$156+ 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 5/8. Fares are subject to change and may not be available on all flights or dates of travel.
AUA — CHI
May 9 — May 161
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
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
Cheapest
Best
Last-minute
One-way
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 April 9, 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 April 9, 2026.
This Gotogate deal was found by Cheapflights users on 4/7. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/253:41 pm
AUA
- ORD
1 stop9h 43m
Spirit Airlines
Mon 5/45:05 am
ORD
- AUA
1 stop8h 31m
Spirit Airlines
Deal found 4/7![Spirit Airlines logo]()
$210
This Expedia deal was found by Cheapflights users on 4/8. 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 5/233:41 pm
AUA
- ORD
1 stop8h 34m
Spirit Airlines
Sat 5/305:05 am
ORD
- AUA
1 stop8h 31m
Spirit Airlines
Deal found 4/8![Spirit Airlines logo]()
$360
This Kiwi.com deal was found by Cheapflights users on 4/8. 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 5/233:41 pm
AUA
- ORD
1 stop17h 41m
Multiple Airlines
Sat 5/307:52 pm
ORD
- AUA
2 stops41h 44m
Multiple Airlines
Deal found 4/8![Multiple Airlines logo]()
$364
This Cheapflightsfares deal was found by Cheapflights users on 4/8. 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 5/83:41 pm
AUA
- ORD
1 stop17h 41m
Spirit Airlines
Fri 5/157:33 pm
ORD
- AUA
1 stop18h 03m
Spirit Airlines
Deal found 4/8![Spirit Airlines logo]()
$388
This Kiwi.com deal was found by Cheapflights users on 4/8. 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 5/83:41 pm
AUA
- ORD
1 stop9h 18m
Multiple Airlines
Fri 5/155:05 am
ORD
- AUA
1 stop8h 31m
Multiple Airlines
Deal found 4/8![Multiple Airlines logo]()
$391
This Kiwi.com deal was found by Cheapflights users on 4/6. 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 5/43:41 pm
AUA
- ORD
1 stop20h 38m
Spirit Airlines
Mon 5/115:05 am
ORD
- AUA
1 stop8h 31m
Spirit Airlines
Deal found 4/6![Spirit Airlines logo]()
$445
This Air Canada deal was found by Cheapflights users on 4/7. 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.
Tue 4/74:15 pm
AUA
- ORD
2 stops19h 38m
Air Canada
Sat 4/116:40 pm
ORD
- AUA
1 stop19h 35m
Air Canada
Deal found 4/7![Air Canada logo]()
$447
This Delta deal was found by Cheapflights users on 4/8. 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 5/211:15 pm
AUA
- MDW
1 stop8h 54m
Delta
Wed 5/275:12 pm
MDW
- AUA
1 stop17h 48m
Delta
Deal found 4/8![Delta logo]()
$541
This Kiwi.com deal was found by Cheapflights users on 4/9. 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.
Thu 5/213:05 pm
AUA
- MDW
1 stop24h 30m
Multiple Airlines
Wed 5/273:20 pm
MDW
- AUA
2 stops18h 25m
Multiple Airlines
Deal found 4/9![Multiple Airlines logo]()
$576
This Delta deal was found by Cheapflights users on 4/8. 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 9/173:25 pm
AUA
- MDW
1 stop7h 21m
Delta
Tue 9/226:00 am
MDW
- AUA
1 stop7h 10m
Delta
Deal found 4/8![Delta logo]()
$622
This Delta deal was found by Cheapflights users on 4/8. 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 4/301:10 pm
AUA
- MDW
1 stop10h 18m
Delta
Wed 5/66:00 am
MDW
- AUA
2 stops29h 40m
Delta
Deal found 4/8![Delta logo]()
$624
This Southwest deal was found by Cheapflights users on 4/9. 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 5/212:35 pm
AUA
- MDW
1 stop10h 40m
Southwest
Wed 5/276:00 am
MDW
- AUA
1 stop6h 35m
Southwest
Deal found 4/9![Southwest logo]()
$651
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 April 9, 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 April 9, 2026.
This Flightnetwork deal was found by Cheapflights users on 4/7. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/253:41 pm
AUA
- ORD
2 stops8h 26m
Spirit Airlines
Mon 5/45:05 am
ORD
- AUA
1 stop8h 31m
Spirit Airlines
Deal found 4/7![Spirit Airlines logo]()
$276
This Priceline deal was found by Cheapflights users on 4/6. 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.
Fri 6/53:41 pm
AUA
- ORD
1 stop8h 34m
Multiple Airlines
Fri 6/121:55 pm
ORD
- AUA
2 stops23h 20m
Multiple Airlines
Deal found 4/6![Multiple Airlines logo]()
$473
This Delta deal was found by Cheapflights users on 4/9. 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 5/213:25 pm
AUA
- ORD
1 stop7h 28m
Delta
Wed 5/277:55 pm
ORD
- AUA
1 stop15h 05m
Delta
Deal found 4/9![Delta logo]()
$540
This United Airlines deal was found by Cheapflights users on 4/8. 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.
Fri 5/84:30 pm
AUA
- ORD
1 stop8h 14m
United Airlines
Fri 5/1511:00 pm
ORD
- AUA
1 stop15h 40m
United Airlines
Deal found 4/8![United Airlines logo]()
$584
This JetBlue deal was found by Cheapflights users on 4/5. 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 5/215:00 pm
AUA
- ORD
1 stop16h 00m
JetBlue
Wed 5/278:30 pm
ORD
- AUA
1 stop19h 16m
JetBlue
Deal found 4/5![JetBlue logo]()
$596
This American Airlines deal was found by Cheapflights users on 4/4. 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 5/211:59 pm
AUA
- ORD
1 stop11h 36m
American Airlines
Wed 5/277:00 am
ORD
- AUA
1 stop8h 59m
American Airlines
Deal found 4/4![American Airlines logo]()
$607
This Copa Airlines deal was found by Cheapflights users on 4/8. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/161:20 pm
AUA
- ORD
1 stop12h 42m
Copa Airlines
Wed 9/238:01 am
ORD
- AUA
1 stop12h 57m
Copa Airlines
Deal found 4/8![Copa Airlines logo]()
$613
This Southwest deal was found by Cheapflights users on 4/9. 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 5/212:35 pm
AUA
- MDW
1 stop10h 40m
Southwest
Wed 5/276:00 am
MDW
- AUA
1 stop6h 35m
Southwest
Deal found 4/9![Southwest logo]()
$651
This Expedia deal was found by Cheapflights users on 4/5. 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.
Wed 4/224:05 pm
AUA
- ORD
1 stop26h 45m
Multiple Airlines
Thu 4/306:00 am
ORD
- AUA
1 stop8h 40m
Multiple Airlines
Deal found 4/5![Multiple Airlines logo]()
$543
This Delta deal was found by Cheapflights users on 4/9. 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 5/211:15 pm
AUA
- MDW
1 stop8h 54m
Delta
Wed 5/275:12 pm
MDW
- AUA
1 stop17h 48m
Delta
Deal found 4/9![Delta logo]()
$547
This Southwest deal was found by Cheapflights users on 4/8. 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 9/171:45 pm
AUA
- MDW
1 stop9h 55m
Southwest
Tue 9/225:20 pm
MDW
- AUA
2 stops18h 25m
Southwest
Deal found 4/8![Southwest logo]()
$656
This Delta deal was found by Cheapflights users on 4/8. 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 9/173:25 pm
AUA
- MDW
1 stop7h 21m
Delta
Tue 9/226:00 am
MDW
- AUA
1 stop7h 10m
Delta
Deal found 4/8![Delta logo]()
$622
This Southwest deal was found by Cheapflights users on 4/8. 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 4/302:45 pm
AUA
- MDW
2 stops17h 25m
Southwest
Wed 5/66:50 pm
MDW
- AUA
2 stops17h 45m
Southwest
Deal found 4/8![Southwest logo]()
$666
This Delta deal was found by Cheapflights users on 4/8. 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 4/303:25 pm
AUA
- MDW
1 stop8h 03m
Delta
Wed 5/66:00 am
MDW
- AUA
1 stop7h 10m
Delta
Deal found 4/8![Delta logo]()
$622
This Delta deal was found by Cheapflights users on 4/8. 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 9/173:25 pm
AUA
- ORD
1 stop9h 32m
Delta
Tue 9/225:30 am
ORD
- AUA
1 stop7h 40m
Delta
Deal found 4/8![Delta logo]()
$622
Last-minute flights from Aruba to ChicagoDiscover last-minute flight deals from Aruba to Chicago. Data last updated April 9, 2026 and is based on user searches.
Discover last-minute flight deals from Aruba to Chicago. Data last updated April 9, 2026 and is based on user searches.
This Mytrip deal was found by Cheapflights users on 4/5. 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.
Wed 4/224:05 pm
AUA
- ORD
2 stops27h 53m
Air Canada
Thu 4/306:21 pm
ORD
- AUA
2 stops42h 54m
Air Canada
Deal found 4/5![Air Canada logo]()
$473
This Gotogate deal was found by Cheapflights users on 4/7. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/253:41 pm
AUA
- ORD
1 stop9h 43m
Spirit Airlines
Mon 5/45:05 am
ORD
- AUA
1 stop8h 31m
Spirit Airlines
Deal found 4/7![Spirit Airlines logo]()
$210
This Delta deal was found by Cheapflights users on 4/8. 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 4/303:25 pm
AUA
- MDW
1 stop8h 03m
Delta
Wed 5/66:00 am
MDW
- AUA
1 stop7h 10m
Delta
Deal found 4/8![Delta logo]()
$622
This Kiwi.com deal was found by Cheapflights users on 4/6. 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 5/43:41 pm
AUA
- ORD
1 stop20h 38m
Spirit Airlines
Mon 5/115:05 am
ORD
- AUA
1 stop8h 31m
Spirit Airlines
Deal found 4/6![Spirit Airlines logo]()
$445
This Kiwi.com deal was found by Cheapflights users on 4/6. 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 5/43:41 pm
AUA
- ORD
2 stops17h 14m
Multiple Airlines
Mon 5/115:05 am
ORD
- AUA
1 stop8h 31m
Multiple Airlines
Deal found 4/6![Multiple Airlines logo]()
$470
This Cheapflightsfares deal was found by Cheapflights users on 4/8. 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 5/83:41 pm
AUA
- ORD
1 stop17h 41m
Spirit Airlines
Fri 5/157:33 pm
ORD
- AUA
1 stop18h 03m
Spirit Airlines
Deal found 4/8![Spirit Airlines logo]()
$388
This Kiwi.com deal was found by Cheapflights users on 4/8. 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 5/83:41 pm
AUA
- ORD
1 stop9h 18m
Multiple Airlines
Fri 5/155:05 am
ORD
- AUA
1 stop8h 31m
Multiple Airlines
Deal found 4/8![Multiple Airlines logo]()
$391
This Delta deal was found by Cheapflights users on 4/8. 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 5/211:15 pm
AUA
- MDW
1 stop8h 54m
Delta
Wed 5/275:12 pm
MDW
- AUA
1 stop17h 48m
Delta
Deal found 4/8![Delta logo]()
$541
This Kiwi.com deal was found by Cheapflights users on 4/9. 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.
Thu 5/213:05 pm
AUA
- MDW
1 stop24h 30m
Multiple Airlines
Wed 5/273:20 pm
MDW
- AUA
2 stops18h 25m
Multiple Airlines
Deal found 4/9![Multiple Airlines logo]()
$576
This Southwest deal was found by Cheapflights users on 4/9. 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 5/212:35 pm
AUA
- MDW
1 stop10h 40m
Southwest
Wed 5/276:00 am
MDW
- AUA
1 stop6h 35m
Southwest
Deal found 4/9![Southwest logo]()
$651
This Expedia deal was found by Cheapflights users on 4/8. 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 5/233:41 pm
AUA
- ORD
1 stop8h 34m
Spirit Airlines
Sat 5/305:05 am
ORD
- AUA
1 stop8h 31m
Spirit Airlines
Deal found 4/8![Spirit Airlines logo]()
$360
This Kiwi.com deal was found by Cheapflights users on 4/8. 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 5/233:41 pm
AUA
- ORD
1 stop17h 41m
Multiple Airlines
Sat 5/307:52 pm
ORD
- AUA
2 stops41h 44m
Multiple Airlines
Deal found 4/8![Multiple Airlines logo]()
$364
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 April 9, 2026.
Search for one-way flight options from Aruba to Chicago. Find affordable one-way fares based on user searches. Data last updated April 9, 2026.
This WAYA deal was found by Cheapflights users on 4/9. 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 WAYA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/83:41 pm
AUA
- ORD
1 stop9h 18m
Multiple Airlines
Deal found 4/9![Multiple Airlines logo]()
$156
This Kiwi.com deal was found by Cheapflights users on 4/8. 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 5/93:41 pm
AUA
- ORD
1 stop8h 34m
Spirit Airlines
Deal found 4/8![Spirit Airlines logo]()
$184
This Kiwi.com deal was found by Cheapflights users on 4/5. 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 5/13:41 pm
AUA
- ORD
2 stops30h 31m
Multiple Airlines
Deal found 4/5![Multiple Airlines logo]()
$189
This Kiwi.com deal was found by Cheapflights users on 4/7. 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 7/33:41 pm
AUA
- ORD
1 stop21h 44m
Multiple Airlines
Deal found 4/7![Multiple Airlines logo]()
$192
This Kiwi.com deal was found by Cheapflights users on 4/9. 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 5/113:41 pm
AUA
- ORD
2 stops29h 10m
Multiple Airlines
Deal found 4/9![Multiple Airlines logo]()
$201
This Kiwi.com deal was found by Cheapflights users on 4/5. 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 5/23:41 pm
AUA
- ORD
2 stops31h 58m
Multiple Airlines
Deal found 4/5![Multiple Airlines logo]()
$215
This Kiwi.com deal was found by Cheapflights users on 4/8. 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 5/93:41 pm
AUA
- ORD
2 stops17h 14m
Multiple Airlines
Deal found 4/8![Multiple Airlines logo]()
$219
This Air Canada deal was found by Cheapflights users on 4/6. 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 6/63:05 pm
AUA
- ORD
1 stop18h 55m
Air Canada
Deal found 4/6![Air Canada logo]()
$220
This Kiwi.com deal was found by Cheapflights users on 4/8. 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 4/273:41 pm
AUA
- MDW
2 stops28h 50m
Multiple Airlines
Deal found 4/8![Multiple Airlines logo]()
$251
This Southwest deal was found by Cheapflights users on 4/6. 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 9/101:45 pm
AUA
- MDW
1 stop9h 55m
Southwest
Deal found 4/6![Southwest logo]()
$353
This Southwest deal was found by Cheapflights users on 4/5. 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
Deal found 4/5![Southwest logo]()
$383
This Southwest deal was found by Cheapflights users on 4/6. 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 7/61:45 pm
AUA
- MDW
2 stops11h 30m
Southwest
Deal found 4/6![Southwest logo]()
$388
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 April 9, 2026.
Round-trip from | $210 (Gotogate) |
|---|---|
One-way from | $156 (WAYA) |
Good round-trip deal | $343 or less |
Good one-way deal | $334 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 April 9, 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
Sat 4/25
3:41 pm-11:07 pm
2 stops8h 26m
Chicago O'Hare Intl
Mon 5/4
5:05 am-2:36 pm
1 stop8h 31m
$276
OranjestadChicago
AUA - ORD
AUAORD
Oranjestad Reina Beatrix
Fri 6/5
3:41 pm-11:15 pm
1 stop8h 34m
Chicago O'Hare Intl
Fri 6/12
1:55 pm-2:15 pm
2 stops23h 20m
$473
OranjestadChicago
AUA - ORD
AUAORD
Oranjestad Reina Beatrix
Thu 5/21
3:25 pm-9:53 pm
1 stop7h 28m
Chicago O'Hare Intl
Wed 5/27
7:55 pm-12:00 pm
1 stop15h 05m
$540
OranjestadChicago
AUA - ORD
AUAORD
Oranjestad Reina Beatrix
Wed 4/22
4:05 pm-5:50 pm
1 stop26h 45m
Chicago O'Hare Intl
Thu 4/30
6:00 am-3:40 pm
1 stop8h 40m
$543
OranjestadChicago
AUA - MDW
AUAMDW
Oranjestad Reina Beatrix
Thu 5/21
1:15 pm-9:09 pm
1 stop8h 54m
Chicago Midway
Wed 5/27
5:12 pm-12:00 pm
1 stop17h 48m
$547
OranjestadChicago
AUA - ORD
AUAORD
Oranjestad Reina Beatrix
Fri 5/8
4:30 pm-11:44 pm
1 stop8h 14m
Chicago O'Hare Intl
Fri 5/15
11:00 pm-3:40 pm
1 stop15h 40m
$584
OranjestadChicago
AUA - ORD
AUAORD
Oranjestad Reina Beatrix
Thu 5/21
5:00 pm-8:00 am
1 stop16h 00m
Chicago O'Hare Intl
Wed 5/27
8:30 pm-4:46 pm
1 stop19h 16m
$596
OranjestadChicago
AUA - ORD
AUAORD
Oranjestad Reina Beatrix
Thu 5/21
1:59 pm-12:35 am
1 stop11h 36m
Chicago O'Hare Intl
Wed 5/27
7:00 am-4:59 pm
1 stop8h 59m
$607
OranjestadChicago
AUA - ORD
AUAORD
Oranjestad Reina Beatrix
Wed 9/16
1:20 pm-1:02 am
1 stop12h 42m
Chicago O'Hare Intl
Wed 9/23
8:01 am-9:58 pm
1 stop12h 57m
$613
Quickest round-trip
OranjestadChicago
AUA - MDW
AUAMDW
Oranjestad Reina Beatrix
Thu 9/17
3:25 pm-9:46 pm
1 stop7h 21m
Chicago Midway
Tue 9/22
6:00 am-2:10 pm
1 stop7h 10m
$622
Showing 1-10 of 34 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 April 9, 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 April 9, 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 locationsLansing
Merrillville
Hammond
Porter
Benton Harbor
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
Other flight options
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 April 9, 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 April 9, 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 April 9, 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% |