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Did you mean flights from Chicago to San Juan, Puerto Rico?

Flights from San Juan, Puerto Rico to Chicago, United States

San Juan, Puerto Rico to Chicago Last modified: Mar 22, 2017 2:34 -04:00Prices shown were found by travelers like you over the past 30 days

We've scanned 33,975,962,565 round trip itineraries and found the cheapest flights to Chicago. Spirit & JetBlue frequently offer the best deals to Chicago flights, or select your preferred carrier below to see the cheapest days to fly.

Spirit
SJUCHI
Thu 5/4
1 stop
CHISJU
Tue 5/9
1 stop
$331
JetBlue
SJUCHI
Wed 4/26
1 stop
CHISJU
Tue 5/9
1 stop
$365
United
SJUCHI
Thu 5/4
nonstop
CHISJU
Tue 5/9
nonstop
$376
American
SJUCHI
Wed 5/10
nonstop
CHISJU
Mon 5/15
nonstop
$381

How Much is a Flight from San Juan, Puerto Rico to Chicago? Prices shown were found by travelers like you over the past 30 days

We have collected flight cost data from across the web for travel from San Juan, Puerto Rico to Chicago, and have found the average flight price for this trip to be $362.

Where To Buy Cheap Flights from San Juan, Puerto Rico to Chicago?

The best way to find a great deal on airfare is to search multiple sites. When you run a search on FareCompare, we search multiple sites and fare sources all at once so you don't have to - which is why we think FareCompare is the best place to find cheap tickets. Airlines can adjust prices for tickets from San Juan, Puerto Rico to Chicago based on the day and time that you decide to book your flight. We have collected data from all airlines, and have found that Tuesdays, Wednesdays, and Saturdays are often the best days to book flights. If you'd like to learn more, read our article about the best time to buy airline tickets.

How far in advance should I book tickets from San Juan, Puerto Rico to Chicago? Prices shown were found by travelers like you over the past 30 days

The chart below shows up-to-date information regarding how far in advance to book your flight from San Juan, Puerto Rico to Chicago.

Non Stop versus Connecting
Advanced PurchaseNon StopConnecting
< 7 days $553 $498
7-14 days $553 $455
14-21 days $452 $436
21-30 days $407 $372
30-60 days $376 $331
60-90 days $409 $377
90+ days $353 $331

Cheapest Day To Fly from San Juan, Puerto Rico to Chicago Prices shown were found by travelers like you over the past 30 days

We've examined 33,993,350,834 itinerary searches that we've seen for departures in the next 90 days and found that the cheapest day to fly from San Juan, Puerto Rico to Chicago is Thursday. See the chart below to compare prices for other days of the week.

Monday Tuesday Wednesday Thursday Friday Saturday Sunday
$439$332$332$331$332$342$421

Compare Flight Prices from San Juan, Puerto Rico to Chicago by Month Prices shown were found by travelers like you over the past 30 days

Low priced flights are most commonly available by purchasing between one and three months in advance. International or holiday flights may need to be purchased even further in advance. The chart below shows the cheapest flight prices by month for San Juan, Puerto Rico to Chicago flights.

Month Origin Destination Carrier Depart Date Return Date Stops Price
March San Juan, Puerto Rico Chicago United 3/29/17 4/3/17 2 $455
April San Juan, Puerto Rico Chicago Spirit 4/28/17 4/30/17 1 $332
May San Juan, Puerto Rico Chicago Spirit 5/4/17 5/9/17 1 $331
June San Juan, Puerto Rico Chicago JetBlue 6/7/17 6/20/17 1 $377
July San Juan, Puerto Rico Chicago American 7/20/17 7/29/17 0 $409
August San Juan, Puerto Rico Chicago Spirit 8/15/17 8/22/17 1 $332
September San Juan, Puerto Rico Chicago Spirit 9/6/17 9/11/17 1 $332
October San Juan, Puerto Rico Chicago Spirit 10/5/17 10/9/17 1 $331

Cheap Last Minute Flights from San Juan, Puerto Rico to Chicago Prices shown were found by travelers like you over the past 30 days

Looking for cheap last minute flights or a weekend getaway? We've got you covered with weekend flight deals from San Juan, Puerto Rico to Chicago. The chart below shows the best last minute deals and cheap flights this weekend we could find.

Next 30 Days

SunMonTueWedThuFriSat
19 20 21 22 23 24 25
$553
26 27 28 29 30 31 1
$553 $620
2 3 4 5 6 7 8
$620 $522
9 10 11 12 13 14 15
$522 $542
16 17 18 19 20 21 22
$542 $372
23 24 25 26 27 28 29
$372

Connecting Flights vs Direct Flights from San Juan, Puerto Rico to Chicago Prices shown were found by travelers like you over the past 30 days

Flights between some cities may be significantly cheaper if you choose 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, Puerto Rico to Chicago is $403.

The average price for direct flights from San Juan, Puerto Rico to Chicago is $403.

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

Weekly Direct Flights from San Juan, Puerto Rico to Chicago - By Carrier
CarrierMonTueWedThuFriSatSunEarliest FlightLatest Flight
American 1 1 1 1 1 1 2 07:00 16:05
United 1 1 1 1 1 2 3 01:55 14:22

One Way Flights vs Round Trip Flights from San Juan, Puerto Rico to Chicago Prices shown were found by travelers like you over the past 30 days

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, Puerto Rico 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, Puerto Rico to Chicago is $195.

The average price for round trip flights from San Juan, Puerto Rico to Chicago is $372.

San Juan, Puerto Rico to Chicago Flight Questions

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

Question: How long is the flight from San Juan, Puerto Rico to Chicago?
Answer: The average San Juan, Puerto Rico to Chicago flight time is 5 hours and 14 minutes.
Question: How far is Chicago from San Juan, Puerto Rico?
Answer: The distance from San Juan, Puerto Rico to Chicago is 3,334 kilometers (2,072 miles).
Question: How common are direct flights from San Juan, Puerto Rico to Chicago?
Answer: There are 18 direct flights from San Juan, Puerto Rico to Chicago.
Question: What are the most popular San Juan, Puerto Rico airlines for direct flights from San Juan, Puerto Rico to Chicago?
Answer: United Airlines provides 55% of the non-stop flights between San Juan, Puerto Rico and Chicago.
Question: What are the most popular connecting cities when flying from San Juan, Puerto Rico to Chicago?
Answer: Newark, NJ

Airlines in San Juan, Puerto Rico flying to Chicago Last modified: Mar 22, 2017 2:34 -04:00Number of routes searched: 248Number of itineraries searched: 589,554

Wondering which airlines fly out of San Juan, Puerto Rico to Chicago? We've gathered the average price of San Juan, Puerto Rico airlines with flights to Chicago. Different airlines offer different levels of comfort and service, so consider convenience when choosing your airline.

Below is the full flight schedule summary showing which days of the week individual carriers offer flights for the next 30 days.

San Juan, Puerto Rico to Chicago
Airline Connections Mon Tue Wed Thu Fri Sat Sun
American -
JetBlue -
United -
American CLT
American DFW
American JFK
American LGA
JetBlue BOS
JetBlue FLL
JetBlue JFK
Copa PTY
Major Airlines ATL
Major Airlines DTW
Major Airlines MSP
Major Airlines JFK
Spirit FLL
Spirit MCO
United CLE
United DFW
United EWR
United IAD

San Juan, Puerto Rico to Chicago Airports

These are the major commercial airports we're currently monitoring in San Juan, Puerto Rico and Chicago. If your route includes a city with multiple airports, you may be able to find substantial savings by choosing an alternate airport.

Farecompare Research Tools

FareCompare's Flight Schedule Search Tool helps you find information about airline schedule filings, including flight numbers, depart times, and travel distance.

Cheap Domestic Flights to Chicago - CHI Last modified: Mar 22, 2017 2:34 -04:00Prices shown were found by travelers like you over the past 30 days

Cheap Flights from San Juan, Puerto Rico to Chicago