$537 Find Cheap Flights from St. Maarten to Chicago Midway 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 Midway departing on 11/28. 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 Midway 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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Flight Deals

Cheap Flights from St. Maarten to Midway

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

Thu, Nov 6 - Wed, Nov 12
Delta Logo
4:14 pm - 8:40 amSXM-MDW
18h 26m2 stops
Delta Logo
6:48 pm - 2:55 pmMDW-SXM
18h 07m2 stops
$600Delta
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Thu, Nov 6 - Wed, Nov 12
Multiple Airlines Logo
4:20 pm - 10:05 amSXM-MDW
19h 45m1 stop
Multiple Airlines Logo
4:15 pm - 3:21 pmMDW-SXM
21h 06m1 stop
$668Multiple Airlines
Find Deal
Fri, Mar 6 - Tue, Mar 10
Delta Logo
4:26 pm - 3:25 pmSXM-MDW
24h 59m2 stops
Delta Logo
9:30 am - 11:15 amMDW-SXM
24h 45m2 stops
$697Delta
Find Deal
Thu, Nov 6 - Wed, Nov 12
Multiple Airlines Logo
4:20 pm - 10:05 amSXM-MDW
19h 45m1 stop
Multiple Airlines Logo
11:00 am - 3:21 pmMDW-SXM
26h 21m1 stop
$698Multiple Airlines
Find Deal
Thu, Nov 6 - Wed, Nov 12
Multiple Airlines Logo
1:05 pm - 10:05 amSXM-MDW
23h 00m2 stops
Multiple Airlines Logo
9:41 am - 3:21 pmMDW-SXM
27h 40m3 stops
$759Multiple Airlines
Find Deal
Fri, Mar 6 - Tue, Mar 10
Delta Logo
1:45 pm - 9:46 pmSXM-MDW
10h 01m1 stop
Delta Logo
6:00 am - 1:53 pmMDW-SXM
6h 53m1 stop
$832Delta
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Sun, Oct 26 - Sun, Nov 2
Multiple Airlines Logo
3:20 pm - 10:05 amSXM-MDW
19h 45m1 stop
Multiple Airlines Logo
11:00 am - 10:50 amMDW-SXM
21h 50m2 stops
$944Multiple Airlines
Find Deal
Fri, Mar 6 - Tue, Mar 10
Delta Logo
1:45 pm - 9:46 pmSXM-MDW
10h 01m1 stop
Delta Logo
6:00 am - 1:53 pmMDW-SXM
6h 53m1 stop
$952Delta
Find Deal
Sat, Oct 11 - Fri, Oct 17
Delta Logo
3:14 pm - 10:14 pmSXM-MDW
8h 00m1 stop
Delta Logo
6:00 am - 1:49 pmMDW-SXM
6h 49m1 stop
$958Delta
Find Deal
Sun, Oct 26 - Sun, Nov 2
Delta Logo
3:14 pm - 10:14 pmSXM-MDW
8h 00m1 stop
Delta Logo
5:00 am - 1:49 pmMDW-SXM
6h 49m1 stop
$978Delta
Find Deal

Everything you should know

Cheapest round-trip
$600
Delta
Thu 11/6Wed 11/12
SXM - MDW • 2 stops
Cheapest one-way
$537
WestJet
Fri 11/28
SXM - MDW • 2 stops
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Midway!
Booking Insights

KAYAK's insights & trends for flights to Midway

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

How long is the flight to Chicago Midway 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 5h 54m.

How many direct flights to Chicago Midway Airport are there each day?

There are around 417 direct flights from within St. Maarten to Chicago Midway Airport every day. Most flights depart in the morning, with 6:00 am the most common departure time and 53% of flights departing in the morning.

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Good to know

Cheapest flight$537
Flight from Simpson Bay to Chicago Midway Airport

FAQs - booking Chicago Midway Airport flights

  • How far is Chicago Midway Airport from central Chicago?

    There are 9 miles between Chicago city center and Chicago Midway Airport.

  • How does KAYAK find such low prices on flights to Chicago Midway 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 Midway Airport.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway 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 Midway 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 Midway 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 Midway 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 Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • How many direct flights to Chicago Midway Airport are there each week?

    Each week there are around 2,914 direct flights from within St. Maarten to Chicago Midway Airport. The most common day for departures is Monday, with 16% of flights taking off on this day.

Top tips for finding cheap flights to Chicago Midway Airport

  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chicago Midway Airport flight deals.

Traveling to a place near Midway?

Book flights to Midway if you plan to visit one of these locations
Merrillville
Saint Joseph
Hammond
Portage
Valparaiso
Lansing
Munster
Chesterton
Schererville
Porter
Monticello
Saint John
Griffith

Everything you need to know for your flight to Midway

Information on the airport you'll fly into in Chicago

Chicago Midway Airport (MDW)

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