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Flight Deals from Chicago to Aguadilla from $194

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Stops

  • Up to 1 stop
    $350
  • Up to 2 stops
    $457

Airlines

  • Frontier Airlines
    $350
  • JetBlue
    $457
  • United Airlines
    $527

Cabin Class

  • Economy
    $350

Departure Airports

  • Chicago Midway Airport
    $361
  • Chicago O Hare Airport
    $350

Arrival Airports

  • Rafael Hernandez Airport
    $350

Layover Airports

  • General Edward Lawrence Logan International Airport
    $457
  • New York John F Kennedy Airport
    $457
  • Newark Liberty Airport
    $527
  • Orlando International Airport
    $350

Best Price. GUARANTEED.

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BUNDLE & SAVE
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On average save $240 per traveler
Frontier Airlines Logo
Frontier Airlines

09/12/25

ORD
13h 7m
MCO

09/13/25

BQN
Frontier Airlines Logo
Frontier Airlines

09/19/25

BQN
17h 12m
MCO

09/19/25

ORD
$350
Frontier Airlines Logo
Frontier Airlines

09/12/25

ORD
28h 38m
MCO

09/14/25

BQN
Frontier Airlines Logo
Frontier Airlines

09/19/25

BQN
17h 12m
MCO

09/19/25

ORD
$361
Frontier Airlines Logo
Frontier Airlines

09/12/25

MDW
24h 8m
MCO

09/13/25

BQN
Frontier Airlines Logo
Frontier Airlines

09/19/25

BQN
17h 12m
MCO

09/19/25

ORD
$361
Frontier Airlines Logo
Frontier Airlines

09/12/25

MDW
15h 39m
MCO

09/13/25

BQN
Frontier Airlines Logo
Frontier Airlines

09/19/25

BQN
17h 12m
MCO

09/19/25

ORD
$364
JetBlue Logo
JetBlue

09/12/25

ORD
11h 58m
JFK

09/13/25

BQN
JetBlue Logo
JetBlue

09/19/25

BQN
28h 55m
JFK
BOS

09/20/25

ORD
$457
JetBlue Logo
JetBlue

09/12/25

ORD
18h 48m
JFK

09/13/25

BQN
JetBlue Logo
JetBlue

09/19/25

BQN
28h 55m
JFK
BOS

09/20/25

ORD
$467
United Airlines Logo
United Airlines

09/12/25

ORD
8h 57m
EWR

09/12/25

BQN
United Airlines Logo
United Airlines

09/19/25

BQN
9h 23m
EWR

09/19/25

ORD
$527
United Airlines Logo
United Airlines

09/12/25

ORD
7h 49m
EWR

09/12/25

BQN
United Airlines Logo
United Airlines

09/19/25

BQN
9h 23m
EWR

09/19/25

ORD
$527
United Airlines Logo
United Airlines

09/12/25

ORD
8h 57m
EWR

09/12/25

BQN
United Airlines Logo
United Airlines

09/19/25

BQN
8h 23m
EWR

09/19/25

ORD
$527
United Airlines Logo
United Airlines

09/12/25

ORD
7h 49m
EWR

09/12/25

BQN
United Airlines Logo
United Airlines

09/19/25

BQN
8h 23m
EWR

09/19/25

ORD
$527
JetBlue Logo
JetBlue

09/12/25

ORD
11h 28m
JFK
MCO

09/12/25

BQN
JetBlue Logo
JetBlue

09/19/25

BQN
28h 55m
JFK
BOS

09/20/25

ORD
$549
JetBlue Logo
JetBlue

09/12/25

ORD
11h 58m
JFK

09/13/25

BQN
JetBlue Logo
JetBlue

09/19/25

BQN
16h 47m
JFK

09/19/25

ORD
$571
JetBlue Logo
JetBlue

09/12/25

ORD
18h 48m
JFK

09/13/25

BQN
JetBlue Logo
JetBlue

09/19/25

BQN
16h 47m
JFK

09/19/25

ORD
$583
United Airlines Logo
United Airlines

09/12/25

ORD
8h 57m
EWR

09/12/25

BQN
United Airlines Logo
United Airlines

09/19/25

BQN
10h 22m
EWR

09/19/25

ORD
$585
United Airlines Logo
United Airlines

09/12/25

ORD
7h 49m
EWR

09/12/25

BQN
United Airlines Logo
United Airlines

09/19/25

BQN
10h 22m
EWR

09/19/25

ORD
$585
United Airlines Logo
United Airlines

09/12/25

ORD
25h 54m
EWR

09/13/25

BQN
United Airlines Logo
United Airlines

09/19/25

BQN
8h 23m
EWR

09/19/25

ORD
$625
United Airlines Logo
United Airlines

09/12/25

ORD
25h 54m
EWR

09/13/25

BQN
United Airlines Logo
United Airlines

09/19/25

BQN
9h 23m
EWR

09/19/25

ORD
$625
United Airlines Logo
United Airlines

09/12/25

ORD
25h 1m
EWR

09/13/25

BQN
United Airlines Logo
United Airlines

09/19/25

BQN
8h 23m
EWR

09/19/25

ORD
$625
United Airlines Logo
United Airlines

09/12/25

ORD
25h 1m
EWR

09/13/25

BQN
United Airlines Logo
United Airlines

09/19/25

BQN
9h 23m
EWR

09/19/25

ORD
$625
United Airlines Logo
United Airlines

09/12/25

ORD
26h 34m
EWR

09/13/25

BQN
United Airlines Logo
United Airlines

09/19/25

BQN
9h 23m
EWR

09/19/25

ORD
$632
United Airlines Logo
United Airlines

09/12/25

ORD
26h 34m
EWR

09/13/25

BQN
United Airlines Logo
United Airlines

09/19/25

BQN
8h 23m
EWR

09/19/25

ORD
$632
United Airlines Logo
United Airlines

09/12/25

ORD
16h 9m
EWR

09/12/25

BQN
United Airlines Logo
United Airlines

09/19/25

BQN
8h 23m
EWR

09/19/25

ORD
$638
United Airlines Logo
United Airlines

09/12/25

ORD
16h 9m
EWR

09/12/25

BQN
United Airlines Logo
United Airlines

09/19/25

BQN
9h 23m
EWR

09/19/25

ORD
$638
United Airlines Logo
United Airlines

09/12/25

ORD
24h 54m
BOS
EWR

09/13/25

BQN
United Airlines Logo
United Airlines

09/19/25

BQN
8h 23m
EWR

09/19/25

ORD
$640
JetBlue Logo
JetBlue

09/12/25

ORD
11h 28m
JFK
MCO

09/12/25

BQN
JetBlue Logo
JetBlue

09/19/25

BQN
16h 47m
JFK

09/19/25

ORD
$672
JetBlue Logo
JetBlue

09/12/25

ORD
11h 28m
JFK
MCO

09/12/25

BQN
JetBlue Logo
JetBlue

09/19/25

BQN
8h 20m
JFK

09/19/25

ORD
$775

Top Deals on flights from Chicago to Aguadilla

Chicago, US (CHI) - Aguadilla, PR (BQN)

JetBlue Logo
JetBlue

Sep 10

ORD
15h 42m
BOS
JFK

Sep 11

BQN

as low as

$194

Chicago, US (CHI) - Aguadilla, PR (BQN)

JetBlue Logo
JetBlue

Sep 10

ORD
11h 56m
JFK

Sep 11

BQN

as low as

$213

Chicago, US (CHI) - Aguadilla, PR (BQN)

United Airlines Logo
United Airlines

Sep 10

ORD
8h 57m
EWR

Sep 10

BQN

as low as

$234

Chicago, US (CHI) - Aguadilla, PR (BQN)

United Airlines Logo
United Airlines

Sep 10

ORD
7h 49m
EWR

Sep 10

BQN

as low as

$234

Chicago, US (CHI) - Aguadilla, PR (BQN)

JetBlue Logo
JetBlue

Sep 10

ORD
39h 41m
BOS
JFK

Sep 12

BQN

as low as

$354

Chicago, US (CHI) - Aguadilla, PR (BQN)

United Airlines Logo
United Airlines

Sep 10

ORD
16h 9m
EWR

Sep 10

BQN

as low as

$358

Chicago, US (CHI) - Aguadilla, PR (BQN)

United Airlines Logo
United Airlines

Sep 10

ORD
14h 59m
EWR

Sep 10

BQN

as low as

$358

Chicago, US (CHI) - Aguadilla, PR (BQN)

United Airlines Logo
United Airlines

Sep 10

ORD
10h 27m
EWR

Sep 10

BQN

as low as

$358

Chicago, US (CHI) - Aguadilla, PR (BQN)

United Airlines Logo
United Airlines

Sep 10

ORD
25h 1m
EWR

Sep 11

BQN

as low as

$375

Chicago, US (CHI) - Aguadilla, PR (BQN)

United Airlines Logo
United Airlines

Sep 10

ORD
11h 34m
EWR

Sep 10

BQN

as low as

$384

Chicago, US (CHI) - Aguadilla, PR (BQN)

United Airlines Logo
United Airlines

Sep 10

ORD
13h 24m
EWR

Sep 10

BQN

as low as

$403

Chicago, US (CHI) - Aguadilla, PR (BQN)

United Airlines Logo
United Airlines

Sep 10

ORD
26h 34m
EWR

Sep 11

BQN

as low as

$511

Frequently Asked Questions

Are there convenient layover flights from Chicago to Aguadilla?
Yes, convenient layover flights from Chicago to Aguadilla include: Frontier Airlines at $350 (13h 7m, Orlando), JetBlue at $457 (11h 58m, New York), and United Airlines at $527 (8h 57m, Newark). For 2 stops, JetBlue costs $549 (11h 28m) and United Airlines is $640 (24h 54m).
What are the most convenient layover airports for my flight?
The most convenient layover airports for your flight from Chicago to Aguadilla are Orlando International Airport with Frontier, Newark Liberty Airport with United, and New York John F. Kennedy Airport with JetBlue.
What are the details of the cheapest and fastest flights from Chicago to Aguadilla?
The cheapest flight is with Frontier Airlines for $350, 1 stop, 13h 7m. The fastest flight is with United Airlines for $527, 1 stop, 7h 49m.
What are all possible destination arrival airports?
Possible destination arrival airports from Chicago include Rafael Hernandez Airport, Orlando International Airport, Newark Liberty Airport, and New York John F Kennedy Airport.
What is the time difference between destination and arrival?
The time difference between Chicago and Aguadilla is one hour; Aguadilla is one hour ahead of Chicago.
Is there a direct flight from Chicago to Aguadilla?
There is no direct flight from Chicago O'Hare Airport to Rafael Hernandez Airport. The available flights have one or two stops, offered by airlines like Frontier Airlines, JetBlue, and United Airlines.
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