Flights from Chicago to San Juan, United States

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Did you mean flights from San Juan, Puerto Rico to Chicago?

Chicago to San Juan, Puerto Rico Last modified: Sep 21, 2018 2:58 -04:00Prices shown were found by travelers like you over the past 30 days

We've scanned 48,195,047,545 round trip itineraries and found the cheapest flights to San Juan, Puerto Rico. Spirit & United frequently offer the best deals to San Juan, Puerto Rico flights, or select your preferred carrier below to see the cheapest days to fly.

Spirit
CHISJU
Tue 10/16
1 stop
SJUCHI
Tue 10/23
1 stop
$240
United
CHISJU
Tue 10/30
nonstop
SJUCHI
Thu 11/8
nonstop
$253
JetBlue
CHISJU
Sat 10/20
2 stops
SJUCHI
Tue 10/23
2 stops
$262
American
CHISJU
Sun 10/28
1 stop
SJUCHI
Fri 11/2
1 stop
$278
Frontier
CHISJU
Sat 10/20
1 stop
SJUCHI
Tue 10/23
1 stop
$383
Alaska
CHISJU
Sat 11/3
nonstop
SJUCHI
Sat 11/10
nonstop
$520

How Much is a Flight from Chicago to San Juan, Puerto Rico? Prices shown were found by travelers like you over the past 30 days

We have collected flight cost data from across the web for travel from Chicago to San Juan, Puerto Rico, and have found the average flight price for this trip to be $246.

Where To Buy Cheap Flights from Chicago to San Juan, Puerto Rico?

The best way to find a great deal on airfare is to search multiple sites. When you run a search on FareCompare, we search multiple sites and fare sources all at once so you don't have to - which is why we think FareCompare is the best place to find cheap tickets. Airlines can adjust prices for tickets from Chicago to San Juan, Puerto Rico based on the day and time that you decide to book your flight. We have collected data from all airlines, and have found that Tuesdays, Wednesdays, and Saturdays are often the best days to book flights. If you'd like to learn more, read our article about the best time to buy airline tickets.

How far in advance should I book tickets from Chicago to San Juan, Puerto Rico? Prices shown were found by travelers like you over the past 30 days

The chart below shows up-to-date information regarding how far in advance to book your flight from Chicago to San Juan, Puerto Rico.

Non Stop versus Connecting
Advanced PurchaseNon StopConnecting
< 7 days $402 $342
7-14 days $379 $309
14-21 days $363 $269
21-30 days $308 $240
30-60 days $253 $240
60-90 days $324 $240
90+ days $253 $256

Cheapest Day To Fly from Chicago to San Juan, Puerto Rico Prices shown were found by travelers like you over the past 30 days

We've examined 57,595,778,181 itinerary searches that we've seen for departures in the next 90 days and found that the cheapest day to fly from Chicago to San Juan, Puerto Rico is Monday. See the chart below to compare prices for other days of the week.

Monday Tuesday Wednesday Thursday Friday Saturday Sunday
$240$240$240$240$261$240$261

Compare Flight Prices from Chicago to San Juan, Puerto Rico by Month Prices shown were found by travelers like you over the past 30 days

Low priced flights are most commonly available by purchasing between one and three months in advance. International or holiday flights may need to be purchased even further in advance. The chart below shows the cheapest flight prices by month for Chicago to San Juan, Puerto Rico flights.

Month Origin Destination Carrier Depart Date Return Date Stops Price
September Chicago San Juan, Puerto Rico United 9/26/18 10/5/18 1 $342
October Chicago San Juan, Puerto Rico Spirit 10/16/18 10/23/18 1 $240
November Chicago San Juan, Puerto Rico Spirit 11/5/18 11/8/18 1 $240
December Chicago San Juan, Puerto Rico Spirit 12/3/18 12/5/18 1 $240
January Chicago San Juan, Puerto Rico American 1/22/19 1/30/19 1 $259
February Chicago San Juan, Puerto Rico American 2/11/19 2/20/19 0 $253
March Chicago San Juan, Puerto Rico American 3/5/19 3/12/19 0 $297
April Chicago San Juan, Puerto Rico United 4/6/19 4/14/19 0 $315

Cheap Last Minute Flights from Chicago to San Juan, Puerto Rico Prices shown were found by travelers like you over the past 30 days

Looking for cheap last minute flights or a weekend getaway? We've got you covered with weekend flight deals from Chicago to San Juan, Puerto Rico. The chart below shows the best last minute deals and cheap flights this weekend we could find.

Next 30 Days

SunMonTueWedThuFriSat
23 24 25 26 27 28 29
$363
30 1 2 3 4 5 6
$363 $329
7 8 9 10 11 12 13
$329 $329
14 15 16 17 18 19 20
$329 $262
21 22 23 24 25 26 27
$262 $288
28 29 30 31 1 2 3
$288

Connecting Flights vs Direct Flights from Chicago to San Juan, Puerto Rico Prices shown were found by travelers like you over the past 30 days

Flights between some cities may be significantly cheaper if you choose a multi-stop airline ticket. Although these connecting flights sacrifice some convenience, on average, travelers save 20%-60% when they choose to fly multi-stop versus a direct flight.

The average price for connecting flights from Chicago to San Juan, Puerto Rico is $295.

The average price for direct flights from Chicago to San Juan, Puerto Rico is $328.

The chart below shows up to date information regarding non-stop flights from Chicago to San Juan, Puerto Rico.

Weekly Direct Flights from Chicago to San Juan, Puerto Rico - By Carrier
CarrierMonTueWedThuFriSatSunEarliest FlightLatest Flight
American 1 0 0 0 1 1 1 08:31 08:31
United 1 1 1 1 1 1 1 07:50 07:50
Major Airlines 1 0 0 0 1 1 1 08:50 08:55

One Way Flights vs Round Trip Flights from Chicago to San Juan, Puerto Rico Prices shown were found by travelers like you over the past 30 days

We have found that there is often no price difference between buying a round trip flight versus a one way flight. Increased flexibility is the main benefit when it comes to buying a one way flight from Chicago to San Juan, Puerto Rico. However, booking a round trip flight can be a simpler process. You can compare round trip and one way flights by using our flight comparison.

The average price for one way flights from Chicago to San Juan, Puerto Rico is $145.

The average price for round trip flights from Chicago to San Juan, Puerto Rico is $290.

Chicago to San Juan, Puerto Rico Flight Questions

Below are some common questions that asked about this flight route:

Question: How long is the flight from Chicago to San Juan, Puerto Rico?
Answer: The average Chicago to San Juan, Puerto Rico flight time is 4 hours and 44 minutes.
Question: How far is San Juan, Puerto Rico from Chicago?
Answer: The distance from Chicago to San Juan, Puerto Rico is 2,058 miles (3,312 kilometers).
Question: How common are direct flights from Chicago to San Juan, Puerto Rico?
Answer: There are 15 direct flights from Chicago to San Juan, Puerto Rico.
Question: What are the most popular Chicago airlines for direct flights from Chicago to San Juan, Puerto Rico?
Answer: United Airlines provides 46% of the non-stop flights between Chicago and San Juan, Puerto Rico.
Question: What are the most popular connecting cities when flying from Chicago to San Juan, Puerto Rico?
Answer: Miami, FL

Airlines in Chicago flying to San Juan, Puerto Rico Last modified: Sep 21, 2018 2:58 -04:00Number of routes searched: 196Number of itineraries searched: 672,680

Wondering which airlines fly out of Chicago to San Juan, Puerto Rico? We've gathered the average price of Chicago airlines with flights to San Juan, Puerto Rico. Different airlines offer different levels of comfort and service, so consider convenience when choosing your airline.

Below is the full flight schedule summary showing which days of the week individual carriers offer flights for the next 30 days.

Chicago to San Juan, Puerto Rico
Airline Connections Mon Tue Wed Thu Fri Sat Sun
American -
JetBlue -
United -
American CLT
American DFW
American MIA
American PHL
JetBlue BOS
JetBlue FLL
JetBlue JFK
Major Airlines ATL
Major Airlines MSP
Major Airlines JFK
Frontier MCO
Spirit BWI
Spirit FLL
Spirit MCO
United EWR
United IAD
United IAH

Chicago to San Juan, Puerto Rico Airports

These are the major commercial airports we're currently monitoring in Chicago and San Juan, Puerto Rico. If your route includes a city with multiple airports, you may be able to find substantial savings by choosing an alternate airport.

Farecompare Research Tools

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Cheap Flights from Chicago to San Juan, Puerto Rico