$213 Find Cheap Flights from St. Maarten 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 to O'Hare Intl departing on 9/8. 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 for flights to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago, as well as popular online travel agencies
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Cheap Flights from St. Maarten to O'Hare Intl

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

Mon, Aug 25 - Tue, Aug 26
Spirit Airlines Logo
3:05 pm - 11:59 pmSXM-ORD
9h 54m1 stop
Spirit Airlines Logo
8:12 pm - 2:00 pmORD-SXM
16h 48m1 stop
$373Spirit Airlines
Find Deal
Sat, Aug 23 - Sat, Aug 30
Spirit Airlines Logo
3:05 pm - 11:59 pmSXM-ORD
9h 54m1 stop
Spirit Airlines Logo
5:05 am - 2:00 pmORD-SXM
7h 55m1 stop
$383Spirit Airlines
Find Deal
Mon, Aug 25 - Tue, Aug 26
 Logo
3:05 pm - 11:59 pmSXM-ORD
9h 54m1 stop
 Logo
10:27 am - 8:12 amORD-SXM
20h 45m2 stops
Fri, Aug 22 - Fri, Aug 29
Spirit Airlines Logo
3:05 pm - 11:59 pmSXM-ORD
9h 54m1 stop
Spirit Airlines Logo
5:05 am - 2:00 pmORD-SXM
7h 55m1 stop
$412Spirit Airlines
Find Deal
Mon, Aug 25 - Tue, Aug 26
Spirit Airlines Logo
3:05 pm - 4:10 pmSXM-ORD
26h 05m3 stops
Spirit Airlines Logo
8:12 pm - 2:00 pmORD-SXM
16h 48m1 stop
$416Spirit Airlines
Find Deal
Fri, Aug 22 - Fri, Aug 29
Spirit Airlines Logo
3:05 pm - 4:10 pmSXM-ORD
26h 05m3 stops
Spirit Airlines Logo
8:12 pm - 2:00 pmORD-SXM
16h 48m1 stop
$451Spirit Airlines
Find Deal
Thu, Oct 9 - Wed, Oct 15
American Airlines Logo
4:25 pm - 2:12 pmSXM-ORD
22h 47m1 stop
American Airlines Logo
7:05 pm - 3:10 pmORD-SXM
19h 05m1 stop
$611American Airlines
Find Deal
Thu, Oct 9 - Wed, Oct 15
American Airlines Logo
4:25 pm - 11:47 pmSXM-ORD
8h 22m1 stop
American Airlines Logo
1:51 pm - 1:34 pmORD-SXM
22h 43m1 stop
$612American Airlines
Find Deal
Thu, Oct 9 - Wed, Oct 15
American Airlines Logo
4:25 pm - 8:24 amSXM-ORD
16h 59m2 stops
American Airlines Logo
8:35 pm - 1:34 pmORD-SXM
15h 59m2 stops
$616American Airlines
Find Deal
Thu, Oct 9 - Wed, Oct 15
American Airlines Logo
4:25 pm - 7:25 amSXM-ORD
16h 00m2 stops
American Airlines Logo
8:35 pm - 1:34 pmORD-SXM
15h 59m2 stops
$617American Airlines
Find Deal
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KAYAK's insights & trends for flights to O'Hare Intl

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

How long is the flight to Chicago O'Hare Intl Airport?

The duration of your flight to Chicago depends on your departure and arrival airports. Obviously, any flights that include a layover will also be longer. The most popular route to Chicago on KAYAK is from Simpson Bay, which takes 9h 54m.

How many direct flights to Chicago O'Hare Intl Airport are there each day?

There are around 1,463 direct flights from within St. Maarten to Chicago O'Hare Intl Airport every day. Most flights depart in the morning, with 6:00 am the most common departure time and 49% of flights departing in the morning.


Good to know

Cheapest flight$213
Flight from Simpson Bay to Chicago O'Hare Airport

FAQs - booking Chicago O'Hare Airport flights

  • How far is Chicago O'Hare Intl Airport from central Chicago?

    There are 16 miles between Chicago city center and Chicago O'Hare Intl Airport.

  • How much is a flight to Chicago?

    On average, a flight to Chicago costs $740. The cheapest price found on KAYAK in the last 2 weeks cost $389 and departed from Simpson Bay Princess Juliana Airport.

  • What is the cheapest day to fly to Chicago?

    Based on KAYAK data, the cheapest day to fly to Chicago is Monday where round-trip tickets can be as cheap as $372. On the other hand, the most expensive day to fly is Sunday, where round-trip prices are $773 on average.

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

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket 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 is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights 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 with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight 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 up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to Chicago O'Hare Intl Airport?

    The cheapest time of day to fly to Chicago O'Hare Intl Airport is generally in the afternoon, when round-trip flights cost $735 on average. The most expensive time of day to fly to Chicago O'Hare Intl Airport is generally in the evening, which is peak travel time and where the average cost of a ticket is $754.

  • How many direct flights to Chicago O'Hare Intl Airport are there each week?

    Each week there are around 10,236 direct flights from within St. Maarten to Chicago O'Hare Intl Airport. The most common day for departures is Friday, with 15% of flights taking off on this day.

Top tips for finding cheap flights to Chicago O'Hare Airport

  • Looking for cheap airfare to Chicago O'Hare Airport? 25% of our users found round-trip tickets to Chicago O'Hare Airport for the following prices or less: From Simpson Bay $550
  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chicago O'Hare Airport flight deals.

Reviews of the top airline flying from St. Maarten to O'Hare Intl

 
See real verified KAYAK customer reviews for airlines flying to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline from St. Maarten to Chicago. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with 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
6.5Food
7.5Boarding
7.2Comfort
6.9Entertainment
8.0Crew
Airline reviews

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.

2.0 MediocreMitchell, Jun 2025CMH - ORD
Read more American Airlines reviews

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 was great. Boarding, early departure, early arrival, and deplaning were smooth. Smooth flight.

Per usual, flight status, staff courtesy and professionalism were excellent

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

Information on the airport you'll fly into in Chicago

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