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Cheap flights from Chicago to San Juan from $289

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 2/15. 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
12:17 pm - 1:28 pm
ORD
-
CPX
23h 11m
1 stop
Multiple Airlines Logo
3:03 pm - 6:16 pm
CPX
-
ORD
29h 13m
2 stops
$613Multiple Airlines
Mon, Feb 2 - Fri, Feb 6
Multiple Airlines Logo
5:05 am - 2:43 pm
ORD
-
CPX
31h 38m
2 stops
Multiple Airlines Logo
3:03 pm - 3:48 pm
CPX
-
ORD
26h 45m
1 stop
$631Multiple Airlines
Sat, Feb 21 - Thu, Feb 26
Multiple Airlines Logo
12:44 pm - 10:53 am
ORD
-
CPX
20h 09m
2 stops
Multiple Airlines Logo
3:03 pm - 6:16 pm
CPX
-
ORD
29h 13m
3 stops
$706Multiple Airlines
Mon, Feb 2 - Fri, Feb 6
Multiple Airlines Logo
3:22 pm - 1:28 pm
ORD
-
CPX
20h 06m
3 stops
Multiple Airlines Logo
3:03 pm - 6:16 pm
CPX
-
ORD
29h 13m
3 stops
$731Multiple Airlines
Mon, Feb 2 - Fri, Feb 6
Multiple Airlines Logo
12:17 pm - 1:28 pm
ORD
-
CPX
23h 11m
1 stop
Multiple Airlines Logo
3:03 pm - 4:37 pm
CPX
-
ORD
27h 34m
1 stop
$758Multiple Airlines
Mon, Feb 2 - Fri, Feb 6
Multiple Airlines Logo
12:17 pm - 2:43 pm
ORD
-
CPX
24h 26m
1 stop
Multiple Airlines Logo
3:03 pm - 3:48 pm
CPX
-
ORD
26h 45m
1 stop
$819Multiple Airlines
Sat, Feb 21 - Thu, Feb 26
United Airlines Logo
9:20 pm - 4:13 pm
ORD
-
CPX
17h 53m
2 stops
United Airlines Logo
10:30 am - 11:15 pm
CPX
-
ORD
13h 45m
2 stops
$1,691United Airlines
Sat, May 2 - Sat, May 9
United Airlines Logo
9:20 pm - 4:13 pm
ORD
-
CPX
17h 53m
2 stops
United Airlines Logo
10:30 am - 9:38 pm
CPX
-
ORD
12h 08m
2 stops
$1,708United Airlines
Fri, May 1 - Sat, May 9
United Airlines Logo
8:55 am - 4:13 pm
ORD
-
CPX
6h 18m
1 stop
United Airlines Logo
10:30 am - 12:45 am
CPX
-
ORD
15h 15m
2 stops
$1,727United Airlines
Thu, Mar 26 - Fri, Apr 3
United Airlines Logo
5:45 pm - 4:13 pm
ORD
-
CPX
21h 28m
2 stops
United Airlines Logo
10:30 am - 9:00 am
CPX
-
ORD
23h 30m
2 stops
$1,841United Airlines
Wed, Mar 25 - Sun, Apr 5

United Airlines flights from Chicago to Culebra

Our best United Airlines deals on Chicago to Culebra flight tickets
United Airlines
May 2
ORD9:20 pmChicago O'Hare Intl
17h 53m
2 stops
CPX4:13 pmCulebra
May 9
CPX10:30 amCulebra
13h 45m
2 stops
ORD11:15 pmChicago O'Hare Intl
$1,691
United Airlines
May 1
ORD9:20 pmChicago O'Hare Intl
17h 53m
2 stops
CPX4:13 pmCulebra
May 10
CPX10:30 amCulebra
13h 45m
2 stops
ORD11:15 pmChicago O'Hare Intl
$1,708
United Airlines
Mar 26
ORD8:55 amChicago O'Hare Intl
6h 18m
1 stop
CPX4:13 pmCulebra
Apr 3
CPX10:30 amCulebra
15h 15m
2 stops
ORD12:45 amChicago O'Hare Intl
$1,727

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 January 20, 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

Mon 2/2

12:17 pm-1:28 pm

1 stop23h 11m

Culebra

Fri 2/6

3:03 pm-6:16 pm

2 stops29h 13m

$613

ChicagoCulebra

ORD - CPX

ORDCPX

Chicago O'Hare Intl

Sat 2/21

5:05 am-2:43 pm

2 stops31h 38m

Culebra

Thu 2/26

3:03 pm-3:48 pm

1 stop26h 45m

$631

ChicagoCulebra

ORD - CPX

ORDCPX

Chicago O'Hare Intl

Mon 2/2

12:44 pm-10:53 am

2 stops20h 09m

Culebra

Fri 2/6

3:03 pm-6:16 pm

3 stops29h 13m

$706

ChicagoCulebra

ORD - CPX

ORDCPX

Chicago O'Hare Intl

Mon 2/2

3:22 pm-1:28 pm

3 stops20h 06m

Culebra

Fri 2/6

3:03 pm-6:16 pm

3 stops29h 13m

$731

ChicagoCulebra

ORD - CPX

ORDCPX

Chicago O'Hare Intl

Mon 2/2

12:17 pm-1:28 pm

1 stop23h 11m

Culebra

Fri 2/6

3:03 pm-4:37 pm

1 stop27h 34m

$758

ChicagoCulebra

ORD - CPX

ORDCPX

Chicago O'Hare Intl

Sat 2/21

12:17 pm-2:43 pm

1 stop24h 26m

Culebra

Thu 2/26

3:03 pm-3:48 pm

1 stop26h 45m

$819

ChicagoCulebra

ORD - CPX

ORDCPX

Chicago O'Hare Intl

Sat 5/2

9:20 pm-4:13 pm

2 stops17h 53m

Culebra

Sat 5/9

10:30 am-11:15 pm

2 stops13h 45m

$1,691

ChicagoCulebra

ORD - CPX

ORDCPX

Chicago O'Hare Intl

Fri 5/1

9:20 pm-4:13 pm

2 stops17h 53m

Culebra

Sat 5/9

10:30 am-9:38 pm

2 stops12h 08m

$1,708

ChicagoCulebra

ORD - CPX

ORDCPX

Chicago O'Hare Intl

Thu 3/26

8:55 am-4:13 pm

1 stop6h 18m

Culebra

Fri 4/3

10:30 am-12:45 am

2 stops15h 15m

$1,727

ChicagoCulebra

ORD - CPX

ORDCPX

Chicago O'Hare Intl

Wed 3/25

5:45 pm-4:13 pm

2 stops21h 28m

Culebra

Sun 4/5

10:30 am-9:00 am

2 stops23h 30m

$1,841

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 46% 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

6h 18m

Direct flights

None
The fastest flight from Chicago to Culebra takes 6h 18m
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 6h 18m, 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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