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Flight Deals from Aguadilla to Chicago from $156

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Bundle + Save

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Save an average of $240 per person when bundling your flight and hotel together with Priceline

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Stops

  • Up to 1 stop
    $295
  • Up to 2 stops
    $500

Airlines

  • Frontier Airlines
    $295
  • JetBlue
    $696
  • United Airlines
    $500

Cabin Class

  • Economy
    $295

Departure Airports

  • Rafael Hernandez Airport
    $295

Arrival Airports

  • Chicago Midway Airport
    $295
  • Chicago O Hare Airport
    $295

Layover Airports

  • Cleveland Hopkins International Airport
    $500
  • Nashville International Airport
    $646
  • New York John F Kennedy Airport
    $696
  • Newark Liberty Airport
    $500
  • Orlando International Airport
    $295

Best Price. GUARANTEED.

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

08/01/25

BQN
13h 7m
MCO

08/01/25

MDW
Frontier Airlines Logo
Frontier Airlines

08/08/25

MDW
16h 26m
MCO

08/09/25

BQN
$295
Frontier Airlines Logo
Frontier Airlines

08/01/25

BQN
13h 7m
MCO

08/01/25

MDW
Frontier Airlines Logo
Frontier Airlines

08/08/25

ORD
8h 35m
MCO

08/09/25

BQN
$295
Frontier Airlines Logo
Frontier Airlines

08/01/25

BQN
21h 32m
MCO

08/01/25

ORD
Frontier Airlines Logo
Frontier Airlines

08/08/25

MDW
16h 26m
MCO

08/09/25

BQN
$305
Frontier Airlines Logo
Frontier Airlines

08/01/25

BQN
21h 32m
MCO

08/01/25

ORD
Frontier Airlines Logo
Frontier Airlines

08/08/25

ORD
8h 35m
MCO

08/09/25

BQN
$305
Frontier Airlines Logo
Frontier Airlines

08/01/25

BQN
13h
MCO

08/01/25

ORD
Frontier Airlines Logo
Frontier Airlines

08/08/25

ORD
8h 35m
MCO

08/09/25

BQN
$375
Frontier Airlines Logo
Frontier Airlines

08/01/25

BQN
13h
MCO

08/01/25

ORD
Frontier Airlines Logo
Frontier Airlines

08/08/25

MDW
16h 26m
MCO

08/09/25

BQN
$375
Frontier Airlines Logo
Frontier Airlines

08/01/25

BQN
21h 36m
MCO

08/02/25

ORD
Frontier Airlines Logo
Frontier Airlines

08/08/25

MDW
16h 26m
MCO

08/09/25

BQN
$388
Frontier Airlines Logo
Frontier Airlines

08/01/25

BQN
21h 36m
MCO

08/02/25

ORD
Frontier Airlines Logo
Frontier Airlines

08/08/25

ORD
8h 35m
MCO

08/09/25

BQN
$388
United Airlines Logo
United Airlines

08/01/25

BQN
9h 24m
EWR

08/01/25

ORD
United Airlines Logo
United Airlines

08/08/25

ORD
26h 34m
CLE
EWR

08/09/25

BQN
$500
United Airlines Logo
United Airlines

08/01/25

BQN
9h 24m
EWR

08/01/25

ORD
United Airlines Logo
United Airlines

08/08/25

ORD
24h 56m
CLE
EWR

08/09/25

BQN
$500
United Airlines Logo
United Airlines

08/01/25

BQN
9h 24m
EWR

08/01/25

ORD
United Airlines Logo
United Airlines

08/08/25

ORD
28h 9m
CLE
EWR

08/09/25

BQN
$500
United Airlines Logo
United Airlines

08/01/25

BQN
8h 23m
EWR

08/01/25

ORD
United Airlines Logo
United Airlines

08/08/25

ORD
26h 34m
CLE
EWR

08/09/25

BQN
$565
United Airlines Logo
United Airlines

08/01/25

BQN
8h 23m
EWR

08/01/25

ORD
United Airlines Logo
United Airlines

08/08/25

ORD
28h 9m
CLE
EWR

08/09/25

BQN
$565
United Airlines Logo
United Airlines

08/01/25

BQN
8h 23m
EWR

08/01/25

ORD
United Airlines Logo
United Airlines

08/08/25

ORD
24h 56m
CLE
EWR

08/09/25

BQN
$565
United Airlines Logo
United Airlines

08/01/25

BQN
9h 24m
EWR

08/01/25

ORD
United Airlines Logo
United Airlines

08/08/25

ORD
24h 44m
EWR

08/09/25

BQN
$610
United Airlines Logo
United Airlines

08/01/25

BQN
10h 24m
EWR

08/01/25

ORD
United Airlines Logo
United Airlines

08/08/25

ORD
26h 34m
CLE
EWR

08/09/25

BQN
$611
United Airlines Logo
United Airlines

08/01/25

BQN
10h 24m
EWR

08/01/25

ORD
United Airlines Logo
United Airlines

08/08/25

ORD
24h 56m
CLE
EWR

08/09/25

BQN
$611
United Airlines Logo
United Airlines

08/01/25

BQN
10h 24m
EWR

08/01/25

ORD
United Airlines Logo
United Airlines

08/08/25

ORD
28h 9m
CLE
EWR

08/09/25

BQN
$611
United Airlines Logo
United Airlines

08/01/25

BQN
9h 24m
EWR

08/01/25

ORD
United Airlines Logo
United Airlines

08/08/25

ORD
26h 34m
EWR

08/09/25

BQN
$640
United Airlines Logo
United Airlines

08/01/25

BQN
9h 24m
EWR

08/01/25

ORD
United Airlines Logo
United Airlines

08/08/25

ORD
24h 39m
BNA
EWR

08/09/25

BQN
$646
United Airlines Logo
United Airlines

08/01/25

BQN
9h 24m
EWR

08/01/25

ORD
United Airlines Logo
United Airlines

08/08/25

ORD
28h 14m
EWR

08/09/25

BQN
$661
United Airlines Logo
United Airlines

08/01/25

BQN
9h 24m
EWR

08/01/25

ORD
United Airlines Logo
United Airlines

08/08/25

ORD
29h 23m
EWR

08/09/25

BQN
$661
JetBlue Logo
JetBlue

08/01/25

BQN
17h 23m
JFK

08/01/25

ORD
JetBlue Logo
JetBlue

08/08/25

ORD
25h 34m
JFK

08/09/25

BQN
$696
JetBlue Logo
JetBlue

08/01/25

BQN
17h 23m
JFK

08/01/25

ORD
JetBlue Logo
JetBlue

08/08/25

ORD
19h 42m
JFK

08/09/25

BQN
$696
JetBlue Logo
JetBlue

08/01/25

BQN
18h 27m
MCO
JFK

08/01/25

ORD
JetBlue Logo
JetBlue

08/08/25

ORD
25h 34m
JFK

08/09/25

BQN
$700
JetBlue Logo
JetBlue

08/01/25

BQN
18h 27m
MCO
JFK

08/01/25

ORD
JetBlue Logo
JetBlue

08/08/25

ORD
19h 42m
JFK

08/09/25

BQN
$700
United Airlines Logo
United Airlines

08/01/25

BQN
8h 23m
EWR

08/01/25

ORD
United Airlines Logo
United Airlines

08/08/25

ORD
24h 39m
BNA
EWR

08/09/25

BQN
$711
JetBlue Logo
JetBlue

08/01/25

BQN
13h 48m
JFK

08/01/25

ORD
JetBlue Logo
JetBlue

08/08/25

ORD
19h 42m
JFK

08/09/25

BQN
$806
JetBlue Logo
JetBlue

08/01/25

BQN
13h 48m
JFK

08/01/25

ORD
JetBlue Logo
JetBlue

08/08/25

ORD
25h 34m
JFK

08/09/25

BQN
$806
JetBlue Logo
JetBlue

08/01/25

BQN
26h 38m
JFK

08/02/25

ORD
JetBlue Logo
JetBlue

08/08/25

ORD
25h 34m
JFK

08/09/25

BQN
$1004

Top Deals on flights from Aguadilla to Chicago

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

Frontier Airlines Logo
Frontier Airlines

Aug 1

BQN
13h 7m
MCO

Aug 1

MDW

as low as

$156

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

Frontier Airlines Logo
Frontier Airlines

Aug 1

BQN
21h 32m
MCO

Aug 1

ORD

as low as

$171

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

Frontier Airlines Logo
Frontier Airlines

Aug 1

BQN
13h
MCO

Aug 1

ORD

as low as

$236

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

United Airlines Logo
United Airlines

Aug 1

BQN
9h 24m
EWR

Aug 1

ORD

as low as

$239

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

Frontier Airlines Logo
Frontier Airlines

Aug 1

BQN
21h 36m
MCO

Aug 2

ORD

as low as

$254

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

United Airlines Logo
United Airlines

Aug 1

BQN
8h 23m
EWR

Aug 1

ORD

as low as

$302

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

JetBlue Logo
JetBlue

Aug 1

BQN
18h 27m
MCO
JFK

Aug 1

ORD

as low as

$313

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

JetBlue Logo
JetBlue

Aug 1

BQN
17h 23m
JFK

Aug 1

ORD

as low as

$316

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

JetBlue Logo
JetBlue

Aug 1

BQN
11h 31m
MCO
BOS

Aug 1

ORD

as low as

$345

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

United Airlines Logo
United Airlines

Aug 1

BQN
10h 24m
EWR

Aug 1

ORD

as low as

$346

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

JetBlue Logo
JetBlue

Aug 1

BQN
18h 45m
MCO
BOS

Aug 2

ORD

as low as

$384

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

United Airlines Logo
United Airlines

Aug 1

BQN
24h 26m
EWR

Aug 1

ORD

as low as

$391

Frequently Asked Questions

What are the most convenient layover airports for the flight?
The most convenient layover airports for your flight from Aguadilla to Chicago are Orlando International Airport, Newark Liberty Airport, and New York John F Kennedy Airport.
What are the cheapest and fastest flights from Aguadilla to Chicago?
The cheapest flight is with Frontier Airlines for $295, taking 13 hours 7 minutes. The fastest is with United Airlines for $565, taking 8 hours 23 minutes.
What are all possible destination arrival airports?
The possible destination arrival airports from Aguadilla include Chicago Midway Airport and Chicago O'Hare Airport.
What is the time difference between destination and arrival?
The time difference between Aguadilla and Chicago is typically 2 hours; Aguadilla is ahead of Chicago. Be mindful of this when planning your travel and arrival times.
Is there a direct flight from Aguadilla to Chicago?
There is no direct flight from Aguadilla to Chicago.
Are there convenient layover flights from Aguadilla to Chicago?
Yes, there are convenient layover flights from Aguadilla to Chicago. You can choose from Frontier Airlines for $295 with a layover in Orlando (13h 7m) or United Airlines for $500 with a layover in Newark (9h 24m). JetBlue also offers a one-stop flight for $696.
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