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$157+ 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 1/31. Fares are subject to change and may not be available on all flights or dates of travel.
AUA — CHI
Feb 5 — Feb 121
Thu 2/5
Thu 2/12
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 January 6, 2026.

This Expedia deal was found by Cheapflights users on 1/4. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/194:40 pmAUA - ORD
1 stop9h 07mSpirit Airlines
Wed 2/258:16 pmORD - AUA
1 stop17h 19mSpirit Airlines
Deal found 1/4$254
This Kiwi.com deal was found by Cheapflights users on 1/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/224:40 pmAUA - ORD
1 stop9h 06mSpirit Airlines
Fri 1/305:32 pmORD - AUA
1 stop20h 03mSpirit Airlines
Deal found 1/4$269
This Cheapflightsfares deal was found by Cheapflights users on 1/4. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/124:40 pmAUA - ORD
1 stop9h 06mSpirit Airlines
Mon 1/195:15 amORD - AUA
1 stop8h 20mSpirit Airlines
Deal found 1/4$278
This Kiwi.com deal was found by Cheapflights users on 1/5. 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.
Thu 2/124:40 pmAUA - ORD
1 stop8h 44mMultiple Airlines
Wed 2/184:43 pmORD - AUA
1 stop20h 52mMultiple Airlines
Deal found 1/5$316
This Kiwi.com deal was found by Cheapflights users on 1/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/194:40 pmAUA - ORD
1 stop8h 44mMultiple Airlines
Wed 2/2512:44 pmORD - AUA
2 stops24h 51mMultiple Airlines
Deal found 1/4$323
This Kiwi.com deal was found by Cheapflights users on 1/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/224:40 pmAUA - ORD
1 stop9h 06mSpirit Airlines
Wed 1/287:20 amORD - AUA
1 stop30h 15mSpirit Airlines
Deal found 1/4$330
This Delta deal was found by Cheapflights users on 1/5. 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 2/124:35 pmAUA - MDW
1 stop7h 56mDelta
Wed 2/1810:49 amMDW - AUA
2 stops25h 06mDelta
Deal found 1/5$449
This Kissandfly.com deal was found by Cheapflights users on 1/5. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/122:10 pmAUA - MDW
1 stop10h 21mKLM
Wed 2/186:40 pmMDW - AUA
1 stop16h 15mKLM
Deal found 1/5$458
This Delta deal was found by Cheapflights users on 1/4. 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.
Thu 1/224:35 pmAUA - MDW
1 stop7h 47mDelta
Fri 1/306:00 amMDW - AUA
1 stop7h 20mDelta
Deal found 1/4$480
This Southwest deal was found by Cheapflights users on 1/5. 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 2/123:25 pmAUA - MDW
1 stop9h 20mSouthwest
Wed 2/185:00 amMDW - AUA
1 stop7h 25mSouthwest
Deal found 1/5$489
This Delta deal was found by Cheapflights users on 1/4. 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.
Thu 2/194:35 pmAUA - MDW
1 stop7h 56mDelta
Wed 2/256:00 amMDW - AUA
1 stop7h 20mDelta
Deal found 1/4$509
This Delta deal was found by Cheapflights users on 1/5. 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 2/194:35 pmAUA - MDW
1 stop7h 56mDelta
Thu 2/266:00 amMDW - AUA
1 stop7h 20mDelta
Deal found 1/5$619

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 January 6, 2026.

Round-trip from

$254
(Expedia)

One-way from

$157
(Frontier)

Good round-trip deal

$342 or less

Good one-way deal

$251 or less
From Aruba to Chicago (CHI)
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One-way flight from Aruba to Chicago (CHI)
Search Deals
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 January 6, 2026.
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

Thu 1/22

4:40 pm-9:12 am

2 stops18h 32m

Chicago O'Hare Intl

Fri 1/30

8:43 pm-3:35 pm

1 stop16h 52m

$276

OranjestadChicago

AUA - ORD

AUAORD

Oranjestad Reina Beatrix

Wed 3/25

3:41 pm-11:41 pm

1 stop9h 00m

Chicago O'Hare Intl

Wed 4/1

7:41 pm-2:26 pm

1 stop17h 45m

$367

OranjestadChicago

AUA - ORD

AUAORD

Oranjestad Reina Beatrix

Thu 2/12

4:05 pm-12:48 pm

2 stops22h 43m

Chicago O'Hare Intl

Wed 2/18

1:55 pm-3:00 pm

2 stops23h 05m

$377

OranjestadChicago

AUA - ORD

AUAORD

Oranjestad Reina Beatrix

Thu 3/26

3:05 pm-1:01 pm

1 stop22h 56m

Chicago O'Hare Intl

Tue 3/31

4:43 pm-3:15 pm

1 stop21h 32m

$394

OranjestadChicago

AUA - ORD

AUAORD

Oranjestad Reina Beatrix

Thu 2/12

1:40 pm-11:21 pm

1 stop11h 41m

Chicago O'Hare Intl

Wed 2/18

6:04 am-1:20 pm

1 stop29h 16m

$420

OranjestadChicago

AUA - ORD

AUAORD

Oranjestad Reina Beatrix

Wed 3/25

3:05 pm-11:18 am

2 stops21h 13m

Chicago O'Hare Intl

Mon 3/30

6:21 pm-3:15 pm

2 stops19h 54m

$448

OranjestadChicago

AUA - MDW

AUAMDW

Oranjestad Reina Beatrix

Thu 2/12

2:10 pm-10:31 pm

1 stop10h 21m

Chicago Midway

Wed 2/18

6:40 pm-12:55 pm

1 stop16h 15m

$449

OranjestadChicago

AUA - ORD

AUAORD

Oranjestad Reina Beatrix

Wed 2/18

5:59 pm-9:41 pm

Nonstop5h 42m

Chicago O'Hare Intl

Wed 2/25

7:10 am-4:59 pm

1 stop7h 49m

$449

OranjestadChicago

AUA - ORD

AUAORD

Oranjestad Reina Beatrix

Thu 2/19

3:00 pm-6:46 pm

Nonstop5h 46m

Chicago O'Hare Intl

Wed 2/25

6:00 am-4:40 pm

1 stop8h 40m

$449

OranjestadChicago

AUA - MDW

AUAMDW

Oranjestad Reina Beatrix

Thu 1/22

4:35 pm-10:22 pm

1 stop7h 47m

Chicago Midway

Wed 1/28

1:26 pm-12:55 pm

2 stops21h 29m

$449

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/4

Showing 1-10 of 31 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 January 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.

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 $449, Spirit Airlines can have you in Chicago from Aruba in 10h 21m. 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 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: Qatar Airways (73%), American Airlines (72%), United Airlines (68%).

  • What are the cheapest flights from Aruba to Chicago?

    Looking for the cheapest flight from Aruba to Chicago? While on average our users pay $581, our data indicates the cheapest price to be $212. The most popular route (Oranjestad Reina Beatrix - Chicago O'Hare Intl), is priced around $254.

  • 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.
Punta Cana to O'Hare Intl flights
Punta Cana to Midway flights
Luis Munoz Marin Intl to O'Hare Intl flights
Oranjestad to O'Hare Intl flights
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Montego Bay to O'Hare Intl flights
Christiansted to O'Hare Intl flights
George Town to O'Hare Intl flights
Port of Spain to O'Hare Intl flights
Santiago de los Caballeros to O'Hare Intl flights
St. John's to O'Hare Intl flights
Montego Bay to Midway flights
Oranjestad to St. Louis flights
Aguadilla to O'Hare Intl flights
Nassau to St. Louis flights
Vieques to O'Hare Intl flights
St. George's to St. Louis flights
Port of Spain to St. Louis flights
Saint Thomas Island to St. Louis flights
Port Au Prince to O'Hare Intl flights
Road Town to O'Hare Intl flights
Roseau to O'Hare Intl flights
Culebra to O'Hare Intl flights
Bridgetown to O'Hare Intl flights
Port Au Prince to Midway flights
Aguadilla to Midway flights

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 January 6, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$343Average$656FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$451Average$790FlexibilityNo cancel feeOn-time71%

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