CHI - BQN

$111 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 5/15. 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, 0 bags

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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Everything you should know

Cheapest round-trip
$243
Overall average: $426
Frontier
Tue 5/12Thu 5/14
ORD - BQN • 1 stop
Cheapest one-way
$111
Typical prices: $153-$155
Frontier
Fri 5/15
ORD - BQN • 1 stop
Nonstop flights
Not available
There are currently no direct flights between Chicago and Aguadilla. You'll need at least 1 connection.
Insights
Insights
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Insights
Top layover airports
Cheapest • Avg $293 (round-trip)
Shortest trip • 7h 55m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 46% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Aguadilla!
Flight Deals
Booking Insights
Flight 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

Tue, May 12 - Thu, May 14
Frontier Logo
3:55 pm - 2:02 am
ORD
-
BQN
9h 07m
1 stop
Frontier Logo
12:28 pm - 11:13 pm
BQN
-
ORD
11h 45m
1 stop
$243Frontier
Mon, May 11 - Thu, May 14
Frontier Logo
5:30 pm - 2:02 am
ORD
-
BQN
7h 32m
1 stop
Frontier Logo
12:28 pm - 11:13 pm
BQN
-
ORD
11h 45m
1 stop
$264Frontier
Fri, May 8 - Sun, May 10
Frontier Logo
5:30 pm - 2:02 am
ORD
-
BQN
7h 32m
1 stop
Frontier Logo
2:59 am - 11:13 pm
BQN
-
ORD
21h 14m
1 stop
$284Frontier
Tue, Mar 31 - Wed, Apr 8
Frontier Logo
9:15 am - 1:42 am
ORD
-
BQN
15h 27m
1 stop
Frontier Logo
2:43 am - 11:36 pm
BQN
-
ORD
21h 53m
1 stop
$299Frontier
Fri, Aug 21 - Mon, Aug 24
Frontier Logo
5:14 pm - 11:51 am
ORD
-
BQN
17h 37m
1 stop
Frontier Logo
12:46 pm - 11:41 pm
BQN
-
ORD
11h 55m
1 stop
$308Frontier
Wed, May 6 - Thu, May 7
Frontier Logo
3:55 pm - 2:02 am
ORD
-
BQN
9h 07m
1 stop
Frontier Logo
12:28 pm - 11:13 pm
BQN
-
ORD
11h 45m
1 stop
$315Frontier
Sat, Apr 11 - Fri, Apr 17
Frontier Logo
4:21 pm - 1:53 am
ORD
-
BQN
8h 32m
1 stop
Frontier Logo
2:38 am - 3:23 pm
BQN
-
ORD
13h 45m
1 stop
$320Frontier
Sat, Apr 25 - Wed, Apr 29
Frontier Logo
8:00 am - 1:43 am
ORD
-
BQN
16h 43m
1 stop
Frontier Logo
2:38 am - 9:30 pm
BQN
-
ORD
19h 52m
1 stop
$325Frontier
Fri, May 8 - Sun, May 10
Frontier Logo
5:30 pm - 2:02 am
ORD
-
BQN
7h 32m
1 stop
Frontier Logo
2:59 am - 11:13 pm
BQN
-
ORD
21h 14m
1 stop
$326Frontier
Fri, May 15 - Sat, May 23
Frontier Logo
5:30 pm - 2:02 am
ORD
-
BQN
7h 32m
1 stop
Frontier Logo
4:28 pm - 11:13 pm
BQN
-
ORD
7h 45m
1 stop
$334Frontier
Booking Insights

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 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 August, where tickets cost $266 (return) on average. On the other hand, the most expensive months are December and May, where the average cost of round-trip tickets is $730 and $676 respectively.

Good to know

Low seasonDecember
Cheapest flight$111
Best time to beat the crowds but there is an average 49% increase in price.
Most popular time to fly and prices are also 41% 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 $111 for a one-way ticket and $243 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 $610 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 $265 and an overall rating of 5.7.

  • 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.

Reviews of the 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 9429 reviews
7.3Comfort
6.6Food
8.1Crew
7.7Boarding
7.1Entertainment
Airline reviews

This trip did not start off well. The inbound flight was delayed about 20 minutes. Then, after initial onboarding, the passengers had to deplane due to a mechanical problem. That took about 30 minutes to fix and be cleared. Then, reboarding was chaotic. It took a long time to sort passengers and two passengers on standby were ticketed but there was no seat. So, they had to deplane. One of the flight crew was trying to help passengers figure out a place to put their carry-on bags and that took more time. In the end, our scheduled 10:30 am departure did not actually take off until about 12:05 pm CST. The flight itself was long but we got to Houston. Some passengers missed their connecting flights and had to rebook. Not the best of flights I've had.

4.0 OkayDr. Joseph, Feb 2026
ORD - IAH
Read more United Airlines reviews

This trip did not start off well. The inbound flight was delayed about 20 minutes. Then, after initial onboarding, the passengers had to deplane due to a mechanical problem. That took about 30 minutes to fix and be cleared. Then, reboarding was chaotic. It took a long time to sort passengers and two passengers on standby were ticketed but there was no seat. So, they had to deplane. One of the flight crew was trying to help passengers figure out a place to put their carry-on bags and that took more time. In the end, our scheduled 10:30 am departure did not actually take off until about 12:05 pm CST. The flight itself was long but we got to Houston. Some passengers missed their connecting flights and had to rebook. Not the best of flights I've had.

We were delayed for about an hour from taking off due to traffic control procedures at the destination airport. But once in the air, the flight went well. The crew members were great and provided cabin service despite moderate turbulence during much of the flight.

Short flight, but no drink/snack service. The flights both going and coming were delayed.

Not being stranded in Chicago for her airport to 11:30 tomorrow morning the 3rd

I was fully checked in the prior night and i was unchecked and then didn’t have a seat when I boarded. Instead of an aisle seat, I was out in the middle seat of the very last row of the plane.

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!

I understand weather is an issue, but making us chase our plane down at five scheduled gates across three terminals in an airport the size of O'Hare was unfair. They'd have probably been better off to leave gates as TBD until the inbound plane is in final approach instead of running us all over the place. Also, props to the consistently-unprepared ground crew in Richmond for once again leaving my lane parked short of the gate because they couldn't have a crew in place on time with 2 hours notice...

cabin crew was OK, food was OK, the trip from the US to Munich was actually pretty bad comfort wise. Noisy aircraft, lights never dimmed even in Business class (night flight) barely sufficient amenities for the price. I have millions of miles with United but TBH American is gaining ground and Delta has always been marginally better then United although on paper United has more longes and cheaper upgrades.

Essy to get on. The hostess gave very little pop, the plane was late getting in, and we are still waiting for our bags. This sucks. :/

There's no seats that lean back with little leg space i wad uncomfortable the entire flight. Your charges for extra baggage is despicable and costly!!

Remind customers of the need to have passport or new ID for boarding.

Flight was canceled. Most upsetting was message from Kayak, stating that the flight was canceled and click with Kayak for details regarding rebook, refund details. THERE'S NO INFORMATION PROVIDED BY KAYAK EXCEPT THAT FLIGHT IS CANCELED. AND NOW THIS SURVEY TO FIND OUT HOW WAS THE FLIGHT !!!!!!!

The flight never took off and we spent 7 hours at the airport

Gate not determined until I got to the airport - hard to plan the trip to the airport.

Our flight was canceled. I will never use Kayak nor Frontier for travel again. The entire experience was a headache.

Frontier.. nickel and dime add-ons. Flight late, on time, late again, last minute gate change, arrival gate required a shuttle to the terminal. They sure keep you guessing.. if you like a little chaos and airport anxiety, this is the airline for you!

This is my second time flying with Frontier. My current experience was very favorable. The staff from the gate to the plane was friendly, warm and professional. The food options lacked in my opinion. This area needs some attention in my opinion.

First of all we hade waited 3 hours in the airplane waiting to leave. Second the return schedule was changed and it messed up my entire vaction. I won't buy never again another flight and recommend to nobody traveling with them.

There was no food and no entertainment, so I'm not sure why these are even in the survey, as my understanding is frontier does not ever offer food without a few, not even a snack, and there are no screens so unless the flight safety talk is our entertainment why ask how we liked it?. One of the flight attendants say in the back of the plane as people filed in to their seats, yelling orders about where to put baggage and telling people to hurry up. It was the least professional experience I've ever had on a flight.

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

Information on your arrival and departure airports