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$577+ Cheap flights from Chicago (CHI) 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 10/1. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — CPX
Okt 17 — Okt 241
Fr 10/17
Fr 10/24
1 adult, Economy
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Cheap 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 September 17, 2025.

Round-trip from

$577
(Mytrip)

Popular in

December

Cheapest in

October

Average price

$380
From Chicago (CHI) to Culebra
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($35 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2025
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Find 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 September 17, 2025.

This Mytrip deal was found by Cheapflights users on 9/16. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mi 10/16:30 amORD - CPX
2 stops9h 21mMultiple Airlines
So 10/58:20 amCPX - ORD
2 stops16h 25mMultiple Airlines
Deal found 9/16$577
This United Airlines deal was found by Cheapflights users on 9/16. 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.
Mi 10/18:52 amORD - CPX
1 stop6h 59mUnited Airlines
So 10/510:13 amCPX - ORD
1 stop10h 50mUnited Airlines
Deal found 9/16$1,166
This Expedia deal was found by Cheapflights users on 9/16. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sa 11/228:45 pmORD - CPX
2 stops14h 00mJetBlue
Sa 11/298:25 amCPX - ORD
2 stops16h 25mJetBlue
Deal found 9/16$1,341
This United deal was found by Cheapflights users on 9/16. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sa 11/222:20 pmORD - CPX
1 stop15h 45mMultiple Airlines
Sa 11/298:25 amCPX - ORD
1 stop29h 07mMultiple Airlines
Deal found 9/16$1,376

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 September 17, 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

Mi 10/1

6:30 am-4:51 pm

2 stops9h 21m

Culebra

So 10/5

8:20 am-11:45 pm

2 stops16h 25m

$577

ChicagoCulebra

ORD - CPX

ORDCPX

Chicago O'Hare Intl

Mi 10/1

8:52 am-4:51 pm

1 stop6h 59m

Culebra

So 10/5

10:13 am-8:03 pm

1 stop10h 50m

$1,166

ChicagoCulebra

ORD - CPX

ORDCPX

Chicago O'Hare Intl

Sa 11/22

8:45 pm-12:45 pm

2 stops14h 00m

Culebra

Sa 11/29

8:25 am-10:50 pm

2 stops16h 25m

$1,341

ChicagoCulebra

ORD - CPX

ORDCPX

Chicago O'Hare Intl

Sa 11/22

2:20 pm-8:05 am

1 stop15h 45m

Culebra

Sa 11/29

8:25 am-11:32 am

1 stop29h 07m

$1,376

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

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
No data available for this route at this time. Please check back soon.

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 59m. 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.

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