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 | FlightHub 3 stars |
---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $194 (Kiwi.com) |
One-way from | $115 (Trip.com) |
Popular in | August |
Cheapest in | January |
Average price | $341 |
Good round-trip deal | $313 or less |
Good one-way deal | $155 or less |
Fly from
Fly to
Route
Depart
Return
Price
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Fri 2/13
10:50 am-7:15 pm
1 stop10h 25m
Chicago Midway
Sun 2/15
6:10 am-9:50 pm
1 stop13h 40m
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Thu 1/22
6:24 pm-11:54 pm
1 stop7h 30m
Chicago O'Hare Intl
Mon 2/2
7:10 am-5:15 pm
1 stop8h 05m
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Fri 2/6
11:20 am-7:45 pm
2 stops10h 25m
Chicago Midway
Sun 2/15
6:10 am-9:50 pm
1 stop13h 40m
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 1/22
9:05 am-2:45 pm
1 stop7h 40m
Chicago Midway
Mon 2/2
7:35 am-7:05 pm
1 stop9h 30m
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 2/12
6:30 am-1:20 pm
2 stops8h 50m
Chicago Midway
Sun 2/15
6:10 am-9:50 pm
1 stop13h 40m
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Wed 11/12
3:59 am-9:12 am
1 stop7h 13m
Chicago Midway
Mon 11/17
6:15 am-3:19 pm
1 stop7h 04m
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Thu 12/4
8:30 am-2:25 pm
1 stop7h 55m
Chicago O'Hare Intl
Wed 12/10
2:20 pm-9:00 pm
Nonstop4h 40m
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Fri 10/31
10:39 pm-10:26 am
1 stop12h 47m
Chicago Midway
Sun 11/2
5:20 am-2:19 pm
1 stop6h 59m
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 3/5
4:11 pm-11:25 pm
1 stop9h 14m
Chicago Midway
Mon 3/9
3:10 pm-1:50 am
1 stop9h 40m
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Fri 12/5
3:59 pm-11:05 pm
1 stop9h 06m
Chicago Midway
Mon 12/8
2:15 pm-2:50 am
1 stop10h 35m
Provider | Price Accuracy | Trust Score* |
---|---|---|
Price Accuracy2 stars | Trust Score*3 stars | |
Price Accuracy3 stars | Trust Score*3 stars | |
Price Accuracy3 stars | Trust Score*3 stars | |
Price Accuracy3 stars | Trust Score*3 stars | |
Price Accuracy3 stars | Trust Score*1 star | |
Price Accuracy3 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 54% 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 (5 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (5 on average).
Comfort
Entertainment
Food
Overall
Boarding
Crew
Reviews
Mike,Aug 2025
OKC - AUS
Comfort
Entertainment
Food
Overall
Boarding
Crew
Reviews
Mike,Aug 2025
OKC - AUS
Comfort
Entertainment
Food
Overall
Boarding
Crew
Reviews
Mike,Aug 2025
OKC - AUS
Comfort
Entertainment
Food
Overall
Boarding
Crew
Reviews
Mike,Aug 2025
OKC - AUS
Comfort
Entertainment
Food
Overall
Boarding
Crew
Reviews
Mike,Aug 2025
OKC - AUS
Comfort
Entertainment
Food
Overall
Boarding
Crew
Reviews
Mike,Aug 2025
OKC - AUS
Airline | Cheapest | Average | Flexibility | On-time |
---|---|---|---|---|
Cheapest$136 | Average$278 | FlexibilityNo cancel fee | On-time65% | |
Cheapest$137 | Average$262 | FlexibilityNo cancel fee | On-time62% | |
Cheapest$162 | Average$487 | FlexibilityNo cancel fee | On-timeN/A | |
Cheapest$262 | Average$483 | FlexibilityNo cancel fee | On-time69% | |
Cheapest$336 | Average$481 | FlexibilityNo cancel fee | On-time71% | |
Cheapest$384 | Average$516 | FlexibilityNo cancel fee | On-time63% |