$139 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 12/24. 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

Fri, Dec 5 - Sun, Dec 7
Multiple Airlines Logo
8:42 pm - 12:00 pmMDW-AUA
13h 18m1 stop
Multiple Airlines Logo
4:40 pm - 9:52 amAUA-MDW
19h 12m2 stops
$416Multiple Airlines
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Tue, Feb 10 - Wed, Feb 18
Delta Logo
1:28 pm - 12:55 pmMDW-AUA
21h 27m2 stops
Delta Logo
4:25 pm - 12:35 pmAUA-MDW
22h 10m2 stops
$447Delta
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Tue, Feb 10 - Fri, Feb 13
Delta Logo
1:28 pm - 12:55 pmMDW-AUA
21h 27m2 stops
Delta Logo
4:25 pm - 12:35 pmAUA-MDW
22h 10m2 stops
$456Delta
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Sun, Jan 11 - Fri, Jan 16
Delta Logo
6:45 am - 3:20 pmMDW-AUA
6h 35m1 stop
Delta Logo
4:35 pm - 10:09 pmAUA-MDW
7h 34m1 stop
$477Delta
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Sat, Feb 14 - Tue, Feb 17
Delta Logo
4:30 pm - 12:30 pmMDW-AUA
18h 00m1 stop
Delta Logo
4:25 pm - 12:35 pmAUA-MDW
22h 10m2 stops
$481Delta
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Sat, Nov 15 - Sat, Nov 22
Southwest Logo
5:05 am - 2:55 pmMDW-AUA
7h 50m1 stop
Southwest Logo
3:55 pm - 11:20 pmAUA-MDW
9h 25m1 stop
$485Southwest
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Sat, Jan 3 - Sat, Jan 10
Frontier Logo
6:12 am - 11:20 amMDW-AUA
27h 08m1 stop
Frontier Logo
4:50 pm - 11:25 pmAUA-MDW
8h 35m1 stop
$506Frontier
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Sat, Jan 17 - Sat, Jan 24
Frontier Logo
6:00 am - 3:33 pmMDW-AUA
7h 33m1 stop
Frontier Logo
2:50 pm - 11:25 pmAUA-MDW
10h 35m1 stop
$507Frontier
Find Deal
Fri, Nov 14 - Fri, Nov 21
Southwest Logo
5:50 am - 3:00 pmMDW-AUA
7h 10m1 stop
Southwest Logo
4:00 pm - 8:55 amAUA-MDW
18h 55m2 stops
$536Southwest
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Thu, Jan 15 - Mon, Jan 19
WestJet Logo
9:50 am - 3:40 pmMDW-AUA
27h 50m3 stops
WestJet Logo
4:30 pm - 6:36 pmAUA-MDW
28h 06m2 stops
$696WestJet
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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.

Which airlines fly non-stop between Chicago Midway Airport and Aruba?

Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for round-trip flights from Chicago Midway Airport to Aruba.

There are 2 airlines that fly nonstop from Chicago Midway Airport to Aruba. They are Southwest and Delta. The cheapest airline for this route is Delta, with the best round-trip deal found costing $458 and arriving in Oranjestad (AUA). On average, Delta offers the best prices for nonstop flights between Chicago Midway Airport and Aruba.

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 Delta ($447) and Southwest ($485).

Good to know

Low seasonJuly
Cheapest flight$139
Best time to beat the crowds with an average 32% drop in price.
Most popular time to fly and prices are also 3% 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.

Reviews of the 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 4241 reviews
7.0Food
8.0Comfort
7.5Entertainment
8.6Crew
8.1Boarding
Airline reviews

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

8.0 ExcellentGreg, Oct 2025OAK - BUR
Read more Southwest reviews

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

Full cans of soda would be nice. A choice between two snacks would be appreciated.

Tried watching free movie and it kept freezing so I couldn’t finish.

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

Sacrament staff are always polite and helpful. Airport is easy to maneuver and boarding is straightforward.

Great flight. Outstanding Service. Southwest was able to put us on a direct flight to Denver when the connection could have been affected by a later arrival to Baltimore. The direct flight was less expensive that the flight with the connection in Baltimore.

Delays delays delays. Late taking off, late landing, wait for a gate, etc.

Boarded on time but once we were ready for take off, the crew determined that, although every seat was taken, somehow someone was on the wrong flight. Delay, delay delay, announcements and ended up with one person checking EVERY ID against their passenger Manifest only to figure out it was a "clerical error." We departed 54 minutes late causing me to run in the St. Louis Airport to make my connection and lose the priority boarding spot I had paid for. Unnecessary delay.

I was re-booked onto another flight because my original flight was delayed and I would have missed my connector. I ended up in the “C” group after paying extra to be in the “A “ group on the original flight. At least if you’re going to re-book people, re-book them into the same group.

Flight was delayed due to plane not passing inspection And one of the crew had to time out and we had to wait for another one A 3 hour delay

Staff were friendly and happy. Delta could make sure passengers that don't have the app know of changes. Without Kayak I would not have known about the change of gate or the delay. Kayak was faster to notify me.

They ended up paying for the bag twice, but the counter wouldn't take my baggage receipt. Left it to me to resolve. Not sure how to resolve the issue.

The customer service before board was very rude and when I expressed my concerns about making the connecting flight she laughed and told me I bought the wrong ticket. I explained once it showed the flight was delayed it no longer let me change seats or anything. I was trying to upgrade to make sure I would get to the next gate on time.

Non stop on long haul is the way to go. Great experience

The aircraft interior is old and tired on this aircraft. The entertainment system never worked despite the crews attempt to reset the system.

The flight used a B767 with a very old interior from before 2014. The entertainment system did not work at all during the flight despite attempts to reset the system. It was like they flew this route just to be competitive.

Old plane and old configuration/seats but still comfortable for a morning flight

They changed planes and the new plane couldn’t carry enough fuel to fly across the country so we had to stop in Kansas City to refuel. Flight was delayed .

Flight was too crowded and seats are too small, especially since passengrs are getting larger. Having a middle seat is ALWAYS tough! Woman on my left was large & kept creeping in to my space. Flight personnel were great! Have more savory rather than sweet snacks please.

Flight was crowded and the woman sitting on my left was large & kept crouching in to my space. You need bigger seats or smaller passengers to fit into the seats you DO have! Snack were OK. Would appreciate if airlines had more savory rather than sweet snacks, thank you!

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

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