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$159+ 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 1/28. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — AUA
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheap flight deals from Midway to Aruba

Cheapest flights from Midway to Aruba
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 December 18, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/17. 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 12/266:12 amMDW - AUA
1 stop27h 08mMultiple Airlines
Tue 12/304:40 pmAUA - MDW
2 stops31h 32mMultiple Airlines
Deal found 12/17$401
This Delta deal was found by Cheapflights users on 12/15. 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.
Tue 12/166:00 amMDW - AUA
1 stop7h 20mDelta
Wed 12/174:35 pmAUA - MDW
1 stop9h 12mDelta
Deal found 12/15$468
This Delta deal was found by Cheapflights users on 12/16. 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 12/229:29 amMDW - AUA
2 stops25h 01mDelta
Wed 12/244:35 pmAUA - MDW
1 stop7h 47mDelta
Deal found 12/16$472
This Delta deal was found by Cheapflights users on 12/16. 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 12/229:29 amMDW - AUA
2 stops25h 01mDelta
Sun 12/284:35 pmAUA - MDW
1 stop7h 47mDelta
Deal found 12/16$502
This Delta deal was found by Cheapflights users on 12/15. 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.
Thu 12/186:00 amMDW - AUA
1 stop7h 20mDelta
Sat 12/204:35 pmAUA - MDW
1 stop7h 47mDelta
Deal found 12/15$528
This Southwest deal was found by Cheapflights users on 12/15. 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 12/166:00 pmMDW - AUA
2 stops19h 00mSouthwest
Tue 12/234:45 pmAUA - MDW
2 stops9h 05mSouthwest
Deal found 12/15$532
This Delta deal was found by Cheapflights users on 12/15. 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.
Mon 12/156:40 pmMDW - AUA
2 stops18h 40mDelta
Fri 12/192:30 pmAUA - MDW
1 stop11h 17mDelta
Deal found 12/15$561
This Delta deal was found by Cheapflights users on 12/17. 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.
Thu 12/186:00 amMDW - AUA
1 stop7h 20mDelta
Thu 12/251:45 pmAUA - MDW
1 stop10h 37mDelta
Deal found 12/17$582
This Delta deal was found by Cheapflights users on 12/17. 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.
Thu 12/186:00 amMDW - AUA
1 stop7h 20mDelta
Sat 12/271:45 pmAUA - MDW
1 stop10h 37mDelta
Deal found 12/17$612
This Kiwi.com deal was found by Cheapflights users on 12/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/266:12 amMDW - AUA
1 stop27h 08mMultiple Airlines
Wed 12/314:15 pmAUA - MDW
1 stop25h 05mMultiple Airlines
Deal found 12/16$620

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 December 18, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$461
(Delta)

One-way from

$159
(Kiwi.com)

Popular in

March

Cheapest in

January

Average price

$785
Provider with most accurate pricing for Chicago (CHI)-Oranjestad Reina Beatrix flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Oranjestad Reina Beatrix flights.
Search Deals
From Chicago Midway to Aruba
Search Deals
One-way flight from Chicago Midway to Aruba
Search Deals
Highest demand for flights based on searches. 3% potential increase in price ($28 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 2,558,603 searches. Data last updated December 18, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Aruba that are best for you.

Fly from

Midway

Fly to

Aruba

Route

Depart

Return

Price

ChicagoOranjestad

MDW - AUA

MDWAUA

Chicago Midway

Tue 3/3

6:00 am-3:20 pm

1 stop7h 20m

Oranjestad Reina Beatrix

Tue 3/10

3:25 pm-10:29 pm

1 stop8h 04m

$468

ChicagoOranjestad

MDW - AUA

MDWAUA

Chicago Midway

Sun 4/26

6:00 am-2:18 pm

1 stop7h 18m

Oranjestad Reina Beatrix

Thu 4/30

1:25 pm-9:45 pm

1 stop9h 20m

$468

ChicagoOranjestad

MDW - AUA

MDWAUA

Chicago Midway

Mon 1/26

6:00 am-3:20 pm

1 stop7h 20m

Oranjestad Reina Beatrix

Thu 1/29

4:35 pm-10:22 pm

1 stop7h 47m

$468

ChicagoOranjestad

MDW - AUA

MDWAUA

Chicago Midway

Wed 1/14

6:45 am-3:20 pm

1 stop6h 35m

Oranjestad Reina Beatrix

Tue 1/20

2:10 pm-10:22 pm

1 stop10h 12m

$468

ChicagoOranjestad

MDW - AUA

MDWAUA

Chicago Midway

Tue 2/3

6:00 am-3:20 pm

1 stop7h 20m

Oranjestad Reina Beatrix

Wed 2/11

2:10 pm-10:22 pm

1 stop10h 12m

$468

ChicagoOranjestad

MDW - AUA

MDWAUA

Chicago Midway

Wed 1/21

5:00 am-2:25 pm

1 stop7h 25m

Oranjestad Reina Beatrix

Mon 1/26

3:20 pm-9:00 pm

1 stop7h 40m

$498

ChicagoOranjestad

MDW - AUA

MDWAUA

Chicago Midway

Mon 1/19

6:00 am-3:20 pm

1 stop7h 20m

Oranjestad Reina Beatrix

Mon 1/26

4:35 pm-10:22 pm

1 stop7h 47m

$498

ChicagoOranjestad

MDW - AUA

MDWAUA

Chicago Midway

Mon 2/2

4:10 pm-2:25 pm

2 stops20h 15m

Oranjestad Reina Beatrix

Tue 2/10

3:20 pm-9:00 pm

1 stop7h 40m

$532

ChicagoOranjestad

MDW - AUA

MDWAUA

Chicago Midway

Wed 1/7

6:45 am-3:20 pm

1 stop6h 35m

Oranjestad Reina Beatrix

Mon 1/12

2:10 pm-10:07 pm

1 stop9h 57m

$538

ChicagoOranjestad

MDW - AUA

MDWAUA

Chicago Midway

Sun 1/11

6:45 am-3:20 pm

1 stop6h 35m

Oranjestad Reina Beatrix

Sun 1/18

1:45 pm-10:07 pm

1 stop10h 22m

$538

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/15

Showing 1-10 of 19 results
1
2

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.
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
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 December 18, 2025.
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.
Southwest
7.9
Good
4,250 reviews

Entertainment

7.5

Food

7.0

Crew

8.6

Boarding

8.1

Overall

7.9

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
7.9
Good
4,250 reviews
Southwest
7.9
Good
4,250 reviews

Entertainment

7.5

Food

7.0

Crew

8.6

Boarding

8.1

Overall

7.9

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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.

  • How long is the flight from Chicago Midway Airport to Aruba?

    There are many flights that can get you from Chicago Midway Airport to Aruba in 7h 20m. Fly via Delta to get the fastest option. Chicago Midway Airport and Aruba are separated by a distance of 2286 mi.

  • Can I find deals for flights from Midway to Aruba that include hotel bookings?

    Yes. In addition to deals on Midway to Aruba flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Aruba?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Aruba.

  • Can I find deals for business class flights from Midway to Aruba?

    Yes. Cheapflights offers flight deals from Midway to Aruba by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

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Alternative routes for Midway to Aruba

See prices for flight routes from nearby airports that may be better suited for you.
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Midway to Castries flights
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Midway to Kingston flights
O'Hare Intl to Fort-de-France flights
O'Hare Intl to Castries flights
Midway to St. John's flights
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Midway to Santiago de los Caballeros flights

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 2,558,603 searches. Data last updated December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$595Average$825FlexibilityNo cancel feeOn-time63%

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