Chicago

$227+ 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 8/12. Fares are subject to change and may not be available on all flights or dates of travel.
AUA — CHI
Jun 17 — Jun 241
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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 May 18, 2026.

This Flysmarter deal was found by Cheapflights users on 5/17. 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.
Thu 7/26:00 pm
AUA
-
ORD
1 stop15h 45m
JetBlue
Wed 7/88:20 pm
ORD
-
AUA
1 stop18h 10m
JetBlue
Deal found 5/17$505
This Flysmarter deal was found by Cheapflights users on 5/16. 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 Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/251:35 pm
AUA
-
ORD
1 stop8h 55m
JetBlue
Wed 7/18:20 pm
ORD
-
AUA
1 stop17h 50m
JetBlue
Deal found 5/16$580
This Avianca deal was found by Cheapflights users on 5/15. 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 Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/2511:50 am
AUA
-
ORD
1 stop10h 30m
Avianca
Wed 7/111:20 pm
ORD
-
AUA
1 stop10h 25m
Avianca
Deal found 5/15$612
This Vliegwinkel deal was found by Cheapflights users on 5/14. 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 Vliegwinkel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/115:20 pm
AUA
-
ORD
1 stop29h 00m
Avianca
Wed 6/1711:20 pm
ORD
-
AUA
1 stop10h 25m
Avianca
Deal found 5/14$622
This Delta deal was found by Cheapflights users on 5/17. 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.
Thu 7/23:25 pm
AUA
-
MDW
1 stop7h 52m
Delta
Wed 7/86:00 am
MDW
-
AUA
1 stop7h 10m
Delta
Deal found 5/17$642
This American Airlines deal was found by Cheapflights users on 5/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/253:00 pm
AUA
-
ORD
1 stop9h 58m
American Airlines
Wed 7/18:30 am
ORD
-
AUA
1 stop7h 29m
American Airlines
Deal found 5/13$646
This Southwest deal was found by Cheapflights users on 5/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/251:45 pm
AUA
-
MDW
2 stops18h 25m
Southwest
Wed 7/14:40 pm
MDW
-
AUA
2 stops19h 05m
Southwest
Deal found 5/15$650
This Cheapflightsfares deal was found by Cheapflights users on 5/13. 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.
Fri 5/226:00 pm
AUA
-
ORD
1 stop20h 01m
JetBlue
Thu 6/48:30 pm
ORD
-
AUA
1 stop15h 00m
JetBlue
Deal found 5/13$658
This Delta deal was found by Cheapflights users on 5/17. 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.
Thu 6/253:25 pm
AUA
-
ORD
1 stop9h 34m
Delta
Wed 7/15:30 am
ORD
-
AUA
1 stop7h 40m
Delta
Deal found 5/17$674
This Cheapflightsfares deal was found by Cheapflights users on 5/15. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/111:35 pm
AUA
-
ORD
1 stop8h 55m
JetBlue
Wed 6/176:27 pm
ORD
-
AUA
1 stop16h 47m
JetBlue
Deal found 5/15$675
This Delta deal was found by Cheapflights users on 5/13. 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.
Thu 6/253:25 pm
AUA
-
MDW
1 stop7h 52m
Delta
Wed 7/16:00 am
MDW
-
AUA
1 stop7h 10m
Delta
Deal found 5/13$676
This United Airlines deal was found by Cheapflights users on 5/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/111:50 pm
AUA
-
ORD
Nonstop5h 48m
United Airlines
Wed 6/179:19 am
ORD
-
AUA
Nonstop5h 16m
United Airlines
Deal found 5/15$682

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 May 18, 2026.

Round-trip from

$505
(Flysmarter)

One-way from

$227
(Super.com)

Good round-trip deal

$232 or less

Good one-way deal

$210 or less
From Aruba to Chicago (CHI)
One-way flight from Aruba to Chicago (CHI)
Price to beat on a round-trip flight from Aruba to Chicago (CHI).
Price to beat on a one-way flight from Aruba to Chicago (CHI).

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 May 18, 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 6/25

1:35 pm-9:30 pm

1 stop8h 55m

Chicago O'Hare Intl

Wed 7/1

8:20 pm-3:10 pm

1 stop17h 50m

$580

OranjestadChicago

AUA - ORD

AUAORD

Oranjestad Reina Beatrix

Thu 6/25

11:50 am-9:20 pm

1 stop10h 30m

Chicago O'Hare Intl

Wed 7/1

11:20 pm-10:45 am

1 stop10h 25m

$612

OranjestadChicago

AUA - MDW

AUAMDW

Oranjestad Reina Beatrix

Thu 7/2

3:25 pm-10:17 pm

1 stop7h 52m

Chicago Midway

Wed 7/8

6:00 am-2:10 pm

1 stop7h 10m

$642

OranjestadChicago

AUA - ORD

AUAORD

Oranjestad Reina Beatrix

Thu 6/25

3:00 pm-11:58 pm

1 stop9h 58m

Chicago O'Hare Intl

Wed 7/1

8:30 am-4:59 pm

1 stop7h 29m

$646

OranjestadChicago

AUA - MDW

AUAMDW

Oranjestad Reina Beatrix

Thu 6/25

1:45 pm-7:10 am

2 stops18h 25m

Chicago Midway

Wed 7/1

4:40 pm-12:45 pm

2 stops19h 05m

$650

OranjestadChicago

AUA - ORD

AUAORD

Oranjestad Reina Beatrix

Thu 6/25

3:25 pm-11:59 pm

1 stop9h 34m

Chicago O'Hare Intl

Wed 7/1

5:30 am-2:10 pm

1 stop7h 40m

$674

OranjestadChicago

AUA - MDW

AUAMDW

Oranjestad Reina Beatrix

Thu 6/25

3:25 pm-10:17 pm

1 stop7h 52m

Chicago Midway

Wed 7/1

6:00 am-2:10 pm

1 stop7h 10m

$676
Quickest round-trip

OranjestadChicago

AUA - ORD

AUAORD

Oranjestad Reina Beatrix

Thu 6/11

1:50 pm-6:38 pm

Nonstop5h 48m

Chicago O'Hare Intl

Wed 6/17

9:19 am-3:35 pm

Nonstop5h 16m

$682

OranjestadChicago

AUA - ORD

AUAORD

Oranjestad Reina Beatrix

Thu 6/11

1:59 pm-12:34 am

1 stop11h 35m

Chicago O'Hare Intl

Wed 6/17

5:10 am-4:59 pm

2 stops10h 49m

$706

OranjestadChicago

AUA - ORD

AUAORD

Oranjestad Reina Beatrix

Thu 6/25

1:50 pm-6:38 pm

Nonstop5h 48m

Chicago O'Hare Intl

Wed 7/1

9:19 am-3:35 pm

Nonstop5h 16m

$753

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/14

Showing 1-10 of 33 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 May 18, 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 $642, JetBlue can have you in Chicago from Aruba in 7h 52m. 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 cheapest flights from Aruba to Chicago?

    Looking for the cheapest flight from Aruba to Chicago? While on average our users pay $513, our data indicates the cheapest price to be $161. The most popular route (Oranjestad Reina Beatrix - Chicago O'Hare Intl), is priced around $579.

  • 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
Benton Harbor
Lansing
Merrillville
Hammond
Porter

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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 May 18, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$343Average$552FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$464Average$735FlexibilityNo cancel feeOn-time71%

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