ORD - SXM

$140 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 10/9. 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

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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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

Sat, Nov 1 - Wed, Nov 5
Spirit Airlines Logo
5:05 am - 2:00 pmORD-SXM
7h 55m1 stop
Spirit Airlines Logo
4:28 pm - 11:42 pmSXM-ORD
9h 14m1 stop
$337Spirit Airlines
Find Deal
Fri, Oct 3 - Fri, Oct 10
Spirit Airlines Logo
5:05 am - 2:00 pmORD-SXM
7h 55m1 stop
Spirit Airlines Logo
3:05 pm - 11:45 pmSXM-ORD
9h 40m1 stop
$342Spirit Airlines
Find Deal
Sat, Nov 8 - Sat, Nov 15
Spirit Airlines Logo
5:05 am - 3:10 pmORD-SXM
8h 05m1 stop
Spirit Airlines Logo
4:28 pm - 11:42 pmSXM-ORD
9h 14m1 stop
$347Spirit Airlines
Find Deal
Thu, Dec 4 - Wed, Dec 10
Multiple Airlines Logo
2:00 pm - 4:00 pmORD-SXM
24h 00m1 stop
Multiple Airlines Logo
4:28 pm - 11:42 pmSXM-ORD
9h 14m1 stop
$373Multiple Airlines
Find Deal
Sat, Jan 24 - Sat, Jan 31
Frontier Logo
5:05 am - 3:20 pmORD-SXM
8h 15m1 stop
Frontier Logo
4:30 pm - 11:35 pmSXM-ORD
9h 05m1 stop
$375Frontier
Find Deal
Wed, Oct 29 - Wed, Nov 5
Multiple Airlines Logo
1:59 pm - 3:00 pmORD-SXM
48h 01m2 stops
Multiple Airlines Logo
4:28 pm - 11:42 pmSXM-ORD
9h 14m1 stop
$383Multiple Airlines
Find Deal
Fri, Dec 12 - Mon, Dec 15
Air Canada Logo
6:28 pm - 2:40 pmORD-SXM
18h 12m2 stops
Air Canada Logo
5:00 pm - 10:00 amSXM-ORD
19h 00m1 stop
$443Air Canada
Find Deal
Sat, Nov 29 - Sat, Dec 6
Air Canada Logo
6:05 pm - 4:00 pmORD-SXM
43h 55m2 stops
Air Canada Logo
3:40 pm - 11:18 amSXM-ORD
21h 38m1 stop
$451Air Canada
Find Deal
Sat, Jan 17 - Sat, Jan 24
Frontier Logo
5:05 am - 3:20 pmORD-SXM
8h 15m1 stop
Frontier Logo
4:30 pm - 11:35 pmSXM-ORD
9h 05m1 stop
$455Frontier
Find Deal
Mon, Oct 6 - Wed, Oct 15
American Airlines Logo
7:05 pm - 1:37 pmORD-SXM
17h 32m1 stop
American Airlines Logo
2:40 pm - 11:58 pmSXM-ORD
10h 18m1 stop
$493American Airlines
Find Deal

Everything you should know

Top airlines
Spirit Airlines
Cheapest • from $337 (round-trip)
Delta
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to book
2 weeks
in advance
Our data shows that travelers who book at least 2 weeks in advance save around 16% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
August
Cheapest • 19% 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
Cheapest round-trip
$337
Overall average: $654
Spirit Airlines
Sat 11/1Wed 11/5
ORD - SXM • 1 stop
Cheapest non-stop
$619
United Airlines
Sun 10/26Sat 11/1
ORD - SXM • Non-stop
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!
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, Tuesday 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 August, where tickets cost $585 (return) on average. On the other hand, the most expensive months are December and March, where the average cost of round-trip tickets is $974 and $899 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 2 weeks before departure, which saves you about 16% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 6 weeks before departure.

Good to know

Low seasonAugust
Cheapest flight$140
Best time to beat the crowds with an average 20% 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 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 $140 for a one-way ticket and $337 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?

    Only American Airlines offers 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 737-700 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?

    Star Alliance, oneworld, and SkyTeam are the airline alliances operating flights between Chicago O'Hare Airport and Simpson Bay, with Star Alliance 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 $806 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 $908 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 $368 or less one-way and $642 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

United Airlines

United Airlines

Sunday

United Airlines

United Airlines

See more direct flights

Direct returns

Simpson Bay Princess Juliana to Chicago O'Hare Intl

Saturday

United Airlines

United Airlines

Sunday

United Airlines

United Airlines

See more direct flights

Reviews of the top 4 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 7954 reviews
7.9Entertainment
8.2Boarding
7.9Comfort
8.5Crew
7.3Food
Airline reviews

Perfect flight both ways. On time, courteous staff, plane comfortable and cool. Best domestic flights I’ve had in awhile.

10.0 ExcellentAnonymous, Sep 2025CLT - BOS
Read more Delta reviews

Perfect flight both ways. On time, courteous staff, plane comfortable and cool. Best domestic flights I’ve had in awhile.

The food was terrible especially for a 15 hour international flight. The crew was unpleasant as well.

Really low quality food especially for an international flight. The crew also was surprisingly unpleasant except couple of ladies. I know we were not in first class but that’s no reason to treat customers as less.

Flight delayed for two and half hours and then canceled altogether due to mechanical issues. No mechanic onsite to fix so had to send one from LAX.

Quick check in. Everything went smooth. I don't know what can be done about airline food.

Crew was good. The reservation got mixed up and they didn't have my TSA number. I am also a Silver Medallion and wasn't able to use Sky Priority.

Delta made it easy, comfortable and timely. The crew was fantastic.

This route with Delta always has delays or is cancelled. Aircrafts seem smaller and older. I fly Delta quite a bit - haven’t had issues with the international flights. But this route has always been the troublesome one

Nothing special. The crew never went out of their way for anything.

Three seats in first class were broken and while they were able to still acommodate us it was looking very touch and go and they had others they could not acommodate

Once we got in the air the pilot made up some of the time of the delay. So that was really nice.

We had a layover from YVR to Denver. We bought 4 bottles of Absolut Vodka at the YVR Duty Free for $116.20, after going through security and American Customs Pre Clearance at YVR, Vancouver. When we landed in Denver, United put us behind the American Customs as well as TSA again for some reason. We were forced to go through American Customs and TSA again. TSA confiscated our rightfully owned Duty Free Absolut Vodka bottles. Because United incorrectly forced our flight behind American border and TSA again, we missed the connecting flight. After United put us on a later flight, we eventually arrived in Chicago very late, with hardly any sleep. I am looking for compensation from United for our incorrectly confiscated Absolut Vodka bottles worth $116.20, as well as compensation for incorrectly putting us behind American Customs and TSA again, causing us to miss our connecting flight, making us arrive extremely late in Chicago.

Excellent flight. Boarding was efficient and departure was on time. Smooth flight with on time arrival. Deplaning was also efficient.

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

The boarding of took of late.The presentation of the food was horrable as was the tast of the food was cold and tastless.

Delay and keep changing gates. I have to run around from B to C then to E.

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

This particular flight wasn't very full at the back, so there were three seats available for spreading out and getting relatively comfortable

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

Everything was fine. I'm average height and I pack light. I'm ready for my Spirit flight.

Changing the flight time to 6:15 am on the return flight is extremely inconvenient. The flight was okay. It was on time. The crew was friendly. The seats were uncomfortable. All the upsells are annoying, and I would prefer paying a single higher fee and not have to purchase so much extra.

Spirit Airlines was ok but TRAVELHELPDESK, the 3rd party travel agent IS A JOKE! VERY RUDE CUSTOMER AGENTS ont he phone. NO HELP AT ALL. But the airlines was ok.

No Tumberlence smooth flight. Try to change the menu on Snacks.

Cancelled my flight last minute and did not help me rebook. It was a horrible experience.

No frills - because you get what you pay for. The crew was amazing!! I had plenty of room to spread out because the flight was half full. Which made it easy to sleep.

The terminal crew is so rude cabin crew is extremely rude flight is very good

Spirit is low fare air line. Food also cost you. No free food.

The flight was delayed twice with minimal explanation. The terminal and airplane were filthy. The food voucher didn’t even cover a tiny pizza from a kiosk in the terminal. All in all, a pretty miserable experience for a flight to attend a funeral

I will use spirit more New clean aircraft Excellent crew ! Quick boarding process !

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

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