$318+ Cheap flights from Midway (MDW) to Aruba
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/28. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — AUA
Sep 18 — Sep 251
Round-trip
1 adult, Economy
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Find cheap flights from Midway to Aruba with Cheapflights
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Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Cheapest flights from Midway to ArubaExplore the most affordable flight options available from Midway to Aruba. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 19, 2026.
Explore the most affordable flight options available from Midway to Aruba. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 19, 2026.
This Southwest deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/175:20 am -
1 stop7h 40m
Tue 11/244:00 pm -
2 stops10h 15m
Deal found 8/18![Southwest logo]()
$578
This Southwest deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/156:05 pm -
2 stops18h 55m
Fri 11/204:00 pm -
2 stops15h 45m
Deal found 8/14![Southwest logo]()
$632
This Southwest deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/274:00 pm -
2 stops19h 40m
Thu 12/33:55 pm -
1 stop7h 20m
Deal found 8/18![Southwest logo]()
$635
This Southwest deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/15:20 am -
1 stop7h 40m
Wed 12/93:55 pm -
1 stop7h 20m
Deal found 8/17![Southwest logo]()
$657
This Delta deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/166:00 am -
1 stop7h 20m
Thu 11/264:35 pm -
1 stop8h 21m
Deal found 8/17![Delta logo]()
$661
This Delta deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/156:00 am -
1 stop7h 20m
Fri 11/204:35 pm -
1 stop8h 21m
Deal found 8/14![Delta logo]()
$671
This Delta deal was found by Cheapflights users on 8/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/235:09 pm -
1 stop17h 51m
Thu 10/292:10 pm -
2 stops27h 04m
Deal found 8/15![Delta logo]()
$676
Best flights from Midway to ArubaDiscover carefully curated flight deals from Midway to Aruba that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 19, 2026.
Discover carefully curated flight deals from Midway to Aruba that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 19, 2026.
This Southwest deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/156:05 pm -
2 stops18h 55m
Fri 11/204:00 pm -
2 stops15h 45m
Deal found 8/14![Southwest logo]()
$632
This Delta deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/156:00 am -
1 stop7h 20m
Fri 11/204:35 pm -
1 stop8h 21m
Deal found 8/14![Delta logo]()
$671
This Southwest deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/35:20 am -
1 stop7h 40m
Tue 11/103:55 pm -
1 stop7h 20m
Deal found 8/17![Southwest logo]()
$701
This Delta deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/96:00 am -
1 stop7h 20m
Sat 1/164:35 pm -
1 stop7h 35m
Deal found 8/18![Delta logo]()
$746
This Delta deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/65:09 pm -
2 stops18h 31m
Wed 10/211:55 pm -
2 stops22h 59m
Deal found 8/19![Delta logo]()
$796
This Delta deal was found by Cheapflights users on 8/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/239:29 am -
2 stops25h 31m
Fri 10/303:35 pm -
2 stops22h 12m
Deal found 8/15![Delta logo]()
$801
This Southwest deal was found by Cheapflights users on 8/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/315:00 am -
1 stop7h 25m
Fri 2/54:45 pm -
1 stop8h 10m
Deal found 8/15![Southwest logo]()
$896
This Southwest deal was found by Cheapflights users on 8/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/145:00 am -
1 stop8h 15m
Fri 9/183:15 pm -
1 stop8h 30m
Deal found 8/15![Southwest logo]()
$931
This Delta deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/285:25 pm -
1 stop17h 45m
Tue 1/56:00 pm -
2 stops16h 45m
Deal found 8/16![Delta logo]()
$926
This Southwest deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/48:25 pm -
2 stops16h 35m
Mon 1/113:20 pm -
2 stops16h 20m
Deal found 8/14![Southwest logo]()
$936
This Delta deal was found by Cheapflights users on 8/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected ” under the list of providers to see comparable flight deals.
Sat 1/236:00 am -
1 stop7h 20m
Sat 1/304:35 pm -
1 stop7h 35m
Deal found 8/15![Delta logo]()
$931
Last-minute flights from Midway to ArubaDiscover last-minute flight deals from Midway to Aruba. Data last updated August 19, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Aruba. Data last updated August 19, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/207:25 am -
1 stop6h 20m
Sun 2/284:45 pm -
1 stop9h 10m
Deal found 8/19![Southwest logo]()
$911
This Southwest deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/225:55 am -
1 stop7h 05m
Sat 8/292:55 pm -
1 stop7h 00m
Deal found 8/17![Southwest logo]()
$921
This Southwest deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/16:15 am -
1 stop7h 30m
Fri 9/43:45 pm -
1 stop8h 00m
Deal found 8/18![Southwest logo]()
$961
This Southwest deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/117:50 pm -
2 stops17h 10m
Fri 9/253:15 pm -
1 stop8h 30m
Deal found 8/18![Southwest logo]()
$936
This Mytrip deal was found by Cheapflights users on 8/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1111:45 am -
2 stops22h 00m
Wed 9/1611:50 am -
2 stops27h 45m
Deal found 8/15![Multiple Airlines logo]()
$943
This Southwest deal was found by Cheapflights users on 8/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/147:55 pm -
2 stops17h 20m
Fri 9/183:15 pm -
2 stops17h 20m
Deal found 8/15![Southwest logo]()
$796
This Southwest deal was found by Cheapflights users on 8/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/296:15 am -
1 stop7h 00m
Tue 10/63:05 pm -
1 stop7h 50m
Deal found 8/15![Southwest logo]()
$930
One-way flights from Midway to ArubaSearch for one-way flight options from Midway to Aruba. Find affordable one-way fares based on user searches. Data last updated August 19, 2026.
Search for one-way flight options from Midway to Aruba. Find affordable one-way fares based on user searches. Data last updated August 19, 2026.
This Southwest deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/288:15 pm -
2 stops17h 00m
Deal found 8/14![Southwest logo]()
$318
This Kiwi.com deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/712:03 pm -
3 stops50h 17m
Deal found 8/18![Multiple Airlines logo]()
$334
This Delta deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/316:00 am -
1 stop7h 20m
Deal found 8/16![Delta logo]()
$338
This Southwest deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/117:50 pm -
2 stops17h 10m
Deal found 8/17![Southwest logo]()
$384
This Kiwi.com deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1112:54 pm -
3 stops44h 21m
Deal found 8/17![Multiple Airlines logo]()
$393
This Southwest deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/287:50 pm -
2 stops17h 10m
Deal found 8/17![Southwest logo]()
$404
This Kiwi.com deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/96:00 am -
3 stops29h 07m
Deal found 8/18![Multiple Airlines logo]()
$412
This Kiwi.com deal was found by Cheapflights users on 8/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/216:04 am -
3 stops29h 10m
Deal found 8/15![Multiple Airlines logo]()
$430
This Kiwi.com deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2810:54 am -
3 stops50h 05m
Deal found 8/17![Multiple Airlines logo]()
$435
Find flight deals from Midway to Aruba
Keep the following information in mind while searching for Midway to Aruba flight deals. Data was last updated August 19, 2026.
Round-trip from | $578 (Southwest) |
|---|---|
One-way from | $318 (Southwest) |
Popular in | August |
Cheapest in | January |
Average price | $786 |
Cheapflights Fare Finder
Customize your flight search to find flights from Midway to Aruba that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated August 19, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Aruba that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoOranjestad
MDW Chicago Midway - AUA Oranjestad Reina Beatrix
MDWAUA
Chicago Midway
Sun 11/15
6:05 pm-3:00 pm
2 stops18h 55m
Oranjestad Reina Beatrix
Fri 11/20
4:00 pm-5:45 am
2 stops15h 45m
$632
ChicagoOranjestad
MDW Chicago Midway - AUA Oranjestad Reina Beatrix
MDWAUA
Chicago Midway
Sun 11/15
6:00 am-3:20 pm
1 stop7h 20m
Oranjestad Reina Beatrix
Fri 11/20
4:35 pm-10:56 pm
1 stop8h 21m
$671
ChicagoOranjestad
MDW Chicago Midway - AUA Oranjestad Reina Beatrix
MDWAUA
Chicago Midway
Tue 11/3
5:20 am-3:00 pm
1 stop7h 40m
Oranjestad Reina Beatrix
Tue 11/10
3:55 pm-9:15 pm
1 stop7h 20m
$701
Quickest round-trip
ChicagoOranjestad
MDW Chicago Midway - AUA Oranjestad Reina Beatrix
MDWAUA
Chicago Midway
Sat 1/9
6:00 am-3:20 pm
1 stop7h 20m
Oranjestad Reina Beatrix
Sat 1/16
4:35 pm-10:10 pm
1 stop7h 35m
$746
ChicagoOranjestad
MDW Chicago Midway - AUA Oranjestad Reina Beatrix
MDWAUA
Chicago Midway
Tue 10/6
5:09 pm-12:40 pm
2 stops18h 31m
Oranjestad Reina Beatrix
Wed 10/21
1:55 pm-11:54 am
2 stops22h 59m
$796
ChicagoOranjestad
MDW Chicago Midway - AUA Oranjestad Reina Beatrix
MDWAUA
Chicago Midway
Fri 10/23
9:29 am-12:00 pm
2 stops25h 31m
Oranjestad Reina Beatrix
Fri 10/30
3:35 pm-12:47 pm
2 stops22h 12m
$801
ChicagoOranjestad
MDW Chicago Midway - AUA Oranjestad Reina Beatrix
MDWAUA
Chicago Midway
Sun 1/31
5:00 am-2:25 pm
1 stop7h 25m
Oranjestad Reina Beatrix
Fri 2/5
4:45 pm-10:55 pm
1 stop8h 10m
$896
ChicagoOranjestad
MDW Chicago Midway - AUA Oranjestad Reina Beatrix
MDWAUA
Chicago Midway
Mon 12/28
5:25 pm-1:10 pm
1 stop17h 45m
Oranjestad Reina Beatrix
Tue 1/5
6:00 pm-8:45 am
2 stops16h 45m
$926
ChicagoOranjestad
MDW Chicago Midway - AUA Oranjestad Reina Beatrix
MDWAUA
Chicago Midway
Mon 9/14
5:00 am-2:15 pm
1 stop8h 15m
Oranjestad Reina Beatrix
Fri 9/18
3:15 pm-10:45 pm
1 stop8h 30m
$931
ChicagoOranjestad
MDW Chicago Midway - AUA Oranjestad Reina Beatrix
MDWAUA
Chicago Midway
Sat 1/23
6:00 am-3:20 pm
1 stop7h 20m
Oranjestad Reina Beatrix
Sat 1/30
4:35 pm-10:10 pm
1 stop7h 35m
$931
Showing 1-10 of 21 resultsSorted by cheapest first
Best time to book a flight from Midway to Aruba
Have a flexible travel schedule? Discover the best time to fly to Aruba from Midway with our price prediction graph.
MDW-AUA
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago Midway Airport to Aruba
MDW-AW0
MDW-AUA
No data available for this route at this time. Please check back soon.
Reviews of airlines servicing Aruba
Get insights into the airlines that provide service to Aruba. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Aruba. Reviews last updated August 19, 2026.
Read through reviews of airlines operating flights from Chicago Midway Airport to Aruba, such as Southwest. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Overall
8.0
Comfort
8.0
Crew
8.6
Entertainment
7.5
Food
7.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Boarding
8.1
Overall
8.0
Comfort
8.0
Crew
8.6
Entertainment
7.5
Food
7.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Related info for your journey
Find useful and relevant information for your journey from Midway to Aruba. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Midway and Aruba flights
Browse other Midway and Aruba flight options. Last updated on August 19, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top airline flying from Midway to Aruba
Discover the top airline that operate flights from Midway to Aruba. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated August 19, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$635 | Average$905 | FlexibilityNo cancel fee | On-time63% |