MDW - AUA

$277 Find Cheap Flights from Chicago Midway Airport to Oranjestad - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to Oranjestad departing on 11/1. 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, 0 bags

Save 20% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Everything you should know

Cheapest round-trip
$520
Southwest
Sun 11/15Wed 11/25
MDW - AUA • 2 stops
Cheapest one-way
$277
Southwest
Sun 11/1
MDW - AUA • 2 stops
Top airlines
Cheapest • from $520 (round-trip)
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Not available
There are currently no direct flights between Midway and Oranjestad. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $852 (round-trip)
Shortest trip • 7h 06m (one-way)
Insights
Insights
Insights
Insights
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Oranjestad!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Midway to Oranjestad (MDW-AUA)

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

Sun, Nov 15 - Wed, Nov 25
Southwest Logo
6:05 pm - 3:00 pm
MDW
-
AUA
18h 55m
2 stops
Southwest Logo
3:15 pm - 11:05 pm
AUA
-
MDW
9h 50m
1 stop
$520Southwest
Sun, Nov 15 - Wed, Nov 25
Southwest Logo
6:05 pm - 3:00 pm
MDW
-
AUA
18h 55m
2 stops
Southwest Logo
3:15 pm - 9:05 am
AUA
-
MDW
19h 50m
2 stops
$520Southwest
Sun, Oct 25 - Tue, Nov 3
Southwest Logo
5:10 am - 2:05 pm
MDW
-
AUA
7h 55m
1 stop
Southwest Logo
3:55 pm - 12:05 pm
AUA
-
MDW
22h 10m
2 stops
$572Southwest
Sun, Oct 25 - Tue, Nov 3
Southwest Logo
5:10 am - 2:05 pm
MDW
-
AUA
7h 55m
1 stop
Southwest Logo
3:55 pm - 9:10 pm
AUA
-
MDW
7h 15m
1 stop
$591Southwest
Fri, Oct 30 - Tue, Nov 3
Southwest Logo
6:25 pm - 1:55 pm
MDW
-
AUA
18h 30m
2 stops
Southwest Logo
3:55 pm - 5:40 am
AUA
-
MDW
15h 45m
2 stops
$592Southwest
Sun, Oct 25 - Tue, Nov 3
Southwest Logo
9:20 pm - 2:10 pm
MDW
-
AUA
15h 50m
2 stops
Southwest Logo
3:55 pm - 12:05 pm
AUA
-
MDW
22h 10m
2 stops
$592Southwest
Fri, Oct 30 - Wed, Nov 18
Southwest Logo
6:25 pm - 1:55 pm
MDW
-
AUA
18h 30m
2 stops
Southwest Logo
3:55 pm - 9:10 pm
AUA
-
MDW
7h 15m
1 stop
$594Southwest
Tue, Nov 3 - Tue, Nov 10
Southwest Logo
5:15 am - 3:00 pm
MDW
-
AUA
7h 45m
1 stop
Southwest Logo
3:55 pm - 5:40 am
AUA
-
MDW
15h 45m
2 stops
$596Southwest
Sat, Nov 7 - Thu, Nov 12
Delta Logo
6:04 am - 3:20 pm
MDW
-
AUA
7h 16m
1 stop
Delta Logo
4:35 pm - 10:56 pm
AUA
-
MDW
8h 21m
1 stop
$661Delta
Fri, Oct 23 - Tue, Nov 3
Delta Logo
5:15 pm - 12:00 pm
MDW
-
AUA
17h 45m
1 stop
Delta Logo
4:35 pm - 10:33 pm
AUA
-
MDW
7h 58m
1 stop
$661Delta
Booking Insights

KAYAK's insights & trends for Midway to Oranjestad flights

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

Which airlines provide the cheapest flights from Chicago Midway Airport to Oranjestad?

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 5 days.

In the past 5 days, the cheapest round-trip tickets from Chicago Midway Airport to Oranjestad were found on Southwest ($520) and Delta ($661).

Good to know

Cheapest flight

$277
Flight from Chicago Midway Airport to Oranjestad

When to book flights from Midway to Oranjestad

Are your dates flexible? Find out the best times to travel from Midway to Oranjestad 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 Chicago Midway Airport to Oranjestad flights

  • What is the cheapest flight from Chicago Midway Airport to Oranjestad?

    In the last 5 days, the lowest price for a flight from Chicago Midway Airport to Oranjestad was $277 for a one-way ticket and $520 for a round-trip.

  • Do I need a passport to fly between Chicago Midway Airport and Oranjestad?

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

  • Which airports will I be using when flying from Chicago Midway Airport to Oranjestad?

    Chicago Midway Airport and Oranjestad are both served by 1 main airport. You will leave Chicago Midway Airport from Chicago Midway and will be arriving at Oranjestad Reina Beatrix.

  • Which aircraft models fly most regularly from Chicago Midway Airport to Oranjestad?

    We unfortunately don’t have that data for this specific route.

  • How does KAYAK find such low prices on flights from Chicago Midway Airport to Oranjestad?

    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 Chicago Midway Airport to Oranjestad.

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

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

    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 Oranjestad with an airline and back to Chicago Midway Airport with another airline. Booking your flights between Chicago Midway Airport and AUA 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 Chicago Midway Airport to Oranjestad?

    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 Oranjestad from Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airline flying from Midway to Oranjestad

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Oranjestad. 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 Midway to Oranjestad? 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.
8.0
SouthwestOverall score based on 4229 reviews
8.1Boarding
7.0Food
8.0Comfort
7.5Entertainment
8.6Crew
Airline reviews

Boarding process of asking for volunteers to check bags goes against the system you had before with 2 bags checked free. This process is more of a guilt trip than a caring attitude toward the customer. In addition bag-size scrutiny has increased which also slows down the process of boarding. My wife said she will not fly on your airline again unless there is no other option.

10.0 ExcellentDenis, Aug 2026
MDW - ATL
Read more Southwest reviews

Boarding process of asking for volunteers to check bags goes against the system you had before with 2 bags checked free. This process is more of a guilt trip than a caring attitude toward the customer. In addition bag-size scrutiny has increased which also slows down the process of boarding. My wife said she will not fly on your airline again unless there is no other option.

Overall good, just screaming kids in the area the whole flight.

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

Everything you need to know for your flight from Midway to Oranjestad

Information on your arrival and departure airports