Chicago

$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 3/17. Fares are subject to change and may not be available on all flights or dates of travel.
AUA — CHI
Apr 5 — Apr 121
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Cheap flight deals from Aruba to Chicago

Cheapest flights from Aruba to Chicago
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 6, 2026.

This Vliegwinkel deal was found by Cheapflights users on 3/2. 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 Vliegwinkel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/164:05 pm
AUA
-
ORD
1 stop26h 45m
Air Canada
Wed 4/226:40 pm
ORD
-
AUA
1 stop19h 35m
Air Canada
Deal found 3/2$380
This Mytrip deal was found by Cheapflights users on 3/1. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/164:05 pm
AUA
-
ORD
1 stop24h 10m
Air Canada
Thu 4/236:21 pm
ORD
-
AUA
2 stops43h 54m
Air Canada
Deal found 3/1$389
This Booking.com deal was found by Cheapflights users on 3/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/183:41 pm
AUA
-
ORD
1 stop9h 43m
Multiple Airlines
Sat 4/255:57 pm
ORD
-
AUA
1 stop20h 18m
Multiple Airlines
Deal found 3/4$412
This Air Canada deal was found by Cheapflights users on 3/1. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/154:05 pm
AUA
-
ORD
1 stop18h 05m
Air Canada
Wed 4/226:40 pm
ORD
-
AUA
1 stop19h 35m
Air Canada
Deal found 3/1$429
This Travelocity deal was found by Cheapflights users on 3/3. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/236:00 pm
AUA
-
ORD
1 stop21h 30m
JetBlue
Sat 5/3010:45 am
ORD
-
AUA
1 stop29h 07m
JetBlue
Deal found 3/3$438
This Cheapflightsfares deal was found by Cheapflights users on 3/1. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/253:40 pm
AUA
-
ORD
1 stop8h 37m
Spirit Airlines
Wed 4/15:05 am
ORD
-
AUA
1 stop8h 30m
Spirit Airlines
Deal found 3/1$441
This Expedia deal was found by Cheapflights users on 3/3. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/2512:40 pm
AUA
-
ORD
1 stop11h 16m
Multiple Airlines
Wed 4/15:05 am
ORD
-
AUA
1 stop8h 30m
Multiple Airlines
Deal found 3/3$445
This Delta deal was found by Cheapflights users on 3/2. 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 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 4/2212:52 pm
MDW
-
AUA
2 stops22h 48m
Delta
Deal found 3/2$503
This Southwest deal was found by Cheapflights users on 3/2. 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
Wed 4/226:00 am
MDW
-
AUA
1 stop6h 45m
Southwest
Deal found 3/2$511
This Delta deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/203:25 pm
AUA
-
MDW
1 stop8h 03m
Delta
Mon 4/276:00 am
MDW
-
AUA
1 stop7h 10m
Delta
Deal found 3/6$552
This Southwest deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/202:45 pm
AUA
-
MDW
1 stop10h 20m
Southwest
Mon 4/276:25 pm
MDW
-
AUA
2 stops18h 20m
Southwest
Deal found 3/6$593
This Southwest deal was found by Cheapflights users on 3/3. 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.
Wed 3/252:25 pm
AUA
-
MDW
1 stop9h 15m
Southwest
Wed 4/16:00 am
MDW
-
AUA
1 stop6h 25m
Southwest
Deal found 3/3$627

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 6, 2026.

Round-trip from

$380
(Vliegwinkel)

One-way from

$162
(Super.com)

Good round-trip deal

$542 or less

Good one-way deal

$285 or less
From Aruba to Chicago (CHI)
One-way flight from Aruba to Chicago (CHI)
Price to beat on a round-trip flight from Aruba to Chicago (CHI).
Price to beat on a one-way flight from Aruba to Chicago (CHI).

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 6, 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

Price

Cheapest round-trip

OranjestadChicago

AUA - ORD

AUAORD

Oranjestad Reina Beatrix

Wed 4/15

4:05 pm-10:53 am

2 stops19h 48m

Chicago O'Hare Intl

Wed 4/22

6:40 pm-3:15 pm

1 stop19h 35m

$432

OranjestadChicago

AUA - ORD

AUAORD

Oranjestad Reina Beatrix

Wed 3/25

12:40 pm-10:56 pm

1 stop11h 16m

Chicago O'Hare Intl

Wed 4/1

5:05 am-2:35 pm

1 stop8h 30m

$445

OranjestadChicago

AUA - ORD

AUAORD

Oranjestad Reina Beatrix

Fri 4/3

11:50 am-9:20 pm

1 stop10h 30m

Chicago O'Hare Intl

Sat 4/11

4:15 pm-3:15 pm

1 stop22h 00m

$452

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

$490
Quickest round-trip

OranjestadChicago

AUA - ORD

AUAORD

Oranjestad Reina Beatrix

Wed 4/15

1:50 pm-6:38 pm

Nonstop5h 48m

Chicago O'Hare Intl

Wed 4/22

9:04 am-3:20 pm

Nonstop5h 16m

$497

OranjestadChicago

AUA - ORD

AUAORD

Oranjestad Reina Beatrix

Sat 6/20

3:05 pm-12:00 pm

1 stop21h 55m

Chicago O'Hare Intl

Fri 6/26

8:40 pm-2:15 pm

1 stop16h 35m

$499

OranjestadChicago

AUA - MDW

AUAMDW

Oranjestad Reina Beatrix

Thu 4/16

3:25 pm-10:28 pm

1 stop8h 03m

Chicago Midway

Wed 4/22

12:52 pm-12:40 pm

2 stops22h 48m

$503

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

$511

OranjestadChicago

AUA - ORD

AUAORD

Oranjestad Reina Beatrix

Thu 4/16

7:19 am-1:13 am

1 stop18h 54m

Chicago O'Hare Intl

Wed 4/22

8:06 am-9:57 pm

1 stop12h 51m

$513

OranjestadChicago

AUA - ORD

AUAORD

Oranjestad Reina Beatrix

Thu 4/16

1:10 pm-8:16 pm

1 stop8h 06m

Chicago O'Hare Intl

Wed 4/22

11:19 am-12:40 pm

2 stops24h 21m

$522

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/2

Showing 1-10 of 30 resultsSorted by cheapest first
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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.
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

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 6, 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.

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated March 6, 2026.
Get a feel of what it's like to fly with American Airlines from Aruba to Chicago by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.

Entertainment

6.9

Comfort

7.2

Food

6.4

Overall

7.1

Crew

8.0

Boarding

7.5

Reviews

1 / 20
2.0
Mediocre

Anonymous,Mar 2026

MIA - SFO

Horrible. When they power flights for other airlines there is nothing they can do to change or accommodate any changes

Entertainment

6.9

Comfort

7.2

Food

6.4

Overall

7.1

Crew

8.0

Boarding

7.5

Reviews

1 / 20
2.0
Mediocre

Anonymous,Mar 2026

MIA - SFO

Horrible. When they power flights for other airlines there is nothing they can do to change or accommodate any changes

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.
  • How long is the flight from Aruba to Chicago?

    For as low as $497, Air Canada can have you in Chicago from Aruba in 5h 48m. Aruba and Chicago are separated by a distance of 2302 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from Aruba to Chicago one-way?

    To fly one-way, consider booking your trip with United Airlines, which is currently one of the cheapest options available, starting at $254. JetBlue flights start at $260 while deals on American Airlines start at $284 one-way.

  • What are the most reliable airlines from Aruba to Chicago?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Aruba to Chicago on time: American Airlines (60%), United Airlines (56%), Qatar Airways (49%).

  • What are the cheapest flights from Aruba to Chicago?

    Looking for the cheapest flight from Aruba to Chicago? While on average our users pay $660, our data indicates the cheapest price to be $224. The most popular route (Oranjestad Reina Beatrix - Chicago O'Hare Intl), is priced around $354.

  • Can I find deals for flights from Aruba to Chicago that include hotel bookings?

    Yes. In addition to deals on Aruba to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Aruba to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Aruba to Chicago.

  • Can I find deals for business class flights from Aruba to Chicago?

    Yes. Cheapflights offers flight deals from Aruba to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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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 6, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$343Average$562FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$464Average$735FlexibilityNo cancel feeOn-time71%

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