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)

All the information you need to plan the best SJU to CHI flight in 2021: compare San Juan to Chicago flight prices with the expected peak season, weather and rainfall in Chicago.
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

$126

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 33% versus a flight at noon.

Cheap flights from San Juan to Chicago in May, June 2021

The best prices found for SJU to CHI flights for May, June
4 Jun - 8 Jun
$192pp
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
18 May - 24 May
$193pp
SJU
San Juan Luis Munoz Marin Intl
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
Non-Stop
SJU
San Juan Luis Munoz Marin Intl
21 May - 22 May
$194pp
SJU
San Juan Luis Munoz Marin Intl
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
Non-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
9 Sep - 13 Sep
$170pp
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 Sep - 13 Sep
$176pp
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 Sep - 29 Sep
$191pp
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

Non-stop flights to Chicago from San Juan

Save time with San Juan to Chicago direct flight deals
9 Sep - 13 Sep
$170pp
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 Sep - 13 Sep
$176pp
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 Sep - 29 Sep
$191pp
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
21 May - 22 May
$194pp
SJU
San Juan Luis Munoz Marin Intl
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
Non-Stop
SJU
San Juan Luis Munoz Marin Intl
21 May - 22 May
$203pp
SJU
San Juan Luis Munoz Marin Intl
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
Non-Stop
SJU
San Juan Luis Munoz Marin Intl
22 May - 24 May
$207pp
SJU
San Juan Luis Munoz Marin Intl
Multiple Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
Non-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
10:00 am - 6:43 pm
JetBlue
1 Stop
9h 43m
SJU - ORD
JetBlue
4:45 am - 8:55 am
United Airlines
Nonstop
5h 10m
SJU - ORD
United Airlines
$133
United
1:13 pm - 7:58 pm
Spirit Airlines
1 Stop
7h 45m
SJU - ORD
Spirit Airlines
$134
Kiwi.com

Related info for your journey

Useful info, stats and facts about <span class="emphasized">San Juan</span> to <span class="emphasized">Chicago</span> 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.

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 $200 on Cheapflights?

Yes, there are multiple flights from San Juan to Chicago for under $200. The cheapest flight booked recently is on Frontier for just $170, but on average you can expect to pay $204.

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 $222.

Are there last-minute flights available from San Juan to Chicago for under $200?

There are currently 20+ open flights from San Juan to Chicago within the next 7 days for less than $200.

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?

United Airlines, Frontier, and Delta can get you from San Juan to Chicago in just under 5h 10m. Your travel time can differ by up to 1h 34m. This flight may include one or multiple stops.

What are the cheapest airlines flying from San Juan to Chicago round-trip?

Our cheapest airline available from San Juan to Chicago is Frontier. Our recent data shows that you can find tickets from as low as $170 on this airline. An additional option worth looking into is Spirit Airlines, starting at $192. You may be able to fly from San Juan to Chicago for 36% less than the average price by searching for these airlines.

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

For one-way options, check prices for Frontier. According to our data, you can fly for as low as $78. Users have also found prices from $95 and $112 on Frontier and Spirit Airlines, respectively.

Destination information for Chicago

Things to know before you go - useful duration and weather info for your trip from San Juan to Chicago.
Today's exchange rate
$1 = $1.00
Flight duration
5h 08m
Average temperature for May in Chicago
71.6 °F
Avg rainfall for May in Chicago
4.3 ″

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

See what time of day planes typically take off from San Juan towards Chicago.
Morning 6 AM to noon 68% of SJU to CHI departures
Afternoon Noon to 6 PM 31% 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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