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Flight Deals from Chicago to Culebra from $329

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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
    $1117
  • Up to 2 stops
    $733

Airlines

  • JetBlue
    $733
  • United Airlines
    $1117

Cabin Class

  • Economy
    $733

Departure Airports

  • Chicago O Hare Airport
    $733

Arrival Airports

  • Benjamin Rivera Noriega Airport
    $733

Layover Airports

  • General Edward Lawrence Logan International Airport
    $733
  • Luis Munoz Marin International Airport
    $733
  • New York John F Kennedy Airport
    $733
  • Newark Liberty Airport
    $1151
  • Washington Dulles Airport
    $1121

Best Price. GUARANTEED.

Exclusively for Priceline Members
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BUNDLE & SAVE
Book a flight & hotel together for extra savings.
On average save $240 per traveler
JetBlue Logo
JetBlue

09/07/25

ORD
9h 6m
JFK
SJU

09/07/25

CPX
JetBlue Logo
JetBlue

09/14/25

CPX
25h 36m
SJU
BOS

09/15/25

ORD
$733
JetBlue Logo
JetBlue

09/07/25

ORD
9h 6m
JFK
SJU

09/07/25

CPX
JetBlue Logo
JetBlue

09/14/25

CPX
18h 51m
SJU
BOS

09/15/25

ORD
$733
JetBlue Logo
JetBlue

09/07/25

ORD
9h 6m
JFK
SJU

09/07/25

CPX
JetBlue Logo
JetBlue

09/14/25

CPX
16h 45m
SJU
BOS

09/15/25

ORD
$733
JetBlue Logo
JetBlue

09/07/25

ORD
9h 6m
JFK
SJU

09/07/25

CPX
JetBlue Logo
JetBlue

09/14/25

CPX
21h 25m
SJU
BOS

09/15/25

ORD
$733
JetBlue Logo
JetBlue

09/07/25

ORD
9h 6m
JFK
SJU

09/07/25

CPX
JetBlue Logo
JetBlue

09/14/25

CPX
23h 43m
SJU
BOS

09/15/25

ORD
$733
JetBlue Logo
JetBlue

09/07/25

ORD
9h 6m
JFK
SJU

09/07/25

CPX
JetBlue Logo
JetBlue

09/14/25

CPX
26h 44m
SJU
BOS

09/15/25

ORD
$744
JetBlue Logo
JetBlue

09/07/25

ORD
9h 6m
JFK
SJU

09/07/25

CPX
JetBlue Logo
JetBlue

09/14/25

CPX
28h 50m
SJU
BOS

09/15/25

ORD
$744
JetBlue Logo
JetBlue

09/07/25

ORD
20h 1m
BOS
SJU

09/08/25

CPX
JetBlue Logo
JetBlue

09/14/25

CPX
25h 36m
SJU
BOS

09/15/25

ORD
$758
JetBlue Logo
JetBlue

09/07/25

ORD
24h 14m
JFK
SJU

09/08/25

CPX
JetBlue Logo
JetBlue

09/14/25

CPX
21h 25m
SJU
BOS

09/15/25

ORD
$773
United Airlines Logo
United Airlines

09/07/25

ORD
6h 59m
SJU

09/07/25

CPX
United Airlines Logo
United Airlines

09/14/25

CPX
10h 50m
SJU

09/14/25

ORD
$1117
United Airlines Logo
United Airlines

09/07/25

ORD
6h 59m
SJU

09/07/25

CPX
United Airlines Logo
United Airlines

09/14/25

CPX
14h 2m
SJU
IAD

09/14/25

ORD
$1121
United Airlines Logo
United Airlines

09/07/25

ORD
22h 7m
SJU

09/08/25

CPX
United Airlines Logo
United Airlines

09/14/25

CPX
10h 50m
SJU

09/14/25

ORD
$1137
United Airlines Logo
United Airlines

09/07/25

ORD
24h 1m
SJU

09/08/25

CPX
United Airlines Logo
United Airlines

09/14/25

CPX
10h 50m
SJU

09/14/25

ORD
$1137
United Airlines Logo
United Airlines

09/07/25

ORD
24h 1m
SJU

09/08/25

CPX
United Airlines Logo
United Airlines

09/14/25

CPX
14h 2m
SJU
IAD

09/14/25

ORD
$1141
United Airlines Logo
United Airlines

09/07/25

ORD
22h 7m
SJU

09/08/25

CPX
United Airlines Logo
United Airlines

09/14/25

CPX
14h 2m
SJU
IAD

09/14/25

ORD
$1141
United Airlines Logo
United Airlines

09/07/25

ORD
6h 59m
SJU

09/07/25

CPX
United Airlines Logo
United Airlines

09/14/25

CPX
22h 33m
SJU
IAD

09/15/25

ORD
$1151
United Airlines Logo
United Airlines

09/07/25

ORD
6h 59m
SJU

09/07/25

CPX
United Airlines Logo
United Airlines

09/14/25

CPX
26h 26m
SJU
EWR

09/15/25

ORD
$1151
United Airlines Logo
United Airlines

09/07/25

ORD
6h 59m
SJU

09/07/25

CPX
United Airlines Logo
United Airlines

09/14/25

CPX
29h 16m
SJU
IAD

09/15/25

ORD
$1169
United Airlines Logo
United Airlines

09/07/25

ORD
24h 1m
SJU

09/08/25

CPX
United Airlines Logo
United Airlines

09/14/25

CPX
22h 33m
SJU
IAD

09/15/25

ORD
$1171
United Airlines Logo
United Airlines

09/07/25

ORD
22h 7m
SJU

09/08/25

CPX
United Airlines Logo
United Airlines

09/14/25

CPX
22h 33m
SJU
IAD

09/15/25

ORD
$1171
United Airlines Logo
United Airlines

09/07/25

ORD
22h 7m
SJU

09/08/25

CPX
United Airlines Logo
United Airlines

09/14/25

CPX
26h 26m
SJU
EWR

09/15/25

ORD
$1171
United Airlines Logo
United Airlines

09/07/25

ORD
24h 1m
SJU

09/08/25

CPX
United Airlines Logo
United Airlines

09/14/25

CPX
26h 26m
SJU
EWR

09/15/25

ORD
$1171
United Airlines Logo
United Airlines

09/07/25

ORD
24h 1m
SJU

09/08/25

CPX
United Airlines Logo
United Airlines

09/14/25

CPX
29h 16m
SJU
IAD

09/15/25

ORD
$1189
United Airlines Logo
United Airlines

09/07/25

ORD
22h 7m
SJU

09/08/25

CPX
United Airlines Logo
United Airlines

09/14/25

CPX
29h 16m
SJU
IAD

09/15/25

ORD
$1189
United Airlines Logo
United Airlines

09/07/25

ORD
6h 59m
SJU

09/07/25

CPX
United Airlines Logo
United Airlines

09/14/25

CPX
10h 50m
SJU

09/14/25

ORD
$1285
United Airlines Logo
United Airlines

09/07/25

ORD
6h 59m
SJU

09/07/25

CPX
United Airlines Logo
United Airlines

09/14/25

CPX
14h 2m
SJU
IAD

09/14/25

ORD
$1290
United Airlines Logo
United Airlines

09/07/25

ORD
6h 59m
SJU

09/07/25

CPX
United Airlines Logo
United Airlines

09/14/25

CPX
26h 26m
SJU
EWR

09/15/25

ORD
$1320
United Airlines Logo
United Airlines

09/07/25

ORD
6h 59m
SJU

09/07/25

CPX
United Airlines Logo
United Airlines

09/14/25

CPX
23h 25m
SJU
EWR

09/15/25

ORD
$1424
United Airlines Logo
United Airlines

09/07/25

ORD
6h 59m
SJU

09/07/25

CPX
United Airlines Logo
United Airlines

09/14/25

CPX
25h 22m
SJU
EWR

09/15/25

ORD
$1424
United Airlines Logo
United Airlines

09/07/25

ORD
6h 59m
SJU

09/07/25

CPX
United Airlines Logo
United Airlines

09/14/25

CPX
24h 25m
SJU
EWR

09/15/25

ORD
$1424

Top Deals on flights from Chicago to Culebra

Chicago, US (CHI) - Culebra, PR (CPX)

United Airlines Logo
United Airlines

Sep 7

ORD
6h 59m
SJU

Sep 7

CPX

as low as

$329

Chicago, US (CHI) - Culebra, PR (CPX)

JetBlue Logo
JetBlue

Sep 7

ORD
9h 6m
JFK
SJU

Sep 7

CPX

as low as

$341

Chicago, US (CHI) - Culebra, PR (CPX)

United Airlines Logo
United Airlines

Sep 7

ORD
22h 7m
SJU

Sep 8

CPX

as low as

$355

Chicago, US (CHI) - Culebra, PR (CPX)

United Airlines Logo
United Airlines

Sep 7

ORD
24h 1m
SJU

Sep 8

CPX

as low as

$355

Chicago, US (CHI) - Culebra, PR (CPX)

JetBlue Logo
JetBlue

Sep 7

ORD
33h 6m
JFK
SJU

Sep 8

CPX

as low as

$361

Chicago, US (CHI) - Culebra, PR (CPX)

JetBlue Logo
JetBlue

Sep 7

ORD
20h 1m
BOS
SJU

Sep 8

CPX

as low as

$375

Chicago, US (CHI) - Culebra, PR (CPX)

JetBlue Logo
JetBlue

Sep 7

ORD
24h 14m
JFK
SJU

Sep 8

CPX

as low as

$387

Chicago, US (CHI) - Culebra, PR (CPX)

JetBlue Logo
JetBlue

Sep 7

ORD
30h
BOS
SJU

Sep 8

CPX

as low as

$426

Chicago, US (CHI) - Culebra, PR (CPX)

United Airlines Logo
United Airlines

Sep 7

ORD
6h 59m
SJU

Sep 7

CPX

as low as

$537

Chicago, US (CHI) - Culebra, PR (CPX)

United Airlines Logo
United Airlines

Sep 7

ORD
22h 51m
EWR
SJU

Sep 8

CPX

as low as

$686

Chicago, US (CHI) - Culebra, PR (CPX)

United Airlines Logo
United Airlines

Sep 7

ORD
24h 6m
EWR
SJU

Sep 8

CPX

as low as

$686

Chicago, US (CHI) - Culebra, PR (CPX)

United Airlines Logo
United Airlines

Sep 7

ORD
20h 16m
EWR
SJU

Sep 8

CPX

as low as

$687

Frequently Asked Questions

What is the cheapest and fastest flight from Chicago to Culebra?
The cheapest flight is with JetBlue for $733, 2 stops, 9h 6m. The fastest flight is with United Airlines for $1117, 1 stop, 6h 59m.
What are all possible destination arrival airports?
The possible destination arrival airport is Benjamin Rivera Noriega Airport. Layover airports include New York John F Kennedy Airport, Luis Munoz Marin International Airport, and Newark Liberty Airport.
What is the time difference between destination and arrival?
The time difference between Chicago and Culebra is typically one hour, with Culebra being one hour ahead of Chicago.
Is there a direct flight from Chicago to Culebra?
There is no direct flight from Chicago to Culebra. The available flights include a 1 stop flight with United Airlines at $1117 and a 2 stops flight with JetBlue at $733.
Are there convenient layover flights from Chicago to Culebra?
Yes, there are convenient layover flights from Chicago to Culebra. You can fly with United Airlines for $1117 (1 stop) or JetBlue for $733 (2 stops).
What are the most convenient layover airports for the flight?
The most convenient layover airports for your flight from Chicago to Culebra are New York John F Kennedy Airport, Luis Munoz Marin International Airport, and Newark Liberty Airport.
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