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CHI - BQN

Find cheap flights from Chicago to Aguadilla from $109

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 9/18. 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
Sun 6/9
Sun 6/16

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 43,156,178 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
5:56 pm - 8:51 amORD-BQN
13h 55m1 stop
5:11 pm - 1:08 amBQN-ORD
8h 57m1 stop
$236Frontier
Find Deal
Thu, May 30 - Mon, Jun 3
5:56 pm - 8:51 amORD-BQN
13h 55m1 stop
2:49 am - 1:08 amBQN-ORD
23h 19m1 stop
$244Frontier
Find Deal
Thu, May 30 - Sun, Jun 2
5:56 pm - 1:49 amORD-BQN
6h 53m1 stop
2:49 am - 1:08 amBQN-ORD
23h 19m1 stop
$252Frontier
Find Deal
Wed, May 22 - Tue, May 28
8:02 pm - 1:48 amORD-BQN
28h 46m1 stop
2:52 am - 6:55 pmBQN-ORD
17h 03m1 stop
$262Frontier
Find Deal
Sun, Jun 9 - Sat, Jun 15
8:25 am - 1:45 amORD-BQN
16h 20m1 stop
2:51 am - 1:08 amBQN-ORD
23h 17m1 stop
$292Frontier
Find Deal
Wed, May 15 - Sat, May 18
5:56 pm - 1:49 amORD-BQN
6h 53m1 stop
2:57 am - 1:08 amBQN-ORD
23h 11m1 stop
$306Frontier
Find Deal
Mon, Jun 3 - Thu, Jun 6
5:56 pm - 1:47 amORD-BQN
6h 51m1 stop
2:47 am - 12:59 amBQN-ORD
23h 12m1 stop
$317Frontier
Find Deal
Tue, Jul 23 - Mon, Jul 29
5:58 pm - 1:48 amORD-BQN
6h 50m1 stop
2:48 am - 6:18 pmBQN-ORD
16h 30m1 stop
$334Frontier
Find Deal
Mon, Jun 24 - Wed, Jun 26
2:25 pm - 11:09 pmORD-BQN
7h 44m1 stop
12:15 am - 9:35 amBQN-ORD
10h 20m1 stop
$502United Airlines
Find Deal
Tue, Jun 18 - Mon, Jun 24
2:25 pm - 11:09 pmORD-BQN
7h 44m1 stop
12:15 am - 7:35 amBQN-ORD
8h 20m1 stop
$509United Airlines
Find Deal
Tue, May 28 - Mon, Jun 3

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 Friday is the most expensive. Flying from Aguadilla back to Chicago, the best deals are generally found on Wednesday, 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 June and December, where the average cost of tickets is $695 and $571 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 $236 on Frontier, followed by United Airlines ($502). One-way flight deals have also been found from as low as $109 on Frontier and from $311 on United Airlines.

Good to know

Low season

January

High season

April

Cheapest flight

$109
Best time to beat the crowds with an average 0% drop in price.
Most popular time to fly and prices are also 26% 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 $109 for a one-way ticket and $236 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 $482 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 $286 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 11014 reviews
7.7Boarding
8.1Crew
7.1Entertainment
6.7Food
7.2Comfort
Airline reviews

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

4.0 OkayJared R., May 2024ORD - SFO
Read more about United Airlines reviews

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 flight experience was very good! Especially the United Club!

I was not able to buy food in the flight. They refer to include your Credit card in the APP, and if you are not from USA (i have a credit card form Canada) it is not possible

Aircraft has better leg room than any of United's larger planes. We had requested mobility assistance for this and related flights. United's response to all was superb.

The flight from Ottawa to Chicago took a lot longer due to DC in Ottawa. We got to Chicago and went to our gate to catch our flight. We only had nine minutes I found that very stressful.

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.

I particularly did not have no problem with my backpack, but a few people in front of me did. The chairs were really uncomfortable. Unless is a super short flight for over a weekend I wouldn't take this airline.

Do I need to call them or will you handle my complaint ? I paid for one carry-on bag. my email said up to 50 pounds when I got to the counter they charged me $79 more for my 48 pound bag!!! they said nope only 40 pounds. My email says 50 pounds. !!! I’m out another $79!!!

Flight attendant very friendly. Seats not adjustable like before. I was in the middle seat and two big guys next to me isn’t to pleasant. No used to have delays in the past and now is too often.

Seats could use more padding. Kind of hard on the tush.

Amazed that Spirit can even get planes in the air, would never use again.

Over an hour delay in departure but I was notified beforehand. Another delay on tarmac upon arrival at LGA. We ended up departing the plane almost 2 hours later than expected

I fly Frontier because it’s affordable. I understand that the seats are tight and not the most comfortable…but that’s part of it. The problem with this flight was that there was a group of travelers directly behind me at the back of the plane who were ridiculously loud and obnoxious the entire flight. I’m pretty sure they were drunk and I could periodically smell an odd odor that I believe was one of them using a smokeless vape pen. The stewards had to remind them to keep quiet during the pre-flight instruction, but that was it. They never said another thing to them for the rest of the flight. It was a miserable.

I checked a bag because it was $5 less than carry on. They managed to lose my bag on a 2.5 hr direct flight! Frontier has no airport staff at baggage claim to help. As soon as I got home around 11 pm I tried to use their online system to file the claim for lost bag - system wouldn't take the # on my baggage claim ticket - said it was not the correct number. Also said that I had not checked a bag, which wasn't true - even my online boarding pass showed that I had checked a bag. Wasted about an hour on that process with no luck. Tried again in the morning - same thing. So tried online chat with Frontier bot - waited 35-40" twice to be connected to a baggage agent and it never happened. Eventually drove to PDX after work and waited 2 hrs for the Frontier ticket agents to arrive prior to the next Frontier flight out of PDX and FINALLY got some help from one of them, to take me to lost luggage area where I was able to retrive my bag. Probably took 4-5 hrs. of my time and endless frustration to get my bag. This was my first -- and LAST -- experience flying Frontier Airlines. Check-in was also extremely difficult and time consuming. The flight itself (and staff) were fine but everything else about the experience was a total disaster! The fact that Frontier literally has NO WAY to connect to a human voice for customer service (in this case for lost luggage) is the WORST!!!!!

Frontier is a crappy airline nothing about it is honest

I didn't get to do this flight l, hard to review

Not good 😐 Over priced baggage fees Small hard seats No wifi or entertainment options 😕

Didn't like anything!! Horrible flight. Small seating area and hard seats. Butt was sore after 2 hour flight to Seattle No entertainment or free refreshments No wifi or USB charging receptacles to charge phone entoute like other airliners Luggage rates were 3 times as much as competitors. Difficult to navigate online luggue process to pre pay before flight Overall bad experience WILL NEVER RIDE OR RECOMMEND FRONTIER TO FRIENDS OR FAMILY MEMBERS!!! THIS IS A SHAME!! MOST MESERIBLE FLIGHT OF MY LIFE!! AND I THOUGHT SPIRIT WAS 👎 YOU GOT THEM BEAD HANDS DOWN!!

Flight was a little late taking off. Seats are too upright, no ports to charge devices, no wifi, no entertainment

Six hour delay. Poor customer service. No voucher. Bad communication. Missed important appointments.

Our flight was delayed an hour, then when we got to board our flight finally, we were waiting in our seats for take off for 45 minutes before it was communicated that there was a maintenance issue therefore we waited on the plane for over an hour while that was resolved. We did not get to Phoenix until almost 3 hours after we were originally supposed to. This was the first and last time I will be flying Frontier.

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.
9/18Wed
1 stopFrontier
6h 51mORD-BQN
$109
6/10Mon
1 stopFrontier
6h 50mORD-BQN
$117
9/19Thu
1 stopFrontier
6h 51mORD-BQN
$129
6/10Mon
1 stopFrontier
6h 50mORD-BQN
$145
6/9Sun
1 stopFrontier
28h 46mORD-BQN
$168
9/18Wed
2 stopsUnited Airlines
14h 24mORD-BQN
$311
9/19Thu
2 stopsUnited Airlines
14h 24mORD-BQN
$341
5/23Thu
1 stopJetBlue
7h 44mORD-BQN
$389
6/9Sun
2 stopsUnited Airlines
24h 37mORD-BQN
$412
6/10Mon
2 stopsUnited Airlines
24h 37mORD-BQN
$434

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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.
5/15Wed
multi-stopFrontier
16h 20mORD-BQN
5/18Sat
multi-stopFrontier
23h 17mBQN-ORD
$292
5/15Wed
multi-stopFrontier
16h 20mORD-BQN
5/19Sun
multi-stopFrontier
13h 12mBQN-ORD
$428
5/11Sat
multi-stopFrontier
16h 20mORD-BQN
5/12Sun
multi-stopFrontier
21h 58mBQN-ORD
$440
5/14Tue
multi-stopUnited Airlines
7h 14mORD-BQN
5/17Fri
multi-stopUnited Airlines
10h 21mBQN-ORD
$739
5/11Sat
multi-stopUnited Airlines
7h 14mORD-BQN
5/12Sun
multi-stopUnited Airlines
19h 35mBQN-ORD
$1,020
5/11Sat
multi-stopUnited Airlines
14h 54mORD-BQN
5/12Sun
multi-stopUnited Airlines
10h 24mBQN-ORD
$1,467

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Flights to Aguadilla

Destination:

Aguadilla (BQN)Puerto Rico

Return flight deals:

Aguadilla - Chicago

Cabin classes: