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$181+ Cheap flights from Aruba to Chicago (CHI)

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 3/28. Fares are subject to change and may not be available on all flights or dates of travel.
AUA — CHI
Apr 22 — Apr 291
Wed 4/22
Wed 4/29
1 adult, Economy
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Cheap flight deals from Aruba to Chicago

Cheapest flights from Aruba to Chicago
Explore the most affordable flight options available from Aruba to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 23, 2026.

This Priceline deal was found by Cheapflights users on 3/19. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/153:41 pm
AUA
-
ORD
1 stop9h 46m
Spirit Airlines
Mon 5/185:05 am
ORD
-
AUA
1 stop8h 31m
Spirit Airlines
Deal found 3/19$289
This Priceline deal was found by Cheapflights users on 3/18. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/23:41 pm
AUA
-
ORD
1 stop9h 43m
Spirit Airlines
Sat 5/95:05 am
ORD
-
AUA
1 stop8h 31m
Spirit Airlines
Deal found 3/18$366
This Kiwi.com deal was found by Cheapflights users on 3/18. 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 5/23:41 pm
AUA
-
ORD
1 stop9h 43m
Multiple Airlines
Sat 5/94:05 pm
ORD
-
AUA
2 stops45h 31m
Multiple Airlines
Deal found 3/18$375
This Vliegwinkel deal was found by Cheapflights users on 3/18. 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 Vliegwinkel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/203:41 pm
AUA
-
ORD
1 stop9h 43m
Multiple Airlines
Sun 4/269:50 am
ORD
-
AUA
1 stop28h 25m
Multiple Airlines
Deal found 3/18$393
This Expedia deal was found by Cheapflights users on 3/21. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/204:05 pm
AUA
-
ORD
1 stop24h 10m
Air Canada
Mon 4/274:15 pm
ORD
-
AUA
1 stop22h 00m
Air Canada
Deal found 3/21$404
This Trip.com deal was found by Cheapflights users on 3/20. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/204:05 pm
AUA
-
ORD
1 stop28h 20m
Air Canada
Sun 4/266:40 pm
ORD
-
AUA
1 stop19h 35m
Air Canada
Deal found 3/20$407
This Expedia deal was found by Cheapflights users on 3/18. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/74:15 pm
AUA
-
ORD
1 stop24h 00m
Multiple Airlines
Tue 4/145:05 am
ORD
-
AUA
1 stop8h 30m
Multiple Airlines
Deal found 3/18$409
This Kiwi.com deal was found by Cheapflights users on 3/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/83:40 pm
AUA
-
ORD
1 stop8h 37m
Spirit Airlines
Tue 4/145:05 am
ORD
-
AUA
1 stop8h 30m
Spirit Airlines
Deal found 3/19$411
This Vliegwinkel deal was found by Cheapflights users on 3/22. 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 Vliegwinkel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/163:41 pm
AUA
-
ORD
1 stop9h 46m
Multiple Airlines
Mon 5/2511:20 pm
ORD
-
AUA
1 stop10h 25m
Multiple Airlines
Deal found 3/22$412
This Kiwi.com deal was found by Cheapflights users on 3/18. 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.
Mon 4/205:20 pm
AUA
-
MDW
2 stops44h 40m
Multiple Airlines
Sun 4/264:05 pm
MDW
-
AUA
1 stop21h 10m
Multiple Airlines
Deal found 3/18$595
This Southwest deal was found by Cheapflights users on 3/18. 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.
Thu 4/162:45 pm
AUA
-
MDW
1 stop10h 20m
Southwest
Wed 4/226:00 am
MDW
-
AUA
1 stop6h 45m
Southwest
Deal found 3/18$631
This Southwest deal was found by Cheapflights users on 3/20. 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 4/202:45 pm
AUA
-
MDW
1 stop10h 20m
Southwest
Sun 4/265:15 am
MDW
-
AUA
1 stop7h 20m
Southwest
Deal found 3/20$661

Find flight deals from Aruba to Chicago

Keep the following information in mind while searching for Aruba to Chicago flight deals. Data was last updated March 23, 2026.

Round-trip from

$289
(Priceline)

One-way from

$181
(Super.com)

Good round-trip deal

$343 or less

Good one-way deal

$288 or less
From Aruba to Chicago (CHI)
Search Deals
One-way flight from Aruba to Chicago (CHI)
Search Deals
Price to beat on a round-trip flight from Aruba to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Aruba to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Aruba to Chicago 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 March 23, 2026.
Use the filters below to find and compare flights from Aruba to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

OranjestadChicago

AUA - ORD

AUAORD

Oranjestad Reina Beatrix

Thu 5/7

5:20 pm-1:05 pm

2 stops20h 45m

Chicago O'Hare Intl

Thu 5/14

7:45 pm-2:36 pm

1 stop17h 51m

$421

OranjestadChicago

AUA - ORD

AUAORD

Oranjestad Reina Beatrix

Sat 5/16

3:41 pm-10:46 am

2 stops20h 05m

Chicago O'Hare Intl

Mon 5/25

5:05 am-2:36 pm

1 stop8h 31m

$629

OranjestadChicago

AUA - MDW

AUAMDW

Oranjestad Reina Beatrix

Thu 4/16

2:45 pm-12:05 am

1 stop10h 20m

Chicago Midway

Wed 4/22

6:00 am-1:45 pm

1 stop6h 45m

$631

OranjestadChicago

AUA - ORD

AUAORD

Oranjestad Reina Beatrix

Thu 5/7

2:30 pm-11:54 pm

2 stops10h 24m

Chicago O'Hare Intl

Thu 5/14

5:00 am-4:25 pm

2 stops10h 25m

$641

OranjestadChicago

AUA - MDW

AUAMDW

Oranjestad Reina Beatrix

Mon 4/20

2:45 pm-12:05 am

1 stop10h 20m

Chicago Midway

Sun 4/26

5:15 am-1:35 pm

1 stop7h 20m

$661

OranjestadChicago

AUA - MDW

AUAMDW

Oranjestad Reina Beatrix

Sat 5/16

1:30 pm-10:35 pm

2 stops10h 05m

Chicago Midway

Mon 5/25

5:15 pm-1:35 pm

2 stops19h 20m

$716

OranjestadChicago

AUA - ORD

AUAORD

Oranjestad Reina Beatrix

Sat 5/16

1:50 pm-6:38 pm

Nonstop5h 48m

Chicago O'Hare Intl

Sun 5/24

9:19 pm-4:40 pm

1 stop18h 21m

$735
Quickest round-trip

OranjestadChicago

AUA - ORD

AUAORD

Oranjestad Reina Beatrix

Sat 5/16

1:50 pm-6:38 pm

Nonstop5h 48m

Chicago O'Hare Intl

Mon 5/25

8:54 am-3:10 pm

Nonstop5h 16m

$736

OranjestadChicago

AUA - ORD

AUAORD

Oranjestad Reina Beatrix

Mon 4/20

1:50 pm-6:38 pm

Nonstop5h 48m

Chicago O'Hare Intl

Sun 4/26

9:04 am-3:20 pm

Nonstop5h 16m

$747

OranjestadChicago

AUA - MDW

AUAMDW

Oranjestad Reina Beatrix

Fri 5/15

2:35 pm-12:05 am

1 stop10h 30m

Chicago Midway

Mon 5/18

5:35 am-1:35 pm

1 stop7h 00m

$751

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/21

Showing 1-10 of 24 resultsSorted by cheapest first
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Best time to book a flight from Aruba to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Aruba 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 Aruba to Chicago

What is the cheapest time of day to fly from AW to CHI?

Find hourly flight availability from Aruba to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated March 23, 2026.

When flying from Aruba to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Weekly flight availability from Aruba to Chicago

Explore weekly flight availability from Aruba to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated March 23, 2026.

The most flights from AW0 to CHI are scheduled on a Monday (2 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (1 on average).

Related info for your journey

Find useful and relevant information for your journey from Aruba to Chicago. 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 Aruba to Chicago?

    For as low as $631, Spirit Airlines can have you in Chicago from Aruba in 10h 20m. Aruba and Chicago are separated by a distance of 2286 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from Aruba to Chicago one-way?

    To fly one-way, consider booking your trip with United Airlines, which is currently one of the cheapest options available, starting at $254. JetBlue flights start at $260 while deals on American Airlines start at $334 one-way.

  • What are the most reliable airlines from Aruba to Chicago?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Aruba to Chicago on time: Qatar Airways (73%), American Airlines (70%), United Airlines (58%).

  • What are the cheapest flights from Aruba to Chicago?

    Looking for the cheapest flight from Aruba to Chicago? While on average our users pay $624, our data indicates the cheapest price to be $188. The most popular route (Oranjestad Reina Beatrix - Chicago O'Hare Intl), is priced around $289.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Aruba to Chicago 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

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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Top 2 airlines flying from Aruba to Chicago

Discover the top 2 airlines that operate flights from Aruba to Chicago. 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 March 23, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$343Average$552FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$464Average$735FlexibilityNo cancel feeOn-time71%

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