CHI - BQN

$146 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 12/8. 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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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

Thu, Nov 13 - Sat, Nov 15
Frontier Logo
5:25 am - 3:04 amORD-BQN
19h 39m1 stop
Frontier Logo
3:59 am - 12:26 pmBQN-ORD
10h 27m1 stop
$168Frontier
Find Deal
Thu, Nov 13 - Wed, Nov 19
Frontier Logo
5:25 am - 3:04 amORD-BQN
19h 39m1 stop
Frontier Logo
3:55 am - 7:26 amBQN-ORD
29h 31m1 stop
$252Frontier
Find Deal
Thu, Nov 13 - Wed, Nov 19
Frontier Logo
5:25 am - 3:04 amORD-BQN
19h 39m1 stop
Frontier Logo
3:55 am - 12:08 amBQN-ORD
22h 13m2 stops
$258Frontier
Find Deal
Wed, Nov 19 - Sun, Nov 23
Multiple Airlines Logo
6:48 am - 3:04 amORD-BQN
18h 16m1 stop
Multiple Airlines Logo
3:55 am - 11:06 pmBQN-ORD
21h 11m1 stop
$265Multiple Airlines
Find Deal
Wed, Nov 19 - Sun, Nov 23
Multiple Airlines Logo
6:48 am - 3:04 amORD-BQN
18h 16m1 stop
Multiple Airlines Logo
3:55 am - 11:06 pmBQN-ORD
21h 11m1 stop
$268Multiple Airlines
Find Deal
Thu, Nov 13 - Wed, Nov 19
Frontier Logo
2:42 pm - 3:04 amORD-BQN
34h 22m2 stops
Frontier Logo
3:55 am - 12:08 amBQN-ORD
22h 13m2 stops
$275Frontier
Find Deal
Sat, Jan 17 - Fri, Jan 23
JetBlue Logo
2:05 pm - 12:27 amORD-BQN
8h 22m1 stop
JetBlue Logo
6:15 am - 1:10 pmBQN-ORD
8h 55m1 stop
$316JetBlue
Find Deal
Thu, Jan 29 - Fri, Feb 6
JetBlue Logo
8:45 am - 10:30 pmORD-BQN
11h 45m1 stop
JetBlue Logo
6:15 am - 1:10 pmBQN-ORD
8h 55m1 stop
$351JetBlue
Find Deal
Mon, Jan 19 - Fri, Jan 23
United Airlines Logo
2:27 pm - 11:57 pmORD-BQN
7h 30m1 stop
United Airlines Logo
1:09 am - 7:54 amBQN-ORD
8h 45m1 stop
$395United Airlines
Find Deal
Wed, Jan 21 - Sat, Jan 24
United Airlines Logo
2:27 pm - 11:57 pmORD-BQN
7h 30m1 stop
United Airlines Logo
1:09 am - 9:40 amBQN-ORD
10h 31m1 stop
$403United Airlines
Find Deal

Everything you should know

Top airlines
Frontier
Cheapest • from $168 (round-trip)
United Airlines
Best reviews • 7.4 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to travel
January
Cheapest • 56% price drop
January
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
$168
Overall average: $574
Frontier
Thu 11/13Sat 11/15
ORD - BQN • 1 stop
Cheapest one-way
$146
Typical prices: $238-$352
Multiple Airlines
Mon 12/8
ORD - BQN • 1 stop
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!
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.

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 $622 respectively.

Good to know

Low seasonSeptember
Cheapest flight$146
Best time to beat the crowds with an average 5% drop in price.
Most popular time to fly and prices are also 56% 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 $146 for a one-way ticket and $168 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 $510 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 $231 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 8999 reviews
8.1Crew
7.1Entertainment
6.6Food
7.7Boarding
7.3Comfort
Airline reviews

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

10.0 ExcellentDr. Joseph, Oct 2025ORD - STL
Read more United Airlines reviews

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

Not the fault of United—weather, reroute around weather, time sitting on tarmac, arrived couple hours late, too late for train into city necessitating a much pricier cab but weather…can’t be helped.

I will never book a flight through Cheap fare. They booked me from Portland Main . And would not give me a refund, so I bought 2 tickets one for 299. From Portland Main to ORD. Then I had to buy a ticket from Oregon PDX to ORD that was another 440. So Just so you know they even told me it was there fault but no refund. Bad bussniess. I did inform United but they said they couldn't help me due to the fact I booked through Cheap Tickets. Never again. And I'm spreding the word. I let everyone know at my 50th class reunion

The flight attendants were rude. Seemed like they didn’t want to be there. Except for one girl that was really nice. Seats are sooooo uncomfortable. They give you a piece of paper and a thin cushion for a pillow and blanket that does nothing. Airlines have gone way downhill, especially United international flights. Food was disguting. Definitely flying ANA next time.

Crew and customer service were excellent. This flight also had plenty of leg room and seat mounted screens for entertainment. A very pleasant flight all around!

It would have been better if the crew has supported my husband's reasons for needing to keep the space clear around his feet, rather than insisting that he put his knapsack in that space.

Subject: Formal Complaint: Discriminatory and Unprofessional Conduct – Request for Immediate Action & Compensation Dear [Airline Customer Relations Team], I am writing to file a formal complaint regarding my recent travel experience with [Airline], which was by far the worst I have ever encountered. What occurred was not only unprofessional, but in several instances discriminatory, unsafe, and unacceptable. On the first leg of my trip, I arrived only four minutes past check-in. Instead of making any attempt to resolve the matter, your representative flatly denied me boarding and made me wait while she attended to passengers who arrived after me. By the time a manager intervened, it was too late to board, costing me time, money, and unnecessary frustration. The second leg of my trip (Chicago–San Francisco) raised even more serious concerns. From the outset, it was apparent that the staff—particularly two attendants—prioritized Caucasian passengers while dismissing African American and minority passengers. • When a Caucasian passenger in the exit row refused to comply with federal safety requirements, I, as a first responder, immediately offered to switch seats and assume the responsibility. My offer was blatantly ignored, and instead, a Caucasian passenger seated further up was chosen. This was discriminatory and deeply insulting, especially as I was actively de-escalating the situation that could have delayed the flight further. • During a lengthy tarmac delay of over 90 minutes, passengers were given conflicting and unreasonable instructions that created unnecessary distress and tension. • Throughout the flight, a visibly intoxicated passenger directly in front of me was disruptive, rude to others, failed to comply with seatbelt and electronic device rules, and yet faced no enforcement from the crew. In stark contrast, I was singled out for repeated compliance checks even though I was following every rule. This unequal treatment was so obvious that multiple passengers around me spoke up in my defense. This pattern of behavior demonstrated a clear lack of professionalism, disregard for passenger safety, and discriminatory treatment. I expect far better from an airline of your stature. As a paying customer subjected to this unacceptable treatment, I am formally requesting: 1. A full investigation into the conduct of the staff on both flights. 2. A written apology acknowledging the discriminatory and unprofessional behavior I endured. 3. Appropriate compensation for the distress, inconvenience, and mishandling of my travel. If this matter is not addressed promptly and thoroughly, I will have no choice but to escalate my complaint further, including filing with the U.S. Department of Transportation and sharing my experience through other channels. I trust [Airline] will take this complaint seriously and provide a timely resolution.

Check in was quick and easy during early hours. Flight was on time, and customer services was a plus.

Once we got in the air the pilot made up some of the time of the delay. So that was really nice.

We had a layover from YVR to Denver. We bought 4 bottles of Absolut Vodka at the YVR Duty Free for $116.20, after going through security and American Customs Pre Clearance at YVR, Vancouver. When we landed in Denver, United put us behind the American Customs as well as TSA again for some reason. We were forced to go through American Customs and TSA again. TSA confiscated our rightfully owned Duty Free Absolut Vodka bottles. Because United incorrectly forced our flight behind American border and TSA again, we missed the connecting flight. After United put us on a later flight, we eventually arrived in Chicago very late, with hardly any sleep. I am looking for compensation from United for our incorrectly confiscated Absolut Vodka bottles worth $116.20, as well as compensation for incorrectly putting us behind American Customs and TSA again, causing us to miss our connecting flight, making us arrive extremely late in Chicago.

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.

Boarding was on time and plane departed as scheduled. There are obviously no amenities (food, drink, entertainment) on Frontier, but there also didn't seem to be any issues with luggage space either.

Inbound plane was on time and flight departed on time with no issues while boarding.

I knew going into this that Frontier, being a low cost carrier, would be pretty bare bones and charge for most extras but this was made up for by the fact that the airplane was a reasonably new Airbus, every employee was great and best of all, Everett Washington is an amazing airport - thanks Frontier for flying there!!!

i was unable to check in the flight. refund requested

It was well done. It was my first time flying with them and I was nervous b/c I have heard of many cancelled and/or delray flights. Everything went smoothly.

Just know that everything, and I mean everything is “ala cart”. 60$ just to put something in the overhead bin. I will never fly Frontier again nor do I recommend them to anyone else.

The single worst check in experience I could imagine. I’ll never do any business with Frontier or any affiliated company

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

Information on your arrival and departure airports

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