at a gate at lax miles away that we had to take a shuttle to a terminal!! I was over 3 hours late to getting the LA! Should have been here at 8:30 and at an appointment at 10:30 and arrived and left lax at 11 am!! Horrible experience!!!

Extra legroom with my upgrade bundle. Clean aircraft, on-time departure, early arrival. Good value for the price.

I didn't have a flight because of a ticking problem that was discovered at the airport at checkin for the initial flight of the round trip.

Even though the plane was delayed from the previous airport, the staff recognized this and kept us informed. The flight crew was absolutely awesome from on my flight from Ft. Meyers to AC. Great experience all around!

Flight was delayed would have liked it to have been on time. I didn't experience the food or entertainment but the boarding process was smooth and the flight crew worked well together and did a great job!

Not seat assigned because overbooking. We could go because some people decided to give their seats.

Spirit loves to pick and choose when to harass you about your personal item. I’ve flown numerous times with the same bag with no problem yet flying out of Orlando they forced me to pay $99 for a carry on and then ran out of overhead space. Do better!

For the price of the fare, there really isn’t much to complain about.

didn't order food on board. there's no way to hold a water botton on the way. otherwise it was a pleasant flight, thanks to the crew.

Even though there was a delay the crew was exceptional.

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

Information on your arrival and departure airports