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Cheap flights from Chicago O'Hare Intl Airport to San Juan from $577

This is the cheapest round-trip 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 10/1. 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

Multiple Airlines Logo
6:30 am - 4:51 pmORD-CPX
9h 21m2 stops
Multiple Airlines Logo
8:20 am - 11:45 pmCPX-ORD
16h 25m2 stops
$577Multiple Airlines
Find Deal
Wed, Oct 1 - Sun, Oct 5
Multiple Airlines Logo
6:30 am - 4:51 pmORD-CPX
9h 21m2 stops
Multiple Airlines Logo
5:11 pm - 8:03 pmCPX-ORD
27h 52m3 stops
$629Multiple Airlines
Find Deal
Wed, Oct 1 - Sun, Oct 5
Multiple Airlines Logo
6:30 am - 12:50 pmORD-CPX
29h 20m3 stops
Multiple Airlines Logo
5:11 pm - 3:49 pmCPX-ORD
23h 38m3 stops
$700Multiple Airlines
Find Deal
Wed, Oct 1 - Sun, Oct 5
United Airlines Logo
8:52 am - 4:51 pmORD-CPX
6h 59m1 stop
United Airlines Logo
10:13 am - 8:03 pmCPX-ORD
10h 50m1 stop
$1,166United Airlines
Find Deal
Wed, Oct 1 - Sun, Oct 5
United Airlines Logo
8:52 am - 4:51 pmORD-CPX
6h 59m1 stop
United Airlines Logo
10:13 am - 9:41 amCPX-ORD
24h 28m2 stops
$1,196United Airlines
Find Deal
Wed, Oct 1 - Sun, Oct 5
JetBlue Logo
8:45 pm - 12:45 pmORD-CPX
14h 00m2 stops
JetBlue Logo
8:25 am - 10:50 pmCPX-ORD
16h 25m2 stops
$1,341JetBlue
Find Deal
Sat, Nov 22 - Sat, Nov 29
Multiple Airlines Logo
2:20 pm - 8:05 amORD-CPX
15h 45m1 stop
Multiple Airlines Logo
8:25 am - 11:32 amCPX-ORD
29h 07m1 stop
$1,376Multiple Airlines
Find Deal
Sat, Nov 22 - Sat, Nov 29
Multiple Airlines Logo
3:07 pm - 12:45 pmORD-CPX
19h 38m2 stops
Multiple Airlines Logo
8:25 am - 8:20 pmCPX-ORD
13h 55m1 stop
$1,380Multiple Airlines
Find Deal
Sat, Nov 22 - Sat, Nov 29

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
Oct 1
ORD8:52 amChicago O'Hare Intl
6h 59m
1 stop
CPX4:51 pmCulebra
Oct 5
CPX10:13 amCulebra
10h 50m
1 stop
ORD8:03 pmChicago O'Hare Intl
$1,166
Find similar
United Airlines
Oct 1
ORD8:52 amChicago O'Hare Intl
6h 59m
1 stop
CPX4:51 pmCulebra
Oct 5
CPX10:13 amCulebra
24h 28m
2 stops
ORD9:41 amChicago O'Hare Intl
$1,196
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 September 17, 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 10/1

6:30 am-4:51 pm

2 stops9h 21m

Culebra

Sun 10/5

8:20 am-11:45 pm

2 stops16h 25m

$577

ChicagoCulebra

ORD - CPX

ORDCPX

Chicago O'Hare Intl

Wed 10/1

6:30 am-4:51 pm

2 stops9h 21m

Culebra

Sun 10/5

5:11 pm-8:03 pm

3 stops27h 52m

$629

ChicagoCulebra

ORD - CPX

ORDCPX

Chicago O'Hare Intl

Wed 10/1

6:30 am-12:50 pm

3 stops29h 20m

Culebra

Sun 10/5

5:11 pm-3:49 pm

3 stops23h 38m

$700

ChicagoCulebra

ORD - CPX

ORDCPX

Chicago O'Hare Intl

Wed 10/1

8:52 am-4:51 pm

1 stop6h 59m

Culebra

Sun 10/5

10:13 am-8:03 pm

1 stop10h 50m

$1,166

ChicagoCulebra

ORD - CPX

ORDCPX

Chicago O'Hare Intl

Wed 10/1

8:52 am-4:51 pm

1 stop6h 59m

Culebra

Sun 10/5

10:13 am-9:41 am

2 stops24h 28m

$1,196

ChicagoCulebra

ORD - CPX

ORDCPX

Chicago O'Hare Intl

Sat 11/22

8:45 pm-12:45 pm

2 stops14h 00m

Culebra

Sat 11/29

8:25 am-10:50 pm

2 stops16h 25m

$1,341

ChicagoCulebra

ORD - CPX

ORDCPX

Chicago O'Hare Intl

Sat 11/22

2:20 pm-8:05 am

1 stop15h 45m

Culebra

Sat 11/29

8:25 am-11:32 am

1 stop29h 07m

$1,376

ChicagoCulebra

ORD - CPX

ORDCPX

Chicago O'Hare Intl

Sat 11/22

3:07 pm-12:45 pm

2 stops19h 38m

Culebra

Sat 11/29

8:25 am-8:20 pm

1 stop13h 55m

$1,380

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

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 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 50% 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.
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  • 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. 6h 59m 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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