$282 Find Cheap Flights from Chicago Midway Airport to Aruba - 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 Aruba departing on 7/15. 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

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Flight Deals

Book Cheap Midway to Aruba Plane Tickets

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

Thu, Jul 16 - Wed, Jul 22
Southwest Logo
6:35 pm - 12:45 pm
MDW
-
AUA
17h 10m
2 stops
Southwest Logo
1:45 pm - 11:15 pm
AUA
-
MDW
10h 30m
2 stops
$634Southwest
Mon, Sep 21 - Fri, Sep 25
Southwest Logo
7:25 am - 2:45 pm
MDW
-
AUA
6h 20m
1 stop
Southwest Logo
3:45 pm - 7:35 am
AUA
-
MDW
16h 50m
2 stops
$638Southwest
Sat, Oct 24 - Wed, Oct 28
Southwest Logo
6:55 pm - 2:50 pm
MDW
-
AUA
18h 55m
2 stops
Southwest Logo
3:05 pm - 10:15 pm
AUA
-
MDW
8h 10m
1 stop
$648Southwest
Mon, Jul 13 - Thu, Jul 16
Southwest Logo
8:50 pm - 12:45 pm
MDW
-
AUA
14h 55m
2 stops
Southwest Logo
1:45 pm - 7:10 am
AUA
-
MDW
18h 25m
2 stops
$650Southwest
Sat, Aug 29 - Wed, Sep 2
Delta Logo
6:05 am - 2:10 pm
MDW
-
AUA
7h 05m
1 stop
Delta Logo
3:25 pm - 10:36 pm
AUA
-
MDW
8h 11m
1 stop
$661Delta
Thu, Jul 23 - Wed, Jul 29
Southwest Logo
8:50 pm - 2:45 pm
MDW
-
AUA
16h 55m
2 stops
Southwest Logo
1:45 pm - 8:10 pm
AUA
-
MDW
7h 25m
1 stop
$666Southwest
Mon, Jul 20 - Mon, Jul 27
Southwest Logo
5:10 am - 2:45 pm
MDW
-
AUA
8h 35m
1 stop
Southwest Logo
1:45 pm - 9:25 pm
AUA
-
MDW
8h 40m
1 stop
$675Southwest
Tue, Jul 14 - Sun, Jul 19
Southwest Logo
7:35 pm - 12:45 pm
MDW
-
AUA
16h 10m
2 stops
Southwest Logo
3:55 pm - 11:45 pm
AUA
-
MDW
8h 50m
1 stop
$680Southwest
Sun, Nov 15 - Wed, Nov 18
Southwest Logo
5:10 am - 3:00 pm
MDW
-
AUA
7h 50m
1 stop
Southwest Logo
3:55 pm - 9:10 pm
AUA
-
MDW
7h 15m
1 stop
$681Southwest
Sun, Sep 27 - Sun, Oct 4
Southwest Logo
8:45 pm - 2:45 pm
MDW
-
AUA
17h 00m
2 stops
Southwest Logo
3:50 pm - 12:10 am
AUA
-
MDW
9h 20m
2 stops
$685Southwest
Booking Insights

KAYAK's insights & trends for Midway to Aruba flights

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

How long does a flight from Chicago Midway Airport to Aruba take?

The duration of a flight to Aruba depends on your arrival airport. The shortest route to Aruba from Chicago Midway Airport is to Oranjestad, which takes 6h 20m.

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Good to know

Cheapest flight$282
Flight from Chicago Midway Airport to Oranjestad

FAQs - booking Aruba flights

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

    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 Aruba.

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

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

    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 from Chicago Midway Airport to Aruba 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 from Chicago Midway Airport to Aruba?

    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 from Chicago Midway Airport to Aruba 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 Aruba

 
Need help choosing which airline to fly with from Midway to Aruba? 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.
7.9
SouthwestOverall score based on 4242 reviews
8.0Comfort
8.1Boarding
8.6Crew
7.5Entertainment
7.0Food
Airline reviews

The flight was late. The crew was rude. There was no food. Cramped and uncomfortable. Nothing about this flight was good.

2.0 MediocreIrene, Jun 2026
DEN - SFO
Read more Southwest reviews

The flight was late. The crew was rude. There was no food. Cramped and uncomfortable. Nothing about this flight was good.

Crew was rude, flight was late, wifi didn't work, no food, basically nothing about this flight was good.

It was just okay, no frills, basic transportation with no luxury. No screens on the seats, no water or drinks on a short flight. Full flight but at least it was on time.

Flight was constantly delayed with significant changes in time, it was supposed to get to Colorado Springs at 8:30 PM but it got there after midnight.

Over a 3 hour flight. The turbulence was almost imperceptible except for 2 short periods which were not bad and over quickly. The attendants claimed "Safety first" and sat looking at their phones for 3 hours with no drink or snack service. This isn't the first time with Southwest. I thinkit may be there new plan of operation. Oh, and it was June 18, Southwest's Birthday which offered free drinks. NOT.

Flight was delayed, full flight and I had to change gates. Southwest flights are always late later in the day.

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

It was great. The gate staff were very helpful in Portland when my son forgot his rolling bag and had to go back to get it just in time to make it on the plane. We really appreciate that. Great job!

Airline is not very senior friendly. Flights are late, forcing us to run to the connecting flight. Food is awful. Wish they would go back to pretzels and peanuts. During flight, pressurization isn’t quite right and all of our ears get plugged. Everything is nickel and dime, charging for boarding, seat selection and legroom. While a screen at the desk in the gate area says check your roll on bag now for free due to space limitation, the employee at the desk will not check the bag without a $100 fee. Insane.

Kayak could’ve posted the correct gate number. Almost missed my flight.

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

Information on your arrival and departure airports

Chicago Midway Airport (MDW)