SXM - ORD

$206 Find Cheap Flights from Simpson Bay to Chicago O'Hare Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Simpson Bay to O'Hare Intl departing on 9/29. 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 Chicago O'Hare Intl Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Simpson Bay to Chicago, 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 Simpson Bay to Chicago, as well as popular online travel agencies
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Cheap Flights from Simpson Bay to O'Hare Intl (SXM-ORD)

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

Mon, Sep 22 - Mon, Sep 29
Spirit Airlines Logo
3:05 pm - 10:48 pmSXM-ORD
8h 43m1 stop
Spirit Airlines Logo
5:05 am - 2:00 pmORD-SXM
7h 55m1 stop
$336Spirit Airlines
Find Deal
Mon, Sep 22 - Mon, Sep 29
Spirit Airlines Logo
3:05 pm - 10:18 amSXM-ORD
20h 13m2 stops
Spirit Airlines Logo
5:05 am - 2:00 pmORD-SXM
7h 55m1 stop
$456Spirit Airlines
Find Deal
Thu, Oct 9 - Wed, Oct 15
American Airlines Logo
2:40 pm - 11:53 pmSXM-ORD
10h 13m2 stops
American Airlines Logo
9:12 pm - 1:37 pmORD-SXM
15h 25m2 stops
$599American Airlines
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Thu, Oct 9 - Wed, Oct 15
American Airlines Logo
4:24 pm - 11:58 pmSXM-ORD
8h 34m1 stop
American Airlines Logo
9:12 pm - 1:37 pmORD-SXM
15h 25m2 stops
$600American Airlines
Find Deal
Thu, Oct 9 - Wed, Oct 15
American Airlines Logo
4:24 pm - 11:58 pmSXM-ORD
8h 34m1 stop
American Airlines Logo
1:51 pm - 1:37 pmORD-SXM
22h 46m1 stop
$608American Airlines
Find Deal
Thu, Oct 9 - Wed, Oct 15
American Airlines Logo
4:24 pm - 11:58 pmSXM-ORD
8h 34m1 stop
American Airlines Logo
1:51 pm - 1:37 pmORD-SXM
22h 46m1 stop
$609American Airlines
Find Deal
Mon, Sep 22 - Mon, Sep 29
American Airlines Logo
2:20 pm - 11:48 pmSXM-ORD
10h 28m2 stops
American Airlines Logo
10:05 pm - 1:19 pmORD-SXM
14h 14m2 stops
$612American Airlines
Find Deal
Thu, Oct 9 - Wed, Oct 15
American Airlines Logo
2:40 pm - 11:53 pmSXM-ORD
10h 13m2 stops
American Airlines Logo
8:44 pm - 1:37 pmORD-SXM
15h 53m2 stops
$613American Airlines
Find Deal
Booking Insights

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

Get data-powered insights and trends into flights from Simpson Bay to O'Hare Intl 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 Simpson Bay to Chicago O'Hare Airport?

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

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

Good to know

Cheapest flight$206
Flight from Simpson Bay to Chicago O'Hare Airport

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

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

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

    In the last 3 days, the lowest price for a flight from Simpson Bay to Chicago O'Hare Intl Airport was $206 for a one-way ticket and $336 for a round-trip.

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

    A passport is required to fly from Simpson Bay to Chicago O'Hare Airport.

  • Which airports will I be using when flying from Simpson Bay to Chicago O'Hare Airport?

    Simpson Bay airport is called Simpson Bay Princess Juliana and the only airport in Chicago O'Hare Airport is Chicago O'Hare Intl.

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

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

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

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

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

    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 Simpson Bay to Chicago O'Hare Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Simpson Bay to Chicago O'Hare Airport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago O'Hare Airport from Simpson Bay 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 Simpson Bay to Chicago O'Hare Airport?

    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 Chicago O'Hare Airport with an airline and back to Simpson Bay with another airline. Booking your flights between Simpson Bay and ORD 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 Simpson Bay to Chicago O'Hare Airport?

    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 Chicago O'Hare Airport from Simpson Bay 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 Simpson Bay to Chicago O'Hare Intl Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for $550 or less one-way.

Reviews of the top airline flying from Simpson Bay to O'Hare Intl

 
See real verified KAYAK customer reviews for airlines flying from Simpson Bay to Chicago. 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 Simpson Bay to O'Hare Intl? 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.
7.2
American AirlinesOverall score based on 10000 reviews
7.2Comfort
7.5Boarding
6.5Food
8.0Crew
6.9Entertainment
Airline reviews

Couldn’t get the door on the plane to close leading to a nearly 2 hour delay. But, hey at least they didn’t cancel the flight.

6.0 GoodMitchell, Jul 2025CMH - ORD
Read more American Airlines reviews

Couldn’t get the door on the plane to close leading to a nearly 2 hour delay. But, hey at least they didn’t cancel the flight.

Very clean and comfortable cabin. Amazing Mediterranean salad for lunch before landing. Great range of films to watch. Really quiet and easy to sleep on the flight also. The initial food was a bit weird: odd fried chicken pieces in some weird white gloop, but that would be my lack of cultural knowledge on the grub. Salad more than made up for it at the other end. Staff were super attentive and helpful. Great and easy flight

The flight was fine and the crew awesome. The problem is ORD and AA. Computers went down, ORD fell apart and a 40 min flight turned into a 3 hour trip. Guess the answer is to not try and fly to ORD after noon. But, as I said, crew was awesome and did everything they could to lesson the flight time.

The flight was fine but the 8 hour delay in Chicago was awful - 5 gate changes and repeated delays without an explanation. No vouchers. Nothing.

Most miserable flight ever. We waited almost 2 hours on the runway because the flight was oversold. American offered $1200 credit. Then there was some nonsense about weight distribution. Ridiculous. No food for 8 plus hours on the flight. I will be writing a letter.

The flight was 2 hour delayed, otherwise everything was excellent. The delay was due to the hourly limit requirement so given that as a reason, I'm happy with the flight!

Not sure the logic of the boarding in Groups. I was loaded first on the aisle. Then the guy in the middle. Then the guy by the window. Constantly holding up the other people boarding behind them with us blocking the aisle and this happened in most of the other rows

To start, I’d like to say that every American Airline personnel I interacted with on the ground, especially flight crew, was very friendly and did their best to help me out. Despite this, however, my experience with the airline was an entire mess. The 7:19 PM flight was heavily delayed due to weather, and pushed to 10:30 AM the next morning. Because of this, I had to spend the night inside of the airport. At some point later in the night, I got an email saying that the flight had been canceled. I called the support number, and the representative on the other line told me that the flight was still on and that I didn’t need to rebook. The next morning, no one came to the gate to open the door for the crew until almost 11 AM. By this time the flight crew had been waiting for over an hour, and they had called management to get someone to open the door for them multiple times. Around 11:30, the gate screen had changed to a different flight. I ended up buying a last minute ticket with Southwest airline just to get to Chicago, because the next flight with American wasn’t until 7:19 pm that day. Now, earlier that morning my suitcase had been sent ahead of me to ORD. I went to baggage claim to ask them if I could have my suitcase forwarded to where I was staying. The representative at SDF baggage claim said they could and put the claim in for me. As I was going back through TSA, I got an email that the airline had found my suitcase, but the next step was to send it BACK to SDF. I called the airline support number again, and I made it clear that my suitcase needed to stay in Chicago and to not come back to SDF. The representative told me that they would hold my suitcase at ORD and that it wasn’t going to be forwarded anywhere. Once I got there, I found that they had loaded my suitcase onto a plane to send it back to SDF. Thankfully, I had gotten to the baggage claim counter in time for them to put in a request to bring my suitcase back up. My refund with the airline is processing already, but because of this entire experience and miscommunication at every turn of the way, I will not book with American Airlines in the future.

The plane was late and then sat on the runway for almost 45 minutes before taking off.

Crew professional. Easy bag drop off. On time. Good entertainment.

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

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