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Did you mean flights from San Juan to Chicago?

Cheap Flights from Chicago to San Juan, PR, United States - CHI to SJU Last modified: Jun 29, 2016 12:54 PM

Popular flights from Chicago to San Juan Last modified: Jun 29, 2016 12:54 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.

JetBlue
CHISJU
Fri 8/19
nonstop
SJUCHI
Fri 8/26
nonstop
$298
Select
JetBlue
CHISJU
Mon 8/22
nonstop
SJUCHI
Fri 8/26
nonstop
$298
Select
JetBlue
CHISJU
Tue 8/23
nonstop
SJUCHI
Fri 8/26
nonstop
$298
Select
JetBlue
CHISJU
Tue 8/23
nonstop
SJUCHI
Tue 9/6
nonstop
$298
Select
JetBlue
CHISJU
Fri 8/26
nonstop
SJUCHI
Tue 9/13
nonstop
$298
Select
United
CHISJU
Fri 8/26
nonstop
SJUCHI
Tue 9/13
nonstop
$298
Select
United
CHISJU
Tue 8/30
nonstop
SJUCHI
Wed 9/7
nonstop
$298
Select
United
CHISJU
Wed 8/31
nonstop
SJUCHI
Wed 9/7
nonstop
$298
Select
United
CHISJU
Wed 8/31
nonstop
SJUCHI
Wed 9/14
nonstop
$298
Select
United
CHISJU
Sun 9/4
nonstop
SJUCHI
Wed 9/7
nonstop
$298
Select
American
CHISJU
Sun 8/14
nonstop
SJUCHI
Thu 8/25
nonstop
$318
Select
American
CHISJU
Wed 8/17
nonstop
SJUCHI
Wed 8/24
nonstop
$318
Select
American
CHISJU
Fri 8/19
nonstop
SJUCHI
Fri 9/2
nonstop
$318
Select
American
CHISJU
Sun 8/21
nonstop
SJUCHI
Fri 9/2
nonstop
$318
Select
American
CHISJU
Sun 8/21
1 stop
SJUCHI
Fri 9/2
1 stop
$318
Select
Spirit
CHISJU
Fri 7/8
1 stop
SJUCHI
Tue 7/12
1 stop
$333
Select
Spirit
CHISJU
Tue 8/9
1 stop
SJUCHI
Wed 8/17
1 stop
$333
Select
Spirit
CHISJU
Tue 8/9
1 stop
SJUCHI
Tue 8/23
1 stop
$333
Select
Spirit
CHISJU
Wed 8/10
1 stop
SJUCHI
Wed 8/17
1 stop
$333
Select
Spirit
CHISJU
Tue 8/16
1 stop
SJUCHI
Tue 8/30
1 stop
$333
Select

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 $298.

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 $393 $376
7-14 days $354 $321
14-21 days $352 $317
21-30 days $332 $313
30-60 days $298 $303
60-90 days $298 $303
90+ days $298 $303

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
$298 $298 $298 $298 $298 $298 $298

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
June Chicago San Juan American 6/30/16 7/6/16 0 $424
July Chicago San Juan United 7/21/16 7/28/16 1 $313
August Chicago San Juan JetBlue 8/19/16 8/26/16 0 $298
September Chicago San Juan JetBlue 9/3/16 9/6/16 0 $298
October Chicago San Juan JetBlue 10/1/16 10/4/16 0 $298
November Chicago San Juan JetBlue 11/1/16 11/5/16 0 $298
December Chicago San Juan Spirit 12/1/16 12/5/16 1 $333
January Chicago San Juan Spirit 1/9/17 1/16/17 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
26 27 28 29 30 1 2
$454
3 4 5 6 7 8 9
$454 $424
10 11 12 13 14 15 16
$424 $371
17 18 19 20 21 22 23
$371 $363
24 25 26 27 28 29 30
$363 $366
31 1 2 3 4 5 6
$366
TIPSave $1 by flying into Punta Cana instead of San Juan from Chicago

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 $332.

The average price for non-stop flights from Chicago to San Juan is $304.

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 08:25 08:25
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 $200.

The average price for round trip flights from Chicago to San Juan is $311.

More Cheap Flights

FlightsAirlineLowest Price
Indianapolis to San Juan Silver, American, JetBlue, Frontier, Allegiant, Spirit, United $352
Milwaukee to San Juan American, JetBlue, Frontier, Spirit, United $354
Grand Rapids to San Juan American, United $382
Madison to San Juan American, Frontier, United $480
Peoria to San Juan American, United $470
Moline to San Juan American, Frontier, United $418
Green Bay to San Juan American, United $502
Toledo to San Juan American, JetBlue, United $518
Bloomington - Normal to San Juan American, United $545
Ft Wayne to San Juan American, United $443
Appleton to San Juan United Check Dates
Kalamazoo to San Juan American, United $581
South Bend to San Juan United $514
Champaign to San Juan American, United $647
Springfield to San Juan American, United $488
Lansing to San Juan American, United $379
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 $333
Chicago to Orlando American, JetBlue, Frontier, Spirit, United $139
Chicago to Miami American, Alaska, Frontier, United $139
Chicago to St Croix Island American, Alaska, JetBlue, United $404
Chicago to Los Angeles American, Alaska, Frontier, Spirit, United, Virgin America $81
Chicago to Las Vegas American, Alaska, Frontier, Spirit, United, Virgin America $133
Chicago to Aguadilla American, JetBlue, Spirit, United $303
Chicago to St Maarten American, JetBlue, Spirit, United $505
Chicago to Atlanta American, Frontier, Spirit, United $81
Chicago to Washington American, Alaska, Frontier, United $99
Chicago to Dallas - Ft Worth American, Alaska, Frontier, Spirit, United $81
Chicago to ViequesCheck Dates

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 44 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: American Airlines provides 33% of the non-stop flights between Chicago and San Juan.
Chicago (CHI) To San Juan, PR (SJU) Flights: Cheap Flights From Chicago To San Juan | FareCompare.