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$157+ 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 2/7. Fares are subject to change and may not be available on all flights or dates of travel.
AUA — CHI
févr. 11 — févr. 181
mer. 2/11
mer. 2/18
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 janvier 12, 2026.

Round-trip from

$289
(Expedia)

One-way from

$157
(Frontier)

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 janvier 12, 2026.

This Expedia deal was found by Cheapflights users on 1/10. 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.
dim. 4/193:41 pm
AUA
-
ORD
2 stops17h 18m
Spirit Airlines
dim. 4/265:15 am
ORD
-
AUA
1 stop8h 18m
Spirit Airlines
Deal found 1/10$355
This Flysmarter deal was found by Cheapflights users on 1/10. 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.
jeu. 2/124:05 pm
AUA
-
ORD
2 stops22h 43m
Air Canada
mer. 2/181:55 pm
ORD
-
AUA
2 stops23h 05m
Air Canada
Deal found 1/10$360
This Cheapflightsfares deal was found by Cheapflights users on 1/12. 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.
mer. 3/253:41 pm
AUA
-
ORD
1 stop9h 00m
Spirit Airlines
mer. 4/17:41 pm
ORD
-
AUA
1 stop17h 45m
Spirit Airlines
Deal found 1/12$363
This Mytrip deal was found by Cheapflights users on 1/12. 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.
lun. 2/164:05 pm
AUA
-
ORD
1 stop29h 40m
Multiple Airlines
ven. 2/204:42 pm
ORD
-
AUA
1 stop16h 13m
Multiple Airlines
Deal found 1/12$367
This Mytrip deal was found by Cheapflights users on 1/11. 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.
jeu. 2/124:40 pm
AUA
-
ORD
1 stop9h 07m
Multiple Airlines
mer. 2/188:40 pm
ORD
-
AUA
1 stop16h 20m
Multiple Airlines
Deal found 1/11$384
This Cheapflightsfares deal was found by Cheapflights users on 1/10. 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.
lun. 2/24:40 pm
AUA
-
ORD
1 stop9h 07m
Spirit Airlines
jeu. 2/125:15 am
ORD
-
AUA
1 stop8h 20m
Spirit Airlines
Deal found 1/10$389
This FlightHub deal was found by Cheapflights users on 1/11. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 3/263:05 pm
AUA
-
ORD
1 stop25h 05m
Air Canada
mar. 3/315:57 pm
ORD
-
AUA
1 stop20h 18m
Air Canada
Deal found 1/11$395
This Kiwi.com deal was found by Cheapflights users on 1/11. 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.
mer. 2/255:50 pm
AUA
-
ORD
2 stops17h 49m
Multiple Airlines
mer. 3/48:16 pm
ORD
-
AUA
1 stop17h 19m
Multiple Airlines
Deal found 1/11$405
This Kiwi.com deal was found by Cheapflights users on 1/12. 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. 2/164:40 pm
AUA
-
MDW
2 stops28h 27m
Multiple Airlines
ven. 2/206:48 pm
MDW
-
AUA
1 stop14h 07m
Multiple Airlines
Deal found 1/12$412
This Delta deal was found by Cheapflights users on 1/12. 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.
jeu. 2/124:35 pm
AUA
-
MDW
1 stop7h 56m
Delta
mer. 2/1812:45 pm
MDW
-
AUA
2 stops23h 10m
Delta
Deal found 1/12$459
This Southwest deal was found by Cheapflights users on 1/12. 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.
jeu. 2/125:55 pm
AUA
-
MDW
2 stops16h 55m
Southwest
mer. 2/187:55 pm
MDW
-
AUA
2 stops16h 30m
Southwest
Deal found 1/12$553
This Southwest deal was found by Cheapflights users on 1/12. 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.
mar. 1/133:20 pm
AUA
-
MDW
1 stop7h 40m
Southwest
lun. 1/195:30 am
MDW
-
AUA
1 stop6h 55m
Southwest
Deal found 1/12$579

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 janvier 12, 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

jeu. 2/12

4:05 pm-12:48 pm

2 stops22h 43m

Chicago O'Hare Intl

mer. 2/18

1:55 pm-3:00 pm

2 stops23h 05m

$360

OranjestadChicago

AUA - ORD

AUAORD

Oranjestad Reina Beatrix

mer. 3/25

3:41 pm-11:41 pm

1 stop9h 00m

Chicago O'Hare Intl

mer. 4/1

5:15 am-2:26 pm

1 stop8h 11m

$363

OranjestadChicago

AUA - ORD

AUAORD

Oranjestad Reina Beatrix

lun. 3/23

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

$417

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

$417

OranjestadChicago

AUA - ORD

AUAORD

Oranjestad Reina Beatrix

lun. 3/23

3:41 pm-10:36 am

1 stop19h 55m

Chicago O'Hare Intl

ven. 4/3

7:41 pm-2:26 pm

1 stop17h 45m

$421

OranjestadChicago

AUA - ORD

AUAORD

Oranjestad Reina Beatrix

mar. 3/24

3:41 pm-10:36 am

1 stop19h 55m

Chicago O'Hare Intl

ven. 4/3

7:41 pm-2:26 pm

1 stop17h 45m

$421

OranjestadChicago

AUA - ORD

AUAORD

Oranjestad Reina Beatrix

mar. 3/24

3:41 pm-10:36 am

1 stop19h 55m

Chicago O'Hare Intl

mer. 4/1

5:15 am-2:26 pm

1 stop8h 11m

$421

OranjestadChicago

AUA - ORD

AUAORD

Oranjestad Reina Beatrix

lun. 3/23

3:41 pm-10:36 am

1 stop19h 55m

Chicago O'Hare Intl

mer. 4/1

7:41 pm-2:26 pm

1 stop17h 45m

$421

OranjestadChicago

AUA - ORD

AUAORD

Oranjestad Reina Beatrix

mer. 5/20

3:41 pm-11:41 pm

1 stop9h 00m

Chicago O'Hare Intl

mar. 7/21

5:15 am-2:33 pm

1 stop8h 18m

$426

OranjestadChicago

AUA - MDW

AUAMDW

Oranjestad Reina Beatrix

jeu. 2/12

2:10 pm-10:31 pm

1 stop10h 21m

Chicago Midway

mer. 2/18

6:40 pm-12:55 pm

1 stop16h 15m

$459

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/10

Showing 1-10 of 35 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 janvier 12, 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 $363, Air Canada can have you in Chicago from Aruba in 9h. Aruba and Chicago are separated by a distance of 2302 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 $338.

  • 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.
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Oranjestad to St. Louis 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 janvier 12, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$343Average$656FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$451Average$790FlexibilityNo cancel feeOn-time71%

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