$165+ 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
Apr 29 — May 61
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 March 30, 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 March 30, 2026.
This Trip.com deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/234:05 pm
AUA
- ORD
1 stop24h 10m
Air Canada
Wed 4/292:00 pm
ORD
- AUA
1 stop24h 15m
Air Canada
Deal found 3/28![Air Canada logo]()
$358
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 Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/94:10 pm
AUA
- ORD
1 stop18h 40m
Air Canada
Sun 4/126:21 pm
ORD
- AUA
2 stops19h 54m
Air Canada
Deal found 3/30![Air Canada logo]()
$447
This Delta deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/231:10 pm
AUA
- MDW
1 stop10h 18m
Delta
Wed 4/296:00 am
MDW
- AUA
1 stop7h 10m
Delta
Deal found 3/29![Delta logo]()
$539
This Southwest deal was found by Cheapflights users on 3/26. 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
Wed 4/226:00 am
MDW
- AUA
1 stop6h 45m
Southwest
Deal found 3/26![Southwest logo]()
$549
This Southwest deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/42:35 pm
AUA
- MDW
2 stops18h 00m
Southwest
Sun 5/105:05 am
MDW
- AUA
1 stop8h 55m
Southwest
Deal found 3/28![Southwest logo]()
$589
This Southwest deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/101:45 pm
AUA
- MDW
1 stop9h 55m
Southwest
Sun 9/135:10 am
MDW
- AUA
1 stop7h 30m
Southwest
Deal found 3/28![Southwest logo]()
$631
This Southwest deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/112:35 pm
AUA
- MDW
1 stop10h 40m
Southwest
Mon 5/185:35 am
MDW
- AUA
1 stop7h 00m
Southwest
Deal found 3/26![Southwest logo]()
$655
This Delta deal was found by Cheapflights users on 3/26. 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 4/163:25 pm
AUA
- MDW
1 stop8h 03m
Delta
Wed 4/2210:41 am
MDW
- AUA
2 stops24h 59m
Delta
Deal found 3/26![Delta logo]()
$667
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 March 30, 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 March 30, 2026.
This Flysmarter deal was found by Cheapflights users on 3/28. 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 3/28![Air Canada logo]()
$365
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 Priceline deal was found by Cheapflights users on 3/27. 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.
Mon 5/113:41 pm
AUA
- ORD
1 stop8h 34m
Spirit Airlines
Mon 5/185:05 am
ORD
- AUA
1 stop8h 31m
Spirit Airlines
Deal found 3/27![Spirit Airlines logo]()
$496
This Avianca deal was found by Cheapflights users on 3/26. 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 4/1611:50 am
AUA
- ORD
1 stop10h 30m
Avianca
Wed 4/2211:20 pm
ORD
- AUA
1 stop10h 25m
Avianca
Deal found 3/26![Avianca logo]()
$528
This JetBlue deal was found by Cheapflights users on 3/28. 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 4/234:45 pm
AUA
- ORD
1 stop15h 56m
JetBlue
Wed 4/299:41 am
ORD
- AUA
1 stop24h 30m
JetBlue
Deal found 3/28![JetBlue logo]()
$532
This Delta deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/231:10 pm
AUA
- MDW
1 stop10h 18m
Delta
Wed 4/296:00 am
MDW
- AUA
1 stop7h 10m
Delta
Deal found 3/29![Delta logo]()
$539
This Southwest deal was found by Cheapflights users on 3/26. 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
Wed 4/226:00 am
MDW
- AUA
1 stop6h 45m
Southwest
Deal found 3/26![Southwest logo]()
$549
This United Airlines deal was found by Cheapflights users on 3/26. 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 4/161:50 pm
AUA
- ORD
Nonstop5h 48m
United Airlines
Wed 4/226:00 am
ORD
- AUA
1 stop9h 40m
United Airlines
Deal found 3/26![United Airlines logo]()
$645
This Delta deal was found by Cheapflights users on 3/27. 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 stop9h 15m
Delta
Wed 4/295:15 am
ORD
- AUA
1 stop7h 55m
Delta
Deal found 3/27![Delta logo]()
$539
This Delta deal was found by Cheapflights users on 3/26. 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 4/161:10 pm
AUA
- ORD
1 stop11h 49m
Delta
Wed 4/227:59 pm
ORD
- AUA
1 stop14h 11m
Delta
Deal found 3/26![Delta logo]()
$540
This Southwest deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/42:35 pm
AUA
- MDW
1 stop10h 40m
Southwest
Sun 5/105:15 am
MDW
- AUA
1 stop7h 20m
Southwest
Deal found 3/28![Southwest logo]()
$604
This Southwest deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/132:35 pm
AUA
- ORD
1 stop8h 20m
Southwest
Wed 5/204:50 pm
ORD
- AUA
2 stops19h 45m
Southwest
Deal found 3/29![Southwest logo]()
$625
This Southwest deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/101:45 pm
AUA
- MDW
2 stops18h 45m
Southwest
Sun 9/135:10 am
MDW
- AUA
1 stop7h 30m
Southwest
Deal found 3/28![Southwest logo]()
$636
This Southwest deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/112:35 pm
AUA
- MDW
1 stop10h 40m
Southwest
Mon 5/185:35 am
MDW
- AUA
1 stop7h 00m
Southwest
Deal found 3/26![Southwest logo]()
$655
Last-minute flights from Aruba to ChicagoDiscover last-minute flight deals from Aruba to Chicago. Data last updated March 30, 2026 and is based on user searches.
Discover last-minute flight deals from Aruba to Chicago. Data last updated March 30, 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 Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/94:10 pm
AUA
- ORD
1 stop18h 40m
Air Canada
Sun 4/126:21 pm
ORD
- AUA
2 stops19h 54m
Air Canada
Deal found 3/30![Air Canada logo]()
$447
This Southwest deal was found by Cheapflights users on 3/27. 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 4/122:35 pm
AUA
- MDW
2 stops10h 45m
Southwest
Thu 4/165:35 am
MDW
- AUA
1 stop7h 10m
Southwest
Deal found 3/27![Southwest logo]()
$1,026
This Southwest deal was found by Cheapflights users on 3/26. 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
Wed 4/226:00 am
MDW
- AUA
1 stop6h 45m
Southwest
Deal found 3/26![Southwest logo]()
$549
This Delta deal was found by Cheapflights users on 3/26. 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 4/163:25 pm
AUA
- MDW
1 stop8h 03m
Delta
Wed 4/2210:41 am
MDW
- AUA
2 stops24h 59m
Delta
Deal found 3/26![Delta logo]()
$667
This Trip.com deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/234:05 pm
AUA
- ORD
1 stop24h 10m
Air Canada
Wed 4/292:00 pm
ORD
- AUA
1 stop24h 15m
Air Canada
Deal found 3/28![Air Canada logo]()
$358
This Delta deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/231:10 pm
AUA
- MDW
1 stop10h 18m
Delta
Wed 4/296:00 am
MDW
- AUA
1 stop7h 10m
Delta
Deal found 3/29![Delta logo]()
$539
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.
Thu 4/232:45 pm
AUA
- MDW
2 stops9h 45m
Southwest
Wed 4/296:05 pm
MDW
- AUA
2 stops18h 40m
Southwest
Deal found 3/30![Southwest logo]()
$716
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 March 30, 2026.
Search for one-way flight options from Aruba to Chicago. Find affordable one-way fares based on user searches. Data last updated March 30, 2026.
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.
Fri 5/13:41 pm
AUA
- ORD
1 stop9h 13m
Multiple Airlines
Deal found 3/30![Multiple Airlines logo]()
$165
This Kiwi.com deal was found by Cheapflights users on 3/28. 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 4/243:41 pm
AUA
- ORD
1 stop30h 36m
Multiple Airlines
Deal found 3/28![Multiple Airlines logo]()
$175
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 Frontier deal was found by Cheapflights users on 3/27. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/411:30 am
AUA
- MDW
1 stop9h 37m
Frontier
Deal found 3/27![Frontier logo]()
$193
This Frontier deal was found by Cheapflights users on 3/27. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/411:30 am
AUA
- ORD
1 stop10h 43m
Frontier
Deal found 3/27![Frontier logo]()
$193
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
2 stops19h 42m
Multiple Airlines
Deal found 3/30![Multiple Airlines logo]()
$210
This Orbitz deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/273:05 pm
AUA
- ORD
1 stop24h 50m
Air Canada
Deal found 3/28![Air Canada logo]()
$242
This Frontier deal was found by Cheapflights users on 3/26. 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 Frontier 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 3/26![Frontier logo]()
$243
This Air Canada deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/263:05 pm
AUA
- ORD
1 stop24h 50m
Air Canada
Deal found 3/29![Air Canada logo]()
$255
This Southwest deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/192:35 pm
AUA
- MDW
1 stop7h 50m
Southwest
Deal found 3/29![Southwest logo]()
$312
This Kiwi.com deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/195:20 pm
AUA
- MDW
3 stops21h 52m
Multiple Airlines
Deal found 3/29![Multiple Airlines logo]()
$326
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
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 March 30, 2026.
Round-trip from | $358 (Trip.com) |
|---|---|
One-way from | $165 (Kiwi.com) |
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 March 30, 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 4/9
4:10 pm-3:15 pm
1 stop24h 05m
Chicago O'Hare Intl
Sun 4/12
5:05 am-2:35 pm
1 stop8h 30m
$432
OranjestadChicago
AUA - ORD
AUAORD
Oranjestad Reina Beatrix
Mon 5/11
3:41 pm-11:15 pm
1 stop8h 34m
Chicago O'Hare Intl
Mon 5/18
5:05 am-2:36 pm
1 stop8h 31m
$496
OranjestadChicago
AUA - ORD
AUAORD
Oranjestad Reina Beatrix
Thu 4/16
11:50 am-9:20 pm
1 stop10h 30m
Chicago O'Hare Intl
Wed 4/22
11:20 pm-10:45 am
1 stop10h 25m
$528
OranjestadChicago
AUA - ORD
AUAORD
Oranjestad Reina Beatrix
Thu 4/23
4:45 pm-7:41 am
1 stop15h 56m
Chicago O'Hare Intl
Wed 4/29
9:41 am-11:11 am
1 stop24h 30m
$532
OranjestadChicago
AUA - MDW
AUAMDW
Oranjestad Reina Beatrix
Thu 4/23
1:10 pm-10:28 pm
1 stop10h 18m
Chicago Midway
Wed 4/29
6:00 am-2:10 pm
1 stop7h 10m
$539
OranjestadChicago
AUA - ORD
AUAORD
Oranjestad Reina Beatrix
Thu 4/23
1:10 pm-9:25 pm
1 stop9h 15m
Chicago O'Hare Intl
Wed 4/29
5:15 am-2:10 pm
1 stop7h 55m
$539
OranjestadChicago
AUA - ORD
AUAORD
Oranjestad Reina Beatrix
Thu 4/16
1:10 pm-11:59 pm
1 stop11h 49m
Chicago O'Hare Intl
Wed 4/22
7:59 pm-11:10 am
1 stop14h 11m
$540
OranjestadChicago
AUA - MDW
AUAMDW
Oranjestad Reina Beatrix
Thu 4/16
2:45 pm-12:05 am
1 stop10h 20m
Chicago Midway
Wed 4/22
6:00 am-1:45 pm
1 stop6h 45m
$549
OranjestadChicago
AUA - MDW
AUAMDW
Oranjestad Reina Beatrix
Mon 5/4
2:35 pm-12:15 am
1 stop10h 40m
Chicago Midway
Sun 5/10
5:15 am-1:35 pm
1 stop7h 20m
$604
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 March 30, 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 March 30, 2026.
The most flights from AW0 to CHI are scheduled on a Monday (2 on average). You will have fewer flight options on Saturday, 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
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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 March 30, 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
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Aruba and Chicago flights
Browse other Aruba and Chicago flight options. Last updated on March 30, 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 March 30, 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% |