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$203+ 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 5/31. Fares are subject to change and may not be available on all flights or dates of travel.
AUA — CHI
May 20 — May 271
Tue 5/20
Tue 5/27
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 May 15, 2025.

Round-trip from

$443
(Cheapflightsfares)

One-way from

$203
(Cheapflightsfares)

Popular in

June

Cheapest in

September

Average price

$754

Good round-trip deal

$393 or less

Good one-way deal

$295 or less
From Aruba to Chicago (CHI)
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One-way flight from Aruba to Chicago (CHI)
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Highest demand for flights based on searches. 19% potential increase in price ($159 potential increase over avg. RT price).
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Cheapest flight prices on average. 8% potential price decrease ($53 potential savings vs. average RT price).
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Average for round-trip flights in May 2025
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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 May 15, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 5/13. 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.
Sun 7/133:45 pmAUA - ORD
1 stop9h 12mSpirit Airlines
Sat 7/195:05 amORD - AUA
1 stop8h 35mSpirit Airlines
Deal found 5/13$443
This Copa Airlines deal was found by Cheapflights users on 5/14. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/81:18 pmAUA - ORD
1 stop12h 02mCopa Airlines
Sat 8/21:07 amORD - AUA
1 stop12h 46mCopa Airlines
Deal found 5/14$557
This Mytrip deal was found by Cheapflights users on 5/15. 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 5/215:35 pmAUA - ORD
2 stops23h 28mMultiple Airlines
Wed 5/2812:41 pmORD - AUA
1 stop24h 59mMultiple Airlines
Deal found 5/15$560
This United Airlines deal was found by Cheapflights users on 5/14. 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.
Tue 7/83:10 pmAUA - ORD
1 stop20h 11mUnited Airlines
Sun 8/38:35 amORD - AUA
Nonstop5h 15mUnited Airlines
Deal found 5/14$571
This Priceline deal was found by Cheapflights users on 5/14. 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.
Tue 7/85:35 pmAUA - ORD
1 stop20h 40mAvianca
Sun 8/33:45 pmORD - AUA
3 stops17h 15mAvianca
Deal found 5/14$605
This JetBlue deal was found by Cheapflights users on 5/15. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2112:20 pmAUA - ORD
1 stop10h 34mJetBlue
Wed 5/287:31 pmORD - AUA
1 stop16h 04mJetBlue
Deal found 5/15$677
This Southwest deal was found by Cheapflights users on 5/14. 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 5/212:35 pmAUA - MDW
1 stop8h 30mSouthwest
Wed 5/285:55 amMDW - AUA
1 stop6h 40mSouthwest
Deal found 5/14$825
This Delta deal was found by Cheapflights users on 5/14. 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.
Sun 6/293:25 pmAUA - MDW
1 stop7h 20mDelta
Sun 7/66:00 amMDW - AUA
1 stop7h 10mDelta
Deal found 5/14$851
This Mytrip deal was found by Cheapflights users on 5/14. 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.
Sun 6/2911:00 amAUA - MDW
3 stops30h 54mMultiple Airlines
Sun 7/69:40 amMDW - AUA
3 stops23h 20mMultiple Airlines
Deal found 5/14$1,475

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 May 15, 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

Sun 7/13

3:45 pm-11:57 pm

1 stop9h 12m

Chicago O'Hare Intl

Sat 7/19

5:05 am-2:40 pm

1 stop8h 35m

$443

OranjestadChicago

AUA - ORD

AUAORD

Oranjestad Reina Beatrix

Tue 7/8

1:18 pm-12:20 am

1 stop12h 02m

Chicago O'Hare Intl

Sat 8/2

1:07 am-2:53 pm

1 stop12h 46m

$557

OranjestadChicago

AUA - ORD

AUAORD

Oranjestad Reina Beatrix

Tue 7/8

3:10 pm-10:21 am

1 stop20h 11m

Chicago O'Hare Intl

Sun 8/3

8:35 am-2:50 pm

Nonstop5h 15m

$571

OranjestadChicago

AUA - ORD

AUAORD

Oranjestad Reina Beatrix

Tue 7/8

5:35 pm-4:04 pm

2 stops23h 29m

Chicago O'Hare Intl

Sun 8/3

2:35 pm-10:00 am

1 stop18h 25m

$577

OranjestadChicago

AUA - ORD

AUAORD

Oranjestad Reina Beatrix

Tue 7/8

5:35 pm-1:15 pm

1 stop20h 40m

Chicago O'Hare Intl

Sun 8/3

3:45 pm-10:00 am

3 stops17h 15m

$605

OranjestadChicago

AUA - MDW

AUAMDW

Oranjestad Reina Beatrix

Sun 6/29

3:25 pm-9:45 pm

1 stop7h 20m

Chicago Midway

Sun 7/6

6:00 am-2:10 pm

1 stop7h 10m

$851

OranjestadChicago

AUA - MDW

AUAMDW

Oranjestad Reina Beatrix

Sun 6/29

11:00 am-4:54 pm

3 stops30h 54m

Chicago Midway

Sun 7/6

9:40 am-10:00 am

3 stops23h 20m

$1,475

OranjestadChicago

AUA - ORD

AUAORD

Oranjestad Reina Beatrix

Sat 5/31

3:45 pm-12:05 am

1 stop9h 20m

$203

OranjestadChicago

AUA - MDW

AUAMDW

Oranjestad Reina Beatrix

Sat 5/31

3:35 pm-10:17 pm

1 stop7h 42m

$219

OranjestadChicago

AUA - ORD

AUAORD

Oranjestad Reina Beatrix

Thu 8/28

2:30 pm-10:28 pm

1 stop8h 58m

$232

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/15

Showing 1-10 of 18 results
1
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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 May 15, 2025.

One of the essential ways to save on airfare from Aruba to Chicago is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight at noon could potentially save you up to 14% on airfare.

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 May 15, 2025.
Southwest
8.0
Very good
4,289 reviews

Entertainment

7.6

Food

7.1

Crew

8.6

Boarding

8.2

Comfort

8.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,289 reviews
Southwest
8.0
Very good
4,289 reviews

Entertainment

7.6

Food

7.1

Crew

8.6

Boarding

8.2

Comfort

8.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,946 reviews
Southwest
8.0
Very good
4,289 reviews

Entertainment

7.6

Food

7.1

Crew

8.6

Boarding

8.2

Comfort

8.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Copa Airlines
7.6
Good
1,423 reviews
Southwest
8.0
Very good
4,289 reviews

Entertainment

7.6

Food

7.1

Crew

8.6

Boarding

8.2

Comfort

8.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
United Airlines
7.4
Good
8,731 reviews
Southwest
8.0
Very good
4,289 reviews

Entertainment

7.6

Food

7.1

Crew

8.6

Boarding

8.2

Comfort

8.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
JetBlue
7.3
Good
2,925 reviews
Southwest
8.0
Very good
4,289 reviews

Entertainment

7.6

Food

7.1

Crew

8.6

Boarding

8.2

Comfort

8.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

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.

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

    To fly one-way, consider booking your trip with Spirit Airlines, which is currently one of the cheapest options available, starting at $203. Frontier flights start at $219 while deals on JetBlue start at $232 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 (75%), Qatar Airways (75%), 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 $516, our data indicates the cheapest price to be $180. The most popular route (Oranjestad Reina Beatrix - Chicago O'Hare Intl), is priced around $426.

  • 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.

  • What is the cheapest month to book a flight from Aruba to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Aruba to Chicago (average of $245). Flying from Aruba to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Aruba?

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

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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 airline flying from Aruba to Chicago

Discover the top airline 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 May 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$571Average$726FlexibilityNo cancel feeOn-time69%

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