
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $192 (Kiwi.com) |
One-way from | $94 (Cheapflightsfares) |
Popular in | December |
Cheapest in | October |
Average price | $408 |
Good round-trip deal | $282 or less |
Good one-way deal | $142 or less |
Fly from
Fly to
Route
Depart
Return
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Wed 4/29
7:10 am-4:23 pm
1 stop8h 13m
San Juan Luis Munoz Marin Intl
Tue 5/5
2:45 pm-10:21 pm
1 stop8h 36m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Wed 4/22
9:50 am-8:24 pm
1 stop9h 34m
San Juan Luis Munoz Marin Intl
Thu 4/30
2:45 pm-11:59 pm
1 stop10h 14m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Mon 4/20
6:00 am-4:23 pm
1 stop9h 23m
San Juan Luis Munoz Marin Intl
Wed 4/29
7:30 am-4:26 pm
1 stop9h 56m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Tue 4/21
12:52 pm-11:12 pm
1 stop9h 20m
San Juan Luis Munoz Marin Intl
Sat 4/25
6:15 am-4:29 pm
1 stop11h 14m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 5/5
2:38 pm-8:34 pm
Nonstop4h 56m
San Juan Luis Munoz Marin Intl
Mon 5/11
7:40 am-11:53 am
Nonstop5h 13m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Mon 5/11
2:40 pm-11:55 pm
2 stops8h 15m
San Juan Luis Munoz Marin Intl
Fri 5/15
5:35 am-9:55 pm
2 stops17h 20m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Mon 5/11
2:38 pm-8:34 pm
Nonstop4h 56m
San Juan Luis Munoz Marin Intl
Sat 5/16
7:40 am-11:53 am
Nonstop5h 13m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Thu 4/23
2:38 pm-8:34 pm
Nonstop4h 56m
San Juan Luis Munoz Marin Intl
Wed 4/29
3:56 pm-8:15 pm
Nonstop5h 19m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Thu 6/4
11:35 am-12:25 am
1 stop11h 50m
San Juan Luis Munoz Marin Intl
Sun 6/7
5:20 am-1:05 pm
2 stops8h 45m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Fri 4/24
2:38 pm-8:34 pm
Nonstop4h 56m
San Juan Luis Munoz Marin Intl
Wed 4/29
7:40 am-11:53 am
Nonstop5h 13m
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*2 stars | |
| Price Accuracy2 stars | Trust Score*2 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 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*1 star |
Booking 28 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, April is the cheapest month in which you can book a flight from Chicago to San Juan Luis Munoz Marin Intl Airport (average of $91). Flying from Chicago to San Juan Luis Munoz Marin Intl Airport in December is currently the most expensive (average of $224). 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 26% 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 evenings 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 Sunday (13 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (7 on average).
Atlanta (ATL) – chosen by Cheapflights users on 45% 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 19% of weekly flights between Chicago and San Juan have experienced delays in the past year, with the average delay time being 139 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, American Airlines have had the lowest number of delays on this route, with just 17% of flights being delayed.
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Dane,Jan 2026
TYS - IAD
Comfort
Boarding
Entertainment
Crew
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Dane,Jan 2026
TYS - IAD
Comfort
Boarding
Entertainment
Crew
Food
Overall
Reviews
Dane,Jan 2026
TYS - IAD
Comfort
Boarding
Entertainment
Crew
Food
Overall
Reviews
Dane,Jan 2026
TYS - IAD
Comfort
Boarding
Entertainment
Crew
Food
Overall
Reviews
Dane,Jan 2026
TYS - IAD
Comfort
Boarding
Entertainment
Crew
Food
Overall
Reviews
Dane,Jan 2026
TYS - IAD
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$106 | Average$289 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$119 | Average$236 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$132 | Average$416 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$138 | Average$311 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$253 | Average$498 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$313 | Average$522 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$377 | Average$488 | FlexibilityNo cancel fee | On-time63% |