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$281+ 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 2/22. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — AUA
Dec 3 — Dec 101
Wed 12/3
Wed 12/10
1 adult, Economy
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Cheap flight deals from Midway to Aruba

Keep the following information in mind while searching for Midway to Aruba flight deals. Data was last updated November 3, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$417
(Booking.com)

One-way from

$281
(Kiwi.com)

Popular in

December

Cheapest in

August

Average price

$688
Provider with most accurate pricing for Chicago (CHI)-Oranjestad Reina Beatrix flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Oranjestad Reina Beatrix flights.
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From Chicago Midway to Aruba
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One-way flight from Chicago Midway to Aruba
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Highest demand for flights based on searches. 6% potential increase in price ($48 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($22 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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Find 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 November 3, 2025.

This Delta deal was found by Cheapflights users on 11/2. 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 12/156:00 amMDW - AUA
1 stop7h 20mDelta
Fri 12/194:35 pmAUA - MDW
1 stop9h 12mDelta
Deal found 11/2$495
This Southwest deal was found by Cheapflights users on 11/1. 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
Thu 12/184:00 pmAUA - MDW
1 stop9h 00mSouthwest
Deal found 11/1$563
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 12/211:00 amMDW - AUA
1 stop29h 45mMultiple Airlines
Fri 12/1212:05 pmAUA - MDW
2 stops36h 25mMultiple Airlines
Deal found 11/1$564
This Kiwi.com deal was found by Cheapflights users on 11/1. 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.
Thu 12/47:23 pmMDW - AUA
2 stops42h 12mMultiple Airlines
Wed 12/107:35 pmAUA - MDW
1 stop16h 30mMultiple Airlines
Deal found 11/1$566
This Delta deal was found by Cheapflights users on 11/2. 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
Tue 12/234:35 pmAUA - MDW
1 stop7h 47mDelta
Deal found 11/2$582
This Delta deal was found by Cheapflights users on 11/1. 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 11/221:26 pmMDW - AUA
2 stops22h 29mDelta
Tue 12/23:10 pmAUA - MDW
2 stops28h 50mDelta
Deal found 11/1$588
This Southwest deal was found by Cheapflights users on 11/2. 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.
Wed 12/175:05 amMDW - AUA
1 stop7h 55mSouthwest
Mon 12/2212:30 pmAUA - MDW
1 stop10h 25mSouthwest
Deal found 11/2$591
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 12/198:15 amMDW - AUA
1 stop25h 05mMultiple Airlines
Wed 12/317:35 pmAUA - MDW
2 stops17h 31mMultiple Airlines
Deal found 11/1$611
This Southwest deal was found by Cheapflights users on 11/2. 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 12/145:50 amMDW - AUA
1 stop7h 10mSouthwest
Thu 12/184:00 pmAUA - MDW
1 stop9h 00mSouthwest
Deal found 11/2$616
This Delta deal was found by Cheapflights users on 11/2. 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 11/76:00 amMDW - AUA
1 stop7h 20mDelta
Fri 11/144:35 pmAUA - MDW
1 stop9h 05mDelta
Deal found 11/2$631
This Delta deal was found by Cheapflights users on 11/1. 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 12/26:00 amMDW - AUA
1 stop7h 20mDelta
Fri 12/123:10 pmAUA - MDW
2 stops20h 44mDelta
Deal found 11/1$644

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 November 3, 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

Mon 3/16

5:25 pm-11:55 am

1 stop17h 30m

Oranjestad Reina Beatrix

Thu 3/19

3:25 pm-9:46 pm

1 stop7h 21m

$546

ChicagoOranjestad

MDW - AUA

MDWAUA

Chicago Midway

Mon 3/16

5:25 pm-11:55 am

1 stop17h 30m

Oranjestad Reina Beatrix

Tue 3/24

3:25 pm-9:46 pm

1 stop7h 21m

$546

ChicagoOranjestad

MDW - AUA

MDWAUA

Chicago Midway

Tue 3/17

1:00 pm-11:55 am

2 stops21h 55m

Oranjestad Reina Beatrix

Tue 3/24

3:25 pm-12:35 pm

2 stops22h 10m

$550

ChicagoOranjestad

MDW - AUA

MDWAUA

Chicago Midway

Mon 3/16

5:59 pm-1:10 pm

2 stops18h 11m

Oranjestad Reina Beatrix

Wed 3/25

3:25 pm-12:35 pm

2 stops22h 10m

$550

ChicagoOranjestad

MDW - AUA

MDWAUA

Chicago Midway

Sun 3/15

1:00 pm-11:55 am

2 stops21h 55m

Oranjestad Reina Beatrix

Tue 3/24

3:25 pm-12:35 pm

2 stops22h 10m

$550

ChicagoOranjestad

MDW - AUA

MDWAUA

Chicago Midway

Sun 3/15

1:00 pm-11:55 am

2 stops21h 55m

Oranjestad Reina Beatrix

Thu 3/19

3:25 pm-9:46 pm

1 stop7h 21m

$550

ChicagoOranjestad

MDW - AUA

MDWAUA

Chicago Midway

Wed 3/11

1:00 pm-11:55 am

2 stops21h 55m

Oranjestad Reina Beatrix

Tue 3/24

1:10 pm-9:46 pm

1 stop9h 36m

$550

ChicagoOranjestad

MDW - AUA

MDWAUA

Chicago Midway

Sun 1/11

6:45 am-3:20 pm

1 stop6h 35m

Oranjestad Reina Beatrix

Fri 1/16

4:35 pm-10:09 pm

1 stop7h 34m

$557

ChicagoOranjestad

MDW - AUA

MDWAUA

Chicago Midway

Thu 12/4

7:23 pm-3:35 pm

2 stops42h 12m

Oranjestad Reina Beatrix

Wed 12/10

7:35 pm-10:05 am

1 stop16h 30m

$566

ChicagoOranjestad

MDW - AUA

MDWAUA

Chicago Midway

Sat 3/14

4:30 pm-11:30 am

1 stop18h 00m

Oranjestad Reina Beatrix

Wed 3/25

3:25 pm-9:46 pm

1 stop7h 21m

$571

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/31

Showing 1-10 of 16 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 November 3, 2025.
Read through reviews of airlines operating flights from Chicago Midway Airport to Aruba, such as Southwest and Delta. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,240 reviews

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,240 reviews
Southwest
8.0
Very good
4,240 reviews

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
7.9
Good
8,001 reviews
Southwest
8.0
Very good
4,240 reviews

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 17h 30m. 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

Browse thousands of different options on Cheapflights for your next trip

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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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Top 2 airlines flying from Midway to Aruba

Discover the top 2 airlines 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 November 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$458Average$759FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$595Average$886FlexibilityNo cancel feeOn-time63%

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