CHI - BQN

$159 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 2/9. 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
$211
Overall average: $502
Frontier
Tue 12/30Fri 1/16
ORD - BQN • 1 stop
Cheapest one-way
$177
Typical prices: $65-$145
JetBlue
Mon 2/9
ORD - BQN • 2 stops
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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, Dec 30 - Fri, Jan 16
Frontier Logo
7:01 pm - 5:47 pm
ORD
-
BQN
20h 46m1 stop
Frontier Logo
3:48 am - 2:39 pm
BQN
-
ORD
12h 51m1 stop
$211Frontier
Thu, Jan 29 - Fri, Feb 6
Frontier Logo
11:51 am - 12:01 pm
ORD
-
BQN
22h 10m1 stop
Frontier Logo
12:56 pm - 4:40 pm
BQN
-
ORD
29h 44m1 stop
$266Frontier
Sun, Feb 1 - Fri, Feb 20
Frontier Logo
12:21 pm - 12:16 pm
ORD
-
BQN
21h 55m1 stop
Frontier Logo
3:55 am - 4:19 pm
BQN
-
ORD
14h 24m1 stop
$286Frontier
Sun, Feb 1 - Fri, Feb 20
Multiple Airlines Logo
7:45 am - 8:53 pm
ORD
-
BQN
11h 08m2 stops
Multiple Airlines Logo
3:55 am - 4:19 pm
BQN
-
ORD
14h 24m1 stop
$288Multiple Airlines
Thu, Jan 1 - Fri, Jan 9
Frontier Logo
11:28 am - 3:10 am
ORD
-
BQN
13h 42m1 stop
Frontier Logo
3:53 am - 7:17 pm
BQN
-
ORD
17h 24m1 stop
$303Frontier
Thu, Dec 25 - Mon, Dec 29
Frontier Logo
11:28 am - 5:47 pm
ORD
-
BQN
28h 19m1 stop
Frontier Logo
3:55 am - 5:51 pm
BQN
-
ORD
15h 56m1 stop
$314Frontier
Mon, Dec 29 - Fri, Jan 16
Frontier Logo
9:47 am - 3:10 am
ORD
-
BQN
15h 23m1 stop
Frontier Logo
3:48 am - 2:39 pm
BQN
-
ORD
12h 51m1 stop
$321Frontier
Fri, Jan 23 - Sun, Jan 25
Multiple Airlines Logo
9:15 am - 2:54 pm
ORD
-
BQN
27h 39m2 stops
Multiple Airlines Logo
12:56 pm - 10:41 am
BQN
-
ORD
23h 45m1 stop
$346Multiple Airlines
Sun, Feb 1 - Fri, Feb 6
Multiple Airlines Logo
12:44 pm - 12:16 pm
ORD
-
BQN
21h 32m1 stop
Multiple Airlines Logo
12:56 pm - 7:41 pm
BQN
-
ORD
8h 45m1 stop
$347Multiple Airlines
Thu, Mar 12 - Sat, Mar 14
Frontier Logo
5:08 pm - 1:58 am
ORD
-
BQN
7h 50m1 stop
Frontier Logo
3:55 am - 9:02 am
BQN
-
ORD
30h 07m1 stop
$350Frontier
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’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.

Good to know

Low seasonAugust
Cheapest flight$177
Best time to beat the crowds with an average 42% drop in price.
Most popular time to fly and prices are also 34% 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 $177 for a one-way ticket and $211 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 $517 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 $249 and an overall rating of 5.8.

  • 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 9094 reviews
7.3Comfort
7.1Entertainment
7.7Boarding
6.6Food
8.1Crew
Airline reviews

The movies offered were great. Staff were very pleasant and very efficient.

10.0 ExcellentAnonymous, Dec 2025
ORD - HND
Read more United Airlines reviews

The movies offered were great. Staff were very pleasant and very efficient.

After a delay at the gate, C3, at Ohare on Sunday, I left my Blk ski coat on the bench at the gate, lost! Please review my lob claim, thx.

Very nice flight love the small aircraft. We had a wonderful flight attendant. Nice to see someone that really enjoys her job. Don't have her name but had a southern accent.

Very thoughtful flight attendant offered me water immediately since I had run to make my connection.

Seats in waiting area and on plane hard as rock. Fast internet on the flight was great! Crew was kind.

Always wish for more healthy, gluten free options. We have to bring our own.

Having a long layover, I was very appreciative of the ability to stand by for an earlier flight. Other airlines like Delta have refused this to me in the past, just to be mean (because my ticket class wasn't high enough). United went out of their way to help me get to my destination early, which I really appreciated given that it was the third leg of a 24+ hour journey for me.

Other than a way way too cold cabinets for the entire flight, all was great

One bag is incorrect and not acceptable for an international flight. The food was not just good. I won't fly with them again.

Excellent flight. Smooth, efficient boarding. Quick flight. Arrived early at STL.

Not clean and was told I would get a great seat and it was not great at all

Flight got delayed for 5 hours no good explanation was offered ;(

Horrible. I would never fly Frontier again. The booking process is tricky at best, but fraudulent in my opinion. Frontier customer service did nothing to rectify my purchase -- I ended up paying more than double what I could have gotten from other airlines and nearly triple what I thought I was buying from Frontier. Their booking practices are unfair to the consumer.

Delayed. Text notifications were slow. Not much information o what was happening. Boarding was slow and confusing. Wasn’t even offered water other flight. Had to ask. No entertainment at all. Felt like.a Greyhound bus.

When I wanted to check in 3 hours prior to boarding time, the employees mentioned “a little over an hour delay” so I waited for an hour then I went to go look for food in the terminal and most people from that flight were in the same area looking for food. Finally I decided after food to check to see if it’s anytime closer and now it’s 2 mins until boarding closes?! What are you kidding me? I didn’t receive anything via sms about boarding now nor via email or on the intercom. I luckily made it through, barely, and then there’s no room for my carry on mind you I’m in the very first row so I had to place my purse in one further row back and my carry on sections down. Not sure who pays for better seats to get your stuff placed all over the plane but that was the worst experience I’ve ever had flying with anyone.

Better than expected. Staff were friendly and nice on both flights.

There was no one at the counter to assist with our check in. The app didn’t work, so I arrived at the airport with time to check in and I couldn’t because no employees were there. When I finally got someone on the phone, it was inside the 60min rule and they said I could no longer check in and they could sell me another ticket. We had to scramble and pay an additional $800 for tickets and THEN AFTER (about 60 min from my original convo with customer service and 10min after original departure time) I had boarded my new flight, there was email saying my original flight from Frontier was delayed and leaving 2hr 50min later, but I STILL wouldn’t have been able to check in. Which means customer service should have been able to see it and let me check in because I was well within my check in time. When I call Frontier, they hang up on me. So their app didn’t work and they employees left and they take zero responsibility or assistance with their “customer service”

Terrible. Flight cancelled with no reasoning and no flights to rebook. Employees were useless and did nothing to help. Did not even know where to retrieve luggage from the cancelled flight. Flyers beware.

No fault of Frontier staff: plane was very late, reached Orlando at 1 am, took a while to get luggage. Weather, gov financial shutdown impact on TSA, air controllers seemed to have multiple flights backed up. Frontier staff seemed to cope as gracefully as possible. It did reassure me that I and my new hip could adapt to travel challenges. Food/entertainment were irrelevant to my trip.

Terrible. The canceled my entire flight when I requested a refund for a trip frontier canceled trip one way.

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

Information on your arrival and departure airports