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Cheap flights from Chicago Midway Airport to Aruba from $252

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Aruba departing on 6/7. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

Find the cheapest flights from Chicago Midway Airport to Aruba

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
3:20 pm - 2:15 pm
MDW
-
AUA
21h 55m
1 stop
Multiple Airlines Logo
3:05 pm - 9:40 am
AUA
-
MDW
19h 35m
1 stop
$603Multiple Airlines
ter, jun 9 - sex, jun 19
Multiple Airlines Logo
3:20 pm - 2:15 pm
MDW
-
AUA
21h 55m
1 stop
Multiple Airlines Logo
3:05 pm - 9:40 am
AUA
-
MDW
19h 35m
1 stop
$614Multiple Airlines
ter, jun 16 - ter, jun 23
Multiple Airlines Logo
3:20 pm - 2:15 pm
MDW
-
AUA
21h 55m
1 stop
Multiple Airlines Logo
3:05 pm - 9:40 am
AUA
-
MDW
19h 35m
1 stop
$623Multiple Airlines
ter, jun 16 - qua, jun 24
Delta Logo
6:00 am - 2:10 pm
MDW
-
AUA
7h 10m
1 stop
Delta Logo
3:25 pm - 9:46 pm
AUA
-
MDW
7h 21m
1 stop
$641Delta
qua, set 9 - qua, set 16
Multiple Airlines Logo
3:20 pm - 2:15 pm
MDW
-
AUA
21h 55m
1 stop
Multiple Airlines Logo
11:50 am - 2:35 pm
AUA
-
MDW
27h 45m
2 stops
$643Multiple Airlines
seg, mai 25 - dom, mai 31
Delta Logo
5:59 pm - 2:10 pm
MDW
-
AUA
19h 11m
2 stops
Delta Logo
3:25 pm - 8:42 am
AUA
-
MDW
18h 17m
2 stops
$646Delta
seg, ago 17 - ter, ago 25
Southwest Logo
6:00 am - 1:35 pm
MDW
-
AUA
6h 35m
1 stop
Southwest Logo
2:35 pm - 9:25 pm
AUA
-
MDW
7h 50m
1 stop
$651Southwest
qua, mai 13 - qua, mai 20
Southwest Logo
7:30 pm - 12:45 pm
MDW
-
AUA
16h 15m
2 stops
Southwest Logo
1:40 pm - 9:50 pm
AUA
-
MDW
9h 10m
2 stops
$656Southwest
dom, set 13 - qua, set 16
Multiple Airlines Logo
3:20 pm - 10:45 am
MDW
-
AUA
18h 25m
2 stops
Multiple Airlines Logo
3:05 pm - 9:40 am
AUA
-
MDW
19h 35m
1 stop
$658Multiple Airlines
qui, jun 18 - ter, jun 23
Delta Logo
1:49 pm - 12:40 pm
MDW
-
AUA
21h 51m
2 stops
Delta Logo
1:55 pm - 10:07 am
AUA
-
MDW
21h 12m
2 stops
$666Delta
ter, jun 9 - qua, jun 17

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Southwest flights from Chicago Midway Airport to Aruba

Our best Southwest deals on Chicago Midway Airport to Aruba flight tickets
Southwest
May 13
MDW6:00 amChicago Midway
6h 35m
1 stop
AUA1:35 pmOranjestad Reina Beatrix
May 20
AUA2:35 pmOranjestad Reina Beatrix
7h 50m
1 stop
MDW9:25 pmChicago Midway
$651
Southwest
Sep 13
MDW7:30 pmChicago Midway
16h 15m
2 stops
AUA12:45 pmOranjestad Reina Beatrix
Sep 16
AUA1:40 pmOranjestad Reina Beatrix
9h 10m
2 stops
MDW9:50 pmChicago Midway
$656
Southwest
Jun 3
MDW6:00 amChicago Midway
6h 35m
1 stop
AUA1:35 pmOranjestad Reina Beatrix
Jun 10
AUA1:45 pmOranjestad Reina Beatrix
9h 15m
1 stop
MDW10:00 pmChicago Midway
$671

Delta flights from Chicago Midway Airport to Aruba

Our best Delta deals on Chicago Midway Airport to Aruba flight tickets
Delta
Sep 9
MDW6:00 amChicago Midway
7h 10m
1 stop
AUA2:10 pmOranjestad Reina Beatrix
Sep 16
AUA3:25 pmOranjestad Reina Beatrix
7h 21m
1 stop
MDW9:46 pmChicago Midway
$641
Delta
Aug 17
MDW5:59 pmChicago Midway
19h 11m
2 stops
AUA2:10 pmOranjestad Reina Beatrix
Aug 27
AUA3:25 pmOranjestad Reina Beatrix
18h 17m
2 stops
MDW8:42 amChicago Midway
$646
Delta
Jun 9
MDW1:49 pmChicago Midway
21h 51m
2 stops
AUA12:40 pmOranjestad Reina Beatrix
Jun 17
AUA1:55 pmOranjestad Reina Beatrix
21h 12m
2 stops
MDW10:07 amChicago Midway
$666

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport 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, momondo users made 832,500 searches. Data last updated abril 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

Price

Cheapest round-trip

ChicagoOranjestad

MDW - AUA

MDWAUA

Chicago Midway

ter 6/9

3:20 pm-2:15 pm

1 stop21h 55m

Oranjestad Reina Beatrix

sex 6/19

3:05 pm-9:40 am

1 stop19h 35m

$603

ChicagoOranjestad

MDW - AUA

MDWAUA

Chicago Midway

ter 6/16

3:20 pm-2:15 pm

1 stop21h 55m

Oranjestad Reina Beatrix

ter 6/23

3:05 pm-9:40 am

1 stop19h 35m

$614

ChicagoOranjestad

MDW - AUA

MDWAUA

Chicago Midway

ter 6/16

3:20 pm-2:15 pm

1 stop21h 55m

Oranjestad Reina Beatrix

qua 6/24

3:05 pm-9:40 am

1 stop19h 35m

$623

ChicagoOranjestad

MDW - AUA

MDWAUA

Chicago Midway

qua 9/9

6:00 am-2:10 pm

1 stop7h 10m

Oranjestad Reina Beatrix

qua 9/16

3:25 pm-9:46 pm

1 stop7h 21m

$641

ChicagoOranjestad

MDW - AUA

MDWAUA

Chicago Midway

seg 5/25

3:20 pm-2:15 pm

1 stop21h 55m

Oranjestad Reina Beatrix

dom 5/31

11:50 am-2:35 pm

2 stops27h 45m

$643

ChicagoOranjestad

MDW - AUA

MDWAUA

Chicago Midway

seg 8/17

5:59 pm-2:10 pm

2 stops19h 11m

Oranjestad Reina Beatrix

ter 8/25

3:25 pm-8:42 am

2 stops18h 17m

$646
Quickest round-trip

ChicagoOranjestad

MDW - AUA

MDWAUA

Chicago Midway

qua 5/13

6:00 am-1:35 pm

1 stop6h 35m

Oranjestad Reina Beatrix

qua 5/20

2:35 pm-9:25 pm

1 stop7h 50m

$651

ChicagoOranjestad

MDW - AUA

MDWAUA

Chicago Midway

dom 9/13

7:30 pm-12:45 pm

2 stops16h 15m

Oranjestad Reina Beatrix

qua 9/16

1:40 pm-9:50 pm

2 stops9h 10m

$656

ChicagoOranjestad

MDW - AUA

MDWAUA

Chicago Midway

qui 6/18

3:20 pm-10:45 am

2 stops18h 25m

Oranjestad Reina Beatrix

ter 6/23

3:05 pm-9:40 am

1 stop19h 35m

$658

ChicagoOranjestad

MDW - AUA

MDWAUA

Chicago Midway

ter 6/9

1:49 pm-12:40 pm

2 stops21h 51m

Oranjestad Reina Beatrix

qua 6/17

1:55 pm-10:07 am

2 stops21h 12m

$666

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Aruba from

How to get the cheapest flight ticket from Chicago Midway Airport to Aruba

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest airline that flies from Chicago Midway to Aruba?

Southwest is the most popular carrier operating from Chicago Midway to Aruba

Cheap Chicago Midway Airport to Aruba flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Aruba

Fastest flight time

6h 45m

Direct flights

None
The fastest flight from Chicago Midway Airport to Aruba takes 6h 45m
There are no direct flights from Chicago Midway Airport to Aruba. There are no popular flight routes from Chicago Midway Airport to Aruba.
Search flight deals

Frequently asked questions about flying from Chicago Midway Airport to Aruba

  • When did momondo last update prices for flights from Chicago Midway Airport to Aruba?

    Prices for flights from Chicago Midway Airport to Aruba were last updated today.

  • How many operators does momondo search for flights from Chicago Midway Airport to Aruba?

  • How old do you have to be to fly from Chicago Midway Airport to Aruba?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago Midway Airport to Aruba.

  • What documentation or ID do you need to fly to Aruba?

    The travel and health documents required for your trip to Aruba can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Aruba. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

Best airlines flying from Chicago Midway Airport to Aruba

Compare and see reviews for airlines that fly from Chicago Midway Airport to Aruba with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $570Free CancellationRating
8.0
4,328 reviews
Search Southwest flights

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Aruba?

It is quick and easy to find Chicago to Aruba flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Aruba that suits you.

Can I find flights from Chicago to Aruba with flexible booking policies on momondo?

Flights from Chicago to Aruba with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Chicago to Aruba?

momondo provides multiple filters to help you find the best flight to Aruba from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Chicago to Aruba right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Chicago to Aruba now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Aruba and let you know when they change.

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ter 5/19
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