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Culebra

$787+ Cheap flights from Illinois to Culebra (CPX)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/13. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — CPX
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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Cheap flight deals from Illinois to Culebra

Keep the following information in mind while searching for Illinois to Culebra flight deals. Data was last updated October 30, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$787
(Kiwi.com)

Popular in

December

Cheapest in

April

Average price

$360
Provider with most accurate pricing for Chicago (CHI)-San Juan Luis Munoz Marin Intl flight deals.
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From Illinois to Culebra
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Highest demand for flights based on searches. 7% potential increase in price ($34 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 October 2025
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Find flight deals from Illinois to Culebra

Cheapest flights from Illinois to Culebra
Explore the most affordable flight options available from Illinois to Culebra. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 30, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/138:26 amORD - CPX
2 stops28h 17mMultiple Airlines
Mon 11/1712:00 pmCPX - ORD
1 stop8h 51mMultiple Airlines
Deal found 10/29$787
This United Airlines deal was found by Cheapflights users on 10/28. 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 12/289:15 pmORD - CPX
2 stops16h 58mUnited Airlines
Mon 1/510:30 amCPX - ORD
2 stops12h 45mUnited Airlines
Deal found 10/28$2,904
This United Airlines deal was found by Cheapflights users on 10/28. 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 12/278:51 amORD - CPX
2 stops29h 22mUnited Airlines
Mon 1/510:30 amCPX - ORD
2 stops12h 45mUnited Airlines
Deal found 10/28$2,944
This United Airlines deal was found by Cheapflights users on 10/28. 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 12/256:21 pmORD - CPX
2 stops19h 52mUnited Airlines
Mon 1/510:30 amCPX - ORD
2 stops12h 45mUnited Airlines
Deal found 10/28$2,950
This United Airlines deal was found by Cheapflights users on 10/28. 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 12/269:15 pmORD - CPX
2 stops16h 58mUnited Airlines
Mon 1/510:30 amCPX - ORD
2 stops12h 45mUnited Airlines
Deal found 10/28$2,979
This United Airlines deal was found by Cheapflights users on 10/27. 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 12/289:05 amORD - CPX
2 stops29h 08mUnited Airlines
Fri 1/210:30 amCPX - ORD
2 stops24h 47mUnited Airlines
Deal found 10/27$3,204
This United Airlines deal was found by Cheapflights users on 10/28. 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 12/289:15 pmORD - CPX
2 stops16h 58mUnited Airlines
Sun 1/410:30 amCPX - ORD
2 stops25h 14mUnited Airlines
Deal found 10/28$3,343
This United Airlines deal was found by Cheapflights users on 10/28. 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 12/256:21 pmORD - CPX
2 stops19h 52mUnited Airlines
Sun 1/410:30 amCPX - ORD
2 stops25h 14mUnited Airlines
Deal found 10/28$3,389
This United Airlines deal was found by Cheapflights users on 10/28. 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 12/289:15 pmORD - CPX
2 stops16h 58mUnited Airlines
Sat 1/310:30 amCPX - ORD
2 stops25h 14mUnited Airlines
Deal found 10/28$3,410
This United Airlines deal was found by Cheapflights users on 10/28. 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 12/269:15 pmORD - CPX
2 stops16h 58mUnited Airlines
Sun 1/410:30 amCPX - ORD
2 stops25h 14mUnited Airlines
Deal found 10/28$3,418
This United Airlines deal was found by Cheapflights users on 10/28. 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 12/256:21 pmORD - CPX
2 stops19h 52mUnited Airlines
Sat 1/310:30 amCPX - ORD
2 stops25h 14mUnited Airlines
Deal found 10/28$3,455
This United Airlines deal was found by Cheapflights users on 10/28. 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 12/269:15 pmORD - CPX
2 stops16h 58mUnited Airlines
Sat 1/310:30 amCPX - ORD
2 stops25h 14mUnited Airlines
Deal found 10/28$3,485

Cheapflights Fare Finder

 
Customize your flight search to find flights from Illinois 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 October 30, 2025.
Use the filters below to find and compare flights from Illinois to Culebra that are best for you.

Fly from

Illinois

Fly to

Culebra

Route

Depart

Return

Price

ChicagoCulebra

ORD - CPX

ORDCPX

Chicago O'Hare Intl

Thu 11/13

8:26 am-2:43 pm

2 stops28h 17m

Culebra

Mon 11/17

12:00 pm-6:51 pm

1 stop8h 51m

$787

ChicagoCulebra

ORD - CPX

ORDCPX

Chicago O'Hare Intl

Sun 12/28

9:15 pm-4:13 pm

2 stops16h 58m

Culebra

Mon 1/5

10:30 am-9:15 pm

2 stops12h 45m

$2,904

ChicagoCulebra

ORD - CPX

ORDCPX

Chicago O'Hare Intl

Sat 12/27

8:51 am-4:13 pm

2 stops29h 22m

Culebra

Mon 1/5

10:30 am-9:15 pm

2 stops12h 45m

$2,944

ChicagoCulebra

ORD - CPX

ORDCPX

Chicago O'Hare Intl

Thu 12/25

6:21 pm-4:13 pm

2 stops19h 52m

Culebra

Mon 1/5

10:30 am-9:15 pm

2 stops12h 45m

$2,950

ChicagoCulebra

ORD - CPX

ORDCPX

Chicago O'Hare Intl

Fri 12/26

9:15 pm-4:13 pm

2 stops16h 58m

Culebra

Mon 1/5

10:30 am-9:15 pm

2 stops12h 45m

$2,979

ChicagoCulebra

ORD - CPX

ORDCPX

Chicago O'Hare Intl

Sun 12/28

9:05 am-4:13 pm

2 stops29h 08m

Culebra

Fri 1/2

10:30 am-9:17 am

2 stops24h 47m

$3,204

ChicagoCulebra

ORD - CPX

ORDCPX

Chicago O'Hare Intl

Sun 12/28

9:15 pm-4:13 pm

2 stops16h 58m

Culebra

Sun 1/4

10:30 am-9:44 am

2 stops25h 14m

$3,343

ChicagoCulebra

ORD - CPX

ORDCPX

Chicago O'Hare Intl

Sun 12/28

9:15 pm-4:13 pm

2 stops16h 58m

Culebra

Sat 1/3

10:30 am-9:44 am

2 stops25h 14m

$3,410

ChicagoCulebra

ORD - CPX

ORDCPX

Chicago O'Hare Intl

Fri 12/26

9:15 pm-4:13 pm

2 stops16h 58m

Culebra

Sun 1/4

10:30 am-9:44 am

2 stops25h 14m

$3,418

ChicagoCulebra

ORD - CPX

ORDCPX

Chicago O'Hare Intl

Sat 12/27

9:15 pm-4:13 pm

2 stops16h 58m

Culebra

Sat 1/3

10:30 am-9:44 am

2 stops25h 14m

$3,485

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

Showing 1-10 of 11 results
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Best time to book a flight from Illinois to Culebra

Have a flexible travel schedule? Discover the best time to fly to Culebra from Illinois 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 Illinois to Culebra

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

Currently, February is the cheapest month in which you can book a flight from Illinois to Culebra (average of $127). Flying from Illinois to Culebra in December is currently the most expensive (average of $188). 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 Illinois 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 Illinois?

    Culebra (CPX) is the airport you will fly into if you book a flight from Illinois to Culebra. It is only a 0.6 mi journey from Culebra (CPX) to Culebra’s city center.

  • How long is the flight from Illinois to Culebra?

    A quick flight from Illinois to Culebra can take about 16h 58m. United Airlines provides one of the quickest options available for as low as $2,904. Airlines will cover a distance of 2105 mi.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Illinois 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 Illinois to Culebra?

    Currently, February is the cheapest month in which you can book a flight from Illinois to Culebra (average of $127). Flying from Illinois to Culebra in December is currently the most expensive (average of $188). 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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Alternative routes for Illinois to Culebra

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