$162+ 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 5/1. Fares are subject to change and may not be available on all flights or dates of travel.
AUA — CHI
May 4 — May 111
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 April 4, 2026.
Explore the most affordable flight options available from Aruba to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 4, 2026.
This Priceline deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/23:41 pm
AUA
- ORD
1 stop9h 43m
Spirit Airlines
Mon 5/45:05 am
ORD
- AUA
1 stop8h 31m
Spirit Airlines
Deal found 4/2![Spirit Airlines logo]()
$295
This Priceline deal was found by Cheapflights users on 3/31. 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 5/13:41 pm
AUA
- ORD
1 stop9h 43m
Spirit Airlines
Mon 5/45:05 am
ORD
- AUA
1 stop8h 31m
Spirit Airlines
Deal found 3/31![Spirit Airlines logo]()
$341
This Flysmarter deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/234:05 pm
AUA
- ORD
1 stop18h 05m
Air Canada
Wed 4/296:21 pm
ORD
- AUA
2 stops19h 54m
Air Canada
Deal found 4/1![Air Canada logo]()
$355
This Gotogate deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/94:10 pm
AUA
- ORD
1 stop24h 05m
Multiple Airlines
Sun 4/125:05 am
ORD
- AUA
1 stop8h 30m
Multiple Airlines
Deal found 3/30![Multiple Airlines logo]()
$432
This Kiwi.com deal was found by Cheapflights users on 3/31. 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 4/233:30 pm
AUA
- MDW
1 stop24h 50m
Multiple Airlines
Wed 4/297:30 am
MDW
- AUA
2 stops11h 00m
Multiple Airlines
Deal found 3/31![Multiple Airlines logo]()
$564
This Delta deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/211:15 pm
AUA
- MDW
1 stop8h 54m
Delta
Wed 5/275:12 pm
MDW
- AUA
1 stop17h 48m
Delta
Deal found 4/3![Delta logo]()
$600
This Delta deal was found by Cheapflights users on 3/31. 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 4/231:10 pm
AUA
- MDW
1 stop10h 18m
Delta
Wed 4/295:21 pm
MDW
- AUA
1 stop17h 34m
Delta
Deal found 3/31![Delta logo]()
$601
This Southwest deal was found by Cheapflights users on 3/31. 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.
Fri 5/12:35 pm
AUA
- MDW
2 stops10h 20m
Southwest
Mon 5/46:25 pm
MDW
- AUA
2 stops18h 10m
Southwest
Deal found 3/31![Southwest logo]()
$656
This Southwest deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/212:35 pm
AUA
- MDW
1 stop10h 40m
Southwest
Wed 5/276:50 pm
MDW
- AUA
2 stops17h 45m
Southwest
Deal found 4/3![Southwest logo]()
$676
This Southwest deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/21:30 pm
AUA
- MDW
2 stops10h 05m
Southwest
Mon 5/47:40 pm
MDW
- AUA
2 stops16h 55m
Southwest
Deal found 4/2![Southwest logo]()
$686
This Mytrip deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/233:30 pm
AUA
- MDW
2 stops18h 17m
WestJet
Wed 4/296:38 pm
MDW
- AUA
2 stops18h 37m
WestJet
Deal found 4/2![WestJet logo]()
$711
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 4, 2026.
Discover carefully curated flight deals from Aruba to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 4, 2026.
This Flysmarter deal was found by Cheapflights users on 3/31. 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 4/234:05 pm
AUA
- ORD
2 stops16h 53m
Air Canada
Wed 4/296:21 pm
ORD
- AUA
2 stops19h 54m
Air Canada
Deal found 3/31![Air Canada logo]()
$365
This JetBlue deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/2312:40 pm
AUA
- ORD
1 stop20h 01m
JetBlue
Wed 4/299:41 am
ORD
- AUA
1 stop24h 30m
JetBlue
Deal found 3/30![JetBlue logo]()
$529
This Expedia deal was found by Cheapflights users on 3/31. 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.
Fri 5/13:41 pm
AUA
- ORD
2 stops8h 26m
Multiple Airlines
Mon 5/46:00 am
ORD
- AUA
2 stops33h 14m
Multiple Airlines
Deal found 3/31![Multiple Airlines logo]()
$529
This Copa Airlines deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/173:43 pm
AUA
- ORD
1 stop10h 32m
Copa Airlines
Sun 5/248:02 am
ORD
- AUA
1 stop12h 55m
Copa Airlines
Deal found 4/2![Copa Airlines logo]()
$593
This Delta deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/211:15 pm
AUA
- MDW
1 stop8h 54m
Delta
Wed 5/275:12 pm
MDW
- AUA
1 stop17h 48m
Delta
Deal found 4/3![Delta logo]()
$600
This United Airlines deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/21:50 pm
AUA
- ORD
Nonstop5h 48m
United Airlines
Mon 5/45:00 am
ORD
- AUA
1 stop8h 00m
United Airlines
Deal found 4/2![United Airlines logo]()
$626
This Southwest deal was found by Cheapflights users on 3/31. 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.
Fri 5/12:35 pm
AUA
- MDW
1 stop10h 30m
Southwest
Mon 5/46:25 pm
MDW
- AUA
2 stops18h 10m
Southwest
Deal found 3/31![Southwest logo]()
$656
This Mytrip deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/233:30 pm
AUA
- MDW
2 stops18h 17m
WestJet
Wed 4/296:38 pm
MDW
- AUA
2 stops18h 37m
WestJet
Deal found 4/2![WestJet logo]()
$711
This Kiwi.com deal was found by Cheapflights users on 3/31. 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 4/233:30 pm
AUA
- MDW
1 stop24h 50m
Multiple Airlines
Wed 4/297:30 am
MDW
- AUA
2 stops11h 00m
Multiple Airlines
Deal found 3/31![Multiple Airlines logo]()
$564
This JetBlue deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/215:00 pm
AUA
- ORD
1 stop16h 00m
JetBlue
Wed 5/278:30 pm
ORD
- AUA
1 stop19h 16m
JetBlue
Deal found 4/3![JetBlue logo]()
$594
This Delta deal was found by Cheapflights users on 3/31. 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 4/231:10 pm
AUA
- MDW
1 stop10h 18m
Delta
Wed 4/295:21 pm
MDW
- AUA
1 stop17h 34m
Delta
Deal found 3/31![Delta logo]()
$601
This Mytrip deal was found by Cheapflights users on 3/31. 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 4/233:30 pm
AUA
- ORD
1 stop18h 40m
Multiple Airlines
Wed 4/297:55 am
ORD
- AUA
1 stop30h 20m
Multiple Airlines
Deal found 3/31![Multiple Airlines logo]()
$586
This Delta deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/211:15 pm
AUA
- ORD
1 stop11h 44m
Delta
Wed 5/277:55 pm
ORD
- AUA
1 stop15h 05m
Delta
Deal found 4/3![Delta logo]()
$602
This Southwest deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/212:35 pm
AUA
- MDW
1 stop10h 40m
Southwest
Wed 5/276:50 pm
MDW
- AUA
2 stops17h 45m
Southwest
Deal found 4/3![Southwest logo]()
$676
This Delta deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/231:10 pm
AUA
- ORD
1 stop8h 06m
Delta
Wed 4/299:50 am
ORD
- AUA
2 stops25h 50m
Delta
Deal found 4/1![Delta logo]()
$604
Last-minute flights from Aruba to ChicagoDiscover last-minute flight deals from Aruba to Chicago. Data last updated April 4, 2026 and is based on user searches.
Discover last-minute flight deals from Aruba to Chicago. Data last updated April 4, 2026 and is based on user searches.
This Gotogate deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/94:10 pm
AUA
- ORD
1 stop24h 05m
Multiple Airlines
Sun 4/125:05 am
ORD
- AUA
1 stop8h 30m
Multiple Airlines
Deal found 3/30![Multiple Airlines logo]()
$432
This Flysmarter deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/234:05 pm
AUA
- ORD
1 stop18h 05m
Air Canada
Wed 4/296:21 pm
ORD
- AUA
2 stops19h 54m
Air Canada
Deal found 4/1![Air Canada logo]()
$355
This Kiwi.com deal was found by Cheapflights users on 3/31. 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 4/233:30 pm
AUA
- MDW
1 stop24h 50m
Multiple Airlines
Wed 4/297:30 am
MDW
- AUA
2 stops11h 00m
Multiple Airlines
Deal found 3/31![Multiple Airlines logo]()
$564
This Delta deal was found by Cheapflights users on 3/31. 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 4/231:10 pm
AUA
- MDW
1 stop10h 18m
Delta
Wed 4/295:21 pm
MDW
- AUA
1 stop17h 34m
Delta
Deal found 3/31![Delta logo]()
$601
This Mytrip deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/233:30 pm
AUA
- MDW
2 stops18h 17m
WestJet
Wed 4/296:38 pm
MDW
- AUA
2 stops18h 37m
WestJet
Deal found 4/2![WestJet logo]()
$711
This Priceline deal was found by Cheapflights users on 3/31. 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 5/13:41 pm
AUA
- ORD
1 stop9h 43m
Spirit Airlines
Mon 5/45:05 am
ORD
- AUA
1 stop8h 31m
Spirit Airlines
Deal found 3/31![Spirit Airlines logo]()
$341
This Southwest deal was found by Cheapflights users on 3/31. 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.
Fri 5/12:35 pm
AUA
- MDW
2 stops10h 20m
Southwest
Mon 5/46:25 pm
MDW
- AUA
2 stops18h 10m
Southwest
Deal found 3/31![Southwest logo]()
$656
This Priceline deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/23:41 pm
AUA
- ORD
1 stop9h 43m
Spirit Airlines
Mon 5/45:05 am
ORD
- AUA
1 stop8h 31m
Spirit Airlines
Deal found 4/2![Spirit Airlines logo]()
$295
This Southwest deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/21:30 pm
AUA
- MDW
2 stops10h 05m
Southwest
Mon 5/47:40 pm
MDW
- AUA
2 stops16h 55m
Southwest
Deal found 4/2![Southwest logo]()
$686
This Delta deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/211:15 pm
AUA
- MDW
1 stop8h 54m
Delta
Wed 5/275:12 pm
MDW
- AUA
1 stop17h 48m
Delta
Deal found 4/3![Delta logo]()
$600
This Southwest deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/212:35 pm
AUA
- MDW
1 stop10h 40m
Southwest
Wed 5/276:50 pm
MDW
- AUA
2 stops17h 45m
Southwest
Deal found 4/3![Southwest 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 April 4, 2026.
Search for one-way flight options from Aruba to Chicago. Find affordable one-way fares based on user searches. Data last updated April 4, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/13:41 pm
AUA
- ORD
1 stop9h 43m
Spirit Airlines
Deal found 4/2![Spirit Airlines logo]()
$162
This Kiwi.com deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/13:41 pm
AUA
- ORD
1 stop9h 13m
Multiple Airlines
Deal found 4/2![Multiple Airlines logo]()
$164
This Kiwi.com deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/23:41 pm
AUA
- ORD
1 stop9h 43m
Spirit Airlines
Deal found 3/30![Spirit Airlines logo]()
$184
This Kiwi.com deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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
Deal found 4/1![Multiple Airlines logo]()
$216
This Air Canada deal was found by Cheapflights users on 3/31. 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 6/273:05 pm
AUA
- ORD
1 stop23h 17m
Air Canada
Deal found 3/31![Air Canada logo]()
$228
This Air Canada deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/303:05 pm
AUA
- ORD
1 stop21h 55m
Air Canada
Deal found 4/2![Air Canada logo]()
$229
This Expedia deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/1111:30 am
AUA
- MDW
1 stop11h 59m
Frontier
Deal found 3/30![Frontier logo]()
$263
This Kiwi.com deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/235:20 pm
AUA
- MDW
3 stops30h 06m
Multiple Airlines
Deal found 3/30![Multiple Airlines logo]()
$332
This Southwest deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/212:45 pm
AUA
- MDW
1 stop7h 40m
Southwest
Deal found 3/30![Southwest logo]()
$343
This Delta deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/231:10 pm
AUA
- MDW
1 stop10h 18m
Delta
Deal found 3/30![Delta logo]()
$359
This Kiwi.com deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/169:34 pm
AUA
- MDW
3 stops46h 03m
Multiple Airlines
Deal found 4/2![Multiple Airlines logo]()
$399
This Southwest deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/162:45 pm
AUA
- MDW
1 stop10h 20m
Southwest
Deal found 4/2![Southwest logo]()
$423
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 4, 2026.
Round-trip from | $295 (Priceline) |
|---|---|
One-way from | $162 (Cheapflightsfares) |
Good round-trip deal | $343 or less |
Good one-way deal | $288 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 4, 2026.
Use the filters below to find and compare flights from Aruba to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
OranjestadChicago
AUA - ORD
AUAORD
Oranjestad Reina Beatrix
Thu 4/23
4:05 pm-7:58 am
2 stops16h 53m
Chicago O'Hare Intl
Wed 4/29
6:21 pm-3:15 pm
2 stops19h 54m
$365
OranjestadChicago
AUA - ORD
AUAORD
Oranjestad Reina Beatrix
Thu 4/23
12:40 pm-7:41 am
1 stop20h 01m
Chicago O'Hare Intl
Wed 4/29
9:41 am-11:11 am
1 stop24h 30m
$529
OranjestadChicago
AUA - ORD
AUAORD
Oranjestad Reina Beatrix
Fri 5/1
3:41 pm-11:07 pm
2 stops8h 26m
Chicago O'Hare Intl
Mon 5/4
6:00 am-4:14 pm
2 stops33h 14m
$529
OranjestadChicago
AUA - MDW
AUAMDW
Oranjestad Reina Beatrix
Thu 4/23
3:30 pm-3:20 pm
1 stop24h 50m
Chicago Midway
Wed 4/29
7:30 am-7:30 pm
2 stops11h 00m
$564
OranjestadChicago
AUA - ORD
AUAORD
Oranjestad Reina Beatrix
Thu 4/23
3:30 pm-9:10 am
1 stop18h 40m
Chicago O'Hare Intl
Wed 4/29
7:55 am-3:15 pm
1 stop30h 20m
$586
OranjestadChicago
AUA - ORD
AUAORD
Oranjestad Reina Beatrix
Sun 5/17
3:43 pm-1:15 am
1 stop10h 32m
Chicago O'Hare Intl
Sun 5/24
8:02 am-9:57 pm
1 stop12h 55m
$593
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
$594
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
$600
OranjestadChicago
AUA - MDW
AUAMDW
Oranjestad Reina Beatrix
Thu 4/23
1:10 pm-10:28 pm
1 stop10h 18m
Chicago Midway
Wed 4/29
5:21 pm-11:55 am
1 stop17h 34m
$601
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
7:55 pm-12:00 pm
1 stop15h 05m
$602
Showing 1-10 of 31 resultsSorted by cheapest first
Best time to book a flight from Aruba to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Aruba with our price prediction graph.
AUA-ORD
AUA-MDW
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Aruba to Chicago
AW0-CHI
AUA-ORD
AUA-MDW
What is the cheapest time of day to fly from AW to CHI?
Find hourly flight availability from Aruba to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 4, 2026.
When flying from Aruba to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
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 4, 2026.
The most flights from AW0 to CHI are scheduled on a Monday (2 on average). You will have fewer flight options on Tuesday, 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
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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 4, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Aruba to Chicago by cabin class
Find flights from Aruba to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Aruba and Chicago flights
Browse other Aruba and Chicago flight options. Last updated on April 4, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 2 airlines flying from Aruba to Chicago
Discover the top 2 airlines that operate flights from Aruba to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 4, 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% |