Spirit's Big Front Seats offer 11 inches extra legroom, ideal for comfort on medium-haul flights.
Spirit's self-service bag drop speeds up airport check-in, saving time for travelers.

Most accurate provider | CheapOair 3 stars |
|---|---|
Most trusted provider | CheapOair 3 stars |
Round-trip from | $168 (JetBlue) |
One-way from | $107 (Super.com) |
Popular in | December |
Cheapest in | January |
Average price | $383 |
Good round-trip deal | $277 or less |
Good one-way deal | $152 or less |
Fly from
Fly to
Route
Depart
Return
Price
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Tue 4/7
12:15 pm-10:59 pm
1 stop11h 44m
Chicago O'Hare Intl
Mon 4/13
1:45 pm-10:47 pm
1 stop8h 02m
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Wed 3/11
4:15 am-11:49 am
1 stop8h 34m
Chicago O'Hare Intl
Tue 3/17
10:56 am-11:23 pm
1 stop11h 27m
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Fri 2/6
11:15 am-7:45 pm
1 stop10h 30m
Chicago O'Hare Intl
Sun 2/8
7:45 am-6:02 pm
1 stop8h 17m
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Sat 4/25
5:40 am-12:50 pm
1 stop8h 10m
Chicago O'Hare Intl
Fri 5/1
3:15 pm-1:59 am
1 stop9h 44m
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Fri 1/16
11:06 am-7:36 pm
1 stop10h 30m
Chicago O'Hare Intl
Sat 1/24
9:40 am-7:26 pm
1 stop7h 46m
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 3/5
9:37 pm-9:58 pm
1 stop26h 21m
Chicago Midway
Mon 3/9
8:00 am-12:45 am
1 stop15h 45m
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Tue 1/27
11:06 am-7:36 pm
1 stop10h 30m
Chicago O'Hare Intl
Thu 1/29
9:40 am-7:26 pm
1 stop7h 46m
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Tue 1/27
11:06 am-7:36 pm
1 stop10h 30m
Chicago O'Hare Intl
Sat 1/31
9:40 am-7:26 pm
1 stop7h 46m
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Fri 1/16
11:06 am-7:36 pm
1 stop10h 30m
Chicago O'Hare Intl
Tue 1/20
7:45 am-6:07 pm
1 stop8h 22m
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Wed 1/21
11:24 am-7:36 pm
1 stop10h 12m
Chicago O'Hare Intl
Fri 1/23
9:15 am-7:26 pm
1 stop8h 11m
| 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 Accuracy3 stars | Trust Score*2 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*1 star |
To ensure you get the cheapest price possible for a flight from San Juan Luis Munoz Marin Intl Airport to Chicago, you should look to book at least 72 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
Currently, January is the cheapest month in which you can book a flight from San Juan Luis Munoz Marin Intl Airport to Chicago (average of $117). Flying from San Juan Luis Munoz Marin Intl Airport to Chicago in June is currently the most expensive (average of $174). 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.
When flying from San Juan Luis Munoz Marin Intl Airport to Chicago, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 62% versus a flight in the afternoon.
Travelers seeking maximum savings on their San Juan Luis Munoz Marin Intl Airport to Chicago flight should consider departing on Thursday afternoons when fares are most often at their lowest. Monday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
The most flights from SJU to CHI are scheduled on a Thursday (10 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (6 on average).
About 9% of weekly flights between San Juan and Chicago have experienced delays in the past year, with the average delay time being 169 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 Saturday 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 6% of flights being delayed.
Crew
Food
Comfort
Overall
Boarding
Entertainment
Reviews
Jim,Nov 2025
AVL - ATL
Crew
Food
Comfort
Overall
Boarding
Entertainment
Reviews
Jim,Nov 2025
AVL - ATL
Crew
Food
Comfort
Overall
Boarding
Entertainment
Reviews
Jim,Nov 2025
AVL - ATL
Crew
Food
Comfort
Overall
Boarding
Entertainment
Reviews
Jim,Nov 2025
AVL - ATL
Crew
Food
Comfort
Overall
Boarding
Entertainment
Reviews
Jim,Nov 2025
AVL - ATL
Crew
Food
Comfort
Overall
Boarding
Entertainment
Reviews
Jim,Nov 2025
AVL - ATL
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$103 | Average$297 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$136 | Average$279 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$138 | Average$269 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$162 | Average$538 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$262 | Average$485 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$274 | Average$482 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$341 | Average$516 | FlexibilityNo cancel fee | On-time63% |