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Cheap flights from Chicago to San Juan from $278

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 to San Juan departing on 4/15. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
2:09 pm - 8:05 am
ORD
-
CPX
16h 56m
2 stops
Multiple Airlines Logo
8:25 am - 8:49 pm
CPX
-
ORD
13h 24m
1 stop
$625Multiple Airlines
Fri, Apr 24 - Mon, Apr 27
Multiple Airlines Logo
7:50 am - 8:05 am
ORD
-
CPX
23h 15m
2 stops
Multiple Airlines Logo
4:33 pm - 10:23 am
CPX
-
ORD
18h 50m
3 stops
$650Multiple Airlines
Fri, Apr 24 - Mon, Apr 27
Multiple Airlines Logo
7:50 am - 10:10 am
ORD
-
CPX
25h 20m
2 stops
Multiple Airlines Logo
3:03 pm - 1:00 pm
CPX
-
ORD
22h 57m
2 stops
$657Multiple Airlines
Fri, Apr 24 - Mon, Apr 27
Multiple Airlines Logo
9:00 am - 12:45 pm
ORD
-
CPX
26h 45m
3 stops
Multiple Airlines Logo
4:33 pm - 10:23 am
CPX
-
ORD
18h 50m
3 stops
$672Multiple Airlines
Fri, Apr 24 - Mon, Apr 27
Multiple Airlines Logo
10:00 am - 8:05 am
ORD
-
CPX
21h 05m
1 stop
Multiple Airlines Logo
8:25 am - 8:49 pm
CPX
-
ORD
13h 24m
1 stop
$865Multiple Airlines
Fri, Apr 24 - Mon, Apr 27
JetBlue Logo
6:00 am - 5:21 pm
ORD
-
CPX
10h 21m
2 stops
JetBlue Logo
5:41 pm - 9:56 am
CPX
-
ORD
17h 15m
2 stops
$1,032JetBlue
Wed, Jun 10 - Sun, Jun 14
United Airlines Logo
5:00 am - 5:21 pm
ORD
-
CPX
11h 21m
2 stops
United Airlines Logo
10:48 am - 9:00 pm
CPX
-
ORD
11h 12m
2 stops
$1,558United Airlines
Wed, Jun 3 - Tue, Jun 9
United Airlines Logo
5:00 am - 4:13 pm
ORD
-
CPX
10h 13m
2 stops
United Airlines Logo
10:30 am - 9:37 am
CPX
-
ORD
24h 07m
2 stops
$1,668United Airlines
Sun, Apr 12 - Sun, Apr 19
United Airlines Logo
8:49 am - 5:21 pm
ORD
-
CPX
7h 32m
1 stop
United Airlines Logo
10:48 am - 9:42 am
CPX
-
ORD
23h 54m
2 stops
$1,681United Airlines
Wed, Jun 10 - Sun, Jun 14
United Airlines Logo
9:35 pm - 4:13 pm
ORD
-
CPX
17h 38m
2 stops
United Airlines Logo
10:30 am - 8:37 pm
CPX
-
ORD
11h 07m
2 stops
$1,684United Airlines
Wed, Apr 15 - Wed, Apr 22

United Airlines flights from Chicago to Culebra

Our best United Airlines deals on Chicago to Culebra flight tickets
United Airlines
Jun 3
ORD8:49 amChicago O'Hare Intl
7h 32m
1 stop
CPX5:21 pmCulebra
Jun 10
CPX10:48 amCulebra
14h 57m
2 stops
ORD12:45 amChicago O'Hare Intl
$1,558
United Airlines
Apr 12
ORD5:00 amChicago O'Hare Intl
10h 13m
2 stops
CPX4:13 pmCulebra
Apr 19
CPX10:30 amCulebra
24h 07m
2 stops
ORD9:37 amChicago O'Hare Intl
$1,668
United Airlines
Jun 10
ORD8:49 amChicago O'Hare Intl
7h 32m
1 stop
CPX5:21 pmCulebra
Jun 14
CPX10:48 amCulebra
23h 54m
2 stops
ORD9:42 amChicago O'Hare Intl
$1,681

momondo 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, momondo users made 832,500 searches. Data last updated March 4, 2026.
Use the filters below to find and compare flights from Chicago to Culebra that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoCulebra

ORD - CPX

ORDCPX

Chicago O'Hare Intl

Fri 4/24

2:09 pm-8:05 am

2 stops16h 56m

Culebra

Mon 4/27

8:25 am-8:49 pm

1 stop13h 24m

$625

ChicagoCulebra

ORD - CPX

ORDCPX

Chicago O'Hare Intl

Fri 4/24

7:50 am-8:05 am

2 stops23h 15m

Culebra

Mon 4/27

4:33 pm-10:23 am

3 stops18h 50m

$650

ChicagoCulebra

ORD - CPX

ORDCPX

Chicago O'Hare Intl

Fri 4/24

7:50 am-10:10 am

2 stops25h 20m

Culebra

Mon 4/27

3:03 pm-1:00 pm

2 stops22h 57m

$657

ChicagoCulebra

ORD - CPX

ORDCPX

Chicago O'Hare Intl

Fri 4/24

9:00 am-12:45 pm

3 stops26h 45m

Culebra

Mon 4/27

4:33 pm-10:23 am

3 stops18h 50m

$672

ChicagoCulebra

ORD - CPX

ORDCPX

Chicago O'Hare Intl

Fri 4/24

10:00 am-8:05 am

1 stop21h 05m

Culebra

Mon 4/27

8:25 am-8:49 pm

1 stop13h 24m

$865

ChicagoCulebra

ORD - CPX

ORDCPX

Chicago O'Hare Intl

Wed 6/10

6:00 am-5:21 pm

2 stops10h 21m

Culebra

Sun 6/14

5:41 pm-9:56 am

2 stops17h 15m

$1,032

ChicagoCulebra

ORD - CPX

ORDCPX

Chicago O'Hare Intl

Wed 6/3

5:00 am-5:21 pm

2 stops11h 21m

Culebra

Tue 6/9

10:48 am-9:00 pm

2 stops11h 12m

$1,558

ChicagoCulebra

ORD - CPX

ORDCPX

Chicago O'Hare Intl

Sun 4/12

5:00 am-4:13 pm

2 stops10h 13m

Culebra

Sun 4/19

10:30 am-9:37 am

2 stops24h 07m

$1,668

ChicagoCulebra

ORD - CPX

ORDCPX

Chicago O'Hare Intl

Wed 6/10

8:49 am-5:21 pm

1 stop7h 32m

Culebra

Sun 6/14

10:48 am-9:42 am

2 stops23h 54m

$1,681

ChicagoCulebra

ORD - CPX

ORDCPX

Chicago O'Hare Intl

Wed 4/15

9:35 pm-4:13 pm

2 stops17h 38m

Culebra

Wed 4/22

10:30 am-8:37 pm

2 stops11h 07m

$1,684

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 13 resultsSorted by cheapest first
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See travel insights to San Juan from

How to get the cheapest flight ticket from Chicago 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 according to our data. Spirit Airlines is the first choice among our users, with 45% 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 to Culebra

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

Cheap Chicago to Culebra (CHI to CPX) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Culebra

Fastest flight time

10h 21m

Direct flights

None
The fastest flight from Chicago to Culebra takes 10h 21m
There are no direct flights from Chicago to Culebra. There are no popular flight routes from Chicago to Culebra.
Search flight deals

  • How far is Chicago to Culebra by plane?

    A flight from Chicago to Culebra will travel around 2090.8 mi. Flights usually cover this in 10h 21m, depending on flying conditions and air traffic around both airports.

  • When did momondo last update prices for flights from Chicago to Culebra Airport?

    Prices for flights from Chicago to Culebra Airport are updated daily.

  • How old do you have to be to fly from Chicago to Culebra Airport?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Culebra Airport.

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

    The necessary travel and health documents for your Culebra Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking 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?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Chicago to Culebra. Millions of users trust and use momondo every year so you are in good hands.

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

Yes. momondo enables you to select and highlight flights to Culebra from Chicago with this policy.

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

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Culebra from Chicago.

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

Yes momondo offers price alerts on flights to Culebra from Chicago. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

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