$107+ Cheap flights from Chicago (CHI) to Aguadilla (BQN)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/18. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BQN
Mar 5 — Mar 121
1 adult, Economy
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Find cheap flights from Chicago to Aguadilla with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Chicago to Aguadilla
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Best
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One-way
Cheapest flights from Chicago to AguadillaExplore the most affordable flight options available from Chicago to Aguadilla. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 3, 2026.
Explore the most affordable flight options available from Chicago to Aguadilla. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 3, 2026.
This Priceline deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/38:30 am
ORD
- BQN
1 stop16h 27m
Frontier
Mon 3/162:42 am
BQN
- ORD
1 stop21h 56m
Frontier
Deal found 2/1![Frontier logo]()
$188
This CheapOair deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/218:15 am
ORD
- BQN
1 stop16h 42m
Frontier
Tue 3/33:59 am
BQN
- ORD
1 stop13h 53m
Frontier
Deal found 2/3![Frontier logo]()
$213
This Priceline deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/233:50 pm
ORD
- BQN
1 stop9h 07m
Frontier
Wed 2/253:58 am
BQN
- ORD
1 stop8h 48m
Frontier
Deal found 2/3![Frontier logo]()
$223
This Kiwi.com deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/412:44 pm
ORD
- BQN
1 stop12h 13m
Multiple Airlines
Mon 3/92:43 am
BQN
- ORD
1 stop16h 03m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$237
This Priceline deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/108:30 am
ORD
- BQN
1 stop16h 27m
Frontier
Mon 3/302:42 am
BQN
- ORD
1 stop21h 56m
Frontier
Deal found 2/1![Frontier logo]()
$244
This Priceline deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/310:00 am
ORD
- BQN
2 stops14h 52m
Multiple Airlines
Mon 3/162:42 am
BQN
- ORD
1 stop13h 46m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$255
This CheapOair deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/218:15 am
ORD
- BQN
1 stop16h 42m
Multiple Airlines
Fri 2/272:30 am
BQN
- ORD
1 stop11h 34m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$260
This Kiwi.com deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/612:05 pm
ORD
- BQN
2 stops37h 37m
Multiple Airlines
Mon 3/92:43 am
BQN
- ORD
1 stop16h 03m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$265
This CheapOair deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/273:11 pm
ORD
- BQN
1 stop9h 46m
Frontier
Sun 3/13:58 am
BQN
- ORD
1 stop21h 17m
Frontier
Deal found 2/1![Frontier logo]()
$266
Best flights from Chicago to AguadillaDiscover carefully curated flight deals from Chicago to Aguadilla that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 3, 2026.
Discover carefully curated flight deals from Chicago to Aguadilla that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 3, 2026.
This Priceline deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/38:30 am
ORD
- BQN
1 stop16h 27m
Frontier
Mon 3/162:42 am
BQN
- ORD
1 stop21h 56m
Frontier
Deal found 2/1![Frontier logo]()
$188
This Kiwi.com deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/412:44 pm
ORD
- BQN
1 stop12h 13m
Multiple Airlines
Mon 3/92:43 am
BQN
- ORD
1 stop16h 03m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$237
This Priceline deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/233:50 pm
ORD
- BQN
1 stop9h 07m
Frontier
Wed 2/253:58 am
BQN
- ORD
1 stop8h 48m
Frontier
Deal found 2/3![Frontier logo]()
$223
This Priceline deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/188:00 am
ORD
- BQN
1 stop16h 43m
Frontier
Sun 4/262:38 am
BQN
- ORD
1 stop12h 39m
Frontier
Deal found 2/3![Frontier logo]()
$223
This Priceline deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/310:00 am
ORD
- BQN
2 stops14h 52m
Multiple Airlines
Mon 3/162:42 am
BQN
- ORD
1 stop13h 46m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$255
This Kiwi.com deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/612:05 pm
ORD
- BQN
2 stops37h 37m
Multiple Airlines
Mon 3/92:43 am
BQN
- ORD
1 stop16h 03m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$265
This Priceline deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/178:30 am
ORD
- BQN
1 stop16h 27m
Frontier
Mon 3/302:42 am
BQN
- ORD
1 stop21h 56m
Frontier
Deal found 2/1![Frontier logo]()
$244
This Kiwi.com deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/412:44 pm
ORD
- BQN
1 stop12h 13m
Multiple Airlines
Sat 3/73:27 am
BQN
- ORD
2 stops32h 29m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$273
This Priceline deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/511:55 am
ORD
- BQN
1 stop13h 02m
Frontier
Sun 3/82:42 am
BQN
- ORD
1 stop13h 46m
Frontier
Deal found 2/2![Frontier logo]()
$270
This CheapOair deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/233:50 pm
ORD
- BQN
1 stop9h 07m
Multiple Airlines
Wed 2/252:30 am
BQN
- ORD
1 stop22h 29m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$289
Last-minute flights from Chicago to AguadillaDiscover last-minute flight deals from Chicago to Aguadilla. Data last updated February 3, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Aguadilla. Data last updated February 3, 2026 and is based on user searches.
This Priceline deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/108:30 am
ORD
- BQN
1 stop16h 27m
Frontier
Mon 3/302:42 am
BQN
- ORD
1 stop21h 56m
Frontier
Deal found 2/1![Frontier logo]()
$244
This CheapOair deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/218:15 am
ORD
- BQN
1 stop16h 42m
Frontier
Tue 3/33:59 am
BQN
- ORD
1 stop13h 53m
Frontier
Deal found 2/3![Frontier logo]()
$213
This CheapOair deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/218:15 am
ORD
- BQN
1 stop16h 42m
Multiple Airlines
Fri 2/272:30 am
BQN
- ORD
1 stop11h 34m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$260
This Priceline deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/233:50 pm
ORD
- BQN
1 stop9h 07m
Frontier
Wed 2/253:58 am
BQN
- ORD
1 stop8h 48m
Frontier
Deal found 2/3![Frontier logo]()
$223
This CheapOair deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/273:11 pm
ORD
- BQN
1 stop9h 46m
Frontier
Sun 3/13:58 am
BQN
- ORD
1 stop21h 17m
Frontier
Deal found 2/1![Frontier logo]()
$266
This Priceline deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/38:30 am
ORD
- BQN
1 stop16h 27m
Frontier
Mon 3/162:42 am
BQN
- ORD
1 stop21h 56m
Frontier
Deal found 2/2![Frontier logo]()
$188
This Priceline deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/310:00 am
ORD
- BQN
2 stops14h 52m
Multiple Airlines
Mon 3/162:42 am
BQN
- ORD
1 stop13h 46m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$255
This Kiwi.com deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/412:44 pm
ORD
- BQN
1 stop12h 13m
Multiple Airlines
Mon 3/92:43 am
BQN
- ORD
1 stop16h 03m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$237
This Kiwi.com deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/612:05 pm
ORD
- BQN
2 stops37h 37m
Multiple Airlines
Mon 3/92:43 am
BQN
- ORD
1 stop16h 03m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$265
One-way flights from Chicago to AguadillaSearch for one-way flight options from Chicago to Aguadilla. Find affordable one-way fares based on user searches. Data last updated February 3, 2026.
Search for one-way flight options from Chicago to Aguadilla. Find affordable one-way fares based on user searches. Data last updated February 3, 2026.
This Expedia deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/186:57 am
ORD
- BQN
1 stop17h 46m
Frontier
Deal found 2/1![Frontier logo]()
$107
This Super.com deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/178:30 am
ORD
- BQN
1 stop16h 27m
Frontier
Deal found 2/1![Frontier logo]()
$120
This Travelocity deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/188:00 am
ORD
- BQN
1 stop16h 43m
Frontier
Deal found 2/3![Frontier logo]()
$122
This Kiwi.com deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/196:31 am
ORD
- BQN
2 stops18h 12m
Frontier
Deal found 2/1![Frontier logo]()
$134
This Super.com deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/151:17 pm
ORD
- BQN
1 stop11h 40m
Frontier
Deal found 2/3![Frontier logo]()
$144
This Priceline deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/169:41 pm
ORD
- BQN
1 stop27h 16m
Frontier
Deal found 2/3![Frontier logo]()
$152
This Kiwi.com deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/147:17 am
ORD
- BQN
2 stops17h 26m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$155
This Priceline deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/139:12 am
ORD
- BQN
1 stop10h 07m
Frontier
Deal found 2/1![Frontier logo]()
$157
This Kiwi.com deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/184:47 pm
ORD
- BQN
2 stops31h 56m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$159
This Kiwi.com deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/134:36 pm
ORD
- BQN
2 stops32h 07m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$171
Find flight deals from Chicago to Aguadilla
Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Aguadilla (BQN). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated February 3, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $188 (Priceline) |
One-way from | $107 (Expedia) |
Popular in | June |
Cheapest in | August |
Average price | $396 |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Aguadilla that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 3, 2026.
Use the filters below to find and compare flights from Chicago to Aguadilla that are best for you.
Fly from
Chicago
Fly to
Aguadilla
Route
Depart
Return
Price
ChicagoAguadilla
ORD - BQN
ORDBQN
Chicago O'Hare Intl
Tue 3/3
8:30 am-2:57 am
1 stop16h 27m
Aguadilla Borinquen
Mon 3/16
2:42 am-11:38 pm
1 stop21h 56m
$188
ChicagoAguadilla
ORD - BQN
ORDBQN
Chicago O'Hare Intl
Mon 2/23
3:50 pm-2:57 am
1 stop9h 07m
Aguadilla Borinquen
Wed 2/25
3:58 am-10:46 am
1 stop8h 48m
$223
ChicagoAguadilla
ORD - BQN
ORDBQN
Chicago O'Hare Intl
Sat 4/18
8:00 am-1:43 am
1 stop16h 43m
Aguadilla Borinquen
Sun 4/26
2:38 am-2:17 pm
1 stop12h 39m
$223
ChicagoAguadilla
ORD - BQN
ORDBQN
Chicago O'Hare Intl
Wed 3/4
12:44 pm-2:57 am
1 stop12h 13m
Aguadilla Borinquen
Mon 3/9
2:43 am-5:46 pm
1 stop16h 03m
$237
ChicagoAguadilla
ORD - BQN
ORDBQN
Chicago O'Hare Intl
Tue 2/17
8:30 am-2:57 am
1 stop16h 27m
Aguadilla Borinquen
Mon 3/30
2:42 am-11:38 pm
1 stop21h 56m
$244
ChicagoAguadilla
ORD - BQN
ORDBQN
Chicago O'Hare Intl
Tue 3/3
10:00 am-2:52 am
2 stops14h 52m
Aguadilla Borinquen
Mon 3/16
2:42 am-3:28 pm
1 stop13h 46m
$255
ChicagoAguadilla
ORD - BQN
ORDBQN
Chicago O'Hare Intl
Fri 3/6
12:05 pm-3:42 am
2 stops37h 37m
Aguadilla Borinquen
Mon 3/9
2:43 am-5:46 pm
1 stop16h 03m
$265
ChicagoAguadilla
ORD - BQN
ORDBQN
Chicago O'Hare Intl
Thu 3/5
11:55 am-2:57 am
1 stop13h 02m
Aguadilla Borinquen
Sun 3/8
2:42 am-3:28 pm
1 stop13h 46m
$270
ChicagoAguadilla
ORD - BQN
ORDBQN
Chicago O'Hare Intl
Wed 3/4
12:44 pm-2:57 am
1 stop12h 13m
Aguadilla Borinquen
Sat 3/7
3:27 am-9:56 am
2 stops32h 29m
$273
ChicagoAguadilla
ORD - BQN
ORDBQN
Chicago O'Hare Intl
Mon 2/23
3:50 pm-2:57 am
1 stop9h 07m
Aguadilla Borinquen
Wed 2/25
2:30 am-10:59 pm
1 stop22h 29m
$289
Showing 1-10 of 20 results
Compare providers for flights from Chicago to Aguadilla
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Aguadilla in February.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*2 stars |
- Most accurate provider: When it comes to deals on Chicago-Aguadilla flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Aguadilla flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Aguadilla flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago-Aguadilla flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Aguadilla flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Chicago to Aguadilla
Have a flexible travel schedule? Discover the best time to fly to Aguadilla from Chicago with our price prediction graph.
CHI-BQN
ORD-BQN
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago to Aguadilla
CHI-BQN
ORD-BQN
What is the cheapest month to book a flight from Chicago to Aguadilla?
Currently, April is the cheapest month in which you can book a flight from Chicago to Aguadilla (average of $91). Flying from Chicago to Aguadilla in December is currently the most expensive (average of $224). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What’s the top layover airport for flights from Chicago to Aguadilla?
Share of 1-stop round-trip flights from Chicago to Aguadilla chosen by Cheapflights users in the past 12 months, using the same layover each way.
Orlando (MCO) – chosen by Cheapflights users on 67% of 1-stop itineraries from Chicago to Aguadilla on Cheapflights.
What’s the cheapest layover airport for flights from Chicago to Aguadilla?
Average round-trip fare for 1-stop flights from Chicago to Aguadilla, chosen by Cheapflights users in the past 12 months, with the same layover each way.
Orlando (MCO) is the most affordable 1-stop option, with an average round-trip price of $292.
What’s the fastest layover option from Chicago to Aguadilla?
Shortest average travel time for 1-stop one-way flights from Chicago to Aguadilla, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.
Flights via Newark (EWR) have the shortest average one-way travel time for 1-stop routes: 7h 42m.
Which airport typically offers the quickest layover for flights from Chicago to Aguadilla?
Average layover duration for 1-stop one-way flights from Chicago to Aguadilla, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.
Flights via Newark (EWR) offer the fastest connection on this route, with an average layover time of 1h 31m.
Reviews of airlines servicing Aguadilla
Get insights into the airlines that provide service to Aguadilla. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Aguadilla. Reviews last updated February 3, 2026.
Peruse reviews from past customers who have flown with United Airlines and Frontier from Chicago to Aguadilla to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
7.3
Food
6.6
Overall
7.4
Crew
8.1
Entertainment
7.1
Boarding
7.7
Reviews
1 / 20
10.0
ExcellentDane,Jan 2026
TYS - IAD
Comfort
7.3
Food
6.6
Overall
7.4
Crew
8.1
Entertainment
7.1
Boarding
7.7
Reviews
1 / 20
10.0
ExcellentDane,Jan 2026
TYS - IAD
Comfort
7.3
Food
6.6
Overall
7.4
Crew
8.1
Entertainment
7.1
Boarding
7.7
Reviews
1 / 20
10.0
ExcellentDane,Jan 2026
TYS - IAD
Related info for your journey
Find useful and relevant information for your journey from Chicago to Aguadilla. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Chicago and Aguadilla flights
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Top 2 airlines flying from Chicago to Aguadilla
Discover the top 2 airlines that operate flights from Chicago to Aguadilla. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 3, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$152 | Average$296 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$385 | Average$536 | FlexibilityNo cancel fee | On-time69% |