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$172+ 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 12/18. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — AUA
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
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 September 16, 2025.

Round-trip from

$492
(Delta)

One-way from

$172
(Priceline)

Popular in

December

Cheapest in

August

Average price

$696
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. 8% potential increase in price ($66 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($22 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 16, 2025.

This Delta deal was found by Cheapflights users on 9/15. 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 11/116:00 amMDW - AUA
1 stop7h 20mDelta
Sat 11/154:35 pmAUA - MDW
1 stop8h 57mDelta
Deal found 9/15$492
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Sat 10/186:15 amMDW - AUA
1 stop8h 25mMultiple Airlines
Fri 10/243:55 pmAUA - MDW
2 stops26h 18mMultiple Airlines
Deal found 9/15$538
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Sat 10/186:15 amMDW - AUA
1 stop8h 25mMultiple Airlines
Thu 10/233:55 pmAUA - MDW
2 stops30h 05mMultiple Airlines
Deal found 9/15$549
This Delta deal was found by Cheapflights users on 9/15. 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 11/116:00 amMDW - AUA
1 stop7h 20mDelta
Tue 11/184:35 pmAUA - MDW
1 stop8h 57mDelta
Deal found 9/15$551
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Sat 10/186:15 amMDW - AUA
1 stop8h 25mMultiple Airlines
Sat 10/253:45 pmAUA - MDW
2 stops16h 40mMultiple Airlines
Deal found 9/15$558
This Delta deal was found by Cheapflights users on 9/15. 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 11/156:00 amMDW - AUA
1 stop7h 20mDelta
Wed 11/194:35 pmAUA - MDW
1 stop8h 57mDelta
Deal found 9/15$576
This Delta deal was found by Cheapflights users on 9/14. 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 12/145:32 pmMDW - AUA
2 stops18h 23mDelta
Wed 12/173:10 pmAUA - MDW
2 stops20h 44mDelta
Deal found 9/14$579
This Cheapflightsfares deal was found by Cheapflights users on 9/16. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/186:00 amMDW - AUA
1 stop7h 39mFrontier
Sat 12/274:40 pmAUA - MDW
1 stop8h 25mFrontier
Deal found 9/16$580
This Delta deal was found by Cheapflights users on 9/15. 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 11/84:23 pmMDW - AUA
2 stops19h 32mDelta
Sat 11/154:35 pmAUA - MDW
1 stop8h 57mDelta
Deal found 9/15$594
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Tue 11/1111:00 amMDW - AUA
1 stop26h 40mMultiple Airlines
Sat 11/155:50 pmAUA - MDW
2 stops18h 36mMultiple Airlines
Deal found 9/15$601
This Delta deal was found by Cheapflights users on 9/15. 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 11/116:00 amMDW - AUA
1 stop7h 20mDelta
Sun 11/164:35 pmAUA - MDW
1 stop8h 57mDelta
Deal found 9/15$611
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Sat 10/116:15 amMDW - AUA
1 stop8h 25mMultiple Airlines
Sat 10/183:45 pmAUA - MDW
2 stops16h 40mMultiple Airlines
Deal found 9/15$629

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 September 16, 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 3/10

6:00 am-2:10 pm

1 stop7h 10m

Oranjestad Reina Beatrix

Wed 3/11

3:25 pm-9:46 pm

1 stop7h 21m

$545

ChicagoOranjestad

MDW - AUA

MDWAUA

Chicago Midway

Mon 1/26

6:00 am-3:10 pm

1 stop7h 10m

Oranjestad Reina Beatrix

Thu 1/29

4:25 pm-9:46 pm

1 stop7h 21m

$582

ChicagoOranjestad

MDW - AUA

MDWAUA

Chicago Midway

Sat 10/18

6:00 am-2:10 pm

1 stop7h 10m

Oranjestad Reina Beatrix

Thu 10/23

3:25 pm-10:14 pm

1 stop7h 49m

$682

ChicagoOranjestad

MDW - AUA

MDWAUA

Chicago Midway

Wed 1/7

6:00 am-3:10 pm

1 stop7h 10m

Oranjestad Reina Beatrix

Mon 1/12

2:10 pm-9:46 pm

1 stop9h 36m

$690

ChicagoOranjestad

MDW - AUA

MDWAUA

Chicago Midway

Wed 11/5

8:20 pm-3:00 pm

2 stops16h 40m

Oranjestad Reina Beatrix

Thu 11/13

4:00 pm-11:00 pm

1 stop9h 00m

$699

ChicagoOranjestad

MDW - AUA

MDWAUA

Chicago Midway

Sat 11/15

5:05 am-2:55 pm

1 stop7h 50m

Oranjestad Reina Beatrix

Sat 11/22

2:40 pm-9:50 pm

2 stops9h 10m

$701

ChicagoOranjestad

MDW - AUA

MDWAUA

Chicago Midway

Fri 11/7

12:14 pm-3:45 pm

3 stops25h 31m

$257

ChicagoOranjestad

MDW - AUA

MDWAUA

Chicago Midway

Tue 12/2

8:20 pm-3:00 pm

2 stops16h 40m

$263

ChicagoOranjestad

MDW - AUA

MDWAUA

Chicago Midway

Mon 11/17

6:00 am-3:20 pm

1 stop7h 20m

$303

ChicagoOranjestad

MDW - AUA

MDWAUA

Chicago Midway

Fri 11/7

5:50 am-3:00 pm

1 stop7h 10m

$408

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 12 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

What is the cheapest month to book a flight from Chicago Midway Airport to Aruba?

Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Aruba (average of $456). Flying from Chicago Midway Airport to Aruba in July is currently the most expensive (average of $595). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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 September 16, 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
4,242 reviews

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Overall

8.0

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
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Overall

8.0

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
8.0
Very good
7,957 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Overall

8.0

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 7h 10m. 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.

  • What is the cheapest month to book a flight from Chicago Midway Airport to Aruba?

    Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Aruba (average of $456). Flying from Chicago Midway Airport to Aruba in July is currently the most expensive (average of $595). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 St. John's flights
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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 September 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$558Average$784FlexibilityNo cancel feeOn-time63%
DeltaCheapest$562Average$759FlexibilityNo cancel feeOn-timeN/A

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