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Most accurate provider | CheapOair 3 stars  | 
|---|---|
Most trusted provider | CheapOair 3 stars  | 
Round-trip from | $210 (Kiwi.com)  | 
One-way from | $112 (Kiwi.com)  | 
Popular in | December | 
Cheapest in | April | 
Average price | $381 | 
Good round-trip deal | $358 or less | 
Good one-way deal | $181 or less | 
Fly from
Fly to
Route
Depart
Return
Price
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Sun 1/25
2:20 pm-9:00 pm
Nonstop4h 40m
San Juan Luis Munoz Marin Intl
Tue 1/27
2:05 am-10:53 am
1 stop10h 48m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Sun 1/25
11:18 am-11:44 pm
1 stop10h 26m
San Juan Luis Munoz Marin Intl
Wed 2/4
7:00 am-5:45 pm
1 stop12h 45m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Mon 1/26
3:15 pm-12:35 am
1 stop7h 20m
San Juan Luis Munoz Marin Intl
Thu 1/29
6:10 am-1:55 pm
2 stops9h 45m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Mon 1/19
6:00 am-2:30 pm
1 stop6h 30m
San Juan Luis Munoz Marin Intl
Fri 1/23
6:15 am-12:01 pm
1 stop7h 46m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Sun 1/18
1:50 pm-12:35 am
2 stops8h 45m
San Juan Luis Munoz Marin Intl
Thu 1/22
6:10 am-1:55 pm
2 stops9h 45m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Sun 1/25
1:35 pm-12:05 am
2 stops8h 30m
San Juan Luis Munoz Marin Intl
Wed 1/28
2:35 pm-10:05 pm
2 stops9h 30m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Mon 2/2
9:50 am-11:10 pm
1 stop11h 20m
San Juan Luis Munoz Marin Intl
Sat 2/7
6:00 am-1:40 pm
2 stops9h 40m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Sun 2/1
2:20 pm-9:00 pm
Nonstop4h 40m
San Juan Luis Munoz Marin Intl
Wed 3/4
8:35 am-11:57 am
Nonstop5h 22m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Thu 12/25
6:45 am-4:26 pm
1 stop7h 41m
San Juan Luis Munoz Marin Intl
Tue 1/6
11:15 am-7:45 pm
1 stop10h 30m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Thu 1/29
2:20 pm-9:00 pm
Nonstop4h 40m
San Juan Luis Munoz Marin Intl
Wed 2/4
8:35 am-11:57 am
Nonstop5h 22m
| Provider | Price Accuracy | Trust Score* | 
|---|---|---|
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*2 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | 
Booking 53 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, February is the cheapest month in which you can book a flight from Chicago to San Juan Luis Munoz Marin Intl Airport (average of $127). Flying from Chicago to San Juan Luis Munoz Marin Intl Airport in December is currently the most expensive (average of $188). 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 28% on the flight price compared to flying at noon, 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 Tuesday mornings when fares are most often at their lowest. Sunday mornings 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 (9 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (6 on average).
Orlando (MCO) – chosen by Cheapflights users on 40% of 1-stop itineraries from Chicago to San Juan Luis Munoz Marin Intl Airport on Cheapflights.
Miami (MIA) is the most affordable 1-stop option, with an average round-trip price of $210.
Flights via Tampa (TPA) have the shortest average one-way travel time for 1-stop routes: 6h 29m.
Flights via Tampa (TPA) offer the fastest connection on this route, with an average layover time of 1h 00m.
Overall
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OKC - AUS
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OKC - AUS
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OKC - AUS
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Boarding
Entertainment
Crew
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Mike,Aug 2025
OKC - AUS
Overall
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Entertainment
Crew
Food
Comfort
Reviews
Mike,Aug 2025
OKC - AUS
| Airline | Cheapest | Average | Flexibility | On-time | 
|---|---|---|---|---|
| Cheapest$106 | Average$285 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$140 | Average$317 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$196 | Average$401 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$271 | Average$406 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$273 | Average$488 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$357 | Average$524 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$380 | Average$490 | FlexibilityNo cancel fee | On-time63% |