$183 Find Cheap Flights from Chicago Midway Airport to Aruba

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 8/16. 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.
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Best Aruba Flight Deals from Midway

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Oranjestad
Oranjestad1 stop$429
Oranjestad
Oranjestad1 stop$429

Cheap Flight Deals from Midway to Aruba (MDW-AW0)

 
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.

Recent round-trip flight deals from Midway to Aruba

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Midway to Aruba.
Discover the best prices for you by selecting your travel dates on KAYAK.
Frontier Logo
6:20 am - 2:39 pmMDW-AUA
7h 19m1 stop
Frontier Logo
3:45 pm - 10:35 pmAUA-MDW
7h 50m1 stop
$429Frontier
Find Deal
Sat, Jul 26 - Sat, Aug 2
Frontier Logo
6:20 am - 2:29 pmMDW-AUA
7h 09m1 stop
Frontier Logo
3:35 pm - 10:28 pmAUA-MDW
7h 53m1 stop
$435Frontier
Find Deal
Sat, Jun 14 - Sat, Jun 21
 Logo
2:45 pm - 4:34 pmMDW-AUA
24h 49m2 stops
 Logo
6:35 pm - 4:37 pmAUA-MDW
24h 02m2 stops
Fri, Oct 24 - Sun, Nov 2
 Logo
2:45 pm - 4:34 pmMDW-AUA
24h 49m2 stops
 Logo
6:35 pm - 4:37 pmAUA-MDW
24h 02m3 stops
Fri, Oct 24 - Sun, Nov 2
Delta Logo
6:00 am - 2:10 pmMDW-AUA
7h 10m1 stop
Delta Logo
3:25 pm - 9:27 pmAUA-MDW
7h 02m1 stop
$585Delta
Find Deal
Tue, May 27 - Tue, Jun 3
Delta Logo
6:00 am - 2:10 pmMDW-AUA
7h 10m1 stop
Delta Logo
3:25 pm - 9:45 pmAUA-MDW
7h 20m1 stop
$610Delta
Find Deal
Fri, May 30 - Wed, Jun 11
Southwest Logo
8:00 pm - 2:45 pmMDW-AUA
17h 45m2 stops
Southwest Logo
1:30 pm - 11:45 pmAUA-MDW
11h 15m1 stop
$615Southwest
Find Deal
Thu, Jun 19 - Wed, Jun 25
Southwest Logo
5:50 am - 1:35 pmMDW-AUA
6h 45m1 stop
Southwest Logo
3:40 pm - 11:40 pmAUA-MDW
9h 00m1 stop
$620Southwest
Find Deal
Mon, May 26 - Fri, Jun 6
LATAM Airlines Logo
4:22 pm - 5:45 pmMDW-AUA
24h 23m2 stops
LATAM Airlines Logo
6:50 pm - 11:53 amAUA-MDW
18h 03m2 stops
$2,337LATAM Airlines
Find Deal
Wed, Jul 30 - Mon, Aug 4
LATAM Airlines Logo
6:47 pm - 5:40 pmMDW-AUA
21h 53m2 stops
LATAM Airlines Logo
6:50 pm - 9:41 amAUA-MDW
15h 51m2 stops
$2,353LATAM Airlines
Find Deal
Fri, Aug 1 - Wed, Aug 6
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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.

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

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 72 hours.

In the past 3 days, the cheapest round-trip tickets from Chicago Midway Airport to Aruba were found on Frontier ($429) and Delta ($585).


Good to know

Low seasonFebruary
High seasonNovember
Cheapest flight$183
Best time to beat the crowds with an average 23% drop in price.
Most popular time to fly and prices are also 0% lower on average.
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.

  • What is the cheapest time of day to fly to Aruba?

    The cheapest time of day to fly to Aruba is generally in the morning, when round-trip flights cost $808 on average. The most expensive time of day to fly to Aruba is generally in the morning, which is peak travel time and where the average cost of a ticket is $808.

Top airlines 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.
8.0
SouthwestOverall score based on 4294 reviews
7.6Entertainment
8.0Comfort
8.2Boarding
8.6Crew
7.1Food
Airline reviews

It is southwest seat was ok. Not the most comfortable seat

8.0 ExcellentJohn, Apr 2025PVD - FLL
Read more Southwest reviews

It is southwest seat was ok. Not the most comfortable seat

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

Plz don't take away free bags and free seating

The seats were a bit cramped and worn, but otherwise okay.

I would have liked to arrive on time - not 5 hours late!

After a 3 hour layover in Denver my flight was delayed over 5 hours! No explanation; no assistance; no offer to provide compensation; no one at Southwest was willing to offer any assistance. 8 hours in the Denver airport - ridiculous!

It was a perfect flight in all aspects! Both legs!

Only one drink pass through the cabin for a 4 hour flight. Quite rough and bumpy landing.

Boarding process, crew were good. But the seats were so uncomfortable that was all I could focus on. I literally had to sit forward so that all 3 of us could fit in row. I will try to avoid Southwest in the future for any flights over 60 minutes.

Our bag was lost so that made unnecessary chaos On our trip

Delta is my preferred airline. I've traveled with them for years. On time in most cases, good communication, easy to use app. Most planes are pretty nice. I was on a CRJ 700/900 however, which was pretty badly aged inside and needed a refresh. No infotainment, unreliable wifi, best to download before boarding or bring a book. Food choices are really just snacks on this flight, nice variety but about what you'd expect. Great staff and prompt in departure and early arrival too. Overall quite satisfied.

Crew was friendly Love the entertainment in the seat head rest.

Delta flight was on time, seats were comfortable, and crew was nice.

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

Delayed take-off. Very small plane so very scary with lots of bumps during the flight. Would never fly Delta on short flights in small 80 seaters plane again! Felt relieved when landed.

The worst part was I was NOT allowed in the lounge even though I was holding a first class ticket and have a premium American Express card. I have flown Business or First Class with many airlines. Delta is the ONLY one who does not extend this courtesy to anyone except people who hold the very expensive American Express card. As a result, I won’t fly Delta if I have any other choice.

It was an overnight flight and I desperately needed coffee before we landed, but Delta does only one beverage service, and that is shortly after takeoff, not before landing at 5 am.

A little bumpy ride . No food was being provided due the the turbulence. That was ok it was a short flight to my standards.

Simply outstanding. Their new lounge for Delta One customers is a cut above the rest.

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

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