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$138+ 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 1/17. Fares are subject to change and may not be available on all flights or dates of travel.
AUA — CHI
Jan 21 — Jan 281
Wed 1/21
Wed 1/28
1 adult, Economy
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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 December 22, 2025.

This American Airlines deal was found by Cheapflights users on 12/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/253:39 pmAUA - ORD
Nonstop5h 52mAmerican Airlines
Wed 12/315:00 amORD - AUA
1 stop9h 54mAmerican Airlines
Deal found 12/19$443
This Delta deal was found by Cheapflights users on 12/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/254:35 pmAUA - MDW
1 stop7h 47mDelta
Wed 12/316:00 amMDW - AUA
1 stop7h 20mDelta
Deal found 12/19$449
This Delta deal was found by Cheapflights users on 12/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/254:35 pmAUA - ORD
1 stop9h 27mDelta
Wed 12/315:30 amORD - AUA
1 stop7h 50mDelta
Deal found 12/19$449
This Delta deal was found by Cheapflights users on 12/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/244:35 pmAUA - ORD
1 stop9h 27mDelta
Sun 12/287:59 pmORD - AUA
1 stop14h 31mDelta
Deal found 12/21$559
This Kissandfly.com deal was found by Cheapflights users on 12/21. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/211:45 pmAUA - MDW
1 stop10h 37mKLM
Thu 12/255:59 pmMDW - AUA
1 stop19h 26mKLM
Deal found 12/21$587
This American Airlines deal was found by Cheapflights users on 12/21. 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.
Sun 12/215:59 pmAUA - ORD
2 stops15h 31mAmerican Airlines
Thu 12/258:51 amORD - AUA
Nonstop4h 59mAmerican Airlines
Deal found 12/21$593
This United Airlines deal was found by Cheapflights users on 12/21. 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.
Sun 12/212:50 pmAUA - ORD
Nonstop5h 46mUnited Airlines
Thu 12/259:25 amORD - AUA
Nonstop5h 15mUnited Airlines
Deal found 12/21$692
This United Airlines deal was found by Cheapflights users on 12/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/242:50 pmAUA - ORD
Nonstop5h 46mUnited Airlines
Sun 12/285:49 amORD - AUA
1 stop9h 01mUnited Airlines
Deal found 12/19$732
This Southwest deal was found by Cheapflights users on 12/21. 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 12/2112:30 pmAUA - MDW
1 stop10h 25mSouthwest
Thu 12/251:15 pmMDW - AUA
2 stops20h 15mSouthwest
Deal found 12/21$870
This Delta deal was found by Cheapflights users on 12/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/244:35 pmAUA - MDW
1 stop7h 47mDelta
Sun 12/286:00 amMDW - AUA
1 stop7h 20mDelta
Deal found 12/21$1,881

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 December 22, 2025.

Round-trip from

$220
(Priceline)

One-way from

$138
(Super.com)

Good round-trip deal

$361 or less

Good one-way deal

$227 or less
From Aruba to Chicago (CHI)
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One-way flight from Aruba to Chicago (CHI)
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Price to beat on a round-trip flight from Aruba to Chicago (CHI).
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Price to beat on a one-way flight from Aruba to Chicago (CHI).
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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 December 22, 2025.
Use the filters below to find and compare flights from Aruba to Chicago that are best for you.

Fly from

Aruba

Fly to

Chicago

Route

Depart

Return

Price

OranjestadChicago

AUA - ORD

AUAORD

Oranjestad Reina Beatrix

Tue 3/24

3:41 pm-5:24 pm

1 stop26h 43m

Chicago O'Hare Intl

Tue 3/31

5:15 am-2:26 pm

1 stop8h 11m

$423

OranjestadChicago

AUA - ORD

AUAORD

Oranjestad Reina Beatrix

Tue 3/24

2:00 pm-6:46 pm

Nonstop5h 46m

Chicago O'Hare Intl

Tue 3/31

9:04 am-3:20 pm

Nonstop5h 16m

$443

OranjestadChicago

AUA - ORD

AUAORD

Oranjestad Reina Beatrix

Wed 3/25

2:00 pm-6:46 pm

Nonstop5h 46m

Chicago O'Hare Intl

Tue 3/31

7:00 am-4:40 pm

1 stop8h 40m

$448

OranjestadChicago

AUA - ORD

AUAORD

Oranjestad Reina Beatrix

Tue 3/24

2:00 pm-6:46 pm

Nonstop5h 46m

Chicago O'Hare Intl

Mon 3/30

9:18 pm-12:40 pm

1 stop14h 22m

$448

OranjestadChicago

AUA - ORD

AUAORD

Oranjestad Reina Beatrix

Tue 3/24

3:25 pm-11:56 pm

1 stop9h 31m

Chicago O'Hare Intl

Mon 3/30

1:56 pm-12:15 pm

2 stops21h 19m

$453

OranjestadChicago

AUA - ORD

AUAORD

Oranjestad Reina Beatrix

Wed 3/25

12:50 pm-10:01 pm

1 stop10h 11m

Chicago O'Hare Intl

Mon 3/30

7:56 pm-12:15 pm

1 stop15h 19m

$453

OranjestadChicago

AUA - ORD

AUAORD

Oranjestad Reina Beatrix

Wed 3/25

1:10 pm-8:57 am

2 stops20h 47m

Chicago O'Hare Intl

Tue 3/31

7:35 pm-11:35 am

1 stop15h 00m

$453

OranjestadChicago

AUA - ORD

AUAORD

Oranjestad Reina Beatrix

Thu 3/26

2:25 pm-11:13 pm

1 stop9h 48m

Chicago O'Hare Intl

Tue 3/31

9:04 am-3:20 pm

Nonstop5h 16m

$453

OranjestadChicago

AUA - MDW

AUAMDW

Oranjestad Reina Beatrix

Thu 2/12

4:35 pm-10:42 pm

1 stop8h 07m

Chicago Midway

Wed 2/18

6:40 pm-12:55 pm

1 stop16h 15m

$458

OranjestadChicago

AUA - ORD

AUAORD

Oranjestad Reina Beatrix

Mon 3/23

2:00 pm-6:46 pm

Nonstop5h 46m

Chicago O'Hare Intl

Wed 4/1

9:04 am-3:20 pm

Nonstop5h 16m

$473

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/20

Showing 1-10 of 30 results
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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 December 22, 2025.

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 December 22, 2025.

The most flights from AW0 to CHI are scheduled on a Monday (3 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (1 on average).

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 December 22, 2025.
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.
American Airlines
7.2
Good
11,052 reviews

Crew

8.0

Comfort

7.2

Entertainment

6.9

Food

6.4

Overall

7.2

Boarding

7.5

Reviews

1 / 20
10.0
Excellent

Jeremy,Dec 2025

OKC - CLT

Was an okay flight. Had extra seat empty beside me so was able to stretch a bit
American Airlines
7.2
Good
11,052 reviews
American Airlines
7.2
Good
11,052 reviews

Crew

8.0

Comfort

7.2

Entertainment

6.9

Food

6.4

Overall

7.2

Boarding

7.5

Reviews

1 / 20
10.0
Excellent

Jeremy,Dec 2025

OKC - CLT

Was an okay flight. Had extra seat empty beside me so was able to stretch a bit

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 $443, United Airlines can have you in Chicago from Aruba in 5h 46m. 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 (67%), Qatar Airways (67%), United Airlines (67%).

  • What are the cheapest flights from Aruba to Chicago?

    Looking for the cheapest flight from Aruba to Chicago? While on average our users pay $728, our data indicates the cheapest price to be $218. The most popular route (Oranjestad Reina Beatrix - Chicago O'Hare Intl), is priced around $242.

  • 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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Alternative routes for Aruba to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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St. George's to St. Louis flights
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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 December 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$343Average$656FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$451Average$790FlexibilityNo cancel feeOn-time71%

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