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Culebra

$249+ Cheap flights from Chicago (CHI) to Culebra (CPX)

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 3/16. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — CPX
Mar 21 — Mar 281
Sat 3/21
Sat 3/28
1 adult, Economy
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Cheap flight deals from Chicago to Culebra

Cheapest flights from Chicago to Culebra
Explore the most affordable flight options available from Chicago to Culebra. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 19, 2026.

This Mytrip deal was found by Cheapflights users on 2/18. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/510:44 am
ORD
-
CPX
2 stops19h 21m
Multiple Airlines
Mon 3/93:03 pm
CPX
-
ORD
3 stops21h 19m
Multiple Airlines
Deal found 2/18$677
This Priceline deal was found by Cheapflights users on 2/18. 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 3/266:20 pm
ORD
-
CPX
2 stops17h 25m
Multiple Airlines
Mon 3/304:33 pm
CPX
-
ORD
2 stops40h 32m
Multiple Airlines
Deal found 2/18$1,188
This United Airlines deal was found by Cheapflights users on 2/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/158:49 am
ORD
-
CPX
1 stop7h 32m
United Airlines
Sat 8/2210:48 am
CPX
-
ORD
2 stops12h 48m
United Airlines
Deal found 2/15$1,558
This United Airlines deal was found by Cheapflights users on 2/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/218:55 am
ORD
-
CPX
1 stop6h 26m
United Airlines
Tue 12/2910:48 am
CPX
-
ORD
2 stops26h 54m
United Airlines
Deal found 2/16$1,696
This United Airlines deal was found by Cheapflights users on 2/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/215:00 am
ORD
-
CPX
2 stops10h 21m
United Airlines
Wed 12/2310:48 am
CPX
-
ORD
2 stops12h 59m
United Airlines
Deal found 2/16$1,727
This United Airlines deal was found by Cheapflights users on 2/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/216:00 pm
ORD
-
CPX
3 stops21h 21m
United Airlines
Fri 12/2510:48 am
CPX
-
ORD
2 stops12h 12m
United Airlines
Deal found 2/16$1,808
This United Airlines deal was found by Cheapflights users on 2/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/178:55 am
ORD
-
CPX
1 stop6h 26m
United Airlines
Tue 12/2910:48 am
CPX
-
ORD
2 stops24h 55m
United Airlines
Deal found 2/16$1,865
This United Airlines deal was found by Cheapflights users on 2/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/239:15 pm
ORD
-
CPX
2 stops18h 06m
United Airlines
Fri 12/2510:48 am
CPX
-
ORD
2 stops12h 12m
United Airlines
Deal found 2/16$1,871
This United Airlines deal was found by Cheapflights users on 2/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/99:18 pm
ORD
-
CPX
2 stops17h 55m
United Airlines
Sun 4/1210:30 am
CPX
-
ORD
2 stops15h 56m
United Airlines
Deal found 2/15$1,877

Find flight deals from Chicago to Culebra

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Culebra (CPX). 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 19, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$677
(Mytrip)

One-way from

$249
(Kiwi.com)

Popular in

December

Cheapest in

April

Average price

$392
Provider with most accurate pricing for Chicago (CHI)-San Juan Luis Munoz Marin Intl flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-San Juan Luis Munoz Marin Intl flights.
Search Deals
From Chicago (CHI) to Culebra
Search Deals
One-way flight from Chicago (CHI) to Culebra
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($49 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($14 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Culebra 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 19, 2026.
Use the filters below to find and compare flights from Chicago to Culebra that are best for you.

Fly from

Chicago

Fly to

Culebra

Route

Depart

Return

Price

ChicagoCulebra

ORD - CPX

ORDCPX

Chicago O'Hare Intl

Thu 3/5

10:44 am-8:05 am

2 stops19h 21m

Culebra

Mon 3/9

3:03 pm-11:22 am

3 stops21h 19m

$677

ChicagoCulebra

ORD - CPX

ORDCPX

Chicago O'Hare Intl

Thu 3/26

6:20 pm-12:45 pm

2 stops17h 25m

Culebra

Mon 3/30

4:33 pm-8:05 am

2 stops40h 32m

$1,188

ChicagoCulebra

ORD - CPX

ORDCPX

Chicago O'Hare Intl

Mon 8/17

6:30 am-5:21 pm

2 stops9h 51m

Culebra

Sun 8/23

10:48 am-10:36 pm

2 stops12h 48m

$1,558

ChicagoCulebra

ORD - CPX

ORDCPX

Chicago O'Hare Intl

Mon 8/17

5:00 am-5:21 pm

2 stops11h 21m

Culebra

Wed 8/19

10:48 am-9:54 pm

2 stops12h 06m

$1,558

ChicagoCulebra

ORD - CPX

ORDCPX

Chicago O'Hare Intl

Tue 8/18

5:30 am-5:21 pm

2 stops10h 51m

Culebra

Wed 8/19

10:48 am-9:00 pm

2 stops11h 12m

$1,558

ChicagoCulebra

ORD - CPX

ORDCPX

Chicago O'Hare Intl

Sat 8/15

5:00 am-5:21 pm

2 stops11h 21m

Culebra

Fri 8/21

10:48 am-9:00 pm

2 stops11h 12m

$1,558

ChicagoCulebra

ORD - CPX

ORDCPX

Chicago O'Hare Intl

Tue 8/18

8:52 am-5:21 pm

1 stop7h 29m

Culebra

Sat 8/22

10:48 am-9:54 pm

2 stops12h 06m

$1,558

ChicagoCulebra

ORD - CPX

ORDCPX

Chicago O'Hare Intl

Mon 3/16

8:56 pm-8:05 am

1 stop10h 09m

$249

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/18

Best time to book a flight from Chicago to Culebra

Have a flexible travel schedule? Discover the best time to fly to Culebra from Chicago with our price prediction graph.
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 Culebra

What is the cheapest month to book a flight from Chicago to Culebra?

Currently, April is the cheapest month in which you can book a flight from Chicago to Culebra (average of $91). Flying from Chicago to Culebra 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.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Culebra. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Culebra from Chicago?

    For a flight from Chicago to Culebra, you will be flying into Culebra. Culebra (CPX) is just 0.6 mi from the center of the city. Culebra is the only Culebra airport and it handles 0 inbound flights from Chicago per day. 0 airlines have flights to Culebra from Chicago on a regular basis.

  • How long is the flight from Chicago to Culebra?

    United Airlines can get you from Chicago to Culebra in just under 9h 51m. Your travel time can differ by up to . The distance from Chicago to Culebra is about 2105 mi.

  • Can I find deals for flights from Chicago to Culebra that include hotel bookings?

    Yes. In addition to deals on Chicago to Culebra flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Culebra?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Culebra.

  • Can I find deals for business class flights from Chicago to Culebra?

    Yes. Cheapflights offers flight deals from Chicago to Culebra by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Culebra?

    Currently, April is the cheapest month in which you can book a flight from Chicago to Culebra (average of $91). Flying from Chicago to Culebra 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.

See more FAQs

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