$220+ 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 10/1. Fares are subject to change and may not be available on all flights or dates of travel.
AUA — CHI
Aug 2 — Aug 91
Round-trip
1 adult, Economy
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Find cheap flights from Aruba to Chicago with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Aruba to Chicago
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Cheapest flights from Aruba to ChicagoExplore 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 July 3, 2026.
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 July 3, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 6/30. 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.
Wed 8/194:50 pm
AUA
- ORD
1 stop18h 21m
JetBlue
Wed 8/266:00 am
ORD
- AUA
1 stop9h 38m
JetBlue
Deal found 6/30![JetBlue logo]()
$500
This Cheapflightsfares deal was found by Cheapflights users on 6/28. 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.
Mon 8/176:00 pm
AUA
- ORD
1 stop17h 11m
JetBlue
Mon 8/316:00 am
ORD
- AUA
1 stop9h 38m
JetBlue
Deal found 6/28![JetBlue logo]()
$515
This Cheapflightsfares deal was found by Cheapflights users on 6/30. 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.
Mon 8/244:50 pm
AUA
- ORD
1 stop18h 21m
JetBlue
Sun 9/68:20 pm
ORD
- AUA
1 stop18h 10m
JetBlue
Deal found 6/30![JetBlue logo]()
$518
This Expedia deal was found by Cheapflights users on 6/30. 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 8/254:50 pm
AUA
- ORD
2 stops30h 08m
JetBlue
Tue 9/16:30 pm
ORD
- AUA
1 stop16h 40m
JetBlue
Deal found 6/30![JetBlue logo]()
$550
This Orbitz deal was found by Cheapflights users on 7/2. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/215:25 pm
AUA
- ORD
1 stop21h 48m
Air Canada
Sun 11/294:30 pm
ORD
- AUA
1 stop21h 55m
Air Canada
Deal found 7/2![Air Canada logo]()
$584
This Cheapflightsfares deal was found by Cheapflights users on 6/30. 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.
Mon 8/314:50 pm
AUA
- ORD
1 stop18h 21m
JetBlue
Mon 9/76:00 am
ORD
- AUA
1 stop9h 40m
JetBlue
Deal found 6/30![JetBlue logo]()
$587
This FlightHub deal was found by Cheapflights users on 6/30. 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.
Wed 8/194:50 pm
AUA
- ORD
1 stop18h 21m
JetBlue
Wed 9/28:20 pm
ORD
- AUA
2 stops19h 18m
JetBlue
Deal found 6/30![JetBlue logo]()
$588
This Cheapflightsfares deal was found by Cheapflights users on 7/2. 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.
Mon 8/176:00 pm
AUA
- ORD
1 stop17h 11m
JetBlue
Mon 8/248:20 pm
ORD
- AUA
1 stop18h 10m
JetBlue
Deal found 7/2![JetBlue logo]()
$600
This Vliegwinkel deal was found by Cheapflights users on 7/2. 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 7/3011:50 am
AUA
- ORD
1 stop10h 30m
Avianca
Wed 8/511:20 pm
ORD
- AUA
1 stop10h 25m
Avianca
Deal found 7/2![Avianca logo]()
$625
This Southwest deal was found by Cheapflights users on 6/28. 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 8/173:45 pm
AUA
- MDW
1 stop7h 55m
Southwest
Mon 8/317:25 am
MDW
- AUA
1 stop6h 20m
Southwest
Deal found 6/28![Southwest logo]()
$643
This Southwest deal was found by Cheapflights users on 6/29. 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 7/271:45 pm
AUA
- MDW
1 stop7h 25m
Southwest
Sun 8/29:25 pm
MDW
- AUA
2 stops16h 20m
Southwest
Deal found 6/29![Southwest logo]()
$720
This Southwest deal was found by Cheapflights users on 7/2. 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 7/301:45 pm
AUA
- MDW
2 stops10h 20m
Southwest
Wed 8/58:20 pm
MDW
- AUA
2 stops17h 25m
Southwest
Deal found 7/2![Southwest logo]()
$756
Best flights from Aruba to ChicagoDiscover carefully curated flight deals from Aruba to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 3, 2026.
Discover carefully curated flight deals from Aruba to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 3, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 6/28. 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.
Mon 8/176:00 pm
AUA
- ORD
1 stop17h 11m
JetBlue
Mon 8/316:00 am
ORD
- AUA
1 stop9h 38m
JetBlue
Deal found 6/28![JetBlue logo]()
$515
This Air Canada deal was found by Cheapflights users on 7/2. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/215:25 pm
AUA
- ORD
2 stops19h 42m
Air Canada
Sun 11/294:30 pm
ORD
- AUA
1 stop21h 55m
Air Canada
Deal found 7/2![Air Canada logo]()
$587
This Vliegwinkel deal was found by Cheapflights users on 7/2. 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 7/3011:50 am
AUA
- ORD
1 stop10h 30m
Avianca
Wed 8/511:20 pm
ORD
- AUA
1 stop10h 25m
Avianca
Deal found 7/2![Avianca logo]()
$625
This Southwest deal was found by Cheapflights users on 6/28. 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 8/173:45 pm
AUA
- MDW
1 stop7h 55m
Southwest
Mon 8/317:35 pm
MDW
- AUA
2 stops18h 10m
Southwest
Deal found 6/28![Southwest logo]()
$648
This United Airlines deal was found by Cheapflights users on 7/2. 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.
Sat 11/212:50 pm
AUA
- ORD
Nonstop5h 58m
United Airlines
Sun 11/296:02 pm
ORD
- AUA
1 stop17h 38m
United Airlines
Deal found 7/2![United Airlines logo]()
$681
This American Airlines deal was found by Cheapflights users on 7/2. 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 7/302:34 pm
AUA
- ORD
2 stops10h 27m
American Airlines
Wed 8/56:10 am
ORD
- AUA
1 stop8h 40m
American Airlines
Deal found 7/2![American Airlines logo]()
$718
This Cheapflightsfares deal was found by Cheapflights users on 6/30. 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.
Mon 8/244:50 pm
AUA
- ORD
1 stop18h 21m
JetBlue
Sun 9/68:20 pm
ORD
- AUA
1 stop18h 10m
JetBlue
Deal found 6/30![JetBlue logo]()
$518
This Southwest deal was found by Cheapflights users on 6/29. 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 7/271:45 pm
AUA
- MDW
1 stop7h 25m
Southwest
Sun 8/29:25 pm
MDW
- AUA
2 stops16h 20m
Southwest
Deal found 6/29![Southwest logo]()
$720
This Cheapflightsfares deal was found by Cheapflights users on 6/30. 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.
Wed 7/152:47 pm
AUA
- ORD
1 stop9h 57m
JetBlue
Sat 7/185:27 pm
ORD
- AUA
1 stop20h 30m
JetBlue
Deal found 6/30![JetBlue logo]()
$660
This American Airlines deal was found by Cheapflights users on 7/3. 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.
Sat 8/14:59 pm
AUA
- ORD
2 stops23h 57m
American Airlines
Fri 8/75:59 pm
ORD
- AUA
1 stop18h 33m
American Airlines
Deal found 7/3![American Airlines logo]()
$765
This United Airlines deal was found by Cheapflights users on 7/1. 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 7/301:50 pm
AUA
- ORD
Nonstop5h 48m
United Airlines
Wed 8/59:40 pm
ORD
- AUA
1 stop14h 00m
United Airlines
Deal found 7/1![United Airlines logo]()
$768
This JetBlue deal was found by Cheapflights users on 6/29. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/274:30 pm
AUA
- ORD
1 stop27h 45m
JetBlue
Sun 8/210:56 am
ORD
- AUA
1 stop27h 14m
JetBlue
Deal found 6/29![JetBlue logo]()
$677
This Southwest deal was found by Cheapflights users on 7/1. 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 7/301:45 pm
AUA
- MDW
2 stops10h 20m
Southwest
Wed 8/58:20 pm
MDW
- AUA
2 stops17h 25m
Southwest
Deal found 7/1![Southwest logo]()
$756
This Southwest deal was found by Cheapflights users on 7/3. 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.
Sat 8/11:15 pm
AUA
- MDW
2 stops11h 05m
Southwest
Fri 8/75:00 am
MDW
- AUA
1 stop8h 45m
Southwest
Deal found 7/3![Southwest logo]()
$1,006
Last-minute flights from Aruba to ChicagoDiscover last-minute flight deals from Aruba to Chicago. Data last updated July 3, 2026 and is based on user searches.
Discover last-minute flight deals from Aruba to Chicago. Data last updated July 3, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 6/29. 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 7/271:45 pm
AUA
- MDW
1 stop7h 25m
Southwest
Sun 8/29:25 pm
MDW
- AUA
2 stops16h 20m
Southwest
Deal found 6/29![Southwest logo]()
$720
This Vliegwinkel deal was found by Cheapflights users on 7/2. 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 7/3011:50 am
AUA
- ORD
1 stop10h 30m
Avianca
Wed 8/511:20 pm
ORD
- AUA
1 stop10h 25m
Avianca
Deal found 7/2![Avianca logo]()
$625
This American Airlines deal was found by Cheapflights users on 6/30. 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 7/304:59 pm
AUA
- ORD
1 stop8h 27m
American Airlines
Wed 8/55:00 am
ORD
- AUA
1 stop9h 50m
American Airlines
Deal found 6/30![American Airlines logo]()
$648
This Southwest deal was found by Cheapflights users on 7/1. 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 7/301:45 pm
AUA
- MDW
2 stops10h 20m
Southwest
Wed 8/58:20 pm
MDW
- AUA
2 stops17h 25m
Southwest
Deal found 7/1![Southwest logo]()
$756
This Cheapflightsfares deal was found by Cheapflights users on 6/28. 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.
Mon 8/176:00 pm
AUA
- ORD
1 stop17h 11m
JetBlue
Mon 8/316:00 am
ORD
- AUA
1 stop9h 38m
JetBlue
Deal found 6/28![JetBlue logo]()
$515
This Cheapflightsfares deal was found by Cheapflights users on 7/2. 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.
Mon 8/176:00 pm
AUA
- ORD
1 stop17h 11m
JetBlue
Mon 8/248:20 pm
ORD
- AUA
1 stop18h 10m
JetBlue
Deal found 7/2![JetBlue logo]()
$600
This Southwest deal was found by Cheapflights users on 6/28. 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 8/173:45 pm
AUA
- MDW
1 stop7h 55m
Southwest
Mon 8/317:25 am
MDW
- AUA
1 stop6h 20m
Southwest
Deal found 6/28![Southwest logo]()
$643
This Cheapflightsfares deal was found by Cheapflights users on 6/30. 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.
Wed 8/194:50 pm
AUA
- ORD
1 stop18h 21m
JetBlue
Wed 8/266:00 am
ORD
- AUA
1 stop9h 38m
JetBlue
Deal found 6/30![JetBlue logo]()
$500
This FlightHub deal was found by Cheapflights users on 6/30. 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.
Wed 8/194:50 pm
AUA
- ORD
1 stop18h 21m
JetBlue
Wed 9/28:20 pm
ORD
- AUA
2 stops19h 18m
JetBlue
Deal found 6/30![JetBlue logo]()
$588
This Cheapflightsfares deal was found by Cheapflights users on 6/30. 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.
Mon 8/244:50 pm
AUA
- ORD
1 stop18h 21m
JetBlue
Sun 9/68:20 pm
ORD
- AUA
1 stop18h 10m
JetBlue
Deal found 6/30![JetBlue logo]()
$518
This Expedia deal was found by Cheapflights users on 6/30. 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 8/254:50 pm
AUA
- ORD
2 stops30h 08m
JetBlue
Tue 9/16:30 pm
ORD
- AUA
1 stop16h 40m
JetBlue
Deal found 6/30![JetBlue logo]()
$550
This Cheapflightsfares deal was found by Cheapflights users on 6/30. 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.
Mon 8/314:50 pm
AUA
- ORD
1 stop18h 21m
JetBlue
Mon 9/76:00 am
ORD
- AUA
1 stop9h 40m
JetBlue
Deal found 6/30![JetBlue logo]()
$587
One-way flights from Aruba to ChicagoSearch for one-way flight options from Aruba to Chicago. Find affordable one-way fares based on user searches. Data last updated July 3, 2026.
Search for one-way flight options from Aruba to Chicago. Find affordable one-way fares based on user searches. Data last updated July 3, 2026.
This JetBlue deal was found by Cheapflights users on 6/30. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/13:25 pm
AUA
- ORD
1 stop9h 06m
JetBlue
Deal found 6/30![JetBlue logo]()
$220
This Cheapflightsfares deal was found by Cheapflights users on 7/2. 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.
Wed 9/303:25 pm
AUA
- ORD
1 stop9h 06m
JetBlue
Deal found 7/2![JetBlue logo]()
$240
This Cheapflightsfares deal was found by Cheapflights users on 6/28. 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.
Wed 8/262:37 pm
AUA
- ORD
1 stop10h 07m
JetBlue
Deal found 6/28![JetBlue logo]()
$267
This JetBlue deal was found by Cheapflights users on 7/2. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/22:37 pm
AUA
- ORD
1 stop10h 07m
JetBlue
Deal found 7/2![JetBlue logo]()
$274
This Kiwi.com deal was found by Cheapflights users on 7/3. 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 9/3011:50 am
AUA
- ORD
2 stops28h 36m
Multiple Airlines
Deal found 7/3![Multiple Airlines logo]()
$279
This Kiwi.com deal was found by Cheapflights users on 7/3. 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 8/311:50 am
AUA
- ORD
2 stops25h 25m
Multiple Airlines
Deal found 7/3![Multiple Airlines logo]()
$292
This Kiwi.com deal was found by Cheapflights users on 7/2. 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 8/3111:50 am
AUA
- ORD
2 stops26h 00m
Multiple Airlines
Deal found 7/2![Multiple Airlines logo]()
$293
This Kiwi.com deal was found by Cheapflights users on 7/2. 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.
Sun 8/3011:50 am
AUA
- ORD
2 stops26h 00m
Multiple Airlines
Deal found 7/2![Multiple Airlines logo]()
$301
This Justfly.com deal was found by Cheapflights users on 7/2. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/314:50 pm
AUA
- ORD
1 stop18h 21m
JetBlue
Deal found 7/2![JetBlue logo]()
$303
This Air Canada deal was found by Cheapflights users on 7/1. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/255:25 pm
AUA
- ORD
1 stop21h 48m
Air Canada
Deal found 7/1![Air Canada logo]()
$308
This Justfly.com deal was found by Cheapflights users on 6/28. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/276:00 pm
AUA
- ORD
1 stop17h 06m
JetBlue
Deal found 6/28![JetBlue logo]()
$310
This Kiwi.com deal was found by Cheapflights users on 6/30. 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.
Sun 8/3011:50 am
AUA
- MDW
3 stops24h 05m
Multiple Airlines
Deal found 6/30![Multiple Airlines logo]()
$376
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 July 3, 2026.
Round-trip from | $500 (Cheapflightsfares) |
|---|---|
One-way from | $220 (JetBlue) |
Good round-trip deal | $482 or less |
Good one-way deal | $228 or less |
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 July 3, 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
Cheapest round-trip
OranjestadChicago
AUA - ORD
AUAORD
Oranjestad Reina Beatrix
Mon 8/17
6:00 pm-10:11 am
1 stop17h 11m
Chicago O'Hare Intl
Mon 8/31
6:00 am-4:38 pm
1 stop9h 38m
$515
OranjestadChicago
AUA - ORD
AUAORD
Oranjestad Reina Beatrix
Mon 8/24
4:50 pm-10:11 am
1 stop18h 21m
Chicago O'Hare Intl
Sun 9/6
8:20 pm-3:30 pm
1 stop18h 10m
$518
OranjestadChicago
AUA - ORD
AUAORD
Oranjestad Reina Beatrix
Sat 11/21
5:25 pm-11:07 am
2 stops19h 42m
Chicago O'Hare Intl
Sun 11/29
4:30 pm-4:25 pm
1 stop21h 55m
$587
OranjestadChicago
AUA - ORD
AUAORD
Oranjestad Reina Beatrix
Thu 7/30
11:50 am-9:20 pm
1 stop10h 30m
Chicago O'Hare Intl
Wed 8/5
11:20 pm-10:45 am
1 stop10h 25m
$625
OranjestadChicago
AUA - MDW
AUAMDW
Oranjestad Reina Beatrix
Mon 8/17
3:45 pm-10:40 pm
1 stop7h 55m
Chicago Midway
Mon 8/31
7:35 pm-2:45 pm
2 stops18h 10m
$648
OranjestadChicago
AUA - ORD
AUAORD
Oranjestad Reina Beatrix
Wed 7/15
2:47 pm-11:44 pm
1 stop9h 57m
Chicago O'Hare Intl
Sat 7/18
5:27 pm-2:57 pm
1 stop20h 30m
$660
OranjestadChicago
AUA - ORD
AUAORD
Oranjestad Reina Beatrix
Mon 7/27
4:30 pm-7:15 pm
1 stop27h 45m
Chicago O'Hare Intl
Sun 8/2
10:56 am-3:10 pm
1 stop27h 14m
$677
OranjestadChicago
AUA - ORD
AUAORD
Oranjestad Reina Beatrix
Sat 11/21
2:50 pm-6:48 pm
Nonstop5h 58m
Chicago O'Hare Intl
Sun 11/29
6:02 pm-1:40 pm
1 stop17h 38m
$681
Quickest round-trip
OranjestadChicago
AUA - ORD
AUAORD
Oranjestad Reina Beatrix
Thu 7/30
2:34 pm-12:01 am
2 stops10h 27m
Chicago O'Hare Intl
Wed 8/5
6:10 am-3:50 pm
1 stop8h 40m
$718
OranjestadChicago
AUA - MDW
AUAMDW
Oranjestad Reina Beatrix
Mon 7/27
1:45 pm-8:10 pm
1 stop7h 25m
Chicago Midway
Sun 8/2
9:25 pm-2:45 pm
2 stops16h 20m
$720
Showing 1-10 of 31 resultsSorted by cheapest first
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.
AUA-ORD
AUA-MDW
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
AW0-CHI
AUA-ORD
AUA-MDW
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 July 3, 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 July 3, 2026.
The most flights from AW0 to CHI are scheduled on a Monday (1 on average). You will have fewer flight options on Monday, 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.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Hammond
Lansing
Merrillville
Valparaiso
Porter
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Chicago flight routes
Complete your trip
Flights by cabin class
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Popular flights
Alternative routes for Aruba to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on July 3, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Aruba to Chicago by cabin class
Find flights from Aruba to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Aruba and Chicago flights
Browse other Aruba and Chicago flight options. Last updated on July 3, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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 July 3, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$343 | Average$514 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$464 | Average$735 | FlexibilityNo cancel fee | On-time71% |