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

Popular flights from San Juan to Chicago

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
Feb 19, 2016 Feb 22, 2016 $276
JetBlue Airways
Departure Date Return Date Lowest Price
Feb 16, 2016 Feb 23, 2016 $282
Feb 22, 2016 Feb 29, 2016 $282
Feb 23, 2016 Feb 29, 2016 $282
Feb 24, 2016 Mar 2, 2016 $282
Feb 26, 2016 Mar 1, 2016 $282
Spirit Airlines
Departure Date Return Date Lowest Price
May 18, 2016 May 25, 2016 $319
United Airlines
Departure Date Return Date Lowest Price
Feb 13, 2016 Feb 13, 2016 $271

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

We have collected flight cost data from across the web for travel from San Juan to Chicago, and have found the average flight price for this trip to be $279.

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

Airlines can adjust prices for plane tickets from San Juan to Chicago 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 San Juan to Chicago

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

Non Stop versus 1-Stop
Advanced PurchaseNon StopOne Stop
< 7 days $271 $285
7-14 days $273 $276
14-21 days $282 $280
21-30 days $282 $287
30-60 days $310 $286
60-90 days $294 $320
90+ days $294 $319

Cheapest Day To Fly from San Juan to Chicago

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

Monday Tuesday Wednesday Thursday Friday Saturday Sunday
$282 $282 $282 $282 $273 $271 $282

Lowest Fares Chart By Month from San Juan to Chicago

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

Month Origin Destination Carrier Depart Date Return Date Stops Price
February San Juan Chicago United 2/13/16 2/13/16 0 $271
March San Juan Chicago American 3/3/16 3/7/16 0 $282
April San Juan Chicago JetBlue 4/13/16 4/27/16 0 $294
May San Juan Chicago JetBlue 5/4/16 5/11/16 0 $294
June San Juan Chicago JetBlue 6/2/16 6/7/16 0 $294
July San Juan Chicago JetBlue 7/14/16 7/20/16 0 $294
August San Juan Chicago JetBlue 8/9/16 8/18/16 0 $294
September San Juan Chicago JetBlue 9/2/16 9/5/16 0 $294

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

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 San Juan to Chicago.

Next 30 Days

SunMonTueWedThuFriSat
14 15 16 17 18 19 20
$273
21 22 23 24 25 26 27
$273 $282
28 29 1 2 3 4 5
$282 $282
6 7 8 9 10 11 12
$282 $282
13 14 15 16 17 18 19
$282 $394
20 21 22 23 24 25 26
$394

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

Your San Juan to Chicago 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 San Juan to Chicago is $295.

The average price for non-stop flights from San Juan to Chicago is $294.

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

Nonstop Flight Details from San Juan to Chicago
CarrierMonTueWedThuFriSatSunEarliest FlightLatest Flight
American 1 1 1 1 1 1 1 15:56 15:56
JetBlue 1 1 1 1 1 1 1 19:48 19:48
United 1 1 1 1 1 3 3 02:45 12:55

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

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 San Juan to Chicago. 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 San Juan to Chicago is $142.

The average price for round trip flights from San Juan to Chicago is $293.

San Juan to Chicago Flight Questions

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

Question: How long is a direct flight from San Juan to Chicago?
Answer: The average San Juan to Chicago flight time is 5 hours and 16 minutes.
Question: How many miles are there between San Juan and Chicago?
Answer: The distance from San Juan to Chicago is 2072 miles.
Question: How common are direct flights from San Juan to Chicago?
Answer: There are 25 direct flights from San Juan to Chicago.
Question: What is the most popular airline for non-stop flights from San Juan to Chicago?
Answer: United Airlines provides 44% of the non-stop flights between San Juan and Chicago.
Question: What are the most popular connecting cities when flying from San Juan to Chicago?
Answer: New York, NY

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

Below are the different airlines that fly from San Juan to Chicago 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 San Juan to Chicago.

San Juan to Chicago
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 MSP X X X X X X X
Spirit FLL X X X X X X X
United - X X X X X X X
United EWR X X X X X X X

Airports for Your Route

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

Cheap Domestic Flights from San Juan - SJU

FlightsAirlineLowest Price
San Juan to Milwaukee American, United $332
San Juan to New York American, JetBlue, Spirit, United $212
San Juan to Atlanta American, JetBlue, Spirit, United $259
San Juan to Detroit American, JetBlue, Spirit, United $254
San Juan to Dallas - Ft Worth American, Spirit, United $283
San Juan to South Bend American, United Check Dates
San Juan to Indianapolis American, United $322
San Juan to Grand Rapids American, United $321
San Juan to Madison American, United $345
San Juan to St Louis American, JetBlue, United $339
San Juan to Washington American, JetBlue, United $250
San Juan to Cleveland American, JetBlue, Spirit, United $281
San Juan to Philadelphia American, JetBlue, United $260

Cheap Domestic Flights to Chicago - CHI

FlightsAirlineLowest Price
Aguadilla to Chicago JetBlue, Spirit, United $247
Ponce to Chicago JetBlue Check Dates
Aguadilla to Milwaukee United $567
Aguadilla to New York JetBlue, Spirit $216

Cheap International Flights to Chicago - CHI

FlightsAirlineLowest Price
St Maarten to Chicago Silver, American, JetBlue, Spirit, United $498
St Croix Island to Chicago Cape Air, American, JetBlue, Seaborne, United $422
St Thomas Island to Chicago Cape Air, American, JetBlue, Seaborne, Spirit, United $405
Punta Cana to Chicago American, JetBlue, Frontier, Spirit, Sun Country, United $204
La Romana to Chicago American, JetBlue, United Check Dates
St Maarten to New York Cape Air, American, JetBlue, Spirit, Sun Country, Tradewind, United $348
St Thomas Island to Milwaukee American, Seaborne, United $460
St Maarten to Milwaukee American, United Check Dates
St Thomas Island to Atlanta Cape Air, American, Seaborne, Spirit, United $372
Punta Cana to Milwaukee American, United $534
St Croix Island to Milwaukee American, Seaborne, United Check Dates
Punta Cana to South Bend American, United Check Dates
St Thomas Island to New York Cape Air, American, JetBlue, Seaborne, Spirit, United $272
Cheap Flights from San Juan to Chicago, IL, United States, from $271 Round trip from SJU to CHI