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Cheap flights from San Juan (SJU) to Chicago (CHI)

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The best prices from San Juan to Chicago are usually found in August or March, booked 2 days in advance, depart on a Wednesday or Tuesday and return on a Tuesday

How to find the cheapest flight from
San Juan (SJU) to Chicago (CHI)

PR1 - CHI
Price
$158 - $368
CHI
Temperature
33.8 - 84.2 °F
CHI
Rainfall
0.7 - 4.3 inches

Popular in

December

High demand for flights, 28% potential price rise

Cheapest in

August

Best time to find cheap flights, 41% potential price drop

Round-trip from

$158

From San Juan to Chicago

One-way from

$78

One-way flight from San Juan to Chicago

Flight route prices based on searches on Cheapflights within the last 3 days, monthly prices based on aggregated historical data.
What is the cheapest day to fly round-trip from San Juan to Chicago?

Tuesday is generally a great day to depart. Flying on this day could help you save up to 39%.

How far in advance should I book a flight from San Juan to Chicago?

To save up to 10% on this flight, we recommend booking at least 20 days prior to travel. The price may fluctuate and will likely increase closer to your departure date. Users on Cheapflights have found tickets from San Juan to Chicago from $137 1-2 weeks out and tickets from $157 for flights departing within the next 72 hours.

What is the cheapest month to fly from San Juan to Chicago?

April is one of the best times of the year to fly to Chicago from San Juan. Prices for April average $135 per person but you can even find prices for as low as $33. The most expensive prices can be found in the month of December. Opting for a April flight can save you 49% on your journey compared to booking in April

When is the cheapest time to fly from San Juan to Chicago (PR1 - CHI)?

When flying from San Juan to Chicago, the time of day you fly usually plays a role in the price. Save by searching for a flight in the morning, which can drop the price by up to 35% versus a flight at noon.

Cheap flights from San Juan to Chicago in January, February 2021

The best prices found for SJU to CHI flights for January, February
25 Feb - 28 Feb
$97pp
SJU
San Juan Luis Munoz Marin Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
26 Feb - 2 Mar
$100pp
SJU
San Juan Luis Munoz Marin Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
19 Feb - 23 Feb
$107pp
SJU
San Juan Luis Munoz Marin Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl

San Juan to Chicago 2021 flight deals

Cheap flights to Chicago from San Juan found for this year
25 Feb - 28 Feb
$97pp
SJU
San Juan Luis Munoz Marin Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
26 Feb - 2 Mar
$100pp
SJU
San Juan Luis Munoz Marin Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
3 Mar - 10 Mar
$107pp
SJU
San Juan Luis Munoz Marin Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl

Non-stop flights to Chicago from San Juan

Save time with San Juan to Chicago direct flight deals
29 Apr - 3 May
$157pp
SJU
San Juan Luis Munoz Marin Intl
Frontier
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
Non-Stop
SJU
San Juan Luis Munoz Marin Intl
24 Mar - 29 Mar
$207pp
SJU
San Juan Luis Munoz Marin Intl
Frontier
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
Non-Stop
SJU
San Juan Luis Munoz Marin Intl
9 Apr - 12 Apr
$208pp
SJU
San Juan Luis Munoz Marin Intl
Frontier
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
Non-Stop
SJU
San Juan Luis Munoz Marin Intl

Last minute flights from San Juan to Chicago

Late deals on round-trip flights to Chicago from San Juan, departing today and this week
4 Feb - 7 Feb
$100pp
SJU
San Juan Luis Munoz Marin Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
4 Feb - 9 Feb
$116pp
SJU
San Juan Luis Munoz Marin Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
4 Feb - 9 Feb
$117pp
SJU
San Juan Luis Munoz Marin Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl

One-way flights to Chicago from San Juan

The cheapest one-way flights from San Juan to Chicago
6:11 pm - 3:05 am
Multiple Airlines
1 Stop
10h 54m
SJU - ORD
Multiple Airlines
$78
SmartFares
10:35 pm - 8:28 am
Spirit Airlines
2 Stops
11h 53m
SJU - ORD
Spirit Airlines
$82
Travelocity
9:10 am - 5:34 pm
JetBlue
1 Stop
10h 24m
SJU - ORD
JetBlue

Related info for your journey

Useful info, stats and facts about San Juan to Chicago flights.

Flight FAQs

From San Juan to Chicago

Are flight prices decreasing from San Juan to Chicago due to COVID-19 (coronavirus)?

At this time, Cheapflights has noticed price decreases for many domestic flights due to COVID-19. Travel is not necessarily recommended at this time, and flights may be prone to cancellation: please check with local authorities in both San Juan and Chicago for travel alerts, and be sure to review the airline's cancellation policy and travel advisories before booking. For more information, please view our post on what to know about COVID-19 (coronavirus) and travel.

What safety measures are being taken by airlines flying from San Juan to Chicago to control the spread of COVID-19?

Airlines globally have implemented additional safety measures to accommodate you. Delta is one of them. Some of the new policies that have been implemented to accommodate travelers flying from San Juan to Chicago are improved sanitation, HEPA filters, mask requirements, social distance seating (for a limited time), and pre-flight testing for antibodies and symptoms. Policies will vary by airline.

Which airlines flying from San Juan to Chicago have flexible cancellations due to COVID-19?

Due to the rapidly changing circumstances due to COVID-19, airlines like United Airlines, American Airlines, and Spirit Airlines flying from San Juan to Chicago have implemented new flexible cancellation policies.

Can I find flights from San Juan to Chicago for under $100 on Cheapflights?

Yes, there are multiple flights from San Juan to Chicago for under $100. The cheapest flight booked recently is on Spirit Airlines for just $97, but on average you can expect to pay $119.

Are there nonstop flights from San Juan to Chicago for under $200 on Cheapflights?

Cheapflights has at least 20 direct flights from San Juan to Chicago under $200. A good price for a nonstop flight from San Juan to Chicago is less than $292.

Are there last-minute flights available from San Juan to Chicago for under $100?

There are currently 20+ open flights from San Juan to Chicago within the next 7 days for less than $100.

What days are nonstop flights available from San Juan to Chicago?

Days when nonstop flights are available for this flight are: Monday, Tuesday.

How many flights depart from San Juan to Chicago on average per day?

2 flight departures from San Juan to Chicago per day on average.
Afternoon (Noon - 6pm) - 100% of flight departures

Is San Juan weather warmer or cooler than Chicago?

We forecast the temperature to be around the 90 °F's in June, on average. The temperature in Chicago is generally colder than in San Juan. Book flights in a timely manner in correlation to your departure date.

How long is the flight from San Juan to Chicago?

Spirit Airlines and Delta can get you from San Juan to Chicago in just under 6h 30m. Your travel time can differ by up to 14m. There are 2085 mi between San Juan and Chicago. This flight may include one or multiple stops.

What is the cheapest airline to fly from San Juan to Chicago round-trip?

Our cheapest airline available from San Juan to Chicago is Spirit Airlines. Our recent data shows that you can find tickets from as low as $97 on this airline. You may be able to fly from San Juan to Chicago for 63% less than the average price by searching for this airline.

What are the cheapest airlines to fly from San Juan to Chicago one-way?

For one-way options, check prices for Spirit Airlines. According to our data, you can fly for as low as $44. Users have also found prices from $74 and $83 on Spirit Airlines and Frontier, respectively.

Destination information for Chicago

Things to know before you go. Useful info for your trip from San Juan to Chicago
Today's exchange rate
$1 = $1.00
Average temperature for January in Chicago
33.8 °F
Avg rainfall for January in Chicago
0.7 ″

Airports servicing San Juan

San Juan Isla Grande (SIG)

Airports servicing Chicago

Chicago Midway (MDW)
Rockford (RFD)

Top 6 airlines flying from San Juan to Chicago

The chart below displays the airlines Cheapflights users traveling from San Juan to Chicago choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.

Airline Cheapest Average Flexibility On-time COVID-19 safety
Frontier
$85 $226 No cancel fee 62%
Spirit Airlines
$118 $276 No cancel fee 65%
JetBlue
$174 $340 No cancel fee 62%
United Airlines
$183 $392 No cancel fee 69%
American Airlines
$182 $470 No cancel fee 71%
Delta
$164 $522 No cancel fee N/A

Hourly flight availability from San Juan to Chicago

Afternoon Noon to 6 PM 72% of SJU to CHI departures
Morning 6 AM to noon 27% of SJU to CHI departures
Early morning Midnight to 6 AM 1% of SJU to CHI departures
Evening 6 PM to midnight 0% of SJU to CHI departures
Midnight
6 AM
Noon
6 PM
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