$163+ 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 5/15. Fares are subject to change and may not be available on all flights or dates of travel.
AUA — CHI
May 19 — May 261
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 April 19, 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 19, 2026.
This Travelocity deal was found by Cheapflights users on 4/18. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/194:15 pm
AUA
- ORD
1 stop26h 35m
Air Canada
Sun 4/266:40 pm
ORD
- AUA
1 stop19h 35m
Air Canada
Deal found 4/18![Air Canada logo]()
$455
This Air Canada deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/204:05 pm
AUA
- ORD
2 stops19h 48m
Air Canada
Mon 4/276:40 pm
ORD
- AUA
1 stop19h 35m
Air Canada
Deal found 4/15![Air Canada logo]()
$458
This Mytrip deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/83:41 pm
AUA
- ORD
1 stop8h 34m
Spirit Airlines
Sun 5/179:20 am
ORD
- AUA
3 stops28h 16m
Spirit Airlines
Deal found 4/14![Spirit Airlines logo]()
$479
This Air Canada deal was found by Cheapflights users on 4/18. 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 4/184:05 pm
AUA
- ORD
2 stops19h 48m
Air Canada
Wed 4/221:55 pm
ORD
- AUA
2 stops24h 20m
Air Canada
Deal found 4/18![Air Canada logo]()
$480
This Mytrip deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/303:41 pm
AUA
- ORD
1 stop17h 41m
Spirit Airlines
Sat 6/65:05 am
ORD
- AUA
1 stop8h 31m
Spirit Airlines
Deal found 4/15![Spirit Airlines logo]()
$492
This Mytrip deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/284:05 pm
AUA
- ORD
1 stop22h 00m
Multiple Airlines
Sun 5/36:40 am
ORD
- AUA
3 stops30h 56m
Multiple Airlines
Deal found 4/17![Multiple Airlines logo]()
$500
This Kiwi.com deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/303:41 pm
AUA
- ORD
2 stops17h 14m
Multiple Airlines
Sat 6/65:05 am
ORD
- AUA
1 stop8h 31m
Multiple Airlines
Deal found 4/15![Multiple Airlines logo]()
$514
This Southwest deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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 4/16![Southwest logo]()
$641
This Delta deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/213:25 pm
AUA
- MDW
2 stops18h 18m
Delta
Wed 5/275:12 pm
MDW
- AUA
1 stop17h 48m
Delta
Deal found 4/17![Delta logo]()
$642
This Southwest deal was found by Cheapflights users on 4/18. 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.
Tue 6/22:35 pm
AUA
- MDW
1 stop7h 50m
Southwest
Tue 6/96:00 pm
MDW
- AUA
2 stops17h 45m
Southwest
Deal found 4/18![Southwest logo]()
$696
This Mytrip deal was found by Cheapflights users on 4/18. 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.
Thu 5/215:20 pm
AUA
- MDW
2 stops22h 15m
Multiple Airlines
Wed 5/2710:30 am
MDW
- AUA
3 stops28h 20m
Multiple Airlines
Deal found 4/18![Multiple Airlines logo]()
$709
This Southwest deal was found by Cheapflights users on 4/18. 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 4/181:30 pm
AUA
- MDW
1 stop7h 55m
Southwest
Wed 4/226:00 am
MDW
- AUA
1 stop6h 45m
Southwest
Deal found 4/18![Southwest logo]()
$961
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 19, 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 19, 2026.
This United Airlines deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/293:10 pm
AUA
- ORD
1 stop10h 35m
United Airlines
Wed 8/55:00 am
ORD
- AUA
1 stop10h 40m
United Airlines
Deal found 4/14![United Airlines logo]()
$628
This Delta deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/293:25 pm
AUA
- ORD
2 stops17h 34m
Delta
Tue 8/47:17 pm
ORD
- AUA
2 stops17h 53m
Delta
Deal found 4/14![Delta logo]()
$628
This Southwest deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/212:35 pm
AUA
- ORD
1 stop8h 20m
Southwest
Wed 5/275:55 am
ORD
- AUA
1 stop6h 40m
Southwest
Deal found 4/16![Southwest logo]()
$631
This Avianca deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2111:50 am
AUA
- ORD
1 stop10h 30m
Avianca
Wed 5/2711:20 pm
ORD
- AUA
1 stop10h 25m
Avianca
Deal found 4/14![Avianca logo]()
$639
This American Airlines deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/82:34 pm
AUA
- ORD
2 stops10h 25m
American Airlines
Mon 7/207:59 am
ORD
- AUA
1 stop7h 10m
American Airlines
Deal found 4/14![American Airlines logo]()
$646
This United Airlines deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/293:10 pm
AUA
- ORD
1 stop10h 35m
United Airlines
Tue 8/45:30 am
ORD
- AUA
1 stop8h 50m
United Airlines
Deal found 4/14![United Airlines logo]()
$628
This Southwest deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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 4/16![Southwest logo]()
$641
This Delta deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/213:25 pm
AUA
- MDW
2 stops18h 18m
Delta
Wed 5/275:12 pm
MDW
- AUA
1 stop17h 48m
Delta
Deal found 4/17![Delta logo]()
$642
This United Airlines deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/81:50 pm
AUA
- ORD
Nonstop5h 48m
United Airlines
Mon 7/209:19 am
ORD
- AUA
Nonstop5h 16m
United Airlines
Deal found 4/14![United Airlines logo]()
$637
This Delta deal was found by Cheapflights users on 4/19. 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
- ORD
1 stop11h 44m
Delta
Wed 5/275:30 am
ORD
- AUA
1 stop7h 40m
Delta
Deal found 4/19![Delta logo]()
$642
This Southwest deal was found by Cheapflights users on 4/18. 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.
Tue 6/22:35 pm
AUA
- MDW
1 stop7h 50m
Southwest
Tue 6/96:00 pm
MDW
- AUA
2 stops17h 45m
Southwest
Deal found 4/18![Southwest logo]()
$696
This United Airlines deal was found by Cheapflights users on 4/18. 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.
Tue 6/21:50 pm
AUA
- ORD
Nonstop5h 48m
United Airlines
Tue 6/99:19 am
ORD
- AUA
Nonstop5h 16m
United Airlines
Deal found 4/18![United Airlines logo]()
$637
Last-minute flights from Aruba to ChicagoDiscover last-minute flight deals from Aruba to Chicago. Data last updated April 19, 2026 and is based on user searches.
Discover last-minute flight deals from Aruba to Chicago. Data last updated April 19, 2026 and is based on user searches.
This Air Canada deal was found by Cheapflights users on 4/18. 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 4/184:05 pm
AUA
- ORD
2 stops19h 48m
Air Canada
Wed 4/221:55 pm
ORD
- AUA
2 stops24h 20m
Air Canada
Deal found 4/18![Air Canada logo]()
$480
This Southwest deal was found by Cheapflights users on 4/18. 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 4/181:30 pm
AUA
- MDW
1 stop7h 55m
Southwest
Wed 4/226:00 am
MDW
- AUA
1 stop6h 45m
Southwest
Deal found 4/18![Southwest logo]()
$961
This Travelocity deal was found by Cheapflights users on 4/18. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/194:15 pm
AUA
- ORD
1 stop26h 35m
Air Canada
Sun 4/266:40 pm
ORD
- AUA
1 stop19h 35m
Air Canada
Deal found 4/18![Air Canada logo]()
$455
This Delta deal was found by Cheapflights users on 4/19. 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.
Sun 4/193:25 pm
AUA
- MDW
1 stop8h 03m
Delta
Thu 4/2312:52 pm
MDW
- AUA
2 stops22h 48m
Delta
Deal found 4/19![Delta logo]()
$1,049
This Air Canada deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/204:05 pm
AUA
- ORD
2 stops19h 48m
Air Canada
Mon 4/276:40 pm
ORD
- AUA
1 stop19h 35m
Air Canada
Deal found 4/15![Air Canada logo]()
$458
This Mytrip deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/284:05 pm
AUA
- ORD
1 stop22h 00m
Multiple Airlines
Sun 5/36:40 am
ORD
- AUA
3 stops30h 56m
Multiple Airlines
Deal found 4/17![Multiple Airlines logo]()
$500
This Mytrip deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/83:41 pm
AUA
- ORD
1 stop8h 34m
Spirit Airlines
Sun 5/179:20 am
ORD
- AUA
3 stops28h 16m
Spirit Airlines
Deal found 4/14![Spirit Airlines logo]()
$479
This Southwest deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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 4/16![Southwest logo]()
$641
This Delta deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/213:25 pm
AUA
- MDW
2 stops18h 18m
Delta
Wed 5/275:12 pm
MDW
- AUA
1 stop17h 48m
Delta
Deal found 4/17![Delta logo]()
$642
This Mytrip deal was found by Cheapflights users on 4/18. 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.
Thu 5/215:20 pm
AUA
- MDW
2 stops22h 15m
Multiple Airlines
Wed 5/2710:30 am
MDW
- AUA
3 stops28h 20m
Multiple Airlines
Deal found 4/18![Multiple Airlines logo]()
$709
This Mytrip deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/303:41 pm
AUA
- ORD
1 stop17h 41m
Spirit Airlines
Sat 6/65:05 am
ORD
- AUA
1 stop8h 31m
Spirit Airlines
Deal found 4/15![Spirit Airlines logo]()
$492
This Kiwi.com deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/303:41 pm
AUA
- ORD
2 stops17h 14m
Multiple Airlines
Sat 6/65:05 am
ORD
- AUA
1 stop8h 31m
Multiple Airlines
Deal found 4/15![Multiple Airlines logo]()
$514
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 19, 2026.
Search for one-way flight options from Aruba to Chicago. Find affordable one-way fares based on user searches. Data last updated April 19, 2026.
This WAYA deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure WAYA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/153:41 pm
AUA
- ORD
1 stop9h 18m
Multiple Airlines
Deal found 4/16![Multiple Airlines logo]()
$163
This Cheapflightsfares deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/163:41 pm
AUA
- ORD
1 stop8h 34m
Spirit Airlines
Deal found 4/17![Spirit Airlines logo]()
$177
This Kiwi.com deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/163:41 pm
AUA
- ORD
2 stops23h 58m
Multiple Airlines
Deal found 4/17![Multiple Airlines logo]()
$215
This Kiwi.com deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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
Spirit Airlines
Deal found 4/17![Spirit Airlines logo]()
$231
This Kiwi.com deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/223:41 pm
AUA
- ORD
2 stops21h 42m
Spirit Airlines
Deal found 4/17![Spirit Airlines logo]()
$241
This Kiwi.com deal was found by Cheapflights users on 4/19. 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
- MDW
2 stops20h 31m
Multiple Airlines
Deal found 4/19![Multiple Airlines logo]()
$320
This Southwest deal was found by Cheapflights users on 4/18. 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
Deal found 4/18![Southwest logo]()
$363
This Kiwi.com deal was found by Cheapflights users on 4/19. 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 6/215:20 pm
AUA
- MDW
2 stops22h 15m
Multiple Airlines
Deal found 4/19![Multiple Airlines logo]()
$377
This Southwest deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/104:00 pm
AUA
- MDW
1 stop8h 40m
Southwest
Deal found 4/16![Southwest logo]()
$393
This Kiwi.com deal was found by Cheapflights users on 4/19. 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 8/105:20 pm
AUA
- MDW
3 stops29h 51m
Multiple Airlines
Deal found 4/19![Multiple Airlines logo]()
$396
This Kiwi.com deal was found by Cheapflights users on 4/19. 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 8/1511:50 am
AUA
- MDW
3 stops27h 17m
Multiple Airlines
Deal found 4/19![Multiple Airlines logo]()
$397
This Southwest deal was found by Cheapflights users on 4/19. 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.
Wed 6/171:45 pm
AUA
- MDW
2 stops10h 35m
Southwest
Deal found 4/19![Southwest logo]()
$418
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 19, 2026.
Round-trip from | $479 (Mytrip) |
|---|---|
One-way from | $163 (WAYA) |
Good round-trip deal | $308 or less |
Good one-way deal | $297 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 19, 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
Wed 7/29
3:10 pm-12:45 am
1 stop10h 35m
Chicago O'Hare Intl
Wed 8/5
5:00 am-4:40 pm
1 stop10h 40m
$628
OranjestadChicago
AUA - ORD
AUAORD
Oranjestad Reina Beatrix
Wed 7/29
3:25 pm-7:59 am
2 stops17h 34m
Chicago O'Hare Intl
Tue 8/4
7:17 pm-2:10 pm
2 stops17h 53m
$628
OranjestadChicago
AUA - ORD
AUAORD
Oranjestad Reina Beatrix
Wed 7/29
3:10 pm-12:45 am
1 stop10h 35m
Chicago O'Hare Intl
Tue 8/4
5:30 am-3:20 pm
1 stop8h 50m
$628
OranjestadChicago
AUA - ORD
AUAORD
Oranjestad Reina Beatrix
Thu 5/21
2:35 pm-9:55 pm
1 stop8h 20m
Chicago O'Hare Intl
Wed 5/27
5:55 am-1:35 pm
1 stop6h 40m
$631
Quickest round-trip
OranjestadChicago
AUA - ORD
AUAORD
Oranjestad Reina Beatrix
Wed 7/8
1:50 pm-6:38 pm
Nonstop5h 48m
Chicago O'Hare Intl
Mon 7/20
9:19 am-3:35 pm
Nonstop5h 16m
$637
OranjestadChicago
AUA - ORD
AUAORD
Oranjestad Reina Beatrix
Tue 6/2
1:50 pm-6:38 pm
Nonstop5h 48m
Chicago O'Hare Intl
Tue 6/9
9:19 am-3:35 pm
Nonstop5h 16m
$637
OranjestadChicago
AUA - ORD
AUAORD
Oranjestad Reina Beatrix
Thu 5/21
11:50 am-9:20 pm
1 stop10h 30m
Chicago O'Hare Intl
Wed 5/27
11:20 pm-10:45 am
1 stop10h 25m
$639
OranjestadChicago
AUA - MDW
AUAMDW
Oranjestad Reina Beatrix
Thu 5/21
2:35 pm-12:15 am
1 stop10h 40m
Chicago Midway
Wed 5/27
6:00 am-1:35 pm
1 stop6h 35m
$641
OranjestadChicago
AUA - MDW
AUAMDW
Oranjestad Reina Beatrix
Thu 5/21
3:25 pm-8:43 am
2 stops18h 18m
Chicago Midway
Wed 5/27
5:12 pm-12:00 pm
1 stop17h 48m
$642
OranjestadChicago
AUA - ORD
AUAORD
Oranjestad Reina Beatrix
Thu 5/21
1:15 pm-11:59 pm
1 stop11h 44m
Chicago O'Hare Intl
Wed 5/27
5:30 am-2:10 pm
1 stop7h 40m
$642
Showing 1-10 of 33 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 19, 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 19, 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
Lansing
Merrillville
Hammond
Porter
Browse thousands of different options on Cheapflights for your next trip
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Alternative routes
Chicago flight routes
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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 April 19, 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 19, 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 19, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$343 | Average$562 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$451 | Average$710 | FlexibilityNo cancel fee | On-time71% |