
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $222 (American Airlines) |
One-way from | $109 (American Airlines) |
Popular in | December |
Cheapest in | January |
Average price | $356 |
Good round-trip deal | $306 or less |
Good one-way deal | $135 or less |
Fly from
Fly to
Route
Depart
Return
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 7/28
8:03 am-4:45 pm
1 stop7h 42m
San Juan Luis Munoz Marin Intl
Sat 8/1
5:56 pm-11:53 pm
1 stop6h 57m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Mon 7/13
9:45 am-10:29 pm
1 stop11h 44m
San Juan Luis Munoz Marin Intl
Tue 7/21
12:56 pm-8:33 pm
1 stop8h 37m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Thu 7/30
5:10 pm-1:20 am
1 stop7h 10m
San Juan Luis Munoz Marin Intl
Wed 8/5
5:15 am-12:05 pm
2 stops7h 50m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Mon 7/27
5:10 pm-1:20 am
1 stop7h 10m
San Juan Luis Munoz Marin Intl
Thu 7/30
10:20 pm-9:15 am
1 stop11h 55m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Mon 6/29
2:38 pm-8:34 pm
Nonstop4h 56m
San Juan Luis Munoz Marin Intl
Tue 7/7
7:40 am-11:53 am
Nonstop5h 13m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Thu 7/16
2:30 pm-12:15 am
1 stop8h 45m
San Juan Luis Munoz Marin Intl
Tue 7/21
6:00 am-2:30 pm
2 stops9h 30m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Fri 7/3
11:35 am-12:25 am
1 stop11h 50m
San Juan Luis Munoz Marin Intl
Mon 7/6
10:20 pm-9:50 am
1 stop12h 30m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Mon 6/29
1:00 pm-12:15 am
2 stops10h 15m
San Juan Luis Munoz Marin Intl
Tue 7/21
6:00 am-2:30 pm
2 stops9h 30m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Thu 7/23
2:30 pm-12:15 am
1 stop8h 45m
San Juan Luis Munoz Marin Intl
Sun 7/26
6:25 am-12:20 pm
1 stop6h 55m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Mon 6/15
11:35 am-12:25 am
1 stop11h 50m
San Juan Luis Munoz Marin Intl
Fri 6/19
10:20 pm-8:50 am
1 stop11h 30m
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*1 star | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy1 star | Trust Score*3 stars |
Booking 56 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago to San Juan Luis Munoz Marin Intl Airport. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
Currently, May is the cheapest month in which you can book a flight from Chicago to San Juan Luis Munoz Marin Intl Airport (average of $319). Flying from Chicago to San Juan Luis Munoz Marin Intl Airport in December is currently the most expensive (average of $635). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
It’s typically best to fly out from Chicago to San Juan Luis Munoz Marin Intl Airport in the evening. Doing so could potentially save you 22% on the flight price compared to flying in the morning, which is usually more expensive.
Travelers seeking maximum savings on their Chicago to San Juan Luis Munoz Marin Intl Airport flight should consider departing on Monday afternoons when fares are most often at their lowest. Saturday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
The most flights from CHI to SJU are scheduled on a Monday (8 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (8 on average).
Orlando (MCO) – chosen by Cheapflights users on 39% of 1-stop itineraries from Chicago to San Juan Luis Munoz Marin Intl Airport on Cheapflights.
Boston (BOS) is the most affordable 1-stop option, with an average round-trip price of $132.
Flights via Philadelphia (PHL) have the shortest average one-way travel time for 1-stop routes: 6h 49m.
Flights via Atlanta (ATL) offer the fastest connection on this route, with an average layover time of 1h 12m.
About 22% of weekly flights between Chicago and San Juan have experienced delays in the past year, with the average delay time being 140 minutes.
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.
Thursday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.
Over the last year, United Airlines have had the lowest number of delays on this route, with just 19% of flights being delayed.
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Anonymous,Apr 2026
DFW - EWR
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Anonymous,Apr 2026
DFW - EWR
Crew
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Anonymous,Apr 2026
DFW - EWR
Crew
Boarding
Entertainment
Overall
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Anonymous,Apr 2026
DFW - EWR
Crew
Boarding
Entertainment
Overall
Comfort
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Anonymous,Apr 2026
DFW - EWR
Crew
Boarding
Entertainment
Overall
Comfort
Food
Reviews
Anonymous,Apr 2026
DFW - EWR
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$119 | Average$235 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$122 | Average$289 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$132 | Average$387 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$140 | Average$314 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$256 | Average$504 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$309 | Average$509 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$352 | Average$489 | FlexibilityNo cancel fee | On-time63% |