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$154+ 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 12/4. Fares are subject to change and may not be available on all flights or dates of travel.
AUA — CHI
Dec 6 — Dec 131
Sat 12/6
Sat 12/13
1 adult, Economy
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Cheap flight deals from Aruba to Chicago

Keep the following information in mind while searching for Aruba to Chicago flight deals. Data was last updated November 6, 2025.

Round-trip from

$329
(American Airlines)

One-way from

$154
(Cheapflightsfares)

Good round-trip deal

$495 or less

Good one-way deal

$655 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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Find 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 November 6, 2025.

This American Airlines deal was found by Cheapflights users on 11/5. 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.
Mon 12/223:39 pmAUA - ORD
Nonstop5h 52mAmerican Airlines
Wed 12/318:51 amORD - AUA
Nonstop4h 59mAmerican Airlines
Deal found 11/5$329
This Delta deal was found by Cheapflights users on 11/5. 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 12/224:35 pmAUA - ORD
2 stops22h 19mDelta
Wed 12/315:31 pmORD - AUA
1 stop16h 59mDelta
Deal found 11/5$334
This United Airlines deal was found by Cheapflights users on 11/6. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/35:35 pmAUA - ORD
1 stop8h 08mUnited Airlines
Sun 12/79:10 amORD - AUA
Nonstop5h 15mUnited Airlines
Deal found 11/6$339
This Expedia deal was found by Cheapflights users on 11/5. 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.
Tue 12/24:05 pmAUA - ORD
2 stops17h 55mMultiple Airlines
Tue 12/95:00 amORD - AUA
1 stop8h 35mMultiple Airlines
Deal found 11/5$347
This American Airlines deal was found by Cheapflights users on 11/5. 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.
Wed 12/35:59 pmAUA - ORD
2 stops15h 20mAmerican Airlines
Sun 12/78:55 pmORD - AUA
2 stops15h 05mAmerican Airlines
Deal found 11/5$348
This Kiwi.com deal was found by Cheapflights users on 11/5. 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.
Wed 12/312:05 pmAUA - ORD
2 stops32h 31mMultiple Airlines
Wed 12/103:26 pmORD - AUA
1 stop22h 09mMultiple Airlines
Deal found 11/5$359
This Cheapflightsfares deal was found by Cheapflights users on 11/6. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/204:40 pmAUA - ORD
1 stop8h 33mSpirit Airlines
Thu 11/275:00 amORD - AUA
1 stop8h 35mSpirit Airlines
Deal found 11/6$368
This Kiwi.com deal was found by Cheapflights users on 11/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/224:30 pmAUA - MDW
1 stop19h 35mMultiple Airlines
Wed 12/318:15 amMDW - AUA
2 stops29h 20mMultiple Airlines
Deal found 11/6$447
This Delta deal was found by Cheapflights users on 11/5. 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 11/134:35 pmAUA - MDW
1 stop9h 05mDelta
Mon 11/176:00 amMDW - AUA
1 stop7h 20mDelta
Deal found 11/5$467
This Delta deal was found by Cheapflights users on 11/4. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/124:35 pmAUA - MDW
2 stops18h 19mDelta
Sun 11/166:48 pmMDW - AUA
2 stops18h 32mDelta
Deal found 11/4$471
This Delta deal was found by Cheapflights users on 11/4. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/124:35 pmAUA - MDW
1 stop9h 05mDelta
Fri 11/146:48 pmMDW - AUA
2 stops16h 27mDelta
Deal found 11/4$497
This Southwest deal was found by Cheapflights users on 11/5. 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 11/134:00 pmAUA - MDW
1 stop9h 00mSouthwest
Mon 11/178:20 pmMDW - AUA
2 stops16h 40mSouthwest
Deal found 11/5$530

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 November 6, 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

Mon 12/22

3:39 pm-7:31 pm

Nonstop5h 52m

Chicago O'Hare Intl

Wed 12/31

8:51 am-3:50 pm

Nonstop4h 59m

$329

OranjestadChicago

AUA - ORD

AUAORD

Oranjestad Reina Beatrix

Fri 12/5

4:10 pm-11:32 pm

1 stop9h 22m

Chicago O'Hare Intl

Sun 12/7

6:15 pm-1:40 pm

1 stop17h 25m

$339

OranjestadChicago

AUA - ORD

AUAORD

Oranjestad Reina Beatrix

Fri 12/5

3:10 pm-8:39 am

2 stops19h 29m

Chicago O'Hare Intl

Mon 12/8

5:07 pm-1:55 pm

2 stops18h 48m

$339

OranjestadChicago

AUA - ORD

AUAORD

Oranjestad Reina Beatrix

Wed 12/3

5:35 pm-9:36 am

1 stop18h 01m

Chicago O'Hare Intl

Fri 12/5

7:45 pm-4:50 pm

1 stop19h 05m

$339

OranjestadChicago

AUA - ORD

AUAORD

Oranjestad Reina Beatrix

Wed 12/3

5:35 pm-11:43 pm

1 stop8h 08m

Chicago O'Hare Intl

Sat 12/6

6:00 am-4:50 pm

1 stop8h 50m

$339

OranjestadChicago

AUA - ORD

AUAORD

Oranjestad Reina Beatrix

Wed 12/3

5:35 pm-9:36 am

1 stop18h 01m

Chicago O'Hare Intl

Sun 12/7

9:10 am-4:25 pm

Nonstop5h 15m

$339

OranjestadChicago

AUA - ORD

AUAORD

Oranjestad Reina Beatrix

Thu 12/18

3:10 pm-10:14 am

2 stops21h 04m

Chicago O'Hare Intl

Sun 12/21

7:59 pm-12:30 pm

1 stop14h 31m

$423

OranjestadChicago

AUA - ORD

AUAORD

Oranjestad Reina Beatrix

Wed 12/17

4:35 pm-8:39 am

1 stop18h 04m

Chicago O'Hare Intl

Tue 12/23

5:29 pm-12:30 pm

1 stop17h 01m

$423

OranjestadChicago

AUA - ORD

AUAORD

Oranjestad Reina Beatrix

Tue 12/2

3:10 pm-10:14 am

2 stops21h 04m

Chicago O'Hare Intl

Sun 12/7

6:30 pm-1:55 pm

1 stop17h 25m

$423

OranjestadChicago

AUA - ORD

AUAORD

Oranjestad Reina Beatrix

Tue 12/2

4:05 pm-11:18 am

2 stops21h 13m

Chicago O'Hare Intl

Sun 12/7

8:15 pm-3:00 pm

1 stop16h 45m

$436

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/4

Showing 1-10 of 36 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 November 6, 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.

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 November 6, 2025.
Get a feel of what it's like to fly with United Airlines and 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.
United Airlines
7.4
Good
9,007 reviews

Comfort

7.3

Entertainment

7.1

Boarding

7.7

Overall

7.4

Crew

8.1

Food

6.6

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
United Airlines
7.4
Good
9,007 reviews
United Airlines
7.4
Good
9,007 reviews

Comfort

7.3

Entertainment

7.1

Boarding

7.7

Overall

7.4

Crew

8.1

Food

6.6

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
American Airlines
7.2
Good
11,040 reviews
United Airlines
7.4
Good
9,007 reviews

Comfort

7.3

Entertainment

7.1

Boarding

7.7

Overall

7.4

Crew

8.1

Food

6.6

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000

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 $329, American Airlines can have you in Chicago from Aruba in 5h 52m. 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 flights from Aruba to Chicago?

    Looking for the cheapest flight from Aruba to Chicago? While on average our users pay $878, our data indicates the cheapest price to be $199. The most popular route (Oranjestad Reina Beatrix - Chicago O'Hare Intl), is priced around $327.

  • 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
Hammond
Porter
Benton Harbor
Merrillville

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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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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 November 6, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$343Average$656FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$519Average$915FlexibilityNo cancel feeOn-time71%

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