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Cheap Flights from Chicago to San Juan - CHI to SJU

Popular flights from Chicago to San Juan

If your flight days are flexible and you looking for a good deal, our charts on cheap flights provide some insight regarding affordable flight options for your next big adventure.

American Airlines
Departure Date Return Date Lowest Price
Mar 2, 2016 Mar 9, 2016 $307
JetBlue Airways
Departure Date Return Date Lowest Price
Feb 22, 2016 Mar 1, 2016 $334
Feb 23, 2016 Mar 1, 2016 $334
Feb 24, 2016 Mar 2, 2016 $334
Feb 25, 2016 Mar 1, 2016 $334
Feb 28, 2016 Mar 2, 2016 $334
Spirit Airlines
Departure Date Return Date Lowest Price
Feb 23, 2016 Mar 5, 2016 $324
Feb 23, 2016 Mar 4, 2016 $324
Feb 23, 2016 Feb 25, 2016 $324
Feb 24, 2016 Mar 7, 2016 $324
Feb 28, 2016 Mar 2, 2016 $324
United Airlines
Departure Date Return Date Lowest Price
Feb 23, 2016 Mar 4, 2016 $322
Feb 23, 2016 Mar 5, 2016 $322
Feb 25, 2016 Mar 5, 2016 $322
Feb 25, 2016 Mar 6, 2016 $322
Mar 7, 2016 Mar 22, 2016 $322

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 $319.

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 $415 $397
7-14 days $333 $324
14-21 days $330 $322
21-30 days $333 $322
30-60 days $330 $322
60-90 days $339 $324
90+ days $339 $322

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
$315 $314 $307 $322 $324 $327 $324

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
February Chicago San Juan American 2/29/16 3/8/16 2 $315
March Chicago San Juan American 3/2/16 3/9/16 2 $307
April Chicago San Juan Spirit 4/10/16 4/20/16 1 $324
May Chicago San Juan Spirit 5/3/16 5/17/16 1 $324
June Chicago San Juan United 6/2/16 6/7/16 1 $331
July Chicago San Juan American 7/13/16 7/20/16 1 $338
August Chicago San Juan Spirit 8/24/16 8/29/16 1 $333
September Chicago San Juan United 9/9/16 9/14/16 1 $322

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
7 8 9 10 11 12 13
$398
14 15 16 17 18 19 20
$398 $358
21 22 23 24 25 26 27
$358 $340
28 29 1 2 3 4 5
$340 $348
6 7 8 9 10 11 12
$348 $340
13 14 15 16 17 18 19
$340

TIPSave $146 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 $331.

The average price for non-stop flights from Chicago to San Juan is $339.

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 08:35 08:35
JetBlue 1 1 1 1 1 1 1 07:25 07:25
United 1 1 1 1 3 3 1 07:30 22:55

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 $167.

The average price for round trip flights from Chicago to San Juan is $325.

More Cheap Flights

FlightsAirlineLowest Price
Indianapolis to San Juan United, Delta, US Airways, American, AirTran $369
Milwaukee to San Juan United, Delta, US Airways, American, AirTran $391
Grand Rapids to San Juan United, Delta, American, US Airways, AirTran $403
Madison to San Juan Delta, United, American, US Airways $427
Peoria to San Juan Delta, United, American $462
Moline to San Juan Delta, United, American, US Airways $452
Green Bay to San Juan Delta, United, American, US Airways $418
Toledo to San Juan American $550
Bloomington - Normal to San Juan Delta, American $532
Ft Wayne to San Juan Delta, United, American $485
Appleton to San Juan Delta, United, US Airways $722
Kalamazoo to San Juan Delta, American $605
South Bend to San Juan Delta, United, US Airways $715
Champaign to San Juan American $507
Springfield to San Juan United, American $525
Lansing to San Juan United, Delta $534
Chicago to New York Alaska, United, American, US Airways, Spirit, JetBlue, AirTran $74
Chicago to St Thomas Island United, Delta, US Airways, American, Spirit, JetBlue $343
Chicago to Punta Cana Air Canada, United, Delta, American, US Airways, Spirit, JetBlue, Frontier, AirTran, Copa $190
Chicago to Orlando Alaska, United, Delta, US Airways, American, Spirit, JetBlue, AirTran $77
Chicago to Miami Alaska, United, Delta, American, US Airways $116
Chicago to St Croix Island United, US Airways, American, JetBlue $396
Chicago to Los Angeles Alaska, United, Delta, US Airways, American, Sun Country, Spirit, Frontier, AirTran, Virgin America $107
Chicago to Las Vegas Alaska, United, Delta, US Airways, American, Sun Country, Spirit, Frontier, Virgin America, AirTran $115
Chicago to Aguadilla United, Spirit, JetBlue $259
Chicago to St Maarten Air Canada, United, Delta, US Airways, American, Spirit, JetBlue, Copa $415
Chicago to Atlanta Alaska, United, Delta, US Airways, American, Spirit, AirTran $78
Chicago to Washington Alaska, United, Delta, US Airways, American, JetBlue, AirTran $80
Chicago to Dallas - Ft Worth Alaska, United, Delta, US Airways, American, Spirit, Frontier $79
Chicago to Vieques United, American Check 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 PHL 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 DTW X X X X X X X
Spirit FLL X X X X X X X
Spirit ATL / FLL X X X X X X X
United - X X X X X X X
United CLE 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 33 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 25 direct flights from Chicago to San Juan.
Question: What is the most popular airline for non-stop flights from Chicago to San Juan?
Answer: United Airlines provides 44% 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 (SJU) Flights: Cheap Flights From Chicago To San Juan | FareCompare.