
Keep the following information in mind while searching for Chicago to Puerto Rico flight deals. Data was last updated September 20, 2026.
Round-trip from | $217 (Kiwi.com) |
|---|---|
One-way from | $110 (Cheapflightsfares) |
Popular in | December |
Cheapest in | August |
Average price | $357 |
Good round-trip deal | $309 or less |
Good one-way deal | $164 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 10/26
2:16 pm-8:00 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 10/30
2:50 pm-12:10 am
2 stops8h 20m
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
Sat 11/14
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
ORD Chicago O'Hare Intl - SJU San Juan Luis Munoz Marin Intl
ORDSJU
Chicago O'Hare Intl
Mon 10/19
6:25 am-3:42 pm
1 stop8h 17m
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 11/11
4:25 pm-12:50 am
1 stop6h 25m
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 11/11
12:59 pm-12:36 am
1 stop9h 37m
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 11/16
1:05 pm-11:15 pm
1 stop8h 10m
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
Thu 10/1
8:40 pm-9:20 am
1 stop11h 40m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
ChicagoAguadilla
ORD Chicago O'Hare Intl - BQN Aguadilla Borinquen
ORDBQN
Chicago O'Hare Intl
Tue 10/6
3:50 pm-10:14 am
1 stop17h 24m
Aguadilla Borinquen
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
ChicagoAguadilla
ORD Chicago O'Hare Intl - BQN Aguadilla Borinquen
ORDBQN
Chicago O'Hare Intl
Sat 10/3
3:50 pm-10:13 am
1 stop17h 23m
Aguadilla Borinquen
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
Everything you need to know about your flight from Chicago to Puerto Rico
Boarding
Comfort
Crew
Overall
Food
Entertainment
Reviews
Steven,Sep 2026
OGG - HNL
Boarding
Comfort
Crew
Overall
Food
Entertainment
Reviews
Steven,Sep 2026
OGG - HNL
Boarding
Comfort
Crew
Overall
Food
Entertainment
Reviews
Steven,Sep 2026
OGG - HNL
Boarding
Comfort
Crew
Overall
Food
Entertainment
Reviews
Steven,Sep 2026
OGG - HNL
Boarding
Comfort
Crew
Overall
Food
Entertainment
Reviews
Steven,Sep 2026
OGG - HNL
Boarding
Comfort
Crew
Overall
Food
Entertainment
Reviews
Steven,Sep 2026
OGG - HNL
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$484 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$262 | Average$532 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$276 | Average$489 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$286 | Average$490 | FlexibilityNo cancel fee | On-time71% |