
Round-trip from | $147 (FlightHub) |
|---|---|
One-way from | $95 (Trip.com) |
Popular in | December |
Cheapest in | February |
Average price | $191 |
Good round-trip deal | $265 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
Mon 3/16
1:29 am-5:45 am
Nonstop5h 16m
Chicago O'Hare Intl
Mon 3/23
8:56 pm-2:29 am
Nonstop4h 33m
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 5/7
3:18 pm-10:19 pm
1 stop8h 01m
Chicago Midway
Sun 5/10
6:00 am-2:08 pm
1 stop7h 08m
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Mon 3/9
3:22 pm-10:39 pm
1 stop8h 17m
Chicago O'Hare Intl
Tue 3/17
8:56 pm-2:29 am
Nonstop4h 33m
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Fri 5/1
3:18 pm-10:19 pm
1 stop8h 01m
Chicago Midway
Mon 5/4
9:14 am-10:48 pm
1 stop12h 34m
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
Fri 5/1
6:00 am-10:57 pm
1 stop17h 57m
Chicago O'Hare Intl
Mon 5/4
2:20 pm-12:29 am
1 stop9h 09m
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Thu 3/12
12:55 pm-7:51 pm
1 stop7h 56m
Chicago O'Hare Intl
Tue 3/17
8:56 pm-2:29 am
Nonstop4h 33m
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Wed 4/22
12:22 pm-4:37 pm
Nonstop5h 15m
Chicago O'Hare Intl
Sat 4/25
5:15 am-2:31 pm
1 stop8h 16m
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Thu 3/12
12:55 pm-7:51 pm
1 stop7h 56m
Chicago O'Hare Intl
Mon 3/16
4:18 pm-2:13 am
1 stop8h 55m
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Thu 3/12
1:29 am-5:45 am
Nonstop5h 16m
Chicago O'Hare Intl
Wed 3/18
9:28 am-7:50 pm
1 stop9h 22m
Currently, February is the cheapest month in which you can book a flight from Puerto Rico to Chicago (average of $101). Flying from Puerto Rico 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 Puerto Rico 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 Puerto Rico to Chicago flight should consider departing on Tuesday afternoons when fares are most often at their lowest. Monday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
The most flights from PR0 to CHI are scheduled on a Monday (12 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (3 on average).
About 9% of weekly flights between Puerto Rico and Chicago have experienced delays in the past year, with the average delay time being 183 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.
Entertainment
Comfort
Overall
Boarding
Crew
Food
Reviews
Anonymous,Oct 2025
YUL - ORD
Entertainment
Comfort
Overall
Boarding
Crew
Food
Reviews
Anonymous,Oct 2025
YUL - ORD
Entertainment
Comfort
Overall
Boarding
Crew
Food
Reviews
Anonymous,Oct 2025
YUL - ORD
Entertainment
Comfort
Overall
Boarding
Crew
Food
Reviews
Anonymous,Oct 2025
YUL - ORD
Entertainment
Comfort
Overall
Boarding
Crew
Food
Reviews
Anonymous,Oct 2025
YUL - ORD
Entertainment
Comfort
Overall
Boarding
Crew
Food
Reviews
Anonymous,Oct 2025
YUL - ORD
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$116 | Average$538 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$122 | Average$265 | 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$479 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$419 | Average$553 | FlexibilityNo cancel fee | On-time63% |