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$207+ 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 7/12. Fares are subject to change and may not be available on all flights or dates of travel.
AUA — CHI
Jul 5 — Jul 121
Sat 7/5
Sat 7/12
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 June 30, 2025.

Round-trip from

$362
(Priceline)

One-way from

$207
(Priceline)

Good round-trip deal

$816 or less

Good one-way deal

$355 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 June 30, 2025.

This Priceline deal was found by Cheapflights users on 6/28. 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.
Sat 8/163:45 pmAUA - ORD
1 stop9h 14mMultiple Airlines
Sat 8/236:00 amORD - AUA
1 stop7h 29mMultiple Airlines
Deal found 6/28$362
This Cheapflightsfares deal was found by Cheapflights users on 6/28. 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 7/173:45 pmAUA - ORD
1 stop9h 08mSpirit Airlines
Sat 7/195:05 amORD - AUA
1 stop8h 35mSpirit Airlines
Deal found 6/28$417
This Expedia deal was found by Cheapflights users on 6/29. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/154:30 pmAUA - ORD
1 stop29h 20mJetBlue
Mon 10/206:45 amORD - AUA
1 stop28h 15mJetBlue
Deal found 6/29$433
This Frontier deal was found by Cheapflights users on 6/28. 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 7/123:35 pmAUA - MDW
1 stop8h 00mFrontier
Sat 7/196:20 amMDW - AUA
1 stop7h 09mFrontier
Deal found 6/28$445
This Frontier deal was found by Cheapflights users on 6/30. 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 7/123:35 pmAUA - ORD
1 stop8h 54mFrontier
Sat 7/195:01 amORD - AUA
1 stop8h 28mFrontier
Deal found 6/30$445
This Southwest deal was found by Cheapflights users on 6/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/153:35 pmAUA - MDW
1 stop7h 50mSouthwest
Sun 8/245:35 amMDW - AUA
1 stop8h 15mSouthwest
Deal found 6/30$515
This Delta deal was found by Cheapflights users on 6/30. 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.
Fri 8/153:25 pmAUA - ORD
1 stop9h 31mDelta
Sun 8/245:45 amORD - AUA
1 stop7h 25mDelta
Deal found 6/30$566
This Kiwi.com deal was found by Cheapflights users on 6/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/152:50 pmAUA - MDW
1 stop18h 55mMultiple Airlines
Sat 7/199:12 pmMDW - AUA
2 stops16h 28mMultiple Airlines
Deal found 6/30$597
This American Airlines deal was found by Cheapflights users on 6/28. 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 7/285:00 pmAUA - ORD
1 stop8h 17mAmerican Airlines
Mon 8/48:41 pmORD - AUA
1 stop15h 54mAmerican Airlines
Deal found 6/28$600
This deal was found by Cheapflights users on 6/30. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/123:25 pmAUA - MDW
1 stop7h 17mDelta
Tue 7/156:00 amMDW - AUA
1 stop7h 10mDelta
Deal found 6/30$1,068
This LATAM Airlines deal was found by Cheapflights users on 6/28. 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 LATAM Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/176:50 pmAUA - MDW
2 stops24h 12mLATAM Airlines
Sat 7/1912:43 pmMDW - AUA
2 stops28h 02mLATAM Airlines
Deal found 6/28$3,092

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 June 30, 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

Sat 8/16

3:45 pm-11:59 pm

1 stop9h 14m

Chicago O'Hare Intl

Sat 8/23

6:00 am-2:29 pm

1 stop7h 29m

$362

OranjestadChicago

AUA - ORD

AUAORD

Oranjestad Reina Beatrix

Thu 7/17

3:45 pm-11:53 pm

1 stop9h 08m

Chicago O'Hare Intl

Sat 7/19

5:05 am-2:40 pm

1 stop8h 35m

$417

OranjestadChicago

AUA - ORD

AUAORD

Oranjestad Reina Beatrix

Wed 10/15

4:30 pm-8:50 pm

1 stop29h 20m

Chicago O'Hare Intl

Mon 10/20

6:45 am-12:00 pm

1 stop28h 15m

$433

OranjestadChicago

AUA - MDW

AUAMDW

Oranjestad Reina Beatrix

Sat 7/12

3:35 pm-10:35 pm

1 stop8h 00m

Chicago Midway

Sat 7/19

6:20 am-2:29 pm

1 stop7h 09m

$445

OranjestadChicago

AUA - ORD

AUAORD

Oranjestad Reina Beatrix

Sat 7/12

3:35 pm-11:29 pm

1 stop8h 54m

Chicago O'Hare Intl

Sat 7/19

5:01 am-2:29 pm

1 stop8h 28m

$445

OranjestadChicago

AUA - MDW

AUAMDW

Oranjestad Reina Beatrix

Fri 8/15

3:35 pm-10:25 pm

1 stop7h 50m

Chicago Midway

Sun 8/24

5:35 am-2:50 pm

1 stop8h 15m

$515

OranjestadChicago

AUA - ORD

AUAORD

Oranjestad Reina Beatrix

Fri 8/15

3:25 pm-11:56 pm

1 stop9h 31m

Chicago O'Hare Intl

Sun 8/24

5:45 am-2:10 pm

1 stop7h 25m

$566

OranjestadChicago

AUA - MDW

AUAMDW

Oranjestad Reina Beatrix

Tue 7/15

2:50 pm-8:45 am

1 stop18h 55m

Chicago Midway

Sat 7/19

9:12 pm-2:40 pm

2 stops16h 28m

$597

OranjestadChicago

AUA - ORD

AUAORD

Oranjestad Reina Beatrix

Mon 7/28

5:00 pm-12:17 am

1 stop8h 17m

Chicago O'Hare Intl

Mon 8/4

8:41 pm-1:35 pm

1 stop15h 54m

$600

OranjestadChicago

AUA - MDW

AUAMDW

Oranjestad Reina Beatrix

Sat 7/12

3:25 pm-9:42 pm

1 stop7h 17m

Chicago Midway

Tue 7/15

6:00 am-2:10 pm

1 stop7h 10m

$1,068

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/28

Showing 1-10 of 25 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 June 30, 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.

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 June 30, 2025.
Get a feel of what it's like to fly with Southwest, Delta, and LATAM 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.
Southwest
8.0
Very good
4,278 reviews

Comfort

8.0

Entertainment

7.6

Overall

8.0

Boarding

8.2

Food

7.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,278 reviews
Southwest
8.0
Very good
4,278 reviews

Comfort

8.0

Entertainment

7.6

Overall

8.0

Boarding

8.2

Food

7.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,973 reviews
Southwest
8.0
Very good
4,278 reviews

Comfort

8.0

Entertainment

7.6

Overall

8.0

Boarding

8.2

Food

7.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
LATAM Airlines
7.5
Good
1,801 reviews
Southwest
8.0
Very good
4,278 reviews

Comfort

8.0

Entertainment

7.6

Overall

8.0

Boarding

8.2

Food

7.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
United Airlines
7.4
Good
8,852 reviews
Southwest
8.0
Very good
4,278 reviews

Comfort

8.0

Entertainment

7.6

Overall

8.0

Boarding

8.2

Food

7.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
JetBlue
7.3
Good
2,920 reviews
Southwest
8.0
Very good
4,278 reviews

Comfort

8.0

Entertainment

7.6

Overall

8.0

Boarding

8.2

Food

7.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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 Frontier, which is currently one of the cheapest options available, starting at $207. Spirit Airlines flights start at $216 while deals on JetBlue start at $260 one-way.

  • What are the cheapest flights from Aruba to Chicago?

    Looking for the cheapest flight from Aruba to Chicago? While on average our users pay $670, our data indicates the cheapest price to be $295. The most popular route (Oranjestad Reina Beatrix - Chicago O'Hare Intl), is priced around $362.

  • 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
Lansing
Benton Harbor
Porter
Hammond
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 June 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$571Average$726FlexibilityNo cancel feeOn-time69%

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