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Cheap flights from Chicago O'Hare Intl Airport to San Juan from $899

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago O'Hare Intl Airport to San Juan departing on 12/26. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Chicago O'Hare Intl Airport to San Juan

Cheap round-trip flights

Enter your travel dates to find the best prices.
United Airlines Logo
8:54 am - 4:13 pmORD-CPX
29h 19m2 stops
United Airlines Logo
10:30 am - 2:28 pmCPX-ORD
29h 58m2 stops
$1,295United Airlines
Find Deal
Wed, Dec 31 - Mon, Jan 5
United Airlines Logo
4:00 pm - 4:13 pmORD-CPX
46h 13m2 stops
United Airlines Logo
10:30 am - 2:25 pmCPX-ORD
29h 55m2 stops
$1,632United Airlines
Find Deal
Thu, Jan 1 - Mon, Jan 5
United Airlines Logo
9:15 pm - 4:13 pmORD-CPX
16h 58m2 stops
United Airlines Logo
10:30 am - 9:15 pmCPX-ORD
12h 45m2 stops
$2,429United Airlines
Find Deal
Sat, Dec 20 - Mon, Jan 5
United Airlines Logo
9:23 pm - 4:13 pmORD-CPX
40h 50m2 stops
United Airlines Logo
10:30 am - 9:15 pmCPX-ORD
12h 45m2 stops
$2,442United Airlines
Find Deal
Fri, Dec 19 - Mon, Jan 5
United Airlines Logo
9:15 pm - 4:13 pmORD-CPX
16h 58m2 stops
United Airlines Logo
10:30 am - 2:20 pmCPX-ORD
29h 50m2 stops
$2,895United Airlines
Find Deal
Sat, Dec 20 - Sat, Jan 3
United Airlines Logo
9:23 pm - 4:13 pmORD-CPX
40h 50m2 stops
United Airlines Logo
10:30 am - 2:20 pmCPX-ORD
29h 50m2 stops
$2,908United Airlines
Find Deal
Fri, Dec 19 - Sat, Jan 3
United Airlines Logo
9:15 pm - 4:13 pmORD-CPX
16h 58m2 stops
United Airlines Logo
10:30 am - 11:59 pmCPX-ORD
15h 29m2 stops
$2,972United Airlines
Find Deal
Sat, Dec 20 - Sun, Jan 4
United Airlines Logo
9:15 pm - 4:13 pmORD-CPX
16h 58m2 stops
United Airlines Logo
10:30 am - 9:15 pmCPX-ORD
12h 45m2 stops
$2,979United Airlines
Find Deal
Sun, Dec 21 - Mon, Jan 5
United Airlines Logo
9:23 pm - 4:13 pmORD-CPX
40h 50m2 stops
United Airlines Logo
10:30 am - 11:59 pmCPX-ORD
15h 29m2 stops
$2,984United Airlines
Find Deal
Fri, Dec 19 - Sun, Jan 4
United Airlines Logo
9:23 pm - 4:13 pmORD-CPX
40h 50m2 stops
United Airlines Logo
10:30 am - 4:37 amCPX-ORD
20h 07m3 stops
$3,064United Airlines
Find Deal
Fri, Dec 19 - Mon, Jan 5

United Airlines flights from Chicago O'Hare Intl Airport to Culebra

Our best United Airlines deals on Chicago O'Hare Intl Airport to Culebra flight tickets
United Airlines
Dec 31
ORD8:54 amChicago O'Hare Intl
29h 19m
2 stops
CPX4:13 pmCulebra
Jan 5
CPX10:30 amCulebra
29h 58m
2 stops
ORD2:28 pmChicago O'Hare Intl
$1,295
Find similar
United Airlines
Jan 1
ORD4:00 pmChicago O'Hare Intl
46h 13m
2 stops
CPX4:13 pmCulebra
Jan 5
CPX10:30 amCulebra
29h 55m
2 stops
ORD2:25 pmChicago O'Hare Intl
$1,632
Find similar
United Airlines
Dec 20
ORD9:15 pmChicago O'Hare Intl
16h 58m
2 stops
CPX4:13 pmCulebra
Jan 5
CPX10:30 amCulebra
12h 45m
2 stops
ORD9:15 pmChicago O'Hare Intl
$2,429
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago O'Hare Intl Airport 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, momondo users made 832,500 searches. Data last updated November 3, 2025.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Culebra that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoCulebra

ORD - CPX

ORDCPX

Chicago O'Hare Intl

Wed 12/31

8:54 am-4:13 pm

2 stops29h 19m

Culebra

Mon 1/5

10:30 am-2:28 pm

2 stops29h 58m

$1,295

ChicagoCulebra

ORD - CPX

ORDCPX

Chicago O'Hare Intl

Thu 1/1

4:00 pm-4:13 pm

2 stops46h 13m

Culebra

Mon 1/5

10:30 am-2:25 pm

2 stops29h 55m

$1,632

ChicagoCulebra

ORD - CPX

ORDCPX

Chicago O'Hare Intl

Sat 12/20

9:15 pm-4:13 pm

2 stops16h 58m

Culebra

Mon 1/5

10:30 am-9:15 pm

2 stops12h 45m

$2,429

ChicagoCulebra

ORD - CPX

ORDCPX

Chicago O'Hare Intl

Fri 12/19

9:23 pm-4:13 pm

2 stops40h 50m

Culebra

Mon 1/5

10:30 am-9:15 pm

2 stops12h 45m

$2,442

ChicagoCulebra

ORD - CPX

ORDCPX

Chicago O'Hare Intl

Sat 12/20

9:15 pm-4:13 pm

2 stops16h 58m

Culebra

Sat 1/3

10:30 am-2:20 pm

2 stops29h 50m

$2,895

ChicagoCulebra

ORD - CPX

ORDCPX

Chicago O'Hare Intl

Fri 12/19

9:23 pm-4:13 pm

2 stops40h 50m

Culebra

Sat 1/3

10:30 am-2:20 pm

2 stops29h 50m

$2,908

ChicagoCulebra

ORD - CPX

ORDCPX

Chicago O'Hare Intl

Sat 12/20

9:15 pm-4:13 pm

2 stops16h 58m

Culebra

Sun 1/4

10:30 am-11:59 pm

2 stops15h 29m

$2,972

ChicagoCulebra

ORD - CPX

ORDCPX

Chicago O'Hare Intl

Sun 12/21

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

Fri 12/19

9:23 pm-4:13 pm

2 stops40h 50m

Culebra

Sun 1/4

10:30 am-11:59 pm

2 stops15h 29m

$2,984

ChicagoCulebra

ORD - CPX

ORDCPX

Chicago O'Hare Intl

Fri 12/19

9:23 pm-4:13 pm

2 stops40h 50m

Culebra

Mon 1/5

10:30 am-4:37 am

3 stops20h 07m

$3,064

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 11 resultsSorted by cheapest first
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See travel insights to San Juan from

How to get the cheapest flight ticket from Chicago O'Hare Intl Airport to Culebra

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest airline that flies from Chicago O'Hare Intl to Culebra?

United Airlines is the most popular carrier operating from Chicago O'Hare Intl to Culebra

What airlines fly to Culebra?

Spirit Airlines, United Airlines and American Airlines are the top three most popular airlines that fly to Culebra from Chicago O'Hare Intl Airport according to our data. Spirit Airlines is the first choice among our users, with 49% of people opting to fly with this airline when traveling to Culebra. Keep in mind that there are 7 different airlines that fly to Culebra on a routine basis, so you have a few additional options to choose from.

When to book flights from Chicago O'Hare Intl Airport to Culebra

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago O'Hare Intl Airport to Culebra according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago O'Hare Intl Airport to Culebra (ORD to CPX) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago O'Hare Intl Airport to Culebra

Direct flights

None
There are no direct flights from Chicago O'Hare Intl Airport to Culebra. There are no popular flight routes from Chicago O'Hare Intl Airport to Culebra.
Search flight deals

  • How far is Chicago O'Hare Intl to Culebra by plane?

    The straight-line distance from Chicago O'Hare Intl to Culebra is 2106.0 mi. 16h 58m is a normal flight duration for this route.

  • When did momondo last update prices for flights from Chicago O'Hare Intl Airport to Culebra Airport?

    Prices for flights from Chicago O'Hare Intl Airport to Culebra Airport are updated daily.

  • How old do you have to be to fly from Chicago O'Hare Intl Airport to Culebra Airport?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago O'Hare Intl Airport to Culebra Airport.

  • What documentation or ID do you need to fly to Culebra Airport?

    The travel and health documents you'll need for your trip to Culebra Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Culebra Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Culebra?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Culebra from Chicago.

Can I find flights from Chicago to Culebra with flexible booking policies on momondo?

Flights from Chicago to Culebra with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Chicago to Culebra?

Once all potential Chicago to Culebra flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Chicago to Culebra right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Chicago to Culebra now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Culebra and let you know when they change.

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