CHI - BQN

$179 Find Cheap Flights from Chicago to Aguadilla - Compare and Save

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 7/17. 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
$352
Typical prices: $347-$299
JetBlue
Wed 8/12Wed 8/19
ORD - BQN • 1 stop
Cheapest one-way
$179
Typical prices: $142-$284
JetBlue
Fri 7/17
ORD - BQN • 1 stop
Top airlines
Cheapest • from $352 (round-trip)
Best reviews • 7.4 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Not available
There are currently no direct flights between Chicago and Aguadilla. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $272 (round-trip)
Shortest trip • 8h 12m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 47% 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

Wed, Aug 12 - Wed, Aug 19
JetBlue Logo
2:35 pm - 12:33 am
ORD
-
BQN
8h 58m
1 stop
JetBlue Logo
5:01 am - 1:39 pm
BQN
-
ORD
9h 38m
1 stop
$352JetBlue
Tue, Aug 11 - Tue, Aug 18
JetBlue Logo
2:35 pm - 12:33 am
ORD
-
BQN
8h 58m
1 stop
JetBlue Logo
5:01 am - 1:39 pm
BQN
-
ORD
9h 38m
1 stop
$358JetBlue
Fri, Jul 10 - Wed, Jul 15
JetBlue Logo
2:35 pm - 12:33 am
ORD
-
BQN
8h 58m
1 stop
JetBlue Logo
5:01 am - 1:39 pm
BQN
-
ORD
9h 38m
1 stop
$368JetBlue
Tue, Nov 10 - Wed, Nov 18
JetBlue Logo
2:35 pm - 1:33 am
ORD
-
BQN
8h 58m
1 stop
JetBlue Logo
6:01 am - 1:39 pm
BQN
-
ORD
9h 38m
1 stop
$369JetBlue
Tue, Jul 28 - Tue, Aug 4
Multiple Airlines Logo
5:13 pm - 2:10 am
ORD
-
BQN
7h 57m
1 stop
Multiple Airlines Logo
2:38 pm - 11:44 pm
BQN
-
ORD
10h 06m
1 stop
$373Multiple Airlines
Sat, Aug 8 - Sat, Aug 15
JetBlue Logo
2:35 pm - 12:33 am
ORD
-
BQN
8h 58m
1 stop
JetBlue Logo
5:01 am - 1:39 pm
BQN
-
ORD
9h 38m
1 stop
$376JetBlue
Tue, Jul 7 - Tue, Jul 14
Multiple Airlines Logo
5:13 pm - 2:10 am
ORD
-
BQN
7h 57m
1 stop
Multiple Airlines Logo
2:38 pm - 11:44 pm
BQN
-
ORD
10h 06m
1 stop
$377Multiple Airlines
Tue, Sep 1 - Wed, Sep 2
JetBlue Logo
2:35 pm - 12:33 am
ORD
-
BQN
8h 58m
1 stop
JetBlue Logo
5:01 am - 1:39 pm
BQN
-
ORD
9h 38m
1 stop
$381JetBlue
Wed, Jul 15 - Tue, Jul 21
JetBlue Logo
9:40 am - 6:37 pm
ORD
-
BQN
7h 57m
1 stop
JetBlue Logo
2:38 pm - 11:44 pm
BQN
-
ORD
10h 06m
1 stop
$389JetBlue
Sat, Aug 8 - Sat, Aug 15
JetBlue Logo
2:35 pm - 12:33 am
ORD
-
BQN
8h 58m
1 stop
JetBlue Logo
5:01 am - 1:39 pm
BQN
-
ORD
9h 38m
1 stop
$397JetBlue
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 July, where tickets cost $152 (return) on average. On the other hand, the most expensive months are January and September, where the average cost of round-trip tickets is $484 and $481 respectively.

Good to know

Low seasonJune
Cheapest flight$179
Best time to beat the crowds with an average 2% drop in price.
Most popular time to fly with an average 15% increase in price.
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 5 days, the lowest price for a flight from Chicago to Aguadilla was $179 for a one-way ticket and $352 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 $586 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 5.6.

  • 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 9831 reviews
7.1Entertainment
7.3Comfort
7.7Boarding
6.6Food
8.1Crew
Airline reviews

Smooth travel. Immediate update prior flight delay so I can arrange myself properly without too rush.

10.0 ExcellentNakin, Jun 2026
ORD - HND
Read more United Airlines reviews

Smooth travel. Immediate update prior flight delay so I can arrange myself properly without too rush.

Boarded early; and arrived home 40 mins early. After a long flight, it’s nice to be back home early. These flights have no amenities; no snacks. So need to bring your own

A long delay. Don't travel late in the day.

Super friendly with lots of drink options an entertainment. Friendly crew.

The crew was great. Very friendly and responsive. The plane was old, small and tight. We ran out of overhead space and I had to check. Middle seat was particularly tight.

Several missed and almost missed connections. It felt like everything was being patched together last minute without enough resources and it ended up being an extremely stressful experience that basically ruined our weekend on the west coast. What a waste.

Crew was friendly. Seats are too narrow, particularly when a big person is in the adjacent seat, but I understand this is due to smaller planes usually flight into Lincoln. I have experienced several flight delays going out and coming into Lincoln airport, I say maybe 50% or higher of the flights I've taken out of this airport have been delayed.

Great flight. Boarded efficiently. Arrived early at CLT. There was no in flight entertainment on this aircraft. Great crew.

The seat was comfortable. There was a lot of turbulence. If it weren't for that,it would have been okay.

Poor communication, flight was delayed for preventable reasons. I missed my connection.

There weren't enough employees at check in took awhile to get bags checked. There wasn't a wheel chair for me, I was sent to someone who turns out to work for a different airline, if My flight hadn't been delayed I probably would have missed my flight as it was, by the time I arrived at my gate, they started boarding in about 15 minutes. I don't know who took me to my gate, definitely was not the normal people who take passengers to the gate. I'm guessing she may have been in a management position. I wish I knew her name, she went beyond to help me. With that said everyone was kind, and were doing the best they could. So, I choose to say it was an Adventure, stressful start, but good. In the end went well. The situation was not only difficult for passengers but the employee's.

The staff at the check in counter was so rude. Made you feel Incompetent

Frontier scheduled a 40 minute connection in DEN. What they failed to mention was that they “close the doors” 20 mins prior to departure, which means you only have 20 mins. Not enough time. Possibly against DOT regulations. Filing complaint.

Flight was scheduled at 9:40pm. Got delayed to 10 am, the next day. crazy

The bag check, flight check-in, and onboard experience convinced my wife and me that we will actively go out of our way to avoid flying Frontier Airlines in the future. At bag check, we were informed that check-in could only be completed via the Frontier mobile app. Unfortunately, the app was extremely frustrating—sending us through repetitive, confusing loops that repeatedly forced us to decline add-on services with nearly every click. While most airline apps upsell, this one felt intentionally exhausting. As the process dragged on, we became genuinely concerned that my phone battery would die before check-in could be completed. We approached the bag check staff—who were standing together talking—and explained both our frustration and our predicament. They laughed. Later, my wife described the interaction as “gaslighting,” which felt accurate. We were then informed it would cost $25 per person simply to have our boarding passes printed. From that point forward, the tone of the experience was consistently hostile. The bag check employees were condescending and combative, behaving more like bullies than customer service staff. Unfortunately, that same attitude continued onboard. One flight attendant argued with me when I attempted to stow my backpack in the overhead bin. I explained that we had each paid $75 to check our bags specifically so we would not need to use carry-on space and could have adequate legroom. She demanded to see my ticket, pointed out that it said “no carry-on”—which I acknowledged—and I reiterated that this was precisely why we paid to check our bags. Her response was, “I don’t make the rules.” She then walked away, but not before asking if I “truly wanted to fly back to Chicago today?”—an unnecessary and unmistakable threat. It is also worth noting that despite booking our tickets together in the same transaction, we were not seated together. Upon our return to Chicago—where we could once again sit together—we compared onboard experiences. We both remarked on how unhappy the flight attendants appeared and how each of us was separately asked whether we would like to purchase a beverage. We declined. At no point was water mentioned as an option, leaving us with the clear impression that even water came at a cost—or that complimentary water, if available at all, was deliberately left unmentioned. Overall, the experience was shocking and deeply disappointing, but it was also a profound learning experience—one we will not forget and will not repeat. -Steve

Plane was hot and miserable and the crew was rude!

12 hour delay required getting on and off plane 3 times - would have at least liked to have been offered a snack or drink

They didn’t offer a water, even after I asked

They switched our terminal 3 times and we were delayed for four plus hours!!!

It was an early flight and most people napped/slept and the crew let us which was nice.

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

Information on your arrival and departure airports