SXM - CHI

$206 Find Cheap Flights from Simpson Bay to Chicago

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 Chicago 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

 
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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Flights Deals

Cheap Flights from Simpson Bay to Chicago (SXM-CHI)

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

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
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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
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Mon, Sep 22 - Mon, Sep 29
Delta Logo
3:20 pm - 12:28 pmSXM-MDW
22h 08m2 stops
Delta Logo
6:00 am - 1:50 pmMDW-SXM
6h 50m1 stop
$599Delta
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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
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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
1:51 pm - 1:37 pmORD-SXM
22h 46m1 stop
$608American 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
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
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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
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Mon, Sep 22 - Mon, Sep 29
Delta Logo
3:20 pm - 11:48 amSXM-MDW
21h 28m1 stop
Delta Logo
6:00 am - 1:50 pmMDW-SXM
6h 50m1 stop
$797Delta
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Booking Insights

KAYAK's insights & trends for Simpson Bay to Chicago flights

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

What is the cheapest Simpson Bay to Chicago flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Simpson Bay to Chicago.

Our data shows that the cheapest route for a return flight from Simpson Bay to Chicago cost $389 and was between Simpson Bay (SXM) and Chicago O'Hare Intl Airport (ORD). On average, the best prices are found if you fly this route. The average price for a return flight for this route is $389.

What’s the cheapest day of the week to fly from Simpson Bay to Chicago?

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

If your flying dates are flexible, you should consider flying to Chicago on a Monday, as we generally find the cheapest rates on that day for this route. On the other hand, Sunday is the most expensive day to fly from Simpson Bay to Chicago. For your return ticket, we recommend flying on a Tuesday and avoiding Saturdays for the best deals.

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Good to know

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

When to book flights from Simpson Bay to Chicago

Are your dates flexible? Find out the best times to travel from Simpson Bay to Chicago 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 Simpson Bay to Chicago

  • What is the cheapest flight from Simpson Bay to Chicago?

    In the last 3 days, the lowest price for a flight from Simpson Bay to Chicago 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?

    Yes, you'll most likely have to show a valid passport before boarding the plane in Simpson Bay and on arrival in Chicago.

  • Which airports will I be using when flying from Simpson Bay to Chicago?

    When flying out of Simpson Bay you will be using Simpson Bay Princess Juliana. You will be landing at one of these airports: Chicago Midway or Chicago O'Hare Intl.

  • Which aircraft models fly most regularly from Simpson Bay to Chicago?

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

  • Which airline alliances offer flights from Simpson Bay to Chicago?

    Star Alliance, SkyTeam, and oneworld are the airline alliances operating flights between Simpson Bay and Chicago, 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?

    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.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago 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?

    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 with an airline and back to Simpson Bay with another airline.

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

    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 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

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

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

Information on your arrival and departure airports

Simpson Bay (SXM)

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