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Cheap Flights from Chicago to San Juan, PR, United States - CHI to SJU

Popular flights from Chicago to San Juan

We’ve got the inside scoop on finding the best time to fly for the best price. Not sure when to travel for your next vacation? Find details below on when-to-fly and when-to-buy.

American Airlines
Departure Date Return Date Lowest Price
May 7, 2016 May 10, 2016 $274
May 9, 2016 May 13, 2016 $274
May 10, 2016 May 12, 2016 $274
May 11, 2016 May 12, 2016 $274
JetBlue Airways
Departure Date Return Date Lowest Price
May 9, 2016 May 13, 2016 $272
May 11, 2016 May 14, 2016 $272
May 13, 2016 May 21, 2016 $272
May 13, 2016 May 18, 2016 $272
May 14, 2016 May 18, 2016 $272
Spirit Airlines
Departure Date Return Date Lowest Price
Aug 10, 2016 Aug 17, 2016 $332
Aug 28, 2016 Aug 31, 2016 $332
United Airlines
Departure Date Return Date Lowest Price
May 13, 2016 May 18, 2016 $277

How Much Does it Cost to Fly from Chicago to San Juan (CHI to SJU)?

We have collected flight cost data from across the web for travel from Chicago to San Juan, and have found the average flight price for this trip to be $274.

When Can I Buy the Cheapest Flight from Chicago to San Juan (CHI to SJU)?

Airlines can adjust prices for plane tickets from Chicago to San Juan based on the day and time that you decide to book your flight. We have collected data from all airlines, and have discovered that the best days to book flights are Tuesdays, Wednesdays, and Saturdays. Read our article to find more information about the best time to buy airline tickets.

How far in advance should you book flights from Chicago to San Juan

The chart below shows up-to-date information regarding how far in advance a flight from Chicago to San Juan should be booked.

Non Stop versus 1-Stop
Advanced PurchaseNon StopOne Stop
< 7 days $272 $277
7-14 days $272 $276
14-21 days $329 $277
21-30 days $313 $278
30-60 days $351 $279
60-90 days $352 $355
90+ days $348 $332

Cheapest Day To Fly from Chicago to San Juan

The chart below shows up-to-date information regarding the cheapest days to fly from Chicago to San Juan.

Monday Tuesday Wednesday Thursday Friday Saturday Sunday
$272 $272 $272 $279 $272 $272 $279

Lowest Fares Chart By Month from Chicago to San Juan

The chart below shows the lowest fare by month when flying from Chicago to San Juan.

Month Origin Destination Carrier Depart Date Return Date Stops Price
May Chicago San Juan JetBlue 5/9/16 5/13/16 0 $272
June Chicago San Juan American 6/1/16 6/4/16 1 $278
July Chicago San Juan American 7/4/16 7/14/16 0 $352
August Chicago San Juan Spirit 8/10/16 8/17/16 1 $332
September Chicago San Juan Spirit 9/16/16 9/23/16 1 $332
October Chicago San Juan Spirit 10/8/16 10/15/16 1 $332
November Chicago San Juan Spirit 11/4/16 11/9/16 1 $332
December Chicago San Juan Spirit 12/1/16 12/5/16 1 $333

Cheapest Weekend Non-Stop Flights for the Next 30 Days from Chicago to San Juan

If you're ready to take a trip in the next 30 days and want to fly on the weekend, you might be wondering which weekend is the cheapest to fly. The chart below shows up-to-date data regarding weekend flight prices from Chicago to San Juan.

Next 30 Days

SunMonTueWedThuFriSat
8 9 10 11 12 13 14
$297
15 16 17 18 19 20 21
$297 $329
22 23 24 25 26 27 28
$329 $405
29 30 31 1 2 3 4
$405 $352
5 6 7 8 9 10 11
$352 $352
12 13 14 15 16 17 18
$352

Non-Stop vs Connecting Flights from Chicago to San Juan (CHI to SJU)

Your Chicago to San Juan flight can be significantly cheaper by choosing 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 is $325.

The average price for non-stop flights from Chicago to San Juan is $331.

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

Nonstop Flight Details from Chicago to San Juan
CarrierMonTueWedThuFriSatSunEarliest FlightLatest Flight
American 1 1 1 1 1 1 1 08:30 08:30
JetBlue 1 1 1 1 1 1 1 11:59 11:59
United 1 1 1 1 1 1 1 07:30 07:30

Round Trip vs One Way Flights from Chicago to San Juan (CHI to SJU)

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. 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 is $226.

The average price for round trip flights from Chicago to San Juan is $320.

More Cheap Flights

FlightsAirlineLowest Price
Indianapolis to San Juan Silver, American, JetBlue, Allegiant, Spirit, United $396
Milwaukee to San Juan American, JetBlue, Frontier, Spirit, United $329
Grand Rapids to San Juan American, United $330
Madison to San Juan American, United $419
Peoria to San Juan American, United $382
Moline to San Juan American, United $475
Green Bay to San Juan American, United $450
Toledo to San Juan American, United $577
Bloomington - Normal to San Juan Silver, American, United $419
Ft Wayne to San Juan American, United $539
Appleton to San Juan United Check Dates
Kalamazoo to San Juan American, United $617
South Bend to San Juan United $630
Champaign to San Juan American, United $666
Springfield to San Juan American, United $508
Lansing to San Juan American, United $602
Chicago to New York American, Alaska, JetBlue, Spirit, United $94
Chicago to St Thomas Island American, JetBlue, Spirit, United $326
Chicago to Punta Cana American, JetBlue, Frontier, Spirit, United, Great Lakes $331
Chicago to Orlando American, JetBlue, Frontier, Spirit, United $137
Chicago to Miami American, Alaska, Frontier, United $108
Chicago to St Croix Island American, Alaska, JetBlue, Spirit, United $402
Chicago to Los Angeles American, Alaska, Frontier, Spirit, United, Virgin America $122
Chicago to Las Vegas American, Alaska, Frontier, Spirit, United, Virgin America $107
Chicago to Aguadilla American, JetBlue, Spirit, United $259
Chicago to St Maarten American, Alaska, JetBlue, Spirit, United $480
Chicago to Atlanta American, Spirit, United $71
Chicago to Washington American, Alaska, Frontier, United $88
Chicago to Dallas - Ft Worth American, Alaska, Frontier, Spirit, United $87
Chicago to ViequesCheck Dates

Airlines Flying from Chicago to San Juan (CHI to SJU)

Below are the different airlines that fly from Chicago to San Juan with the average price of their plane tickets. Just remember that different airlines offer different levels of comfort and service, so consider convenience when choosing your airline.

Below is the full flight schedule summary of the next 30 days for flights from Chicago to San Juan.

Chicago to San Juan
Airline Connections Mon Tue Wed Thu Fri Sat Sun
American - X X X X X X X
American JFK X X X X X X X
JetBlue - X X X X X X X
JetBlue BOS X X X X X X X
Delta ATL X X X X X X X
Spirit MCO X X X X X X X
Spirit ACY / FLL X X X X X X X
United - X X X X X X X
United IAH X X X X X X X

Airports for Your Route

These pages contain information about the major airports in Chicago and San Juan, so you can feel comfortable knowing how to get around whether you are about to take off or you just landed.

Chicago to San Juan Flight Questions

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

Question: How long is a direct flight from Chicago to San Juan?
Answer: The average Chicago to San Juan flight time is 4 hours and 43 minutes.
Question: How many miles are there between Chicago and San Juan?
Answer: The distance from Chicago to San Juan is 2072 miles.
Question: How common are direct flights from Chicago to San Juan?
Answer: There are 21 direct flights from Chicago to San Juan.
Question: What is the most popular airline for non-stop flights from Chicago to San Juan?
Answer: JetBlue Airways provides 33% of the non-stop flights between Chicago and San Juan.
Question: What are the most popular connecting cities when flying from Chicago to San Juan?
Answer: New York, NY
Chicago (CHI) To San Juan, PR (SJU) Flights: Cheap Flights From Chicago To San Juan | FareCompare.