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$152+ 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 1/29. Fares are subject to change and may not be available on all flights or dates of travel.
AUA — CHI
Dec 31 — Jan 71
Wed 12/31
Wed 1/7
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 December 1, 2025.

Round-trip from

$256
(Kiwi.com)

One-way from

$152
(Super.com)

Good round-trip deal

$361 or less

Good one-way deal

$328 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 December 1, 2025.

This Frontier deal was found by Cheapflights users on 11/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/2712:40 pmAUA - MDW
1 stop11h 32mFrontier
Fri 1/26:12 amMDW - AUA
1 stop27h 08mFrontier
Deal found 11/30$270
This Mytrip deal was found by Cheapflights users on 11/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/2712:40 pmAUA - ORD
1 stop12h 06mFrontier
Sat 1/36:10 amORD - AUA
1 stop27h 10mFrontier
Deal found 11/29$278
This Gotogate deal was found by Cheapflights users on 11/30. 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.
Sat 12/2712:40 pmAUA - ORD
1 stop12h 06mFrontier
Fri 1/212:39 pmORD - AUA
1 stop20h 41mFrontier
Deal found 11/30$279
This Kiwi.com deal was found by Cheapflights users on 11/29. 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.
Thu 12/254:40 pmAUA - ORD
1 stop9h 50mSpirit Airlines
Wed 12/313:26 pmORD - AUA
1 stop22h 09mSpirit Airlines
Deal found 11/29$284
This Mytrip deal was found by Cheapflights users on 11/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/244:05 pmAUA - ORD
1 stop22h 56mMultiple Airlines
Wed 1/215:53 pmORD - AUA
2 stops19h 42mMultiple Airlines
Deal found 11/29$362
This Mytrip deal was found by Cheapflights users on 11/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/274:40 pmAUA - ORD
1 stop9h 50mSpirit Airlines
Sat 1/37:57 pmORD - AUA
2 stops17h 38mSpirit Airlines
Deal found 11/29$376
This Priceline deal was found by Cheapflights users on 11/29. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/244:05 pmAUA - ORD
1 stop22h 56mAir Canada
Wed 1/219:15 pmORD - AUA
1 stop15h 45mAir Canada
Deal found 11/29$381
This Delta deal was found by Cheapflights users on 11/30. 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.
Wed 12/34:35 pmAUA - MDW
1 stop9h 12mDelta
Sun 12/76:00 amMDW - AUA
1 stop7h 20mDelta
Deal found 11/30$489
This Delta deal was found by Cheapflights users on 11/29. 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.
Fri 12/53:10 pmAUA - MDW
2 stops26h 34mDelta
Fri 12/125:13 pmMDW - AUA
1 stop18h 02mDelta
Deal found 11/29$519
This Delta deal was found by Cheapflights users on 11/29. 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 12/251:45 pmAUA - MDW
1 stop10h 37mDelta
Wed 12/316:00 amMDW - AUA
1 stop7h 20mDelta
Deal found 11/29$538
This Delta deal was found by Cheapflights users on 12/1. 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.
Tue 12/24:35 pmAUA - MDW
1 stop9h 12mDelta
Sat 12/66:00 amMDW - AUA
1 stop7h 20mDelta
Deal found 12/1$559
This Delta deal was found by Cheapflights users on 11/30. 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.
Sat 12/273:10 pmAUA - MDW
2 stops19h 55mDelta
Fri 1/29:29 amMDW - AUA
2 stops27h 51mDelta
Deal found 11/30$703

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 1, 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 - MDW

AUAMDW

Oranjestad Reina Beatrix

Sat 12/27

12:40 pm-10:12 pm

1 stop11h 32m

Chicago Midway

Fri 1/2

6:12 am-11:20 am

1 stop27h 08m

$270

OranjestadChicago

AUA - ORD

AUAORD

Oranjestad Reina Beatrix

Thu 1/22

4:40 pm-11:46 pm

1 stop9h 06m

Chicago O'Hare Intl

Sun 1/25

8:43 pm-3:35 pm

1 stop16h 52m

$271

OranjestadChicago

AUA - ORD

AUAORD

Oranjestad Reina Beatrix

Sat 12/27

12:40 pm-10:46 pm

1 stop12h 06m

Chicago O'Hare Intl

Sat 1/3

6:10 am-11:20 am

1 stop27h 10m

$278

OranjestadChicago

AUA - ORD

AUAORD

Oranjestad Reina Beatrix

Sat 12/27

12:40 pm-10:46 pm

1 stop12h 06m

Chicago O'Hare Intl

Fri 1/2

12:39 pm-11:20 am

1 stop20h 41m

$279

OranjestadChicago

AUA - ORD

AUAORD

Oranjestad Reina Beatrix

Sat 1/17

4:40 pm-11:46 pm

1 stop9h 06m

Chicago O'Hare Intl

Thu 1/29

5:15 am-3:35 pm

1 stop8h 20m

$284

OranjestadChicago

AUA - ORD

AUAORD

Oranjestad Reina Beatrix

Mon 1/19

4:40 pm-11:22 am

1 stop20h 42m

Chicago O'Hare Intl

Sat 1/24

5:15 am-3:35 pm

1 stop8h 20m

$301

OranjestadChicago

AUA - ORD

AUAORD

Oranjestad Reina Beatrix

Thu 1/15

4:40 pm-11:46 pm

1 stop9h 06m

Chicago O'Hare Intl

Sat 1/24

4:38 pm-3:45 pm

3 stops21h 07m

$324

OranjestadChicago

AUA - ORD

AUAORD

Oranjestad Reina Beatrix

Wed 1/21

12:05 pm-8:18 am

2 stops22h 13m

Chicago O'Hare Intl

Thu 1/29

5:15 am-3:35 pm

1 stop8h 20m

$348

OranjestadChicago

AUA - ORD

AUAORD

Oranjestad Reina Beatrix

Wed 12/24

4:05 pm-11:18 am

2 stops21h 13m

Chicago O'Hare Intl

Wed 1/21

5:53 pm-3:35 pm

2 stops19h 42m

$362

OranjestadChicago

AUA - MDW

AUAMDW

Oranjestad Reina Beatrix

Thu 1/22

4:35 pm-10:22 pm

1 stop7h 47m

Chicago Midway

Sun 1/25

6:00 am-3:20 pm

1 stop7h 20m

$458

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/30

Showing 1-10 of 27 results
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2
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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 1, 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 December 1, 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
11,039 reviews

Overall

7.2

Entertainment

6.9

Food

6.5

Boarding

7.5

Crew

8.0

Comfort

7.2

Reviews

1 / 20
8.0
Excellent

Monica,Nov 2025

JAC - DFW

At least there was an option of entertainment on this flight.
American Airlines
7.2
Good
11,039 reviews
American Airlines
7.2
Good
11,039 reviews

Overall

7.2

Entertainment

6.9

Food

6.5

Boarding

7.5

Crew

8.0

Comfort

7.2

Reviews

1 / 20
8.0
Excellent

Monica,Nov 2025

JAC - DFW

At least there was an option of entertainment on this flight.

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 $458, Frontier can have you in Chicago from Aruba in 7h 47m. Aruba and Chicago are separated by a distance of 2286 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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: United Airlines (100%), American Airlines (50%), Qatar Airways (50%).

  • What are the cheapest flights from Aruba to Chicago?

    Looking for the cheapest flight from Aruba to Chicago? While on average our users pay $412, our data indicates the cheapest price to be $241. The most popular route (Oranjestad Reina Beatrix - Chicago O'Hare Intl), is priced around $269.

  • 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 December 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$343Average$656FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$451Average$790FlexibilityNo cancel feeOn-time71%

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