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

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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 2022: compare San Juan to Chicago flight prices with the expected peak season, weather and rainfall in Chicago.
SJU - CHI
Price
$187 - $472
CHI
Temperature
23 - 73.4 °F
CHI
Rainfall
1.7 - 4.9 inches

Popular in

June

High demand for flights, 35% potential price rise

Cheapest in

October

Best time to find cheap flights, 39% potential price drop

Round-trip from

$187

From San Juan to Chicago (CHI)

One-way from

$122

One-way flight from San Juan to Chicago (CHI)

Flight route prices based on searches on Cheapflights within the last 3 days, monthly prices based on aggregated historical data.
How far in advance should I book a flight from San Juan to Chicago?

When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 43 days in advance, which can save you up to 30% on flights from San Juan to Chicago compared to booking the week you need them. Waiting 43 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at $375. For sooner than that we have options available in the next 3 days from $423.

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

The best pricing can be found in the month of October. Prices to Chicago from San Juan average $307. You can even find prices in October for less than $307, as users have found deals to Chicago from as low as $104. The month of June appears to be one of the more expensive times to travel to Chicago from San Juan. Flying in the targeted month can save you up to 53%.

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

When flying from San Juan to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Cheap flights from San Juan to Chicago in August, September 2022

The best prices found for SJU to CHI flights for August, September
3 Sep - 13 Sep
$200pp
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 Sep - 10 Sep
$202pp
SJU
San Juan Luis Munoz Marin Intl
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
29 Aug - 30 Aug
$203pp
SJU
San Juan Luis Munoz Marin Intl
Multiple 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 2022 flight deals

Cheap flights to Chicago from San Juan found for this year
3 Sep - 13 Sep
$200pp
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 Sep - 10 Sep
$202pp
SJU
San Juan Luis Munoz Marin Intl
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
29 Aug - 30 Aug
$203pp
SJU
San Juan Luis Munoz Marin Intl
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl

Cheap Spirit Airlines flights from San Juan to Chicago

3 Sep - 13 Sep
$200pp
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
16 Sep - 19 Sep
$208pp
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
16 Sep - 19 Sep
$215pp
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

Cheap Delta flights from San Juan to Chicago

16 Aug - 22 Aug
$429pp
SJU
San Juan Luis Munoz Marin Intl
Delta
 
1 STOP
MDW
Chicago Midway
MDW
Chicago Midway
Delta
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
18 Aug - 31 Aug
$479pp
SJU
San Juan Luis Munoz Marin Intl
Delta
 
1 STOP
MDW
Chicago Midway
MDW
Chicago Midway
Delta
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
17 Aug - 22 Aug
$484pp
SJU
San Juan Luis Munoz Marin Intl
Delta
 
1 STOP
MDW
Chicago Midway
MDW
Chicago Midway
Delta
 
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
19 Jan - 22 Jan
$300pp
SJU
San Juan Luis Munoz Marin Intl
American Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
Non-Stop
SJU
San Juan Luis Munoz Marin Intl
14 Dec - 17 Jan
$314pp
SJU
San Juan Luis Munoz Marin Intl
Multiple Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
Non-Stop
SJU
San Juan Luis Munoz Marin Intl
2 Nov - 7 Nov
$325pp
SJU
San Juan Luis Munoz Marin Intl
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
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
17 Aug - 24 Aug
$228pp
SJU
San Juan Luis Munoz Marin Intl
Multiple Airlines
 
1 STOP
MDW
Chicago Midway
MDW
Chicago Midway
Multiple Airlines
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
16 Aug - 30 Aug
$248pp
SJU
San Juan Luis Munoz Marin Intl
Multiple Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
17 Aug - 24 Aug
$259pp
SJU
San Juan Luis Munoz Marin Intl
Spirit Airlines
   
2 STOPS
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
4:26 am - 11:31 am
Frontier
1 Stop
9h 05m
SJU - MDW
Frontier
$122
Kiwi.com
4:29 pm - 6:50 am
Spirit Airlines
2 Stops
15h 21m
SJU - ORD
Spirit Airlines
$123
JustFly
10:26 pm - 7:18 am
Multiple Airlines
1 Stop
9h 52m
SJU - ORD
Multiple Airlines
$124
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

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 American Airlines, United Airlines, and Frontier 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 Multiple Airlines for just $188, but on average you can expect to pay $207.

Are there nonstop flights from San Juan to Chicago for under $300 on Cheapflights?

Cheapflights has at least 20 direct flights from San Juan to Chicago under $300. A good price for a nonstop flight from San Juan to Chicago is less than $383.

Are there last-minute flights available from San Juan to Chicago for under $300?

There are currently 20+ open flights from San Juan to Chicago within the next 7 days for less than $300.

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

Cheapflights users have booked flights from San Juan to Chicago round-trip from $200. Another airline that can offer you cheap pricing is Frontier. Spirit Airlines is 34% cheaper than the average price of flights available within the next 90 days to this destination.

What are the cheapest flights from San Juan to Chicago?

While on average a flight from San Juan to Chicago is generally $757, our data shows the cheapest flight currently is $150. When looking at the most popular route, (San Juan Luis Munoz Marin Intl - Chicago O'Hare Intl), you can expect to pay $208 for that flight.

What are the most popular airlines that fly from San Juan to Chicago?

Consider Undisclosed Carrier, American Airlines or JetBlue when booking your flight. These represent the most popular airlines when flying from San Juan to Chicago.

What are the most reliable airlines from San Juan to Chicago?

No one likes to see their flight delayed. When booking a flight from San Juan to Chicago consider choosing Air Canada (83%), United Airlines (83%) or Air New Zealand (83%) as they are the most reliable in getting you off to your destination on time.

COVID Restrictions

View COVID Travel Restrictions for Chicago, IL

Do I need a COVID test to fly to Chicago from San Juan?

Information is based on travel restrictions from San Juan to Chicago

Most visitors from San Juan can enter Chicago without restrictions.

COVID-19 testing requirements
Visitors from San Juan are not required to present a negative COVID-19 PCR test or antigen result upon entering Chicago.

Quarantine requirements
Visitors from San Juan are not required to quarantine after entering Chicago.

Do I need a test to fly back to San Juan from Chicago?

Returning to San Juan from Chicago

COVID-19 testing requirements
Visitors from Chicago are not required to present a negative COVID-19 PCR test or antigen result upon entering San Juan.

Quarantine requirements
Visitors from Chicago are not required to quarantine after entering San Juan.

Hide COVID Travel Restrictions for Chicago, IL

Top 7 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
Juneyao Airlines
$13 $23 No cancel fee 66%

We couldn't confirm the COVID-19 safety measures taken by Juneyao Airlines. Please check directly on their website for additional information.

Delta
$63 $398 No cancel fee N/A
Spirit Airlines
$87 $314 No cancel fee 65%
Frontier
$93 $277 No cancel fee 62%
United Airlines
$112 $388 No cancel fee 69%
JetBlue
$117 $279 No cancel fee 62%
American Airlines
$161 $463 No cancel fee 71%

Hourly flight availability from San Juan to Chicago

See what time of day planes typically take off from San Juan towards Chicago.
Early morning Midnight to 6 AM 71% of SJU to CHI departures
Afternoon Noon to 6 PM 27% of SJU to CHI departures
Morning 6 AM to noon 2% of SJU to CHI departures
Evening 6 PM to midnight 0% of SJU to CHI departures
Midnight
6 AM
Noon
6 PM
Weekly flight availability
from San Juan to Chicago
See how many times per day planes take to the skies headed from San Juan to Chicago.
Sunday
7 daily flights
Monday
4 daily flights
Tuesday
4 daily flights
Wednesday
4 daily flights
Thursday
4 daily flights
Friday
4 daily flights
Saturday
10 daily flights