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 | $183 (Orbitz) |
One-way from | $107 (Kiwi.com) |
Popular in | December |
Cheapest in | January |
Average price | $337 |
Good round-trip deal | $339 or less |
Good one-way deal | $179 or less |
Fly from
Fly to
Route
Depart
Return
Price
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
vie. 1/16
7:00 am-6:35 pm
1 stop13h 35m
Chicago Midway
lun. 1/19
1:35 pm-12:05 am
2 stops8h 30m
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
lun. 11/24
7:09 pm-5:15 pm
1 stop24h 06m
Chicago Midway
mié. 11/26
3:47 pm-3:00 pm
1 stop21h 13m
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
vie. 1/30
5:40 am-11:15 am
1 stop7h 35m
Chicago Midway
mié. 2/4
8:25 am-5:05 pm
1 stop6h 40m
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
vie. 12/12
4:31 pm-10:12 pm
1 stop7h 41m
Chicago Midway
lun. 12/15
3:10 pm-2:50 am
1 stop9h 40m
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
dom. 3/29
1:59 am-12:50 pm
1 stop11h 51m
Chicago O'Hare Intl
lun. 4/6
1:45 pm-1:47 am
1 stop11h 02m
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
mar. 4/7
5:40 am-12:50 pm
1 stop8h 10m
Chicago O'Hare Intl
mar. 4/14
1:45 pm-10:47 pm
1 stop8h 02m
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
mié. 11/26
10:40 am-4:57 pm
1 stop8h 17m
Chicago Midway
vie. 11/28
6:05 am-8:27 pm
2 stops12h 22m
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
mar. 11/25
4:52 pm-8:20 pm
Nonstop5h 28m
Chicago O'Hare Intl
sáb. 11/29
8:55 am-3:40 pm
Nonstop4h 45m
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
vie. 2/6
8:00 am-5:10 pm
2 stops11h 10m
Chicago Midway
dom. 2/8
2:20 pm-12:35 am
2 stops8h 15m
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
vie. 4/24
1:59 am-12:50 pm
1 stop11h 51m
Chicago O'Hare Intl
vie. 5/1
3:15 pm-12:59 am
1 stop8h 44m
| 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 59 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 $116). Flying from San Juan Luis Munoz Marin Intl Airport to Chicago in June is currently the most expensive (average of $193). 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 Monday (8 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (6 on average).
Comfort
Overall
Crew
Boarding
Food
Entertainment
Reviews
Mike,Aug 2025
OKC - AUS
Comfort
Overall
Crew
Boarding
Food
Entertainment
Reviews
Mike,Aug 2025
OKC - AUS
Comfort
Overall
Crew
Boarding
Food
Entertainment
Reviews
Mike,Aug 2025
OKC - AUS
Comfort
Overall
Crew
Boarding
Food
Entertainment
Reviews
Mike,Aug 2025
OKC - AUS
Comfort
Overall
Crew
Boarding
Food
Entertainment
Reviews
Mike,Aug 2025
OKC - AUS
Comfort
Overall
Crew
Boarding
Food
Entertainment
Reviews
Mike,Aug 2025
OKC - AUS
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$137 | Average$279 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$139 | Average$261 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$162 | Average$487 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$290 | Average$485 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$334 | Average$482 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$384 | Average$516 | FlexibilityNo cancel fee | On-time63% |