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Culebra

$922+ 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 4/4. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — CPX
Jan 25 — Feb 11
Sun 1/25
Sun 2/1
1 adult, Economy
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Cheap flight deals from Chicago to Culebra

Best flights from Chicago to Culebra
Discover carefully curated flight deals from Chicago to Culebra that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated December 26, 2025.

This United Airlines deal was found by Cheapflights users on 12/24. 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 3/198:55 amORD - CPX
1 stop6h 18mUnited Airlines
Wed 3/2510:30 amCPX - ORD
2 stops13h 43mUnited Airlines
Deal found 12/24$1,726
This United Airlines deal was found by Cheapflights users on 12/25. 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.
Sun 3/158:55 amORD - CPX
1 stop6h 18mUnited Airlines
Fri 3/2010:30 amCPX - ORD
2 stops29h 03mUnited Airlines
Deal found 12/25$1,795
This United Airlines deal was found by Cheapflights users on 12/25. 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 3/149:32 pmORD - CPX
2 stops17h 41mUnited Airlines
Fri 3/2010:30 amCPX - ORD
2 stops33h 20mUnited Airlines
Deal found 12/25$1,905
This United Airlines deal was found by Cheapflights users on 12/24. 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.
Fri 3/208:55 amORD - CPX
1 stop6h 18mUnited Airlines
Wed 3/2510:30 amCPX - ORD
2 stops13h 43mUnited Airlines
Deal found 12/24$2,129

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 December 26, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$1,471
(United Airlines)

One-way from

$922
(United Airlines)

Popular in

December

Cheapest in

January

Average price

$565
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.
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From Chicago (CHI) to Culebra
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One-way flight from Chicago (CHI) to Culebra
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Highest demand for flights based on searches. 10% potential increase in price ($46 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($15 potential savings vs. average RT price).
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Average for round-trip flights in December 2025
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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 December 26, 2025.
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 3/19

8:55 am-4:13 pm

1 stop6h 18m

Culebra

Wed 3/25

10:30 am-11:13 pm

2 stops13h 43m

$1,726

ChicagoCulebra

ORD - CPX

ORDCPX

Chicago O'Hare Intl

Sun 3/15

8:55 am-4:13 pm

1 stop6h 18m

Culebra

Fri 3/20

10:30 am-2:33 pm

2 stops29h 03m

$1,795

ChicagoCulebra

ORD - CPX

ORDCPX

Chicago O'Hare Intl

Sat 3/14

9:32 pm-4:13 pm

2 stops17h 41m

Culebra

Fri 3/20

10:30 am-6:50 pm

2 stops33h 20m

$1,905

ChicagoCulebra

ORD - CPX

ORDCPX

Chicago O'Hare Intl

Fri 3/20

8:55 am-4:13 pm

1 stop6h 18m

Culebra

Wed 3/25

10:30 am-11:13 pm

2 stops13h 43m

$2,129

ChicagoCulebra

ORD - CPX

ORDCPX

Chicago O'Hare Intl

Sat 4/4

6:01 pm-4:13 pm

2 stops21h 12m

$922

ChicagoCulebra

ORD - CPX

ORDCPX

Chicago O'Hare Intl

Sun 4/5

6:01 pm-4:13 pm

2 stops21h 12m

$929

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/26

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, September is the cheapest month in which you can book a flight from Chicago to Culebra (average of $127). Flying from Chicago to Culebra in December is currently the most expensive (average of $220). 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 6h 18m. 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, September is the cheapest month in which you can book a flight from Chicago to Culebra (average of $127). Flying from Chicago to Culebra in December is currently the most expensive (average of $220). 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.

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