Find cheap airline tickets from Chicago to San Juan by date

Departure: Return: Sorted by:

$163

outward: Sep 6, 2020
1:28a ORD » 7:16p SJU
Spirit Airlines 1 stop (17h48m)

inbound: Sep 19, 2020
8:11p SJU » 7:14a ORD
Spirit Airlines 1 stop (11h03m)

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$163

outward: Sep 6, 2020
1:28a ORD » 7:16p SJU
Spirit Airlines 1 stop (17h48m)

inbound: Sep 19, 2020
8:11p SJU » 2:44a ORD
Spirit Airlines 1 stop (6h33m)

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$181

outward: Jul 18, 2020
3:14a ORD » 4:54p SJU
Spirit Airlines 1 stop (13h40m)

inbound: Jul 21, 2020
3:55a SJU » 11:36p ORD
Unknown Company 1 stop (19h41m)

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$190

outward: Jul 14, 2020
12:10a ORD » 8:13a SJU
Spirit Airlines 1 stop (8h03m)

inbound: Jul 21, 2020
9:23a SJU » 4:27p ORD
Spirit Airlines 1 stop (7h04m)

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$190

outward: Jul 14, 2020
12:10a ORD » 8:13a SJU
Spirit Airlines 1 stop (8h03m)

inbound: Jul 21, 2020
9:23a SJU » 4:27p ORD
Spirit Airlines 1 stop (7h04m)

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$190

outward: Jul 14, 2020
3:14p ORD » 8:13a SJU
Spirit Airlines 1 stop (16h59m)

inbound: Jul 22, 2020
9:23a SJU » 4:27p ORD
Spirit Airlines 1 stop (7h04m)

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$212

outward: Jul 20, 2020
4:11p ORD » 2:51a SJU
Spirit Airlines 1 stop (10h40m)

inbound: Jul 27, 2020
9:23a SJU » 4:27p ORD
Spirit Airlines 1 stop (7h04m)

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$241

outward: Jul 14, 2020
12:10a ORD » 8:13a SJU
Spirit Airlines 1 stop (8h03m)

inbound: Jul 21, 2020
3:18a SJU » 7:40p ORD
Unknown Company 1 stop (16h22m)

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$289

outward: Dec 31, 2020
6:45p ORD » 4:09a SJU
American Airlines 1 stop (9h24m)

inbound: Jan 12, 2021
8:17p SJU » 1:50a ORD
American Airlines direct (5h33m)

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$530

outward: Dec 21, 2020
4:45p ORD » 9:36p SJU
Frontier Airlines direct (4h51m)

inbound: Jan 2, 2021
12:39a SJU » 6:20a ORD
Frontier Airlines direct (5h41m)

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Return

Departure

Choose when you'd like to depart to San Juan (Puerto Rico):

Find the cheapest Chicago San Juan flight by browsing the dates below to find alternative flight prices found in the last days. To launch a flight search for Chicago - San Juan with these new dates, click on an offer. Want to depart from another city? Choose:

Airlines operating flights from Chicago to San Juan

Departure: Airline

Spirit Airlines

outbound: Jul 13, 2020
Spirit Airlines 1 stop

return: Jul 21, 2020
Spirit Airlines 1 stop

$186 Verify

American Airlines

outbound: Sep 5, 2020
American Airlines 1 stop

return: Sep 19, 2020
American Airlines 2 stops

$264 Verify

United Airlines

outbound: Dec 31, 2020
United Airlines 1 stop

return: Jan 12, 2021
United Airlines 1 stop

$302 Verify

Frontier Airlines

outbound: Dec 31, 2020
Frontier Airlines direct

return: Jan 12, 2021
United Airlines direct

$483 Verify

Airline tickets Chicago - San Juan found in the last 30 days.

Travel tips for flights Chicago - San Juan

Information on San Juan

Route

Average flight duration: 9h47m (flight with stopovers)

Arrival city:
San Juan, Puerto Rico
Airport(s):
Fernando Luis Ribas Dominicci Airport (SIG)
Luis Muñoz Marín International Airport (SJU)
Local time:
Jul 11, 2020 9:41 AM, GMT-4
Weather:
min. 41ºF, max. 59ºF

Departure city:
Chicago, USA
Airport(s):
Midway International Airport (MDW)
O'Hare International Airport (ORD)
Local time:
Jul 11, 2020 8:41 AM, GMT-5
Weather:
min. 72ºF, max. 80ºF

Why travel by plane from Chicago to San Juan?

When traveling from Chicago to San Juan, travelers are able to take advantage of daily non-stop flights between the two cities, operated by a number of airlines including regular and low-cost operators. These include American Airlines, Southwest Airlines and United Airlines, which operate direct flights to San Juan with a flight time of around 4h 40m. Connecting flights are also available with a flight time of upwards of 6h. Departing from either O'Hare International Airport or Chicago Midway International Airport, flights touch down in San Juan's Luis Muñoz Marín International Airport.

What is there to see and do in San Juan?

The Puerto Rican capital city of San Juan is home to a host of activities and sights for visitors to enjoy. As well as the must-visit area of Old San Juan, filled with colorful houses and interesting attractions, there's also the opportunity to learn more about Bacardi rum at the Casa Bacardi factory and museum. Other museums to visit include the Museo de las Americas, the Museum of the Sea, and the Museum of Art Puerto Rico. After a day of exploring, relax in one of San Juan's restaurants or bars – the city boasts a lively nightlife scene!

Find a cheap rental car in San Juan