$303 Find Cheap Flights from St. Maarten to Chicago Midway Airport - Compare and Save

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Cheap Flights from St. Maarten to Midway

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from St. Maarten to Midway

Thu, Dec 17 - Wed, Dec 23
Delta Logo
4:05 pm - 10:54 pmSXM  Simpson Bay Princess Juliana-MDW Chicago Midway
8h 49m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:00 am - 2:49 pmMDW  Chicago Midway-SXM Simpson Bay Princess Juliana
6h 49m1 stop Atlanta Hartsfield-Jackson
$626Delta
Thu, Dec 17 - Wed, Dec 23
Delta Logo
4:05 pm - 10:54 pmSXM  Simpson Bay Princess Juliana-MDW Chicago Midway
8h 49m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:00 am - 2:49 pmMDW  Chicago Midway-SXM Simpson Bay Princess Juliana
6h 49m1 stop Atlanta Hartsfield-Jackson
$646Delta
Thu, Dec 17 - Wed, Dec 23
Southwest Logo
3:15 pm - 11:00 pmSXM  Simpson Bay Princess Juliana-MDW Chicago Midway
9h 45m1 stop Orlando
Southwest Logo
3:15 pm - 2:15 pmMDW  Chicago Midway-SXM Simpson Bay Princess Juliana
21h 00m2 stops Denver Intl Orlando
$692Southwest
Sun, Nov 29 - Wed, Dec 2
Southwest Logo
3:15 pm - 8:40 amSXM  Simpson Bay Princess Juliana-MDW Chicago Midway
19h 25m2 stops Orlando Baltimore/Washington
Southwest Logo
4:10 pm - 2:15 pmMDW  Chicago Midway-SXM Simpson Bay Princess Juliana
20h 05m2 stops Las Vegas Harry Reid Intl Orlando
$852Southwest
Sun, Nov 29 - Thu, Dec 3
Southwest Logo
3:15 pm - 8:40 amSXM  Simpson Bay Princess Juliana-MDW Chicago Midway
19h 25m2 stops Orlando Baltimore/Washington
Southwest Logo
8:50 pm - 2:15 pmMDW  Chicago Midway-SXM Simpson Bay Princess Juliana
15h 25m2 stops Phoenix Sky Harbor Intl Orlando
$861Southwest
Sun, Nov 29 - Wed, Dec 2
Southwest Logo
3:15 pm - 8:40 amSXM  Simpson Bay Princess Juliana-MDW Chicago Midway
19h 25m2 stops Orlando Baltimore/Washington
Southwest Logo
5:20 am - 2:15 pmMDW  Chicago Midway-SXM Simpson Bay Princess Juliana
6h 55m1 stop Orlando
$865Southwest
Sun, Nov 29 - Wed, Dec 2
Southwest Logo
4:40 pm - 12:05 amSXM  Simpson Bay Princess Juliana-MDW Chicago Midway
9h 25m1 stop Baltimore/Washington
Southwest Logo
4:10 pm - 2:15 pmMDW  Chicago Midway-SXM Simpson Bay Princess Juliana
20h 05m2 stops Las Vegas Harry Reid Intl Orlando
$872Southwest
Sun, Nov 29 - Wed, Dec 2
Southwest Logo
3:15 pm - 8:40 amSXM  Simpson Bay Princess Juliana-MDW Chicago Midway
19h 25m2 stops Orlando Baltimore/Washington
Southwest Logo
5:20 am - 2:15 pmMDW  Chicago Midway-SXM Simpson Bay Princess Juliana
6h 55m1 stop Orlando
$908Southwest
Sun, Nov 29 - Wed, Dec 2
Southwest Logo
4:40 pm - 12:05 amSXM  Simpson Bay Princess Juliana-MDW Chicago Midway
9h 25m1 stop Baltimore/Washington
Southwest Logo
5:20 am - 2:15 pmMDW  Chicago Midway-SXM Simpson Bay Princess Juliana
6h 55m1 stop Orlando
$923Southwest
Sun, Nov 29 - Wed, Dec 2
Southwest Logo
3:15 pm - 12:40 amSXM  Simpson Bay Princess Juliana-MDW Chicago Midway
11h 25m1 stop Orlando
Southwest Logo
5:20 am - 2:15 pmMDW  Chicago Midway-SXM Simpson Bay Princess Juliana
6h 55m1 stop Orlando
$938Southwest
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 6h 01m.

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

There are around 229 direct flights from within St. Maarten to Chicago Midway Airport every day. Most flights depart in the morning, with 41% of flights departing in the morning.

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 1,597 direct flights from within St. Maarten to Chicago Midway Airport. The most common day for departures is Sunday, with 17% 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
Hammond
Saint Joseph
Portage
Lansing
Valparaiso
Chesterton
Munster
Schererville
Porter
Monticello
Saint John
Griffith

More options for your flight to Midway