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CHI - BQN

$96 Find cheap flights from Chicago to Aguadilla

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Aguadilla departing on 6/20. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
Thu 7/11
Thu 7/18

Search hundreds of travel sites at once for deals on flights to Aguadilla

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Aguadilla, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Aguadilla, as well as popular online travel agencies
In the last 7 days travelers have searched 44,212,782 times on KAYAK, and here is why:

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Cheap flight deals from Chicago to Aguadilla (CHI-BQN)

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Aguadilla that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
5:58 pm - 1:48 amORD-BQN
6h 50m1 stop
5:53 pm - 1:13 amBQN-ORD
8h 20m1 stop
$285Frontier
Find Deal
Fri, Jun 28 - Thu, Jul 4
5:56 pm - 1:47 amORD-BQN
6h 51m1 stop
2:47 am - 12:59 amBQN-ORD
23h 12m1 stop
$341Frontier
Find Deal
Wed, Aug 14 - Sat, Aug 17
5:58 pm - 1:48 amORD-BQN
6h 50m1 stop
2:57 am - 6:18 pmBQN-ORD
16h 21m1 stop
$377Frontier
Find Deal
Fri, Jun 28 - Wed, Jul 3
5:56 pm - 1:47 amORD-BQN
6h 51m1 stop
2:47 am - 12:59 amBQN-ORD
23h 12m1 stop
$384Frontier
Find Deal
Fri, Oct 4 - Sun, Oct 6
5:37 pm - 1:54 amORD-BQN
7h 17m1 stop
2:54 am - 12:59 amBQN-ORD
23h 05m1 stop
$424Frontier
Find Deal
Tue, Jul 16 - Tue, Jul 23
9:13 pm - 11:57 pmORD-BQN
25h 44m2 stops
1:09 am - 8:30 amBQN-ORD
9h 21m1 stop
$512United Airlines
Find Deal
Fri, Nov 1 - Mon, Nov 4
6:38 pm - 2:50 amORD-BQN
7h 12m1 stop
9:41 am - 5:43 pmBQN-ORD
9h 02m1 stop
$515JetBlue
Find Deal
Tue, Jul 30 - Mon, Aug 5
7:45 am - 11:09 pmORD-BQN
14h 24m2 stops
12:15 am - 8:34 amBQN-ORD
9h 19m1 stop
$519United Airlines
Find Deal
Fri, Oct 4 - Sun, Oct 6
9:13 pm - 11:57 pmORD-BQN
25h 44m2 stops
1:09 am - 6:38 pmBQN-ORD
19h 29m2 stops
$606United Airlines
Find Deal
Fri, Nov 1 - Mon, Nov 4
6:17 pm - 11:09 pmORD-BQN
27h 52m2 stops
12:15 am - 8:34 amBQN-ORD
9h 19m1 stop
$670United Airlines
Find Deal
Sun, Oct 13 - Sat, Oct 19

Flights from Chicago to Aguadilla - Travel Insights & Trends

Get data-powered insights and trends into flights from Chicago to Aguadilla to help you find the cheapest flights, the best time to fly and much more.

What’s the cheapest day of the week to fly from Chicago to Aguadilla?

The average price of all flights from Chicago to Aguadilla clicked on KAYAK for each day over the last 12 months.
For Chicago to Aguadilla, Wednesday is the cheapest day to fly on average and Sunday is the most expensive. Flying from Aguadilla back to Chicago, the best deals are generally found on Monday, with Friday being the most expensive.

What is the cheapest month to fly from Chicago to Aguadilla?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Chicago to Aguadilla, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.
The cheapest month for flights from Chicago to Aguadilla is September, where tickets cost $240 on average. On the other hand, the most expensive months are December and June, where the average cost of tickets is $571 and $520 respectively.

How far in advance should I book a flight from Chicago to Aguadilla?

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from Chicago to Aguadilla, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price on the flight from Chicago to Aguadilla, you should book around 3 days before departure. For the absolute cheapest price, our data suggests you should book 23 days before departure.

Which airlines provide the cheapest flights from Chicago to Aguadilla?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
The cheapest return flight ticket from Chicago to Aguadilla found by KAYAK users in the last 72 hours was for $285 on Frontier, followed by United Airlines ($512). One-way flight deals have also been found from as low as $96 on Frontier and from $274 on JetBlue.

Good to know

Low season

January

High season

April

Cheapest flight

$96
Best time to beat the crowds but there is an average 5% increase in price.
Most popular time to fly and prices are also 23% lower on average.
Flight from Chicago O'Hare Airport to Aguadilla

When to book flights from Chicago to Aguadilla

Are your dates flexible? Find out the best times to travel from Chicago to Aguadilla based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Chicago to Aguadilla

  • What is the cheapest flight from Chicago to Aguadilla?

    In the last 3 days, the lowest price for a flight from Chicago to Aguadilla was $96 for a one-way ticket and $285 for a round-trip.

  • Do I need a passport to fly between Chicago and Aguadilla?

    Yes

  • Which airports will I be using when flying from Chicago to Aguadilla?

    Chicago is served by 2 major airports and there is only 1 main airport in Aguadilla. You will leave Chicago from one of these airports: Chicago Midway or Chicago O'Hare Intl. You will be arriving at Aguadilla Borinquen.

  • Which aircraft models fly most regularly from Chicago to Aguadilla?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Chicago to Aguadilla?

    Star Alliance is the only airline alliance operating flights between Chicago and Aguadilla.

  • Which is the best airline for flights from Chicago to Aguadilla, United Airlines or Frontier?

    The two airlines most popular with KAYAK users for flights from Chicago to Aguadilla are United Airlines and Frontier. With an average price for the route of $432 and an overall rating of 7.4, United Airlines is the most popular choice. Frontier is also a great choice for the route, with an average price of $293 and an overall rating of 6.2.

  • How does KAYAK find such low prices on flights from Chicago to Aguadilla?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Aguadilla.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Aguadilla?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Aguadilla from Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Aguadilla?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Aguadilla with an airline and back to Chicago with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Aguadilla?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Aguadilla from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top 3 airlines serving from Chicago to Aguadilla

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Aguadilla. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Chicago to Aguadilla? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.4
United AirlinesOverall score based on 10629 reviews
7.2Comfort
6.7Food
7.1Entertainment
8.1Crew
7.7Boarding
Airline reviews

Flighty delayed on boarding - then group 1 had to check their carry on bags but groups 3 and beyond could carry bags on - very inconvenient for weekend business trip with no checked baggage. Then delayed on the runway - before take off. No communication from pilot on why or how long. Wifi/Entertainment didn't work for 4+ flight. Upon arrival, attendants announced wrong carousel for baggage claim - everyone was waiting at the wrong place for their checked bags. This was a mess united!

8.0 ExcellentBob, Jun 2024ORD - LAX
Read more about United Airlines reviews

Flighty delayed on boarding - then group 1 had to check their carry on bags but groups 3 and beyond could carry bags on - very inconvenient for weekend business trip with no checked baggage. Then delayed on the runway - before take off. No communication from pilot on why or how long. Wifi/Entertainment didn't work for 4+ flight. Upon arrival, attendants announced wrong carousel for baggage claim - everyone was waiting at the wrong place for their checked bags. This was a mess united!

There was no screens on board AND the WiFi didn’t work. My seat was broken and couldn’t recline so I couldn’t even sleep. The flight attendants didn’t offer anything to make it more comfortable. It was such an old cramped plane, when the person in front of me reclined I couldn’t even open my tray table. All the United ads talk about guaranteeing everyone gets a screen!

Standard flight experience, but there is only power at the seat to row 20 on the aircraft, on my initial check in it did not say that was the case

Energetic crew - flight full of swiftied going to Taylor's opening show in Paris! Long lines for bathroom made out kind of suck though

I’ve had a couple flights this week on United that were delayed by an hour or more

Great! The plane was decently sized and comfortable. The staff was nice and there was great in flight entertainment

Last minute gate change nearly caused us to miss our flight. Change was not announced or displayed in the main board at the old gate. Terrible communication. When we landed we had to wait 20 minutes because there was another plane at the assigned gate. Not the crew’s fault, but adding 20 minutes to a 45 minute flight sucked.

Nothing beats ANA customer service on my opinion. Maybe because of their Japanese culture (and food). Arigatō

delay several times and wait extra long to board. no entertainment service because there are problem for some rows. always encounter some delays for the last flight of the day.

Flight delayed for 2 hours due to a part. The plane sat waiting for boarding for a long time and during final preflight inspection the issue was found. Why not do the preflight inspection sooner if you know the plane is being used?

The plane was not on time for boarding or departure or arrivals.

Flight expected to leave at 6:40 pm ended leaving at 8:00 am the following day. I slept in a cold airport. Never again Spirit for me…

This was the return leg of my journey with Spirit Airlines. Despite its reputation, I found no issues as it got me from point A to B safely and without delay, especially with no mechanical delays, which is fantastic in my book! The staff, from ground crew to cabin crew, were all pleasant and hassle-free. The flight was smooth from takeoff to landing. I have absolutely no complaints about this no-frills airline!

It was the worst ever, i will be filing a lawsuit to get a refund. Our flight was delayed 4 hours so we would miss our connecting flight, we were not rebooked to our destination the same day, we were not offered any options to get home on the same day despite being clear that we absolutely cannot get stranded at night due to family, we were forced to book our own flights on a different airline to get home, and spririt is refusing a refund because our flight wasn't cancelled, only delayed. oh yeah, and they lost our luggage on the first part of the trip and you cannot get a hold of customer service when anything goes wrong, on hold for 30+ minutes. and their app breaks so you can't use that either.

My flight was cancelled!!! I had to spend 200.00 on another flight!!

The flight attendants were very personable, extremely friendly, and had a very good feeling of the energy around them not to mention they’re very funny and engaging. What made up for the discomfort of the seats and the fact that the plane sat for a long time on the Turmac. Not sure if the pilot was new, but the landing was very rough sort of like I was at a magic mountain theme park ride that was built in 1959

Didn’t happen. They stranded us in Orlando and had to book a flight on frontier to get to our destination.

Flight was delayed 2+ hours missed a concert because of it…

Flight left very close to original projected time. Paid for checked bag weight overage (my fault). Plane was literally brand new & this was its 2nd flight. Seats were alittle uncomfortable (I'm 5'11 * 175lbs and was alittle cramped, & brand new seats had little cushion). Food options were good. Main thing was flight took off & landed on time.

Flight left very close to original projected time. Plane was literally brand new & this was its 2nd flight. Seats were alittle uncomfortable (I'm 5'11 * 175lbs and was alittle cramped, & brand new seats had little cushion). Food options were good. Main thing was flight took off & landed on time.

Did not realize seats did not recline. Best to travel in an exit row... No question

I strongly dislike Frontier. I find them barebones, the seats not particularly comfortable, the nickel and diming is maddening, the app is TERRIBLE - super confusing to navigate, and the last 4 frontier flights I have flown have been on AVERAGE 2 hours late, one ruining a fancy night out in Vegas with reservations made well in advance, which was nodded to with a measly 5000 miles, which translates to almost nothing. At least credit a free checked bag or something.

8 hr delay. had to buy another ticket with another airline

Four and a half hour delay in total. What frustrates me most is the poor communication and disorganization.

I appreciated the upgrade to free cary-on bag and seat selection at no charge

FRONTIER SUCKS! The agent downstairs tricked me into booking, just to get to the gate. At the gate, they told me they couldn't help. I then called Customer Service. They and the gate attendants kept blaming each other. Neither side was willing to help the customer.

The agent at check-in was strident, unwelcoming, and condescending to customers ahead of me.

Flight was delay 9hrs and nothing was provided at airport, had to go and get a room to sleep in, paid for Uber back and fort with no offers until we landed back home a 1hr later for a $75 voucher for a future flight.

Didn't like anything..entire crew was very rude to everyone on the flight. Plane old and the trays fall down on you the while time you're flying. Charged more for a carry on bag than for the plane ticket itself. Did make it from point a to point b, but worth the extra money to fly with another airline

9 hours of delay!! Was not able to check my luggage that I paid for!!!

Book cheap flights from Chicago to Aguadilla

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Chicago to Aguadilla found on KAYAK in the last 72 hours.
6/20Thu
1 stopFrontier
29h 35mORD-BQN
$96
9/11Wed
1 stopFrontier
6h 51mORD-BQN
$126
8/29Thu
1 stopFrontier
6h 51mORD-BQN
$132
6/21Fri
1 stopFrontier
6h 50mORD-BQN
$136
6/17Mon
1 stopFrontier
6h 50mORD-BQN
$146
7/10Wed
1 stopJetBlue
9h 23mORD-BQN
$274
9/11Wed
2 stopsUnited Airlines
15h 54mORD-BQN
$319
9/13Fri
2 stopsUnited Airlines
24h 59mORD-BQN
$359
9/12Thu
2 stopsUnited Airlines
24h 51mORD-BQN
$369
8/29Thu
2 stopsUnited Airlines
15h 54mORD-BQN
$375

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Last minute flights from Chicago to Aguadilla

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Chicago to Aguadilla that are departing in the next 10 days.
6/14Fri
multi-stopFrontier
6h 50mORD-BQN
6/18Tue
multi-stopFrontier
23h 19mBQN-ORD
$474
6/14Fri
multi-stopUnited Airlines
7h 44mORD-BQN
6/15Sat
multi-stopUnited Airlines
8h 05mBQN-ORD
$774
6/14Fri
multi-stopUnited Airlines
14h 59mORD-BQN
6/15Sat
multi-stopUnited Airlines
10h 20mBQN-ORD
$894
6/14Fri
multi-stopUnited Airlines
7h 44mORD-BQN
6/29Sat
multi-stopUnited Airlines
9h 20mBQN-ORD
$944
6/14Fri
multi-stopUnited Airlines
7h 44mORD-BQN
6/29Sat
multi-stopUnited Airlines
10h 10mBQN-ORD
$1,054
6/14Fri
multi-stopUnited Airlines
14h 59mORD-BQN
6/15Sat
multi-stopUnited Airlines
10h 28mBQN-ORD
$1,301

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Flights to Aguadilla

Destination:

Aguadilla (BQN)Puerto Rico

Return flight deals:

Aguadilla - Chicago

Cabin classes: