Spirit's Big Front Seats offer 11 inches more legroom, ideal for medium-haul comfort.
Use Spirit's Bag-O-Tron tool to compare baggage fees and save money.

Most accurate provider | CheapOair 3 stars |
|---|---|
Most trusted provider | CheapOair 3 stars |
Round-trip from | $192 (JetBlue) |
One-way from | $99 (Kiwi.com) |
Popular in | December |
Cheapest in | April |
Average price | $361 |
Good round-trip deal | $308 or less |
Good one-way deal | $141 or less |
Fly from
Fly to
Route
Depart
Return
Price
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Thu 3/12
10:56 am-11:23 pm
1 stop11h 27m
San Juan Luis Munoz Marin Intl
Wed 3/18
3:26 am-11:25 am
1 stop8h 59m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Wed 4/1
10:00 am-10:01 pm
1 stop11h 01m
San Juan Luis Munoz Marin Intl
Wed 4/15
11:25 pm-8:51 am
1 stop10h 26m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Wed 3/11
12:41 pm-10:44 pm
1 stop9h 03m
San Juan Luis Munoz Marin Intl
Sun 3/15
1:30 am-10:05 am
1 stop9h 35m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Mon 2/9
7:45 am-6:05 pm
1 stop8h 20m
San Juan Luis Munoz Marin Intl
Fri 2/13
5:22 pm-11:21 pm
1 stop7h 59m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Sat 2/21
6:04 am-4:56 pm
1 stop8h 52m
San Juan Luis Munoz Marin Intl
Sat 2/28
5:10 am-12:04 pm
1 stop8h 54m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Fri 2/6
9:15 am-7:23 pm
1 stop8h 08m
San Juan Luis Munoz Marin Intl
Wed 2/11
9:25 am-7:31 pm
1 stop12h 06m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 3/3
10:00 am-9:56 pm
1 stop9h 56m
San Juan Luis Munoz Marin Intl
Sat 3/7
4:15 am-11:49 am
1 stop8h 34m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 2/24
2:20 pm-9:00 pm
Nonstop4h 40m
San Juan Luis Munoz Marin Intl
Fri 3/6
8:30 am-11:52 am
Nonstop5h 22m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Sat 2/28
12:59 pm-12:29 am
1 stop9h 30m
San Juan Luis Munoz Marin Intl
Fri 3/13
1:30 am-10:05 am
1 stop9h 35m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Mon 3/16
10:56 am-11:23 pm
1 stop11h 27m
San Juan Luis Munoz Marin Intl
Mon 3/16
1:30 am-10:05 am
1 stop9h 35m
| 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 Accuracy- | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*1 star |
Booking 34 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, September 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 $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 33% 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 Tuesday mornings 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 (11 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (8 on average).
Orlando (MCO) – chosen by Cheapflights users on 41% 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 Philadelphia (PHL) have the shortest average one-way travel time for 1-stop routes: 6h 49m.
Flights via Tampa (TPA) offer the fastest connection on this route, with an average layover time of 1h 20m.
About 17% of weekly flights between Chicago and San Juan have experienced delays in the past year, with the average delay time being 142 minutes.
Historically, flights departing at night are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.
Tuesday 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 13% of flights being delayed.
Crew
Overall
Food
Boarding
Entertainment
Comfort
Reviews
Dane,Jan 2026
IAD - TYS
Crew
Overall
Food
Boarding
Entertainment
Comfort
Reviews
Dane,Jan 2026
IAD - TYS
Crew
Overall
Food
Boarding
Entertainment
Comfort
Reviews
Dane,Jan 2026
IAD - TYS
Crew
Overall
Food
Boarding
Entertainment
Comfort
Reviews
Dane,Jan 2026
IAD - TYS
Crew
Overall
Food
Boarding
Entertainment
Comfort
Reviews
Dane,Jan 2026
IAD - TYS
Crew
Overall
Food
Boarding
Entertainment
Comfort
Reviews
Dane,Jan 2026
IAD - TYS
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$114 | Average$289 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$135 | Average$286 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$150 | Average$314 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$190 | Average$400 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$276 | Average$531 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$361 | Average$534 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$383 | Average$488 | FlexibilityNo cancel fee | On-time63% |