CHI - BQN

$184 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 8/17. 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

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Everything you should know

Cheapest round-trip
$362
Typical prices: $462-$481
Frontier
Wed 9/9Wed 9/16
ORD - BQN • 1 stop
Cheapest one-way
$190
Typical prices: $135-$298
Frontier
Mon 8/17
ORD - BQN • 1 stop
Top airlines
Cheapest • from $362 (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 • 6h 56m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 29% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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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

Wed, Sep 9 - Wed, Sep 16
Frontier Logo
3:50 pm - 10:13 am
ORD
-
BQN
17h 23m
1 stop
Frontier Logo
11:12 am - 10:59 pm
BQN
-
ORD
12h 47m
1 stop
$362Frontier
Tue, Sep 8 - Tue, Sep 15
Frontier Logo
7:44 pm - 9:57 am
ORD
-
BQN
13h 13m
1 stop
Frontier Logo
10:52 am - 11:55 pm
BQN
-
ORD
14h 03m
1 stop
$365Frontier
Mon, Aug 31 - Mon, Sep 7
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
$369JetBlue
Sat, Aug 15 - Sat, Aug 29
JetBlue Logo
3:20 pm - 12:33 am
ORD
-
BQN
8h 13m
1 stop
JetBlue Logo
2:30 pm - 11:44 pm
BQN
-
ORD
10h 14m
1 stop
$369JetBlue
Wed, Aug 26 - Sat, Sep 5
JetBlue Logo
2:35 pm - 12:33 am
ORD
-
BQN
8h 58m
1 stop
JetBlue Logo
5:01 am - 2:24 pm
BQN
-
ORD
10h 23m
1 stop
$369JetBlue
Tue, Aug 25 - Sat, Aug 29
Multiple Airlines Logo
5:59 pm - 2:10 am
ORD
-
BQN
7h 11m
1 stop
Multiple Airlines Logo
2:30 pm - 11:44 pm
BQN
-
ORD
10h 14m
1 stop
$372Multiple Airlines
Wed, Aug 26 - Sun, Sep 6
Frontier Logo
5:59 pm - 11:09 am
ORD
-
BQN
16h 10m
1 stop
Frontier Logo
12:04 pm - 11:08 pm
BQN
-
ORD
12h 04m
1 stop
$384Frontier
Sat, Sep 12 - Sun, Sep 20
Multiple Airlines Logo
6:00 am - 1:56 pm
ORD
-
BQN
6h 56m
1 stop
Multiple Airlines Logo
11:08 am - 10:59 pm
BQN
-
ORD
12h 51m
1 stop
$402Multiple Airlines
Wed, Aug 26 - Fri, Sep 4
United Airlines Logo
1:30 pm - 11:09 pm
ORD
-
BQN
8h 39m
1 stop
United Airlines Logo
12:15 am - 9:13 am
BQN
-
ORD
9h 58m
1 stop
$497United Airlines
Mon, Jan 18 - Sat, Jan 23
United Airlines Logo
2:20 pm - 11:57 pm
ORD
-
BQN
7h 37m
1 stop
United Airlines Logo
1:09 am - 8:30 am
BQN
-
ORD
9h 21m
1 stop
$597United Airlines
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 April, where tickets cost $356 (return) on average. On the other hand, the most expensive months are December and November, where the average cost of round-trip tickets is $784 and $610 respectively.

Good to know

Low season

August

Cheapest flight

$184
Best time to beat the crowds with an average 49% drop in price.
Most popular time to fly with an average 11% 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 $190 for a one-way ticket and $362 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 $274 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 10047 reviews
7.1Entertainment
6.6Food
8.1Crew
7.7Boarding
7.3Comfort
Airline reviews

It was hot and not as comfortable as the flight to Chicago. Must have been a different plane that needs to be worked on or replaced.

8.0 ExcellentArmedrest, Jul 2026
ORD - PAH
Read more United Airlines reviews

It was hot and not as comfortable as the flight to Chicago. Must have been a different plane that needs to be worked on or replaced.

The SFO lounge closes at 12 midnight. My flight took off at 2AM

It was extremely hot in the cabin the entire flight, vent air was worn

Have not had a flight out or returning to Norfolk that has not required maintenance, and a gate delay. Properly staff the crew so maintenance can be performed without last minute emergencies on each flight and there is enough staff to have gates prepared for inbound flights. Staff to ensure the safety and on time service vs. profit.

We were forced to eat vegetarian food because non veg food ran out. The breakfast was mediocre.

My original flight was cancelled and that affected my trip and my plans and I got no compensation and customer service was hard to reach as well

The kid in the middle seat kicked me almost the whole flight, almost kicked my hot tea off my tray. The flight was delayed due to the first plane not being able to be de-iced in July! We had to get a new plane. Now I drive 3 hours back to Edmonton because direct flights from PVR were way to expensive

The flight was delayed by a hour and I wish they had communicated it sooner. No issues on the plane, it did take a while for food to come.

Know that the movies that you are going to be offered are the oldest be rated movies they could possibly get. They may have one or two new movies that they keep advertising but when you’re flying 15 hours, there is nothing to see past the first new movie.

Agents at gate were not immediately available to solve problems and once they did they didn’t fix all the fight connections

During the flight I suddenly felt very sick, and no one from the crew even tried to help me or check on my condition. They seemed completely indifferent and showed no concern for my well-being. I was very disappointed by the lack of care and compassion. I hope the airline improves its customer service and trains its crew to respond better when passengers need assistance.

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 !!!!!!!

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

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.

Great for the price. No wifi or entertainment, but gate agents and crew were fantastic and we boarded quickly and left on time.

Our flight was canceled for no known reason. We weren’t told until we were checking in at 5:00 am. This was after our last flight with Frontier where we sat on the plane for three hours (not an exaggeration) before we took off because of a mechanical issue. We won’t be flying Frontier again.

I didn’t have enough time to catch my connecting flight and had to use a different Airline. I will be requesting a refund.

I brought a ticket and car rental through Travelocity. There was no where to add a KTN. So I thought i’d add it by looking up ticket on frontier website. I tried 3 times with the frontier chat bot to add my KTN it never updated my boarding pass. So then I tried showing up early to do it in person at the airport. The first employee update my ktn in the system and gave me a new boarding pass. I was sent back by tsa to join regular line. Then I was told to add my Ktn. It would cost me $25 extra. Given the length of the cue I did pay. Congratulations! BUT I will NEVER fly frontier again. Plus the plane was very old. It had actual ashtrays and old looking tray backs. Worst travel experience ever. Im warning my friends and family not to use frontier ever.

It was delayed 9 hours for operational reasons, despite the plane arriving to the airport on time.

Was just ok with over selling I guess. A lot of people in a short space and when we finally arrive i20 minutes, waiting to get out from the plain because we were waiting authorization for out boarding? Something like that.

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

Information on your arrival and departure airports