
Keep the following information in mind while searching for Chicago to Puerto Rico flight deals. Data was last updated September 11, 2026.
Round-trip from | $217 (United Airlines) |
|---|---|
One-way from | $106 (Frontier) |
Popular in | December |
Cheapest in | August |
Average price | $376 |
Good round-trip deal | $319 or less |
Good one-way deal | $156 or less |
Fly from
Fly to
Route
Depart
Return
ChicagoSan Juan
ORD Chicago O'Hare Intl - SJU San Juan Luis Munoz Marin Intl
ORDSJU
Chicago O'Hare Intl
Mon 10/5
5:00 am-1:45 pm
1 stop7h 45m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
ChicagoSan Juan
ORD Chicago O'Hare Intl - SJU San Juan Luis Munoz Marin Intl
ORDSJU
Chicago O'Hare Intl
Wed 11/18
1:00 pm-1:13 am
1 stop10h 13m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Fri 12/4
8:07 pm-6:32 pm
1 stop20h 25m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Wed 9/16
9:40 am-6:10 pm
1 stop7h 30m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
ChicagoSan Juan
ORD Chicago O'Hare Intl - SJU San Juan Luis Munoz Marin Intl
ORDSJU
Chicago O'Hare Intl
Mon 11/23
2:30 pm-12:36 am
1 stop8h 06m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Mon 9/28
6:05 am-4:49 pm
1 stop9h 44m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
ChicagoSan Juan
ORD Chicago O'Hare Intl - SJU San Juan Luis Munoz Marin Intl
ORDSJU
Chicago O'Hare Intl
Wed 9/30
5:00 am-1:45 pm
1 stop7h 45m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Tue 9/15
8:30 am-6:10 pm
1 stop8h 40m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
ChicagoSan Juan
ORD Chicago O'Hare Intl - SJU San Juan Luis Munoz Marin Intl
ORDSJU
Chicago O'Hare Intl
Mon 11/2
2:16 pm-9:00 pm
Nonstop4h 44m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Fri 10/9
4:15 pm-1:25 am
2 stops8h 10m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
Everything you need to know about your flight from Chicago to Puerto Rico
Entertainment
Overall
Comfort
Crew
Food
Boarding
Reviews
Sarah,Aug 2024
MDW - AUS
Entertainment
Overall
Comfort
Crew
Food
Boarding
Reviews
Sarah,Aug 2024
MDW - AUS
Entertainment
Overall
Comfort
Crew
Food
Boarding
Reviews
Sarah,Aug 2024
MDW - AUS
Entertainment
Overall
Comfort
Crew
Food
Boarding
Reviews
Sarah,Aug 2024
MDW - AUS
Entertainment
Overall
Comfort
Crew
Food
Boarding
Reviews
Sarah,Aug 2024
MDW - AUS
Entertainment
Overall
Comfort
Crew
Food
Boarding
Reviews
Sarah,Aug 2024
MDW - AUS
Find useful and relevant information for your journey from Chicago to Puerto Rico. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$91 | Average$376 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$118 | Average$491 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$118 | Average$326 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$264 | Average$523 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$276 | Average$486 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$292 | Average$494 | FlexibilityNo cancel fee | On-time71% |