$214+ 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 5/30. Fares are subject to change and may not be available on all flights or dates of travel.
AUA — CHI
Jun 3 — Jun 101
Round-trip
1 adult, Economy
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Find cheap flights from Aruba to Chicago with Cheapflights
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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
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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 May 4, 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 May 4, 2026.
This Orbitz deal was found by Cheapflights users on 4/29. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/133:05 pm
AUA
- ORD
1 stop23h 20m
Multiple Airlines
Sat 6/205:10 am
ORD
- AUA
1 stop8h 26m
Multiple Airlines
Deal found 4/29![Multiple Airlines logo]()
$416
This Expedia deal was found by Cheapflights users on 5/3. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/303:05 pm
AUA
- ORD
1 stop23h 20m
Multiple Airlines
Mon 6/88:30 pm
ORD
- AUA
1 stop15h 00m
Multiple Airlines
Deal found 5/3![Multiple Airlines logo]()
$489
This JetBlue deal was found by Cheapflights users on 5/2. 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.
Sat 5/234:30 pm
AUA
- ORD
1 stop16h 30m
JetBlue
Sun 5/318:30 pm
ORD
- AUA
1 stop18h 10m
JetBlue
Deal found 5/2![JetBlue logo]()
$519
This Justfly.com deal was found by Cheapflights users on 5/2. 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.
Wed 7/14:17 pm
AUA
- ORD
1 stop17h 28m
JetBlue
Sun 7/56:00 am
ORD
- AUA
1 stop27h 30m
JetBlue
Deal found 5/2![JetBlue logo]()
$533
This JetBlue deal was found by Cheapflights users on 5/2. 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.
Tue 6/306:00 pm
AUA
- ORD
1 stop15h 45m
JetBlue
Mon 7/66:00 am
ORD
- AUA
1 stop9h 40m
JetBlue
Deal found 5/2![JetBlue logo]()
$543
This Cheapflightsfares deal was found by Cheapflights users on 5/2. 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.
Thu 7/26:00 pm
AUA
- ORD
1 stop15h 45m
JetBlue
Mon 7/66:00 am
ORD
- AUA
1 stop9h 40m
JetBlue
Deal found 5/2![JetBlue logo]()
$555
This Expedia deal was found by Cheapflights users on 5/1. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/154:17 pm
AUA
- ORD
1 stop30h 13m
JetBlue
Mon 6/226:00 am
ORD
- AUA
1 stop9h 38m
JetBlue
Deal found 5/1![JetBlue logo]()
$558
This Delta deal was found by Cheapflights users on 5/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/13:25 pm
AUA
- MDW
1 stop7h 52m
Delta
Sun 7/56:00 am
MDW
- AUA
1 stop7h 10m
Delta
Deal found 5/2![Delta logo]()
$568
This Delta deal was found by Cheapflights users on 5/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/33:25 pm
AUA
- MDW
1 stop7h 52m
Delta
Wed 7/811:05 am
MDW
- AUA
2 stops24h 35m
Delta
Deal found 5/2![Delta logo]()
$574
This Kiwi.com deal was found by Cheapflights users on 5/2. 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 6/293:05 pm
AUA
- MDW
1 stop19h 35m
Multiple Airlines
Wed 7/83:20 pm
MDW
- AUA
1 stop21h 55m
Multiple Airlines
Deal found 5/2![Multiple Airlines logo]()
$606
This Delta deal was found by Cheapflights users on 5/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/11:35 pm
AUA
- MDW
1 stop9h 42m
Delta
Thu 7/96:00 am
MDW
- AUA
1 stop7h 10m
Delta
Deal found 5/2![Delta logo]()
$609
This Kiwi.com deal was found by Cheapflights users on 5/2. 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 6/293:05 pm
AUA
- MDW
1 stop19h 35m
Multiple Airlines
Tue 7/73:20 pm
MDW
- AUA
1 stop21h 55m
Multiple Airlines
Deal found 5/2![Multiple Airlines logo]()
$628
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 May 4, 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 May 4, 2026.
This Delta deal was found by Cheapflights users on 5/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/11:35 pm
AUA
- MDW
1 stop9h 42m
Delta
Wed 7/89:19 am
MDW
- AUA
2 stops26h 21m
Delta
Deal found 5/2![Delta logo]()
$574
This United Airlines deal was found by Cheapflights users on 5/1. 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.
Mon 6/155:50 pm
AUA
- ORD
1 stop16h 10m
United Airlines
Mon 6/229:19 am
ORD
- AUA
Nonstop5h 16m
United Airlines
Deal found 5/1![United Airlines logo]()
$608
This American Airlines deal was found by Cheapflights users on 5/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/151:59 pm
AUA
- ORD
1 stop17h 58m
American Airlines
Mon 6/225:00 am
ORD
- AUA
2 stops10h 59m
American Airlines
Deal found 5/1![American Airlines logo]()
$617
This Mytrip deal was found by Cheapflights users on 4/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/133:41 pm
AUA
- ORD
2 stops21h 42m
Multiple Airlines
Sat 6/2010:27 am
ORD
- AUA
3 stops22h 48m
Multiple Airlines
Deal found 4/29![Multiple Airlines logo]()
$621
This Southwest deal was found by Cheapflights users on 5/2. 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 7/21:45 pm
AUA
- MDW
2 stops18h 25m
Southwest
Mon 7/68:50 pm
MDW
- AUA
2 stops14h 55m
Southwest
Deal found 5/2![Southwest logo]()
$836
This Delta deal was found by Cheapflights users on 5/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/33:25 pm
AUA
- MDW
2 stops22h 21m
Delta
Wed 7/81:18 pm
MDW
- AUA
2 stops23h 52m
Delta
Deal found 5/2![Delta logo]()
$574
This Delta deal was found by Cheapflights users on 5/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/33:25 pm
AUA
- ORD
1 stop9h 34m
Delta
Sun 7/55:30 am
ORD
- AUA
1 stop7h 40m
Delta
Deal found 5/2![Delta logo]()
$574
This United Airlines deal was found by Cheapflights users on 5/2. 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.
Wed 7/11:50 pm
AUA
- ORD
Nonstop5h 48m
United Airlines
Mon 7/69:19 am
ORD
- AUA
Nonstop5h 16m
United Airlines
Deal found 5/2![United Airlines logo]()
$643
This Delta deal was found by Cheapflights users on 5/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/11:35 pm
AUA
- MDW
1 stop9h 42m
Delta
Thu 7/96:00 am
MDW
- AUA
1 stop7h 10m
Delta
Deal found 5/2![Delta logo]()
$609
This Kiwi.com deal was found by Cheapflights users on 5/3. 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.
Sat 5/303:05 pm
AUA
- MDW
1 stop19h 40m
Multiple Airlines
Mon 6/810:15 am
MDW
- AUA
1 stop27h 00m
Multiple Airlines
Deal found 5/3![Multiple Airlines logo]()
$743
This American Airlines deal was found by Cheapflights users on 5/3. 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.
Sun 5/242:33 pm
AUA
- ORD
2 stops10h 26m
American Airlines
Sun 5/317:58 am
ORD
- AUA
1 stop7h 12m
American Airlines
Deal found 5/3![American Airlines logo]()
$754
This United Airlines deal was found by Cheapflights users on 5/2. 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.
Sun 7/51:50 pm
AUA
- ORD
Nonstop5h 48m
United Airlines
Wed 7/89:19 am
ORD
- AUA
Nonstop5h 16m
United Airlines
Deal found 5/2![United Airlines logo]()
$708
This Delta deal was found by Cheapflights users on 5/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/11:35 pm
AUA
- MDW
1 stop9h 42m
Delta
Fri 7/36:00 am
MDW
- AUA
1 stop7h 10m
Delta
Deal found 5/2![Delta logo]()
$609
This United Airlines deal was found by Cheapflights users on 5/2. 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.
Mon 6/291:50 pm
AUA
- ORD
Nonstop5h 48m
United Airlines
Sat 7/48:44 am
ORD
- AUA
Nonstop5h 16m
United Airlines
Deal found 5/2![United Airlines logo]()
$733
This Delta deal was found by Cheapflights users on 4/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/293:25 pm
AUA
- ORD
1 stop9h 25m
Delta
Mon 11/25:30 am
ORD
- AUA
1 stop7h 40m
Delta
Deal found 4/29![Delta logo]()
$622
This Southwest deal was found by Cheapflights users on 5/3. 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 5/301:30 pm
AUA
- MDW
2 stops10h 05m
Southwest
Mon 6/88:50 pm
MDW
- AUA
2 stops14h 55m
Southwest
Deal found 5/3![Southwest logo]()
$916
This Southwest deal was found by Cheapflights users on 5/3. 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.
Sun 5/242:35 pm
AUA
- MDW
1 stop9h 10m
Southwest
Sun 5/315:05 am
MDW
- AUA
1 stop8h 55m
Southwest
Deal found 5/3![Southwest logo]()
$921
This Southwest deal was found by Cheapflights users on 5/1. 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.
Mon 6/151:45 pm
AUA
- MDW
2 stops10h 15m
Southwest
Mon 6/225:10 am
MDW
- AUA
1 stop8h 35m
Southwest
Deal found 5/1![Southwest logo]()
$946
This Delta deal was found by Cheapflights users on 5/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/301:15 pm
AUA
- MDW
1 stop8h 54m
Delta
Mon 6/86:00 am
MDW
- AUA
1 stop7h 10m
Delta
Deal found 5/3![Delta logo]()
$754
Last-minute flights from Aruba to ChicagoDiscover last-minute flight deals from Aruba to Chicago. Data last updated May 4, 2026 and is based on user searches.
Discover last-minute flight deals from Aruba to Chicago. Data last updated May 4, 2026 and is based on user searches.
This JetBlue deal was found by Cheapflights users on 5/3. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/145:35 pm
AUA
- ORD
1 stop15h 09m
JetBlue
Tue 5/199:49 am
ORD
- AUA
1 stop28h 51m
JetBlue
Deal found 5/3![JetBlue logo]()
$669
This JetBlue deal was found by Cheapflights users on 5/2. 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.
Sat 5/234:30 pm
AUA
- ORD
1 stop16h 30m
JetBlue
Sun 5/318:30 pm
ORD
- AUA
1 stop18h 10m
JetBlue
Deal found 5/2![JetBlue logo]()
$519
This Kissandfly.com deal was found by Cheapflights users on 5/2. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/231:50 pm
AUA
- ORD
Nonstop5h 48m
Lufthansa
Sun 5/319:14 am
ORD
- AUA
Nonstop5h 16m
Lufthansa
Deal found 5/2![Lufthansa logo]()
$674
This Southwest deal was found by Cheapflights users on 5/2. 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.
Sat 5/231:30 pm
AUA
- MDW
1 stop7h 55m
Southwest
Sun 5/315:05 am
MDW
- AUA
1 stop8h 55m
Southwest
Deal found 5/2![Southwest logo]()
$705
This Flighttix deal was found by Cheapflights users on 5/3. 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 Flighttix is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/2411:50 am
AUA
- ORD
1 stop10h 30m
Multiple Airlines
Sun 5/316:15 am
ORD
- AUA
1 stop9h 38m
Multiple Airlines
Deal found 5/3![Multiple Airlines logo]()
$664
This Delta deal was found by Cheapflights users on 4/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/283:25 pm
AUA
- ORD
1 stop9h 34m
Delta
Wed 6/35:30 am
ORD
- AUA
1 stop7h 40m
Delta
Deal found 4/30![Delta logo]()
$605
This Kissandfly.com deal was found by Cheapflights users on 4/30. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/281:50 pm
AUA
- ORD
Nonstop5h 48m
Lufthansa
Wed 6/38:54 am
ORD
- AUA
Nonstop5h 16m
Lufthansa
Deal found 4/30![Lufthansa logo]()
$617
This American Airlines deal was found by Cheapflights users on 4/30. 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 5/282:33 pm
AUA
- ORD
2 stops10h 26m
American Airlines
Wed 6/36:55 am
ORD
- AUA
1 stop7h 45m
American Airlines
Deal found 4/30![American Airlines logo]()
$623
This Flysmarter deal was found by Cheapflights users on 4/30. 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 Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/286:00 pm
AUA
- ORD
1 stop15h 00m
Multiple Airlines
Wed 6/38:54 am
ORD
- AUA
Nonstop5h 16m
Multiple Airlines
Deal found 4/30![Multiple Airlines logo]()
$634
This Expedia deal was found by Cheapflights users on 5/3. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/303:05 pm
AUA
- ORD
1 stop23h 20m
Multiple Airlines
Mon 6/88:30 pm
ORD
- AUA
1 stop15h 00m
Multiple Airlines
Deal found 5/3![Multiple Airlines logo]()
$489
This Expedia deal was found by Cheapflights users on 5/3. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/3011:55 am
AUA
- ORD
2 stops21h 05m
JetBlue
Mon 6/88:30 pm
ORD
- AUA
2 stops17h 50m
JetBlue
Deal found 5/3![JetBlue logo]()
$667
This Kissandfly.com deal was found by Cheapflights users on 5/2. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/301:50 pm
AUA
- ORD
Nonstop5h 48m
Lufthansa
Sun 6/79:14 am
ORD
- AUA
Nonstop5h 16m
Lufthansa
Deal found 5/2![Lufthansa logo]()
$672
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 May 4, 2026.
Search for one-way flight options from Aruba to Chicago. Find affordable one-way fares based on user searches. Data last updated May 4, 2026.
This Trip.com deal was found by Cheapflights users on 5/2. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/303:05 pm
AUA
- ORD
1 stop26h 54m
Air Canada
Deal found 5/2![Air Canada logo]()
$214
This Kiwi.com deal was found by Cheapflights users on 4/30. 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.
Fri 5/153:41 pm
AUA
- ORD
1 stop8h 34m
Spirit Airlines
Deal found 4/30![Spirit Airlines logo]()
$239
This Kiwi.com deal was found by Cheapflights users on 4/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/293:41 pm
AUA
- ORD
1 stop8h 34m
Spirit Airlines
Deal found 4/29![Spirit Airlines logo]()
$242
This Priceline deal was found by Cheapflights users on 4/30. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/273:05 pm
AUA
- ORD
2 stops17h 40m
Air Canada
Deal found 4/30![Air Canada logo]()
$244
This OneTravel deal was found by Cheapflights users on 5/2. 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 OneTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/203:05 pm
AUA
- ORD
1 stop23h 17m
Air Canada
Deal found 5/2![Air Canada logo]()
$248
This Air Canada deal was found by Cheapflights users on 4/29. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/233:05 pm
AUA
- ORD
2 stops28h 39m
Air Canada
Deal found 4/29![Air Canada logo]()
$251
This Kiwi.com deal was found by Cheapflights users on 4/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/243:41 pm
AUA
- ORD
1 stop9h 18m
Spirit Airlines
Deal found 4/29![Spirit Airlines logo]()
$257
This Kiwi.com deal was found by Cheapflights users on 4/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/253:41 pm
AUA
- ORD
2 stops41h 14m
Multiple Airlines
Deal found 4/29![Multiple Airlines logo]()
$266
This Kiwi.com deal was found by Cheapflights users on 4/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/293:41 pm
AUA
- ORD
2 stops17h 14m
Multiple Airlines
Deal found 4/29![Multiple Airlines logo]()
$274
This Kiwi.com deal was found by Cheapflights users on 5/2. 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.
Tue 6/233:05 pm
AUA
- MDW
1 stop19h 35m
Multiple Airlines
Deal found 5/2![Multiple Airlines logo]()
$311
This Kiwi.com deal was found by Cheapflights users on 4/30. 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.
Fri 5/153:41 pm
AUA
- MDW
2 stops31h 21m
Multiple Airlines
Deal found 4/30![Multiple Airlines logo]()
$316
This Kiwi.com deal was found by Cheapflights users on 5/2. 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.
Wed 6/1711:50 am
AUA
- MDW
2 stops22h 50m
Multiple Airlines
Deal found 5/2![Multiple Airlines logo]()
$362
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 4, 2026.
Round-trip from | $416 (Orbitz) |
|---|---|
One-way from | $214 (Trip.com) |
Good round-trip deal | $232 or less |
Good one-way deal | $231 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 May 4, 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 - MDW
AUAMDW
Oranjestad Reina Beatrix
Wed 7/1
1:35 pm-10:17 pm
1 stop9h 42m
Chicago Midway
Wed 7/8
9:19 am-12:40 pm
2 stops26h 21m
$574
OranjestadChicago
AUA - MDW
AUAMDW
Oranjestad Reina Beatrix
Fri 7/3
3:25 pm-12:46 pm
2 stops22h 21m
Chicago Midway
Wed 7/8
1:18 pm-2:10 pm
2 stops23h 52m
$574
OranjestadChicago
AUA - ORD
AUAORD
Oranjestad Reina Beatrix
Fri 7/3
3:25 pm-11:59 pm
1 stop9h 34m
Chicago O'Hare Intl
Sun 7/5
5:30 am-2:10 pm
1 stop7h 40m
$574
OranjestadChicago
AUA - ORD
AUAORD
Oranjestad Reina Beatrix
Mon 6/15
5:50 pm-9:00 am
1 stop16h 10m
Chicago O'Hare Intl
Mon 6/22
9:19 am-3:35 pm
Nonstop5h 16m
$608
OranjestadChicago
AUA - MDW
AUAMDW
Oranjestad Reina Beatrix
Wed 7/1
1:35 pm-10:17 pm
1 stop9h 42m
Chicago Midway
Thu 7/9
6:00 am-2:10 pm
1 stop7h 10m
$609
OranjestadChicago
AUA - MDW
AUAMDW
Oranjestad Reina Beatrix
Wed 7/1
1:35 pm-10:17 pm
1 stop9h 42m
Chicago Midway
Fri 7/3
6:00 am-2:10 pm
1 stop7h 10m
$609
OranjestadChicago
AUA - ORD
AUAORD
Oranjestad Reina Beatrix
Mon 6/15
1:59 pm-6:57 am
1 stop17h 58m
Chicago O'Hare Intl
Mon 6/22
5:00 am-4:59 pm
2 stops10h 59m
$617
OranjestadChicago
AUA - ORD
AUAORD
Oranjestad Reina Beatrix
Sat 6/13
3:41 pm-12:23 pm
2 stops21h 42m
Chicago O'Hare Intl
Sat 6/20
10:27 am-10:15 am
3 stops22h 48m
$621
OranjestadChicago
AUA - ORD
AUAORD
Oranjestad Reina Beatrix
Thu 10/29
3:25 pm-11:50 pm
1 stop9h 25m
Chicago O'Hare Intl
Mon 11/2
5:30 am-3:10 pm
1 stop7h 40m
$622
Quickest round-trip
OranjestadChicago
AUA - ORD
AUAORD
Oranjestad Reina Beatrix
Wed 7/1
1:50 pm-6:38 pm
Nonstop5h 48m
Chicago O'Hare Intl
Mon 7/6
9:19 am-3:35 pm
Nonstop5h 16m
$643
Showing 1-10 of 41 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 May 4, 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.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Hammond
Porter
Browse thousands of different options on Cheapflights for your next trip
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Alternative routes
Chicago flight routes
Complete your trip
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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.
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 May 4, 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 May 4, 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 May 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$343 | Average$562 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$464 | Average$735 | FlexibilityNo cancel fee | On-time71% |