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$147+ 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 2/28. Fares are subject to change and may not be available on all flights or dates of travel.
AUA — CHI
feb. 14 — feb. 211
sáb. 2/14
sáb. 2/21
1 adult, Economy
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Cheap flight deals from Aruba to Chicago

Keep the following information in mind while searching for Aruba to Chicago flight deals. Data was last updated enero 15, 2026.

Round-trip from

$299
(Expedia)

One-way from

$147
(Cheapflightsfares)

Good round-trip deal

$342 or less

Good one-way deal

$282 or less
From Aruba to Chicago (CHI)
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One-way flight from Aruba to Chicago (CHI)
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Price to beat on a round-trip flight from Aruba to Chicago (CHI).
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Price to beat on a one-way flight from Aruba to Chicago (CHI).
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Find 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 enero 15, 2026.

This Expedia deal was found by Cheapflights users on 1/15. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 3/253:41 pm
AUA
-
ORD
1 stop8h 36m
Spirit Airlines
mié. 4/15:05 am
ORD
-
AUA
1 stop8h 21m
Spirit Airlines
Deal found 1/15$299
This Vliegwinkel deal was found by Cheapflights users on 1/15. 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 Vliegwinkel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 2/44:05 pm
AUA
-
ORD
1 stop25h 05m
Multiple Airlines
lun. 2/95:15 am
ORD
-
AUA
1 stop8h 20m
Multiple Airlines
Deal found 1/15$301
This Kiwi.com deal was found by Cheapflights users on 1/15. 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.
lun. 3/233:41 pm
AUA
-
ORD
1 stop19h 55m
Multiple Airlines
mar. 3/316:36 pm
ORD
-
AUA
1 stop18h 50m
Multiple Airlines
Deal found 1/15$343
This Kiwi.com deal was found by Cheapflights users on 1/15. 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.
lun. 3/233:41 pm
AUA
-
ORD
1 stop19h 55m
Multiple Airlines
mié. 4/15:05 am
ORD
-
AUA
1 stop8h 21m
Multiple Airlines
Deal found 1/15$347
This Mytrip deal was found by Cheapflights users on 1/15. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 3/14:50 pm
AUA
-
ORD
1 stop8h 57m
Multiple Airlines
dom. 3/810:00 am
ORD
-
AUA
1 stop27h 00m
Multiple Airlines
Deal found 1/15$358
This Flysmarter deal was found by Cheapflights users on 1/15. 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 Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 2/44:05 pm
AUA
-
ORD
1 stop19h 08m
Air Canada
lun. 2/91:55 pm
ORD
-
AUA
2 stops23h 05m
Air Canada
Deal found 1/15$360
This Expedia deal was found by Cheapflights users on 1/14. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 2/184:05 pm
AUA
-
ORD
1 stop19h 08m
Multiple Airlines
lun. 2/235:15 am
ORD
-
AUA
1 stop8h 20m
Multiple Airlines
Deal found 1/14$366
This Kiwi.com deal was found by Cheapflights users on 1/15. 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.
lun. 3/233:41 pm
AUA
-
ORD
1 stop8h 36m
Spirit Airlines
lun. 3/308:41 pm
ORD
-
AUA
1 stop16h 45m
Spirit Airlines
Deal found 1/15$374
This Kiwi.com deal was found by Cheapflights users on 1/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 1/305:50 pm
AUA
-
ORD
2 stops16h 28m
Multiple Airlines
dom. 2/85:15 am
ORD
-
AUA
1 stop8h 30m
Multiple Airlines
Deal found 1/14$375
This Kiwi.com deal was found by Cheapflights users on 1/15. 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.
mié. 3/253:41 pm
AUA
-
ORD
2 stops20h 11m
Multiple Airlines
mar. 3/316:36 pm
ORD
-
AUA
1 stop18h 50m
Multiple Airlines
Deal found 1/15$382
This Delta deal was found by Cheapflights users on 1/15. 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.
jue. 2/122:10 pm
AUA
-
MDW
1 stop10h 21m
Delta
mié. 2/186:40 pm
MDW
-
AUA
1 stop16h 15m
Delta
Deal found 1/15$470
This Southwest deal was found by Cheapflights users on 1/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 2/183:20 pm
AUA
-
MDW
1 stop7h 40m
Southwest
lun. 2/235:30 am
MDW
-
AUA
1 stop6h 55m
Southwest
Deal found 1/14$479

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 enero 15, 2026.
Use the filters below to find and compare flights from Aruba to Chicago that are best for you.

Fly from

Aruba

Fly to

Chicago

Route

Depart

Return

Price

OranjestadChicago

AUA - ORD

AUAORD

Oranjestad Reina Beatrix

mié. 2/4

4:05 pm-3:10 pm

1 stop25h 05m

Chicago O'Hare Intl

lun. 2/9

5:15 am-3:35 pm

1 stop8h 20m

$301

OranjestadChicago

AUA - ORD

AUAORD

Oranjestad Reina Beatrix

mar. 3/24

3:41 pm-10:36 am

1 stop19h 55m

Chicago O'Hare Intl

mar. 3/31

6:36 pm-2:26 pm

1 stop18h 50m

$343

OranjestadChicago

AUA - ORD

AUAORD

Oranjestad Reina Beatrix

mié. 3/25

3:41 pm-11:21 am

1 stop20h 40m

Chicago O'Hare Intl

mar. 3/31

6:36 pm-2:26 pm

1 stop18h 50m

$347

OranjestadChicago

AUA - ORD

AUAORD

Oranjestad Reina Beatrix

mié. 3/25

3:41 pm-11:41 pm

1 stop9h 00m

Chicago O'Hare Intl

mié. 4/1

7:05 am-2:26 pm

1 stop6h 21m

$363

OranjestadChicago

AUA - ORD

AUAORD

Oranjestad Reina Beatrix

lun. 3/23

3:41 pm-11:17 pm

1 stop8h 36m

Chicago O'Hare Intl

lun. 3/30

8:41 pm-2:26 pm

1 stop16h 45m

$374

OranjestadChicago

AUA - ORD

AUAORD

Oranjestad Reina Beatrix

jue. 2/12

4:05 pm-8:00 am

2 stops17h 55m

Chicago O'Hare Intl

mié. 2/18

1:55 pm-3:00 pm

2 stops23h 05m

$387

OranjestadChicago

AUA - ORD

AUAORD

Oranjestad Reina Beatrix

mié. 3/25

3:41 pm-10:52 am

2 stops20h 11m

Chicago O'Hare Intl

mié. 4/1

5:05 am-2:26 pm

1 stop8h 21m

$387

OranjestadChicago

AUA - ORD

AUAORD

Oranjestad Reina Beatrix

jue. 3/26

3:41 pm-10:52 am

2 stops20h 11m

Chicago O'Hare Intl

mié. 4/1

5:05 am-2:26 pm

1 stop8h 21m

$387

OranjestadChicago

AUA - ORD

AUAORD

Oranjestad Reina Beatrix

lun. 3/23

12:05 pm-8:25 am

2 stops21h 20m

Chicago O'Hare Intl

mar. 3/31

6:36 pm-2:26 pm

1 stop18h 50m

$405

OranjestadChicago

AUA - MDW

AUAMDW

Oranjestad Reina Beatrix

jue. 2/12

2:10 pm-10:31 pm

1 stop10h 21m

Chicago Midway

mié. 2/18

6:40 pm-12:55 pm

1 stop16h 15m

$470

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/15

Showing 1-10 of 36 results
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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 enero 15, 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.

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 $479, Spirit Airlines can have you in Chicago from Aruba in 7h 40m. 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 $284 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 (72%), United Airlines (68%).

  • What are the cheapest flights from Aruba to Chicago?

    Looking for the cheapest flight from Aruba to Chicago? While on average our users pay $670, our data indicates the cheapest price to be $212. The most popular route (Oranjestad Reina Beatrix - Chicago O'Hare Intl), is priced around $356.

  • 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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Alternative routes for Aruba to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Punta Cana to O'Hare Intl flights
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Montego Bay to Midway flights
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Road Town to O'Hare Intl flights
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Oranjestad to St. Louis flights
St. George's to St. Louis flights
Nassau to St. Louis flights
Port of Spain to St. Louis flights
Saint Thomas Island to St. Louis flights
Port Au Prince to O'Hare Intl flights
Roseau to O'Hare Intl flights
Culebra to O'Hare Intl flights
Bridgetown to O'Hare Intl flights
Port Au Prince to Midway flights
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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 enero 15, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$343Average$591FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$451Average$790FlexibilityNo cancel feeOn-time71%

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