Cheap flights from Chicago (CHI) to San Juan
How to find the cheapest flight from Chicago (CHI) to San Juan
All the information you need to plan the best CHI to PR1 flight in 2023: compare Chicago to San Juan flight prices with the expected peak season, weather and rainfall in San Juan.
CHI - SJU Price | $275 - $578 |
|---|---|
SJU Temperature | 77 - 82.4 °F |
SJU Rainfall | 2.2 - 6.1 inches |
| Popular in | December | High demand for flights, 30% potential price rise |
|---|---|---|
| Cheapest in | February | Best time to find cheap flights, 32% potential price drop |
| Round-trip from | $275 | From Chicago (CHI) to San Juan |
| One-way from | $94 | One-way flight from Chicago (CHI) to San Juan |
How far in advance should I book a flight from Chicago to San Juan?
Travelers have found it’s best to book a flight 38 days in advance to save up to 16% compared to booking the same week of travel. As your travel date approaches, the cost of this flight route may potentially increase. While opting to book 38 days out may not be an option for all, there are still additional ways to secure a deal in the near future. You might find a flight from Chicago to San Juan 1-2 weeks in advance for as low as $402, or $467 for flights within the next 24 hours.
What is the cheapest month to fly from Chicago to San Juan?
The best pricing can be found in the month of February. Prices to San Juan from Chicago average $403. You can even find prices in February for less than $403, as users have found deals to San Juan from as low as $168. The month of December appears to be one of the more expensive times to travel to San Juan from Chicago. Flying in the targeted month can save you up to 43%.
When is the cheapest time to fly from Chicago to San Juan (CHI - SJU)?
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago to San Juan as you normally would.
Cheap flights from Chicago to San Juan in February, March 2023
The best prices found for CHI to San Juan flights for February, March
Chicago O'Hare Intl
San Juan Luis Munoz Marin Intl
1 stop
17h 31mSan Juan Luis Munoz Marin Intl
Chicago O'Hare Intl
1 stop
20h 04mMultiple Airlines
Chicago Midway
San Juan Luis Munoz Marin Intl
1 stop
8h 57mSan Juan Luis Munoz Marin Intl
Chicago Midway
1 stop
26h 51mFrontier
Chicago O'Hare Intl
San Juan Luis Munoz Marin Intl
1 stop
12h 42mSan Juan Luis Munoz Marin Intl
Chicago O'Hare Intl
1 stop
15h 05mFrontier
Chicago to San Juan 2023 flight deals
Cheap flights to San Juan from Chicago found for this year
Chicago O'Hare Intl
San Juan Luis Munoz Marin Intl
1 stop
17h 31mSan Juan Luis Munoz Marin Intl
Chicago O'Hare Intl
1 stop
20h 04mMultiple Airlines
Chicago Midway
San Juan Luis Munoz Marin Intl
1 stop
8h 57mSan Juan Luis Munoz Marin Intl
Chicago Midway
1 stop
26h 51mFrontier
Chicago O'Hare Intl
San Juan Luis Munoz Marin Intl
1 stop
12h 42mSan Juan Luis Munoz Marin Intl
Chicago O'Hare Intl
1 stop
15h 05mFrontier
Cheap Frontier flights from Chicago to San Juan
Chicago Midway
San Juan Luis Munoz Marin Intl
1 stop
8h 57mSan Juan Luis Munoz Marin Intl
Chicago Midway
1 stop
26h 51mFrontier
Chicago Midway
San Juan Luis Munoz Marin Intl
1 stop
18h 51mSan Juan Luis Munoz Marin Intl
Chicago Midway
1 stop
26h 51mFrontier
Chicago O'Hare Intl
San Juan Luis Munoz Marin Intl
1 stop
15h 50mSan Juan Luis Munoz Marin Intl
Chicago O'Hare Intl
1 stop
15h 05mFrontier
Cheap Spirit Airlines flights from Chicago to San Juan
Chicago O'Hare Intl
San Juan Luis Munoz Marin Intl
1 stop
13h 49mSan Juan Luis Munoz Marin Intl
Chicago O'Hare Intl
1 stop
12h 18mSpirit Airlines
Chicago O'Hare Intl
San Juan Luis Munoz Marin Intl
1 stop
14h 53mSan Juan Luis Munoz Marin Intl
Chicago O'Hare Intl
2 stops
16h 43mSpirit Airlines
Chicago O'Hare Intl
San Juan Luis Munoz Marin Intl
1 stop
14h 01mSan Juan Luis Munoz Marin Intl
Chicago O'Hare Intl
2 stops
22h 20mSpirit Airlines
Non-stop flights to San Juan from Chicago
Save time with Chicago to San Juan direct flight deals
Chicago O'Hare Intl
San Juan Luis Munoz Marin Intl
Nonstop
4h 46mSan Juan Luis Munoz Marin Intl
Chicago O'Hare Intl
Nonstop
5h 15mMultiple Airlines
Chicago O'Hare Intl
San Juan Luis Munoz Marin Intl
Nonstop
4h 31mSan Juan Luis Munoz Marin Intl
Chicago O'Hare Intl
Nonstop
5h 15mAmerican Airlines
Chicago O'Hare Intl
San Juan Luis Munoz Marin Intl
Nonstop
4h 46mSan Juan Luis Munoz Marin Intl
Chicago O'Hare Intl
Nonstop
5h 10mUnited Airlines
Last minute flights from Chicago to San Juan
Late deals on return flights to San Juan from Chicago, departing today and this week
Chicago Midway
San Juan Luis Munoz Marin Intl
1 stop
8h 57mSan Juan Luis Munoz Marin Intl
Chicago Midway
1 stop
26h 51mFrontier
Chicago Midway
San Juan Luis Munoz Marin Intl
1 stop
18h 51mSan Juan Luis Munoz Marin Intl
Chicago Midway
1 stop
26h 51mFrontier
Chicago O'Hare Intl
San Juan Luis Munoz Marin Intl
1 stop
15h 50mSan Juan Luis Munoz Marin Intl
Chicago O'Hare Intl
1 stop
15h 05mFrontier
One-way flights to San Juan from Chicago
The cheapest one-way flights from Chicago to San Juan
Chicago Midway
San Juan Luis Munoz Marin Intl
1 stop
13h 10mFrontier
Chicago Midway
San Juan Luis Munoz Marin Intl
1 stop
17h 42mFrontier
Chicago Midway
San Juan Luis Munoz Marin Intl
1 stop
12h 41mFrontier
Reviews of Airlines Servicing San Juan
Crew
Food
Boarding
Entertainment
Overall
Comfort
Reviews
Seats are small, hard and don’t recline. Some arm rests are stationary. Flight took longer on Spirit than other airlines. Baggage claim was ridiculous slow. Took over an hour to get bags in Dallas and Las Vegas. Not worth the small savings! I’ll fly SWA or some other airline.
Crew
Food
Boarding
Entertainment
Overall
Comfort
Reviews
Seats are small, hard and don’t recline. Some arm rests are stationary. Flight took longer on Spirit than other airlines. Baggage claim was ridiculous slow. Took over an hour to get bags in Dallas and Las Vegas. Not worth the small savings! I’ll fly SWA or some other airline.
Crew
Food
Boarding
Entertainment
Overall
Comfort
Reviews
Seats are small, hard and don’t recline. Some arm rests are stationary. Flight took longer on Spirit than other airlines. Baggage claim was ridiculous slow. Took over an hour to get bags in Dallas and Las Vegas. Not worth the small savings! I’ll fly SWA or some other airline.
Related info for your journey
Useful info, stats and facts about Chicago to San Juan flights.
Which airlines flying from Chicago to San Juan have flexible cancellations due to COVID-19?
Some of the carriers operating flights from Chicago to San Juan that may be offering flexible cancellation policies are American Airlines, United Airlines, and Frontier. Our site will let you filter for all airlines offering greater flexibility due to COVID-19.
Can I find flights from Chicago to San Juan for under $200 on Cheapflights?
Yes, there are multiple flights from Chicago to San Juan for under $200. The cheapest flight booked recently is on Multiple Airlines for just $148, but on average you can expect to pay $161.
Are there nonstop flights from Chicago to San Juan for under $400 on Cheapflights?
Cheapflights has at least 20 direct flights from Chicago to San Juan under $400. A good price for a nonstop flight from Chicago to San Juan is less than $428.
Are there last-minute flights available from Chicago to San Juan for under $200?
There are currently 20+ open flights from Chicago to San Juan within the next 7 days for less than $200.
What are the cheapest airlines flying from Chicago to San Juan round-trip?
Cheapflights users have booked flights from Chicago to San Juan round-trip from $156. Another airline that can offer you cheap pricing is Spirit Airlines. Frontier is priced at 61% lower than the current average price of a flight leaving 3 months from now.
What are the most popular airlines that fly from Chicago to San Juan?
Consider American Airlines, Alaska Airlines or JetBlue when booking your flight. These represent the most popular airlines when flying from Chicago to San Juan.
What are the most reliable airlines from Chicago to San Juan?
Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Chicago to San Juan on time: Air Canada (85%), Air New Zealand (85%), American Airlines (77%).
What are the cheapest flights from Chicago to San Juan?
Looking at all options, your cheapest flight can be booked for $185. While the most popular route (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl) can be booked for $161 on average our data indicates $1,038 when flying from Chicago to San Juan.
Other flights from Chicago
Top 8 airlines flying from Chicago to San Juan
The chart below displays the airlines Cheapflights users traveling from Chicago to San Juan choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
Hourly flight availability from Chicago to San Juan
See what time of day planes typically take off from Chicago to San Juan
| 1%of flight departures | Early morningMidnight to 6 am |
|---|---|
| 44%of flight departures | Morning6 am to noon |
| 55%of flight departures | AfternoonNoon to 6 pm |
| 0%of flight departures | Evening6 pm to midnight |
Weekly flight availability from Chicago to San Juan
See how many times per day planes take to the skies headed from Chicago to San Juan
| Sunday | 7daily flights |
|---|---|
| Monday | 9daily flights |
| Tuesday | 9daily flights |
| Wednesday | 9daily flights |
| Thursday | 9daily flights |
| Friday | 9daily flights |
| Saturday | 7daily flights |