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  1. Flights
  2. Puerto Rico
  3. San Juan
  4. Chicago - San Juan

Cheap Flights from Chicago (CHI) to San Juan (SJU)

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Discover the cheapest flights from Chicago to San Juan
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Sun, Jul 20 - Thu, Jul 24
Spirit Airlines
Spirit AirlinesDirect
CHI - SJU
Spirit Airlines
Spirit AirlinesDirect
SJU - CHI
149$
144$
Prime price per passenger
Mon, May 19 - Sat, May 24
Spirit Airlines
Spirit AirlinesDirect
CHI - SJU
Spirit Airlines
Spirit Airlines1 stop
SJU - CHI
210$
203$
Prime price per passenger
Tue, Jun 3 - Thu, Jun 5
Spirit Airlines
Spirit AirlinesDirect
CHI - SJU
Spirit Airlines
Spirit AirlinesDirect
SJU - CHI
233$
225$
Prime price per passenger
Mon, Jun 16 - Wed, Jun 18
Spirit Airlines
Spirit AirlinesDirect
CHI - SJU
Spirit Airlines
Spirit AirlinesDirect
SJU - CHI
236$
230$
Prime price per passenger
Mon, Jun 23 - Tue, Jun 24
Spirit Airlines
Spirit AirlinesDirect
CHI - SJU
Spirit Airlines
Spirit Airlines1 stop
SJU - CHI
254$
248$
Prime price per passenger
Sat, Jul 5 - Fri, Jul 11
Spirit Airlines
Spirit AirlinesDirect
CHI - SJU
Spirit Airlines
Spirit AirlinesDirect
SJU - CHI
256$
250$
Prime price per passenger
Mon, May 19
Spirit Airlines
Spirit AirlinesDirect
CHI - SJU
99$
Prime price per passenger
Sun, May 25
Spirit Airlines
Spirit AirlinesDirect
CHI - SJU
114$
Prime price per passenger
Sun, Jun 8
Spirit Airlines
Spirit AirlinesDirect
CHI - SJU
114$
Prime price per passenger
Sat, Jun 21
Spirit Airlines
Spirit AirlinesDirect
CHI - SJU
114$
Prime price per passenger
Sun, Jul 20
Spirit Airlines
Spirit AirlinesDirect
CHI - SJU
114$
Prime price per passenger
Wed, Jul 9
Spirit Airlines
Spirit AirlinesDirect
CHI - SJU
134$
133$
Prime price per passenger
Prices shown below were available within the past 3 days for the period specified and should not be considered the final price offered. Please note that availability and prices are subject to change.

Cheapest time to fly from Chicago to San Juan

Flexible with dates? We find the best price for the week of the day you select *Prices may vary after you search.
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week: May 5 - May 11
Flights from just $85
$85
$87
$92
$128
$136
$138
$184
$218
$166
$187
$137
$154
MayJuneJuly
Flying Time5 h and 2 mWhen flying from Chicago to San Juan, this can take around 5 h and 2 m in flying time, however this flight duration can vary due to other factors
Cheapest flight$99The best price for flights from Chicago to San Juan offered by eDreams, which have been found by our customers in the last 3 days
Departure AirportO'hare International AirportO'hare International Airport is where you'll take off when flying from Chicago to San Juan
Arrival AirportLuis Munoz Marin InternationalYou'll land at Luis Munoz Marin International when flying from Chicago to San Juan
Peak seasonDecemberDecember is the busiest time to fly from Chicago to San Juan according to search data results from our customers
Airlines operating this routeSpirit Airlines, American AirlinesAirline(s) that fly from Chicago to San Juan
Best time to bookDecemberDecember is one of the most frequent times to fly to San Juan from Chicago according to real data from our customers

Route information

Distance: 2055 miles
Chicago airports
O'hare International Airport (ORD)How far from city center: 14 miles
Midway Airport (MDW)How far from city center: 4 miles
San Juan airports
Luis Munoz Marin International (SJU)How far from city center: 7 miles

Are you searching for flights from Chicago to San Juan?

Are you planning to travel to San Juan for vacations, business or family visits? eDreams offers you the cheapest flights and best deals departing from Chicago. With our fast search engine you will get a large selection of airfares from standard and low cost airlines worldwide and easily book your tickets for this route. If you are flexible we help you identify the cheapest day to fly to San Juan and if you need to leave soon you can check our most convenient last minute fares. Read all the useful information about your next destination and proceed to the reservation, indicating your flight dates and completing your travel booking with hotels and car rental!

Frequently asked questions about flights from Chicago to San Juan

What are the benefits of booking flexible flight tickets?
Using the flexible flight ticket, you're guaranteed a refund or a rebooking option (without fees) in case of flight cancellations when travelling to Puerto Rico. At eDreams have you covered!
For flights from Chicago to San Juan, how can I find the cheapest price?
The cheapest price for a flight from Chicago to San Juan is $99. At eDreams we use different machine learned based methodologies to find our costumers the best option available, considering airline combinations, stopovers and direct flights as well as different criteria for inbound and outbound journeys.
When booking, when is the best time to get the best prices for flights from Chicago to San Juan?
The most popular months to book a trip from Chicago to San Juan are December, March and September, based on the searches of our customers.
When is the best time to travel from Chicago to San Juan?
The best time of the year to visit San Juan depends on lots of personal preferences, especially the price. Regarding popularity, December is the best month to fly to San Juan from Chicago in terms of searches from our customers, followed by July and June. If you prefer to avoid the busy season and get away from the crowds September, August and October are the months with fewer searches for Chicago - San Juan.
How long does the flight from Chicago to San Juan take?
Flight length from Chicago to San Juan is around 05:02 hours on average, at an average distance of 3,382 km, for flights for the route (which may have 1 or more stops in other cities in between).
Which airports have flights between Chicago and San Juan?

The main route from Chicago to San Juan is: O'hare International Airport (ORD) to Luis Munoz Marin International (SJU). The following airlines fly this route:

Spirit Airlines.

Frontier Airlines.

American Airlines.

Alternatively, you can find Chicago - San Juan flights between Midway Airport (MDW) to Luis Munoz Marin International (SJU) with the following airline(s) flying the route: Frontier Airlines.

Which airlines fly from Chicago to San Juan?

The airlines that fly non-stop from Chicago to San Juan are:

  • American Airlines.
  • United Airlines.

American Airlines, stopping at Dallas, TX during at least 61 minutes.

  • United Airlines, with 183 minutes of layover in Washington, D.C..

Plan your trip

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