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$101+ Cheap flights from Aguadilla (BQN) 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 4/15. Fares are subject to change and may not be available on all flights or dates of travel.
BQN — CHI
Mar 14 — Mar 211
Sat 3/14
Sat 3/21
1 adult, Economy
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Cheap flight deals from Aguadilla to Chicago

Cheapest flights from Aguadilla to Chicago
Explore the most affordable flight options available from Aguadilla to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 12, 2026.

This Expedia deal was found by Cheapflights users on 2/10. 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.
Sun 4/122:43 am
BQN
-
MDW
1 stop18h 26m
Frontier
Mon 4/209:14 am
MDW
-
BQN
1 stop15h 29m
Frontier
Deal found 2/10$259
This Expedia deal was found by Cheapflights users on 2/10. 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.
Sun 4/122:43 am
BQN
-
ORD
1 stop21h 53m
Frontier
Mon 4/206:57 am
ORD
-
BQN
1 stop17h 46m
Frontier
Deal found 2/10$259
This Frontier deal was found by Cheapflights users on 2/9. 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.
Wed 3/43:58 am
BQN
-
MDW
1 stop12h 28m
Frontier
Tue 3/1011:19 am
MDW
-
BQN
1 stop13h 23m
Frontier
Deal found 2/9$268
This Frontier deal was found by Cheapflights users on 2/9. 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.
Wed 3/43:58 am
BQN
-
ORD
1 stop8h 48m
Frontier
Tue 3/104:18 pm
ORD
-
BQN
1 stop8h 24m
Frontier
Deal found 2/9$268
This Frontier deal was found by Cheapflights users on 2/8. 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.
Wed 2/253:58 am
BQN
-
ORD
1 stop8h 48m
Frontier
Mon 3/23:50 pm
ORD
-
BQN
1 stop9h 07m
Frontier
Deal found 2/8$288
This Travelocity deal was found by Cheapflights users on 2/10. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/193:58 am
BQN
-
MDW
1 stop12h 28m
Frontier
Sat 2/218:00 am
MDW
-
BQN
1 stop16h 57m
Frontier
Deal found 2/10$309
This Expedia deal was found by Cheapflights users on 2/10. 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 2/193:58 am
BQN
-
ORD
1 stop18h 14m
Frontier
Sat 2/218:15 am
ORD
-
BQN
1 stop16h 42m
Frontier
Deal found 2/10$309
This Kiwi.com deal was found by Cheapflights users on 2/11. 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 4/132:38 am
BQN
-
ORD
1 stop15h 18m
Multiple Airlines
Tue 4/215:34 pm
ORD
-
BQN
2 stops31h 09m
Multiple Airlines
Deal found 2/11$348
This Kiwi.com deal was found by Cheapflights users on 2/10. 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 4/139:14 pm
BQN
-
ORD
1 stop20h 42m
Multiple Airlines
Mon 4/204:47 pm
ORD
-
BQN
2 stops31h 56m
Multiple Airlines
Deal found 2/10$351
This Kiwi.com deal was found by Cheapflights users on 2/10. 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 4/139:14 pm
BQN
-
MDW
2 stops16h 46m
Multiple Airlines
Mon 4/209:14 am
MDW
-
BQN
1 stop15h 29m
Multiple Airlines
Deal found 2/10$373
This eDestinos deal was found by Cheapflights users on 2/11. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/132:38 am
BQN
-
MDW
2 stops20h 41m
Frontier
Tue 4/212:20 pm
MDW
-
BQN
2 stops34h 23m
Frontier
Deal found 2/11$383
This eDestinos deal was found by Cheapflights users on 2/11. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/132:38 am
BQN
-
ORD
2 stops33h 06m
Frontier
Tue 4/214:28 pm
ORD
-
BQN
2 stops32h 15m
Frontier
Deal found 2/11$383

Find flight deals from Aguadilla to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Aguadilla (BQN) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated February 12, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$259
(Expedia)

One-way from

$101
(Priceline)
Provider with most accurate pricing for Aguadilla Borinquen-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Aguadilla Borinquen-Chicago (CHI) flights.
Search Deals
From Aguadilla Borinquen to Chicago (CHI)
Search Deals
One-way flight from Aguadilla Borinquen to Chicago (CHI)
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Aguadilla 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 February 12, 2026.
Use the filters below to find and compare flights from Aguadilla to Chicago that are best for you.

Fly from

Aguadilla

Fly to

Chicago

Route

Depart

Return

Price

AguadillaChicago

BQN - MDW

BQNMDW

Aguadilla Borinquen

Sun 4/12

2:43 am-8:09 pm

1 stop18h 26m

Chicago Midway

Mon 4/20

9:14 am-1:43 am

1 stop15h 29m

$259

AguadillaChicago

BQN - ORD

BQNORD

Aguadilla Borinquen

Sun 4/12

2:43 am-11:36 pm

1 stop21h 53m

Chicago O'Hare Intl

Mon 4/20

6:57 am-1:43 am

1 stop17h 46m

$259

AguadillaChicago

BQN - MDW

BQNMDW

Aguadilla Borinquen

Wed 3/4

3:58 am-2:26 pm

1 stop12h 28m

Chicago Midway

Tue 3/10

11:19 am-1:42 am

1 stop13h 23m

$268

AguadillaChicago

BQN - ORD

BQNORD

Aguadilla Borinquen

Wed 3/4

3:58 am-10:46 am

1 stop8h 48m

Chicago O'Hare Intl

Tue 3/10

4:18 pm-1:42 am

1 stop8h 24m

$268

AguadillaChicago

BQN - ORD

BQNORD

Aguadilla Borinquen

Wed 2/25

3:58 am-10:46 am

1 stop8h 48m

Chicago O'Hare Intl

Mon 3/2

3:50 pm-2:57 am

1 stop9h 07m

$288

AguadillaChicago

BQN - ORD

BQNORD

Aguadilla Borinquen

Wed 2/25

3:58 am-10:46 am

1 stop8h 48m

Chicago O'Hare Intl

Sat 2/28

8:15 am-2:57 am

1 stop16h 42m

$309

AguadillaChicago

BQN - ORD

BQNORD

Aguadilla Borinquen

Mon 4/13

2:38 am-4:56 pm

1 stop15h 18m

Chicago O'Hare Intl

Tue 4/21

5:34 pm-1:43 am

2 stops31h 09m

$348

AguadillaChicago

BQN - ORD

BQNORD

Aguadilla Borinquen

Mon 4/13

9:14 pm-4:56 pm

1 stop20h 42m

Chicago O'Hare Intl

Mon 4/20

4:47 pm-1:43 am

2 stops31h 56m

$351

AguadillaChicago

BQN - MDW

BQNMDW

Aguadilla Borinquen

Mon 4/13

9:14 pm-1:00 pm

2 stops16h 46m

Chicago Midway

Mon 4/20

9:14 am-1:43 am

1 stop15h 29m

$373

AguadillaChicago

BQN - MDW

BQNMDW

Aguadilla Borinquen

Mon 4/13

2:38 am-10:19 pm

2 stops20h 41m

Chicago Midway

Tue 4/21

2:20 pm-1:43 am

2 stops34h 23m

$383

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/10

Showing 1-10 of 21 results
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Compare providers for flights from Aguadilla to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Aguadilla to Chicago in February.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Aguadilla-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Aguadilla-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Aguadilla-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Aguadilla-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Aguadilla-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Aguadilla to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Aguadilla 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 Aguadilla to Chicago

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

Currently, February is the cheapest month in which you can book a flight from Aguadilla to Chicago (average of $101). Flying from Aguadilla to Chicago in December is currently the most expensive (average of $157). 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.

Related info for your journey

Find useful and relevant information for your journey from Aguadilla to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Aguadilla to Chicago?

    If you book a flight to Chicago from Aguadilla, you will be flying from Borinquen, which is the city’s only airport. Aguadilla Borinquen (BQN) is located 4.8 mi from the center of Aguadilla. There are 0 flights from Borinquen to Chicago per day from 0 different airlines.

  • How long is the flight from Aguadilla to Chicago?

    Frontier can get you from Aguadilla to Chicago in just under 18h 26m. Your travel time can differ by up to . There are 2013 mi between Aguadilla and Chicago.

  • Can I find deals for flights from Aguadilla to Chicago that include hotel bookings?

    Yes. In addition to deals on Aguadilla to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Aguadilla to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Aguadilla to Chicago.

  • Can I find deals for business class flights from Aguadilla to Chicago?

    Yes. Cheapflights offers flight deals from Aguadilla 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 Aguadilla to Chicago?

    Currently, February is the cheapest month in which you can book a flight from Aguadilla to Chicago (average of $101). Flying from Aguadilla to Chicago in December is currently the most expensive (average of $157). 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 Chicago?

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