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Cheap Flights from Chicago to San Juan, PR, United States - CHI to SJU Last modified: May 30, 2016 12:56 PM

Popular flights from Chicago to San Juan Last modified: May 30, 2016 12:56 PM

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
Jun 28, 2016 Jul 8, 2016 $315
Jun 28, 2016 Jul 12, 2016 $315
Jun 28, 2016 Jul 13, 2016 $315
JetBlue Airways
Departure Date Return Date Lowest Price
Jul 7, 2016 Jul 13, 2016 $362
Jul 19, 2016 Jul 23, 2016 $362
Jul 19, 2016 Jul 27, 2016 $362
Jul 21, 2016 Jul 27, 2016 $362
Jul 21, 2016 Aug 1, 2016 $362
Silver Airways
Departure Date Return Date Lowest Price
Aug 6, 2016 Aug 14, 2016 $2,559
Spirit Airlines
Departure Date Return Date Lowest Price
Sep 10, 2016 Sep 17, 2016 $331
United Airlines
Departure Date Return Date Lowest Price
Jul 4, 2016 Jul 8, 2016 $362
Jul 4, 2016 Jul 12, 2016 $362
Jul 4, 2016 Jul 13, 2016 $362
Jul 4, 2016 Jul 13, 2016 $362
Jul 7, 2016 Jul 13, 2016 $362

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 $335.

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 $390 $395
7-14 days $390 $351
14-21 days $394 $369
21-30 days $380 $315
30-60 days $362 $355
60-90 days $362 $333
90+ days $362 $331

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
$348 $315 $333 $348 $333 $333 $333

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 American 5/31/16 6/7/16 1 $407
June Chicago San Juan American 6/28/16 7/8/16 1 $315
July Chicago San Juan American 7/4/16 7/20/16 1 $355
August Chicago San Juan Spirit 8/9/16 8/10/16 1 $333
September Chicago San Juan Spirit 9/10/16 9/17/16 1 $331
October Chicago San Juan Spirit 10/1/16 10/4/16 1 $333
November Chicago San Juan Spirit 11/1/16 11/5/16 1 $333
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
29 30 31 1 2 3 4
$453
5 6 7 8 9 10 11
$453 $482
12 13 14 15 16 17 18
$482 $450
19 20 21 22 23 24 25
$450 $454
26 27 28 29 30 1 2
$454 $450
3 4 5 6 7 8 9
$450

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 $799.

The average price for non-stop flights from Chicago to San Juan is $362.

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 11:55 11:55
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 $224.

The average price for round trip flights from Chicago to San Juan is $790.

More Cheap Flights

FlightsAirlineLowest Price
Indianapolis to San Juan American, JetBlue, Allegiant, Spirit, United $353
Milwaukee to San Juan American, JetBlue, Spirit, United $355
Grand Rapids to San Juan American, Allegiant, Spirit, United $353
Madison to San Juan American, United $544
Peoria to San Juan American, United $470
Moline to San Juan American, United $516
Green Bay to San Juan Silver, American, United $467
Toledo to San Juan American, United $692
Bloomington - Normal to San Juan American, United $466
Ft Wayne to San Juan American, United $503
Appleton to San Juan United Check Dates
Kalamazoo to San Juan American, United $596
South Bend to San Juan United $574
Champaign to San Juan American, United $608
Springfield to San Juan American, United $518
Lansing to San Juan American, United $632
Chicago to New York American, Alaska, JetBlue, Spirit, United $81
Chicago to St Thomas Island American, JetBlue, Spirit, United $326
Chicago to Punta Cana American, JetBlue, Frontier, Spirit, Sun Country, United $337
Chicago to Orlando American, JetBlue, Frontier, Spirit, United $137
Chicago to Miami American, Alaska, Frontier, United $119
Chicago to St Croix Island American, Alaska, JetBlue, United $355
Chicago to Los Angeles American, Alaska, Frontier, Spirit, United, Virgin America $183
Chicago to Las Vegas American, Alaska, Frontier, Spirit, United, Virgin America $118
Chicago to Aguadilla American, JetBlue, Spirit, United $259
Chicago to St Maarten Cape Air, American, JetBlue, Spirit, United $499
Chicago to Atlanta American, Spirit, United $81
Chicago to Washington American, Alaska, Frontier, United $98
Chicago to Dallas - Ft Worth American, Alaska, Frontier, Spirit, United $117
Chicago to ViequesCheck Dates

Airlines Flying from Chicago to San Juan (CHI to SJU) Number of flights searched: 187Last modified: May 30, 2016 12:56 PM

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 CLT 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 MYR / 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 45 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.