$227+ Cheap flights from Aruba to Chicago (CHI)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/12. Fares are subject to change and may not be available on all flights or dates of travel.
AUA — CHI
Jun 17 — Jun 241
Round-trip
1 adult, Economy
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Find cheap flights from Aruba to Chicago with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Aruba to Chicago
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Cheapest flights from Aruba to ChicagoExplore the most affordable flight options available from Aruba to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 18, 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 18, 2026.
This Flysmarter deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/26:00 pm
AUA
- ORD
1 stop15h 45m
JetBlue
Wed 7/88:20 pm
ORD
- AUA
1 stop18h 10m
JetBlue
Deal found 5/17![JetBlue logo]()
$505
This Flysmarter deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/251:35 pm
AUA
- ORD
1 stop8h 55m
JetBlue
Wed 7/18:20 pm
ORD
- AUA
1 stop17h 50m
JetBlue
Deal found 5/16![JetBlue logo]()
$580
This Avianca deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/2511:50 am
AUA
- ORD
1 stop10h 30m
Avianca
Wed 7/111:20 pm
ORD
- AUA
1 stop10h 25m
Avianca
Deal found 5/15![Avianca logo]()
$612
This Vliegwinkel deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Vliegwinkel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/115:20 pm
AUA
- ORD
1 stop29h 00m
Avianca
Wed 6/1711:20 pm
ORD
- AUA
1 stop10h 25m
Avianca
Deal found 5/14![Avianca logo]()
$622
This Delta deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/23:25 pm
AUA
- MDW
1 stop7h 52m
Delta
Wed 7/86:00 am
MDW
- AUA
1 stop7h 10m
Delta
Deal found 5/17![Delta logo]()
$642
This American Airlines deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/253:00 pm
AUA
- ORD
1 stop9h 58m
American Airlines
Wed 7/18:30 am
ORD
- AUA
1 stop7h 29m
American Airlines
Deal found 5/13![American Airlines logo]()
$646
This Southwest deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/251:45 pm
AUA
- MDW
2 stops18h 25m
Southwest
Wed 7/14:40 pm
MDW
- AUA
2 stops19h 05m
Southwest
Deal found 5/15![Southwest logo]()
$650
This Cheapflightsfares deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/226:00 pm
AUA
- ORD
1 stop20h 01m
JetBlue
Thu 6/48:30 pm
ORD
- AUA
1 stop15h 00m
JetBlue
Deal found 5/13![JetBlue logo]()
$658
This Delta deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/253:25 pm
AUA
- ORD
1 stop9h 34m
Delta
Wed 7/15:30 am
ORD
- AUA
1 stop7h 40m
Delta
Deal found 5/17![Delta logo]()
$674
This Cheapflightsfares deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/111:35 pm
AUA
- ORD
1 stop8h 55m
JetBlue
Wed 6/176:27 pm
ORD
- AUA
1 stop16h 47m
JetBlue
Deal found 5/15![JetBlue logo]()
$675
This Delta deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/253:25 pm
AUA
- MDW
1 stop7h 52m
Delta
Wed 7/16:00 am
MDW
- AUA
1 stop7h 10m
Delta
Deal found 5/13![Delta logo]()
$676
This United Airlines deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/111:50 pm
AUA
- ORD
Nonstop5h 48m
United Airlines
Wed 6/179:19 am
ORD
- AUA
Nonstop5h 16m
United Airlines
Deal found 5/15![United Airlines logo]()
$682
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 18, 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 18, 2026.
This Flysmarter deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/251:35 pm
AUA
- ORD
1 stop8h 55m
JetBlue
Wed 7/18:20 pm
ORD
- AUA
1 stop17h 50m
JetBlue
Deal found 5/16![JetBlue logo]()
$580
This Avianca deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/2511:50 am
AUA
- ORD
1 stop10h 30m
Avianca
Wed 7/111:20 pm
ORD
- AUA
1 stop10h 25m
Avianca
Deal found 5/15![Avianca logo]()
$612
This Delta deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/23:25 pm
AUA
- MDW
1 stop7h 52m
Delta
Wed 7/86:00 am
MDW
- AUA
1 stop7h 10m
Delta
Deal found 5/17![Delta logo]()
$642
This American Airlines deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/253:00 pm
AUA
- ORD
1 stop9h 58m
American Airlines
Wed 7/18:30 am
ORD
- AUA
1 stop7h 29m
American Airlines
Deal found 5/13![American Airlines logo]()
$646
This Southwest deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/251:45 pm
AUA
- MDW
2 stops18h 25m
Southwest
Wed 7/14:40 pm
MDW
- AUA
2 stops19h 05m
Southwest
Deal found 5/15![Southwest logo]()
$650
This United Airlines deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/111:50 pm
AUA
- ORD
Nonstop5h 48m
United Airlines
Wed 6/179:19 am
ORD
- AUA
Nonstop5h 16m
United Airlines
Deal found 5/15![United Airlines logo]()
$682
This Delta deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/253:25 pm
AUA
- ORD
1 stop9h 34m
Delta
Wed 7/15:30 am
ORD
- AUA
1 stop7h 40m
Delta
Deal found 5/17![Delta logo]()
$674
This American Airlines deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/111:59 pm
AUA
- ORD
1 stop11h 35m
American Airlines
Wed 6/175:10 am
ORD
- AUA
2 stops10h 49m
American Airlines
Deal found 5/15![American Airlines logo]()
$706
This Delta deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/253:25 pm
AUA
- MDW
1 stop7h 52m
Delta
Wed 7/16:00 am
MDW
- AUA
1 stop7h 10m
Delta
Deal found 5/13![Delta logo]()
$676
This United Airlines deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/251:50 pm
AUA
- ORD
Nonstop5h 48m
United Airlines
Wed 7/19:19 am
ORD
- AUA
Nonstop5h 16m
United Airlines
Deal found 5/17![United Airlines logo]()
$753
This United Airlines deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/21:50 pm
AUA
- ORD
Nonstop5h 48m
United Airlines
Wed 7/89:19 am
ORD
- AUA
Nonstop5h 16m
United Airlines
Deal found 5/17![United Airlines logo]()
$753
This Southwest deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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
Wed 7/85:10 am
MDW
- AUA
1 stop6h 35m
Southwest
Deal found 5/17![Southwest logo]()
$846
This Southwest deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/111:45 pm
AUA
- MDW
2 stops10h 15m
Southwest
Wed 6/175:10 am
MDW
- AUA
1 stop6h 35m
Southwest
Deal found 5/14![Southwest logo]()
$896
Last-minute flights from Aruba to ChicagoDiscover last-minute flight deals from Aruba to Chicago. Data last updated May 18, 2026 and is based on user searches.
Discover last-minute flight deals from Aruba to Chicago. Data last updated May 18, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/226:00 pm
AUA
- ORD
1 stop20h 01m
JetBlue
Thu 6/48:30 pm
ORD
- AUA
1 stop15h 00m
JetBlue
Deal found 5/13![JetBlue logo]()
$658
This Vliegwinkel deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Vliegwinkel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/115:20 pm
AUA
- ORD
1 stop29h 00m
Avianca
Wed 6/1711:20 pm
ORD
- AUA
1 stop10h 25m
Avianca
Deal found 5/14![Avianca logo]()
$622
This Cheapflightsfares deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/111:35 pm
AUA
- ORD
1 stop8h 55m
JetBlue
Wed 6/176:27 pm
ORD
- AUA
1 stop16h 47m
JetBlue
Deal found 5/15![JetBlue logo]()
$675
This United Airlines deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/111:50 pm
AUA
- ORD
Nonstop5h 48m
United Airlines
Wed 6/179:19 am
ORD
- AUA
Nonstop5h 16m
United Airlines
Deal found 5/15![United Airlines logo]()
$682
This American Airlines deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/111:59 pm
AUA
- ORD
1 stop11h 35m
American Airlines
Wed 6/175:10 am
ORD
- AUA
2 stops10h 49m
American Airlines
Deal found 5/15![American Airlines logo]()
$706
This Southwest deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/111:45 pm
AUA
- MDW
2 stops10h 15m
Southwest
Wed 6/175:30 pm
MDW
- AUA
2 stops18h 15m
Southwest
Deal found 5/15![Southwest logo]()
$866
This Flysmarter deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/251:35 pm
AUA
- ORD
1 stop8h 55m
JetBlue
Wed 7/18:20 pm
ORD
- AUA
1 stop17h 50m
JetBlue
Deal found 5/16![JetBlue logo]()
$580
This Avianca deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/2511:50 am
AUA
- ORD
1 stop10h 30m
Avianca
Wed 7/111:20 pm
ORD
- AUA
1 stop10h 25m
Avianca
Deal found 5/15![Avianca logo]()
$612
This American Airlines deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/253:00 pm
AUA
- ORD
1 stop9h 58m
American Airlines
Wed 7/18:30 am
ORD
- AUA
1 stop7h 29m
American Airlines
Deal found 5/13![American Airlines logo]()
$646
This Southwest deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/251:45 pm
AUA
- MDW
2 stops18h 25m
Southwest
Wed 7/14:40 pm
MDW
- AUA
2 stops19h 05m
Southwest
Deal found 5/15![Southwest logo]()
$650
This Delta deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/253:25 pm
AUA
- ORD
1 stop9h 34m
Delta
Wed 7/15:30 am
ORD
- AUA
1 stop7h 40m
Delta
Deal found 5/17![Delta logo]()
$674
This Delta deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/253:25 pm
AUA
- MDW
1 stop7h 52m
Delta
Wed 7/16:00 am
MDW
- AUA
1 stop7h 10m
Delta
Deal found 5/13![Delta logo]()
$676
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 18, 2026.
Search for one-way flight options from Aruba to Chicago. Find affordable one-way fares based on user searches. Data last updated May 18, 2026.
This Super.com deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/122:39 pm
AUA
- ORD
1 stop10h 05m
JetBlue
Deal found 5/16![JetBlue logo]()
$227
This Super.com deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/112:29 pm
AUA
- ORD
1 stop10h 15m
JetBlue
Deal found 5/14![JetBlue logo]()
$228
This JetBlue deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/103:39 pm
AUA
- ORD
1 stop10h 05m
JetBlue
Deal found 5/15![JetBlue logo]()
$237
This Super.com deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/92:39 pm
AUA
- ORD
1 stop10h 05m
JetBlue
Deal found 5/14![JetBlue logo]()
$254
This Super.com deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/202:39 pm
AUA
- ORD
1 stop10h 05m
JetBlue
Deal found 5/13![JetBlue logo]()
$255
This Air Canada deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/133:05 pm
AUA
- ORD
2 stops17h 40m
Air Canada
Deal found 5/16![Air Canada logo]()
$256
This Cheapflightsfares deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/272:39 pm
AUA
- ORD
1 stop10h 05m
JetBlue
Deal found 5/13![JetBlue logo]()
$260
This JetBlue deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/102:39 pm
AUA
- ORD
1 stop10h 05m
JetBlue
Deal found 5/13![JetBlue logo]()
$265
This Air Canada deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/293:05 pm
AUA
- ORD
1 stop18h 55m
Air Canada
Deal found 5/13![Air Canada logo]()
$276
This Air Canada deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/113:05 pm
AUA
- ORD
1 stop24h 50m
Air Canada
Deal found 5/13![Air Canada logo]()
$281
This Southwest deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/201:45 pm
AUA
- MDW
1 stop8h 45m
Southwest
Deal found 5/13![Southwest logo]()
$337
This Kiwi.com deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/113:02 pm
AUA
- MDW
3 stops44h 56m
Multiple Airlines
Deal found 5/15![Multiple Airlines logo]()
$436
Find flight deals from Aruba to Chicago
Keep the following information in mind while searching for Aruba to Chicago flight deals. Data was last updated May 18, 2026.
Round-trip from | $505 (Flysmarter) |
|---|---|
One-way from | $227 (Super.com) |
Good round-trip deal | $232 or less |
Good one-way deal | $210 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Aruba to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 18, 2026.
Use the filters below to find and compare flights from Aruba to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
OranjestadChicago
AUA - ORD
AUAORD
Oranjestad Reina Beatrix
Thu 6/25
1:35 pm-9:30 pm
1 stop8h 55m
Chicago O'Hare Intl
Wed 7/1
8:20 pm-3:10 pm
1 stop17h 50m
$580
OranjestadChicago
AUA - ORD
AUAORD
Oranjestad Reina Beatrix
Thu 6/25
11:50 am-9:20 pm
1 stop10h 30m
Chicago O'Hare Intl
Wed 7/1
11:20 pm-10:45 am
1 stop10h 25m
$612
OranjestadChicago
AUA - MDW
AUAMDW
Oranjestad Reina Beatrix
Thu 7/2
3:25 pm-10:17 pm
1 stop7h 52m
Chicago Midway
Wed 7/8
6:00 am-2:10 pm
1 stop7h 10m
$642
OranjestadChicago
AUA - ORD
AUAORD
Oranjestad Reina Beatrix
Thu 6/25
3:00 pm-11:58 pm
1 stop9h 58m
Chicago O'Hare Intl
Wed 7/1
8:30 am-4:59 pm
1 stop7h 29m
$646
OranjestadChicago
AUA - MDW
AUAMDW
Oranjestad Reina Beatrix
Thu 6/25
1:45 pm-7:10 am
2 stops18h 25m
Chicago Midway
Wed 7/1
4:40 pm-12:45 pm
2 stops19h 05m
$650
OranjestadChicago
AUA - ORD
AUAORD
Oranjestad Reina Beatrix
Thu 6/25
3:25 pm-11:59 pm
1 stop9h 34m
Chicago O'Hare Intl
Wed 7/1
5:30 am-2:10 pm
1 stop7h 40m
$674
OranjestadChicago
AUA - MDW
AUAMDW
Oranjestad Reina Beatrix
Thu 6/25
3:25 pm-10:17 pm
1 stop7h 52m
Chicago Midway
Wed 7/1
6:00 am-2:10 pm
1 stop7h 10m
$676
Quickest round-trip
OranjestadChicago
AUA - ORD
AUAORD
Oranjestad Reina Beatrix
Thu 6/11
1:50 pm-6:38 pm
Nonstop5h 48m
Chicago O'Hare Intl
Wed 6/17
9:19 am-3:35 pm
Nonstop5h 16m
$682
OranjestadChicago
AUA - ORD
AUAORD
Oranjestad Reina Beatrix
Thu 6/11
1:59 pm-12:34 am
1 stop11h 35m
Chicago O'Hare Intl
Wed 6/17
5:10 am-4:59 pm
2 stops10h 49m
$706
OranjestadChicago
AUA - ORD
AUAORD
Oranjestad Reina Beatrix
Thu 6/25
1:50 pm-6:38 pm
Nonstop5h 48m
Chicago O'Hare Intl
Wed 7/1
9:19 am-3:35 pm
Nonstop5h 16m
$753
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 May 18, 2026.
When flying from Aruba to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
Related info for your journey
Find useful and relevant information for your journey from Aruba to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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 for Aruba to Chicago
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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 18, 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 18, 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 18, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$343 | Average$552 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$464 | Average$735 | FlexibilityNo cancel fee | On-time71% |