ORD - SXM

$74 Find Cheap Flights from Chicago O'Hare Airport 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 O'Hare Intl 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
Travelers love KAYAK
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Everything you should know

Cheapest round-trip
$220
Overall average: $672
Spirit Airlines
Wed 2/18Wed 2/25
ORD - SXM • 1 stop
Cheapest non-stop
$610
American Airlines
Sat 2/28Sat 3/7
ORD - SXM • Non-stop
When to book
3 weeks
in advance
Our data shows that travelers who book at least 3 weeks in advance save around 38% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
September
Cheapest • 25% price drop
May
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 O'Hare Intl to Simpson Bay 2 days a week: Sat, Sun.
Direct flights
Direct flights
Direct flights
Direct flights
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 O'Hare Intl to Simpson Bay (ORD-SXM)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from O'Hare Intl 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 O'Hare Intl to Simpson Bay

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
$220Spirit Airlines
Sun, Feb 8 - Fri, Feb 13
Spirit Airlines Logo
8:43 pm - 2:15 pm
ORD
-
SXM
15h 32m
1 stop
Spirit Airlines Logo
3:20 pm - 11:47 pm
SXM
-
ORD
10h 27m
1 stop
$222Spirit 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
$227Spirit Airlines
Mon, Feb 16 - Fri, Feb 20
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
$237Spirit Airlines
Tue, Feb 24 - Tue, Mar 3
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
$242Spirit 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
$249Spirit Airlines
Sun, Feb 15 - 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
$250Spirit Airlines
Sat, Feb 28 - Wed, Mar 4
Spirit Airlines Logo
8:16 pm - 2:15 pm
ORD
-
SXM
15h 59m
1 stop
Spirit Airlines Logo
3:20 pm - 11:47 pm
SXM
-
ORD
10h 27m
1 stop
$258Spirit Airlines
Mon, Feb 9 - Thu, Feb 12
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
$259Spirit 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 - 11:22 am
SXM
-
ORD
22h 02m
1 stop
$262Spirit Airlines
Booking Insights

KAYAK's insights & trends for O'Hare Intl to Simpson Bay flights

Get data-powered insights and trends into flights from O'Hare Intl to Simpson Bay to help you find the cheapest flights, the best time to fly and much more.

What’s the cheapest day of the week to fly from Chicago O'Hare Airport to Simpson Bay?

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

For Chicago O'Hare Airport to Simpson Bay, Sunday is the cheapest day to fly on average and Saturday is the most expensive. Flying from Simpson Bay back to Chicago O'Hare Airport, the best deals are generally found on Monday, with Saturday being the most expensive.

What is the cheapest month to fly from Chicago O'Hare Intl Airport 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 O'Hare Intl Airport 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 O'Hare Intl Airport to Simpson Bay is September, where tickets cost $489 (return) on average. On the other hand, the most expensive months are March and June, where the average cost of round-trip tickets is $744 and $680 respectively.

How far in advance should I book a flight from Chicago O'Hare Intl Airport 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 O'Hare Intl Airport 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 O'Hare Intl Airport to Simpson Bay, you should book around 3 weeks before departure, which saves you about 38% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 8 weeks before departure.

Good to know

Low seasonAugust
Cheapest flight$74
Most popular time to fly with an average 2% increase in price.
Flight from Chicago O'Hare Airport to Simpson Bay

When to book flights from O'Hare Intl to Simpson Bay

Are your dates flexible? Find out the best times to travel from O'Hare Intl 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 Chicago O'Hare Airport to Simpson Bay flights

  • What is the cheapest flight from Chicago O'Hare Intl Airport to Simpson Bay?

    In the last 3 days, the lowest price for a flight from Chicago O'Hare Intl Airport to Simpson Bay was $74 for a one-way ticket and $220 for a round-trip.

  • Do I need a passport to fly between Chicago O'Hare Airport and Simpson Bay?

    Yes

  • Which airlines offer Wi-Fi service onboard planes from Chicago O'Hare Airport to Simpson Bay?

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

  • Which aircraft models fly most regularly from Chicago O'Hare Airport to Simpson Bay?

    The Boeing 737 MAX 8 is the aircraft model that flies most regularly on the Chicago O'Hare Airport to Simpson Bay flight route.

  • Which airline alliances offer flights from Chicago O'Hare Airport to Simpson Bay?

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

  • On which days can I fly direct from Chicago O'Hare Airport to Simpson Bay?

    You can catch a nonstop flight from Chicago O'Hare Airport to Simpson Bay 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 $595 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 $769 and an overall rating of 7.4.

  • How does KAYAK find such low prices on flights from Chicago O'Hare Airport 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 O'Hare Airport to Simpson Bay.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago O'Hare Airport 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 O'Hare Airport 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 O'Hare Airport 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 O'Hare Airport with another airline. Booking your flights between Chicago O'Hare Airport and SXM can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago O'Hare Airport 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 O'Hare Airport 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 O'Hare Intl Airport to Simpson Bay

  • Looking for a cheap flight? 25% of our users found flights on this route for $596 or less round-trip.

Prefer to fly direct from Chicago O'Hare Airport 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 O'Hare Intl to Simpson Bay Princess Juliana.
Find which airlines fly direct from Chicago O'Hare Intl Airport to Simpson Bay Princess Juliana Airport, which days they fly and book direct flights.

Direct departures

Chicago O'Hare Intl 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 O'Hare Intl

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 O'Hare Intl 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 O'Hare Intl 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 8128 reviews
7.9Comfort
7.8Entertainment
7.2Food
8.5Crew
8.1Boarding
Airline reviews

Timing, quality of service, promptness and courtesy of the staff

10.0 ExcellentAjai, Jan 2026
DFW - ATL
Read more Delta reviews

Timing, quality of service, promptness and courtesy of the staff

It was last minute due to weather - considering - it was amazing! Good smiles, friendly staff and they were making sure we knew what was going on when and where.

delta last minute gave me a boarding pass for a different flight with no confirmation that they were changing it

The flight was comfortable and uneventful, which is what I desire

The service from the flight attendants were of supreme quality. They greeted and treated everyone with a wide smile. This is totally absent nowadays. Kudos to them!!!!

Excellent flight and got us around tough weather. Only issue was seat TV did not work and crew tried to reboot.

Very large passenger too space from my own seat. Arm board couldn’t be lowered because of his size. It wads very uncomfortable trip, as the flight was full couldn’t move anywhere having back pain because of the position in which I was the entire flight.

was sitting in the jet bridge for 10 minutes in -20 degree weather waiting for my bag

Outdated equipment in disrepair, wifi inoperable. Broken seats, taped air vents, generally poor condition, the 717 showed its age and lack of upkeep.

My flight out of Baton Rouge to Atlanta was delayed by a half hour. This got us into Atlanta airport 30 minutes late. I ran through the airport to get to my connecting flight. As I approached the boarding gate, I saw the boarding door was still open and a passenger was being checked in. But when I got to the gate, the boarding agent told me they had already given away my seat and there were no empty seats on that flight. So I had to take a later flight. That has never happened to me before. Very frustrating.

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.

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.

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.

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.

Terrible. They canceled our early morning flight after midnight on the day of and had no available flights to rebook my family on for the next 72 hours. Yet they still had other flights that were not cancelled from JFK so it couldn’t be based on the weather. It felt like they canceled the flight based on it not being profitable enough for them. I am not interested in traveling with the again. The absolute worse customer service and lack of accountability.

Horribly rude check in at airport, worst in 25 years of flying. All over a simple issue they could have googled to resolve.

First time flying with JetBlue and never again. I went to the counter to request meet and assist because I'm 74 and my wife is 79. I walk with a cane and my wife is handicapped and has her own wheel chair. I told the agent that my wife and luggage was at the entrance door. The ticketing agent said to me that they don't offer meet and assist. I need to bring them our luggage and then go back and get my wife in order to get my boarding pass. As I went back to get my luggage a Southwest agent along with a TSA agent recognized the situation and came over and took my wife and luggage to the JetBlue ticketing counter alongside the line and told the JetBlue agent to issue to take our luggage as soon as they could.

Flight was fine, price was good but food onboard was abysmal. I was on there for breakfast and lunch and dinner 845am EST to 845pm GMT and all I got was a yoghurt parfait, fruit and a piece of cake. Later snacks included an ice-cream brownie and a pizza twist. I was hungry by the time I landed and the airport amenities were closed. Not happy.

1) No pilot available for 1 hour 2) no room for most passengers careyon in overhead—-> stowed below 3) when we landed we had to wait 45 min. Before docking at gate as gate was not ready

Good. No issues except a slight delay. Crew came in late.

Not a pleasant experience, service was poor. Didn't like it

It was good. I prefer JB over other airlines.I just wish we had headphones for the films, but other than that - good.

The ride share experience in JFK is terrible. After traveling on a flight, then you need to take a subway to the last stop to get an uber or lyft. Unacceptable. Bad job JetBlue for permitting JFK and Port Authority to do this to your passengers.

Checking In on JetBlue site was impossible. It hung up on REAL ID. Even my Global Entry did not help. Luckily, on Kayak site it was a breeze. Entire flight the temperature was COLD! Otherwise the crew was great!

I know it's a low-cost airline. However, the seats are very basic, so after two hours of travel, they feel very uncomfortable and cannot be reclined. The two flights from Bogota to Orlando and the return flight were very punctual. The check-in process on the app works very well. I really liked the self-check-in process for luggage at the Orlando airport; it was quick, easy, and very convenient.

The entire experience was so surprisingly pleasant. And the blocked extra seat between us was such an amazing and nice bonus. Great experience all around and I can’t wait to fly with spirit again!

Everything was OK, the deicing took a long time, our connections were almost missed.

All very good except they didn’t load our walker so haven’t gotten it yet

Flight was cancelled. But kayak thought it was still on time.

For the cost you can't e too critical, but the inablitiy to recline the seat and minimal cushioning in the seats made for a less than comfortable flight. Other than that we had an ealry departure and arrival, boarding was smooth.

The flight was delayed by 2 hours and we had no food or water or chargers

Spirit was on time. They maintained updates and information. The crew was friendly and professional. Because this is a budget friendly airline, they have dispensed with a lot of frills and part of that comes with a price, for example, the seats are not quite as comfortable as others. I am ok with a pay for beverage and snack service as I prefer my own anyway so this was not a concern. I thought overall, having a great flight crew and on time service was definitely worth losing some of the frills from other carriers.

Nothing everything cost money a bottle of water is 5 dollars and there wasn't even an outlet to plug 🔌 in my 📱 phone

You can’t beat Spirit’s prices on tickets, especially with the positive experience that comes with it! I appreciated the timeliness of Spirit airlines. The crew in the airport was very kind and wished you a good flight by name. The crew on the flight was attentive and friendly. Overall, I am very pleased with my experience with Spirit.

Everything you need to know for your flight from O'Hare Intl to Simpson Bay

Information on your arrival and departure airports