
Most accurate provider | CheapOair 3 stars |
|---|---|
Most trusted provider | CheapOair 3 stars |
Round-trip from | $120 (Trip.com) |
One-way from | $96 (JetBlue) |
Popular in | December |
Cheapest in | February |
Average price | $301 |
Good round-trip deal | $261 or less |
Good one-way deal | $205 or less |
Fly from
Fly to
Route
Depart
Return
Price
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Fri 5/1
11:59 pm-9:48 am
1 stop10h 49m
Chicago O'Hare Intl
Mon 5/4
3:15 pm-2:07 am
1 stop9h 52m
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Wed 4/29
11:59 pm-9:48 am
1 stop10h 49m
Chicago O'Hare Intl
Mon 5/4
3:15 pm-2:07 am
1 stop9h 52m
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Mon 5/4
11:25 pm-8:51 am
1 stop10h 26m
Chicago O'Hare Intl
Thu 5/7
10:35 am-9:01 pm
1 stop9h 26m
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 2/26
6:00 am-1:56 pm
1 stop9h 56m
Chicago Midway
Mon 3/2
9:22 pm-9:54 am
1 stop10h 32m
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Sat 5/2
11:59 pm-9:48 am
1 stop10h 49m
Chicago O'Hare Intl
Wed 5/6
3:15 pm-12:07 am
1 stop7h 52m
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Thu 2/12
12:32 pm-3:48 pm
Nonstop5h 16m
Chicago O'Hare Intl
Sun 2/15
12:17 pm-6:49 pm
Nonstop4h 32m
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Thu 4/9
11:00 am-9:33 pm
1 stop11h 33m
Chicago O'Hare Intl
Mon 4/13
10:00 am-10:01 pm
1 stop11h 01m
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Fri 2/27
5:10 am-11:54 am
1 stop8h 44m
Chicago O'Hare Intl
Mon 3/2
12:41 pm-12:29 am
1 stop9h 48m
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Wed 2/18
5:25 pm-2:26 pm
1 stop23h 01m
Chicago Midway
Mon 3/2
9:22 pm-9:54 am
1 stop10h 32m
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Wed 4/22
11:07 am-6:15 pm
1 stop8h 08m
Chicago O'Hare Intl
Sat 4/25
12:22 pm-5:54 pm
Nonstop4h 32m
| 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, February is the cheapest month in which you can book a flight from San Juan Luis Munoz Marin Intl Airport to Chicago (average of $118). Flying from San Juan Luis Munoz Marin Intl Airport to Chicago in December is currently the most expensive (average of $157). 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 53% 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. Sunday afternoons 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 Saturday (13 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (10 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 171 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, United Airlines have had the lowest number of delays on this route, with just 5% of flights being delayed.
Boarding
Food
Entertainment
Comfort
Overall
Crew
Reviews
Anonymous,Oct 2025
YUL - ORD
Boarding
Food
Entertainment
Comfort
Overall
Crew
Reviews
Anonymous,Oct 2025
YUL - ORD
Boarding
Food
Entertainment
Comfort
Overall
Crew
Reviews
Anonymous,Oct 2025
YUL - ORD
Boarding
Food
Entertainment
Comfort
Overall
Crew
Reviews
Anonymous,Oct 2025
YUL - ORD
Boarding
Food
Entertainment
Comfort
Overall
Crew
Reviews
Anonymous,Oct 2025
YUL - ORD
Boarding
Food
Entertainment
Comfort
Overall
Crew
Reviews
Anonymous,Oct 2025
YUL - ORD
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$116 | Average$538 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$118 | Average$270 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$131 | Average$201 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$137 | Average$258 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$256 | Average$480 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$258 | Average$484 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$419 | Average$559 | FlexibilityNo cancel fee | On-time63% |