CHI - BQN

$129 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 8/12. 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
1 adult, Economy

KAYAK searches 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
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Flights Deals

Cheap Flights 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 for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Aguadilla

Thu, Jul 10 - Wed, Jul 16
Frontier Logo
4:37 pm - 2:01 amORD-BQN
8h 24m1 stop
Frontier Logo
2:59 am - 3:27 pmBQN-ORD
13h 28m1 stop
$297Frontier
Find Deal
Tue, Jul 22 - Sat, Jul 26
Frontier Logo
11:28 am - 2:01 amORD-BQN
13h 33m1 stop
Frontier Logo
2:59 am - 3:43 pmBQN-ORD
13h 44m1 stop
$323Frontier
Find Deal
Thu, Jul 10 - Fri, Jul 18
Frontier Logo
4:37 pm - 2:01 amORD-BQN
8h 24m1 stop
Frontier Logo
11:11 am - 8:07 amBQN-ORD
21h 56m1 stop
$327Frontier
Find Deal
Thu, Jun 26 - Mon, Jun 30
Frontier Logo
8:14 am - 1:59 amORD-BQN
16h 45m1 stop
Frontier Logo
2:59 am - 10:17 amBQN-ORD
8h 18m1 stop
$329Frontier
Find Deal
Thu, Jul 10 - Thu, Jul 17
Frontier Logo
4:37 pm - 2:01 amORD-BQN
8h 24m1 stop
Frontier Logo
2:59 am - 11:31 pmBQN-ORD
21h 32m1 stop
$337Frontier
Find Deal
Tue, Oct 14 - Fri, Oct 17
United Airlines Logo
1:10 pm - 11:09 pmORD-BQN
8h 59m1 stop
United Airlines Logo
12:15 am - 11:49 amBQN-ORD
12h 34m2 stops
$458United Airlines
Find Deal
Tue, Oct 14 - Fri, Oct 17
United Airlines Logo
2:20 pm - 11:09 pmORD-BQN
7h 49m1 stop
United Airlines Logo
12:15 am - 9:05 amBQN-ORD
9h 50m1 stop
$471United Airlines
Find Deal
Tue, Oct 14 - Fri, Oct 17
United Airlines Logo
2:20 pm - 11:09 pmORD-BQN
7h 49m1 stop
United Airlines Logo
12:15 am - 9:29 amBQN-ORD
10h 14m1 stop
$491United Airlines
Find Deal
Thu, Jul 10 - Fri, Jul 18
 Logo
4:37 pm - 10:21 amORD-BQN
16h 44m1 stop
 Logo
11:11 am - 11:53 pmBQN-ORD
13h 42m2 stops
Tue, Oct 14 - Fri, Oct 17
United Airlines Logo
7:30 am - 11:09 pmORD-BQN
14h 39m2 stops
United Airlines Logo
12:15 am - 9:29 amBQN-ORD
10h 14m1 stop
$536United Airlines
Find Deal
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KAYAK's insights & trends for Chicago to Aguadilla flights

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 round-trip flights from Chicago to Aguadilla clicked on KAYAK for each day over the last 12 months.

If your flying dates are flexible, you should consider flying to Aguadilla on a Monday, as we generally find the cheapest rates on that day for this route. On the other hand, Sunday is the most expensive day to fly from Chicago to Aguadilla. For your return ticket, we recommend flying on a Tuesday and avoiding Wednesdays for the best deals.

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 round-trip 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 January, where tickets cost $188 (return) on average. On the other hand, the most expensive months are June and December, where the average cost of round-trip tickets is $740 and $638 respectively.

Good to know

Low seasonJune
High seasonJanuary
Cheapest flight$129
Best time to beat the crowds but there is an average 60% increase in price.
Most popular time to fly and prices are also 60% 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 $129 for a one-way ticket and $297 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 $506 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 $210 and an overall rating of 5.9.

  • 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.

Top airlines flying 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 8801 reviews
8.1Crew
7.0Entertainment
7.3Comfort
7.7Boarding
6.6Food
Airline reviews

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

8.0 ExcellentStacie, Jun 2025ORD - ALB
Read more United Airlines reviews

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

The boarding of took of late.The presentation of the food was horrable as was the tast of the food was cold and tastless.

Delay and keep changing gates. I have to run around from B to C then to E.

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

A bit rush for transit. Food and entertainment are not available

Boarding was a little difficult. The gate area at O'Hare was very small and crowded due to multiple gates in the area. Could not hear the intercom, so had to rely on signage to see when my group was boarding and the signage was blocked by passengers standing in the gate. Flight was great and we arrived in Montreal on time.

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

I do prefer to fly United and have always had excellent service, except for bad weather. Flights are on time and staff is alway curtious and helpful

Since you have to pay for overhead bags then they shouldn't be running out of space and asking individuals who paid to remove stuff from the overhead

Cancelled flight after I arrived at airport after 75 min drive and parking. Next flight was 4 days in the future. Had to scramble and buy a much more expensive flight on another carrier.

Book with frontier airlines with the mentality that they'll cancel your flight, kick you off and lose your luggage. Anything besides that is a win. Compare prices with other airlines (to include luggage) and if frontier is still worth it, book it but know all of their policies.

You get what you pay for nothing essentially but a hard uncomfortable seat that doesn’t recline and kids screaming all around you and chaotic boarding and limited check bag weight allowance when compared to other airlines

I never got to experience the flight because they delayed my first flight and I missed this one. Then Frontier didn't want to help me rebook a flight to get me to my final destination.

The Boarding process in Denver was chaotic, and since the line was so long, we were lined up very far from the gate. If there were any announcements from the gate staff, we didn't hear them. The flight attendants were spectacular. The only negative part of the flight was sitting by a 2 1/2 year old who was unruly and unfortunately had parents that matched his behaviors. Also, the restaurants in Denver on the E concourse, they didn't have food (passengers could only order 1 item on the entire menu) or the restaurants had 12-14 people waiting for orders to be prepared and another 6 people waiting to order. If you have a layover in Denver and need to grab food, be prepared to visit the shops with pre-packaged sandwiches, or you can visit another concourse but it may take a while to transit throughout the airport.

I liked the turn-style feature at gate 209B at LAX. Very efficient process. The gate staff also made several, clearly directed announcements so I felt very informed.

Although an hour and a half early was told by staff at check in they had overbooked and could not check us in for the flight.

The crew was delayed because they came on another flight that was delayed due to weather 10pm flight left at 1.30 am The airline made no effort to align alternate crew

I liked the price of the flight and the chance to buy a seat with no person seated in the middle seat.. Also the flight was right on time.

Everything you need to know for your flight from Chicago to Aguadilla

Information on your arrival and departure airports

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