$101+ Cheap flights from Midway (MDW) to Puerto Rico
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/13. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJU
Mar 24 — Mar 311
1 adult, Economy
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Find cheap flights from Midway to Puerto Rico with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Midway to Puerto Rico
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Cheapest flights from Midway to Puerto RicoExplore the most affordable flight options available from Midway to Puerto Rico. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 22, 2026.
Explore the most affordable flight options available from Midway to Puerto Rico. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 22, 2026.
This Frontier deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/112:56 pm
MDW
- SJU
1 stop8h 18m
Frontier
Thu 4/163:03 pm
SJU
- MDW
1 stop8h 16m
Frontier
Deal found 2/20![Frontier logo]()
$202
This CheapOair deal was found by Cheapflights users on 2/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/199:14 am
MDW
- SJU
1 stop15h 47m
Frontier
Thu 4/303:18 pm
SJU
- MDW
1 stop8h 01m
Frontier
Deal found 2/19![Frontier logo]()
$213
This Frontier deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/1011:19 am
MDW
- SJU
1 stop10h 26m
Frontier
Wed 3/116:30 am
SJU
- MDW
1 stop12h 43m
Frontier
Deal found 2/20![Frontier logo]()
$218
This CheapOair deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/112:56 pm
MDW
- SJU
1 stop8h 18m
Frontier
Wed 4/156:30 am
SJU
- MDW
1 stop26h 34m
Frontier
Deal found 2/20![Frontier logo]()
$221
This Frontier deal was found by Cheapflights users on 2/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/29:22 pm
MDW
- SJU
1 stop10h 32m
Frontier
Tue 3/106:30 am
SJU
- MDW
1 stop12h 43m
Frontier
Deal found 2/19![Frontier logo]()
$223
This Trip.com deal was found by Cheapflights users on 2/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/29:22 pm
MDW
- SJU
1 stop10h 32m
Frontier
Wed 3/116:30 am
SJU
- MDW
1 stop12h 43m
Frontier
Deal found 2/19![Frontier logo]()
$229
This Kiwi.com deal was found by Cheapflights users on 2/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/16:15 am
MDW
- SJU
1 stop17h 54m
Frontier
Thu 3/56:00 am
SJU
- MDW
1 stop9h 56m
Frontier
Deal found 2/19![Frontier logo]()
$233
This CheapOair deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/106:30 am
MDW
- SJU
1 stop17h 31m
Frontier
Sat 4/183:47 pm
SJU
- MDW
1 stop7h 27m
Frontier
Deal found 2/20![Frontier logo]()
$234
This Frontier deal was found by Cheapflights users on 2/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/106:00 am
MDW
- SJU
1 stop7h 17m
Frontier
Fri 3/1312:44 pm
SJU
- MDW
1 stop10h 35m
Frontier
Deal found 2/19![Frontier logo]()
$239
This Priceline deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/239:51 pm
MDW
- SJU
1 stop11h 06m
Frontier
Tue 3/243:08 am
SJU
- MDW
1 stop16h 05m
Frontier
Deal found 2/20![Frontier logo]()
$242
This CheapOair deal was found by Cheapflights users on 2/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/36:00 am
MDW
- SJU
1 stop7h 08m
Frontier
Sun 5/176:30 am
SJU
- MDW
1 stop26h 34m
Frontier
Deal found 2/22![Frontier logo]()
$243
This Travelocity deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/89:14 am
MDW
- SJU
1 stop12h 34m
Frontier
Sun 5/176:30 am
SJU
- MDW
1 stop26h 34m
Frontier
Deal found 2/20![Frontier logo]()
$244
Best flights from Midway to Puerto RicoDiscover carefully curated flight deals from Midway to Puerto Rico that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 22, 2026.
Discover carefully curated flight deals from Midway to Puerto Rico that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 22, 2026.
This Delta deal was found by Cheapflights users on 2/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/206:00 am
MDW
- SJU
1 stop9h 23m
Delta
Sat 4/256:15 am
SJU
- MDW
1 stop11h 14m
Delta
Deal found 2/19![Delta logo]()
$266
This Southwest deal was found by Cheapflights users on 2/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/1111:25 am
MDW
- SJU
1 stop9h 00m
Southwest
Tue 4/145:35 am
SJU
- MDW
1 stop9h 10m
Southwest
Deal found 2/18![Southwest logo]()
$266
This Frontier deal was found by Cheapflights users on 2/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/42:56 pm
MDW
- SJU
1 stop8h 18m
Frontier
Fri 4/103:16 am
SJU
- MDW
1 stop7h 24m
Frontier
Deal found 2/18![Frontier logo]()
$336
This Southwest deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/41:00 pm
MDW
- SJU
1 stop9h 25m
Southwest
Sat 5/95:45 am
SJU
- MDW
2 stops9h 10m
Southwest
Deal found 2/20![Southwest logo]()
$311
This Delta deal was found by Cheapflights users on 2/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/1210:46 am
MDW
- SJU
1 stop10h 31m
Delta
Tue 5/196:15 am
SJU
- MDW
1 stop11h 02m
Delta
Deal found 2/19![Delta logo]()
$316
This Travelocity deal was found by Cheapflights users on 2/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/1111:19 am
MDW
- SJU
1 stop10h 26m
Frontier
Sun 3/156:30 am
SJU
- MDW
1 stop10h 22m
Frontier
Deal found 2/18![Frontier logo]()
$336
This Southwest deal was found by Cheapflights users on 2/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/281:25 pm
MDW
- SJU
1 stop6h 40m
Southwest
Sun 5/35:00 am
SJU
- MDW
1 stop9h 45m
Southwest
Deal found 2/18![Southwest logo]()
$316
This Southwest deal was found by Cheapflights users on 2/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/251:50 pm
MDW
- SJU
2 stops8h 45m
Southwest
Wed 3/46:10 am
SJU
- MDW
2 stops9h 45m
Southwest
Deal found 2/18![Southwest logo]()
$336
This Southwest deal was found by Cheapflights users on 2/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/31:15 pm
MDW
- SJU
1 stop7h 55m
Southwest
Thu 3/56:00 am
SJU
- MDW
2 stops16h 25m
Southwest
Deal found 2/19![Southwest logo]()
$336
This Southwest deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/189:05 am
MDW
- SJU
1 stop13h 10m
Southwest
Wed 4/225:05 am
SJU
- MDW
2 stops11h 45m
Southwest
Deal found 2/20![Southwest logo]()
$366
Last-minute flights from Midway to Puerto RicoDiscover last-minute flight deals from Midway to Puerto Rico. Data last updated February 22, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Puerto Rico. Data last updated February 22, 2026 and is based on user searches.
This CheapOair deal was found by Cheapflights users on 2/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/267:30 am
MDW
- SJU
1 stop15h 13m
Frontier
Mon 3/211:15 am
SJU
- MDW
1 stop11h 12m
Frontier
Deal found 2/19![Frontier logo]()
$255
This Orbitz deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/288:00 am
MDW
- SJU
1 stop16h 53m
Frontier
Mon 3/211:15 am
SJU
- MDW
1 stop11h 12m
Frontier
Deal found 2/20![Frontier logo]()
$244
This Kiwi.com deal was found by Cheapflights users on 2/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/16:15 am
MDW
- SJU
1 stop17h 54m
Frontier
Thu 3/56:00 am
SJU
- MDW
1 stop9h 56m
Frontier
Deal found 2/19![Frontier logo]()
$233
This Frontier deal was found by Cheapflights users on 2/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/29:22 pm
MDW
- SJU
1 stop10h 32m
Frontier
Tue 3/106:30 am
SJU
- MDW
1 stop12h 43m
Frontier
Deal found 2/19![Frontier logo]()
$223
This Trip.com deal was found by Cheapflights users on 2/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/29:22 pm
MDW
- SJU
1 stop10h 32m
Frontier
Wed 3/116:30 am
SJU
- MDW
1 stop12h 43m
Frontier
Deal found 2/19![Frontier logo]()
$229
This Frontier deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/72:56 pm
MDW
- SJU
1 stop11h 02m
Frontier
Wed 3/116:30 am
SJU
- MDW
1 stop12h 43m
Frontier
Deal found 2/20![Frontier logo]()
$249
This Priceline deal was found by Cheapflights users on 2/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/1011:19 am
MDW
- SJU
1 stop13h 44m
Frontier
Wed 3/1110:04 am
SJU
- MDW
1 stop9h 09m
Frontier
Deal found 2/21![Frontier logo]()
$202
This Frontier deal was found by Cheapflights users on 2/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/106:00 am
MDW
- SJU
1 stop7h 17m
Frontier
Fri 3/1312:44 pm
SJU
- MDW
1 stop10h 35m
Frontier
Deal found 2/19![Frontier logo]()
$239
This Priceline deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/239:51 pm
MDW
- SJU
1 stop11h 06m
Frontier
Tue 3/243:08 am
SJU
- MDW
1 stop16h 05m
Frontier
Deal found 2/20![Frontier logo]()
$242
This Frontier deal was found by Cheapflights users on 2/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/314:33 pm
MDW
- SJU
1 stop8h 30m
Frontier
Wed 4/11:11 pm
SJU
- MDW
1 stop10h 08m
Frontier
Deal found 2/21![Frontier logo]()
$254
One-way flights from Midway to Puerto RicoSearch for one-way flight options from Midway to Puerto Rico. Find affordable one-way fares based on user searches. Data last updated February 22, 2026.
Search for one-way flight options from Midway to Puerto Rico. Find affordable one-way fares based on user searches. Data last updated February 22, 2026.
This Mytrip deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/136:30 am
MDW
- SJU
1 stop16h 23m
Frontier
Deal found 2/20![Frontier logo]()
$101
This CheapOair deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/256:48 pm
MDW
- SJU
1 stop29h 33m
Frontier
Deal found 2/20![Frontier logo]()
$107
This Trip.com deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/16:15 am
MDW
- SJU
1 stop17h 54m
Frontier
Deal found 2/20![Frontier logo]()
$117
This Priceline deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/239:51 pm
MDW
- SJU
1 stop11h 06m
Frontier
Deal found 2/20![Frontier logo]()
$120
This Super.com deal was found by Cheapflights users on 2/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/288:00 am
MDW
- SJU
1 stop14h 43m
Frontier
Deal found 2/19![Frontier logo]()
$121
This Priceline deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/89:14 am
MDW
- SJU
1 stop12h 34m
Frontier
Deal found 2/20![Frontier logo]()
$122
This Southwest deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/51:25 pm
MDW
- SJU
1 stop6h 40m
Southwest
Deal found 2/20![Southwest logo]()
$123
This Kiwi.com deal was found by Cheapflights users on 2/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/16:15 am
MDW
- SJU
1 stop10h 43m
Multiple Airlines
Deal found 2/22![Multiple Airlines logo]()
$130
This Kiwi.com deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/137:30 am
MDW
- SJU
2 stops33h 25m
Multiple Airlines
Deal found 2/20![Multiple Airlines logo]()
$132
This Delta deal was found by Cheapflights users on 2/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/1712:47 pm
MDW
- SJU
1 stop9h 28m
Delta
Deal found 2/19![Delta logo]()
$133
Find flight deals from Midway to Puerto Rico
Keep the following information in mind while searching for Midway to Puerto Rico flight deals. Data was last updated February 22, 2026.
Round-trip from | $202 (Orbitz) |
|---|---|
One-way from | $101 (Mytrip) |
Popular in | December |
Cheapest in | April |
Average price | $396 |
Cheapflights Fare Finder
Customize your flight search to find flights from Midway to Puerto Rico that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 22, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Puerto Rico that are best for you.
Fly from
Midway
Fly to
Puerto Rico
Route
Depart
Return
Price
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Mon 4/20
6:00 am-4:23 pm
1 stop9h 23m
San Juan Luis Munoz Marin Intl
Sat 4/25
6:15 am-4:29 pm
1 stop11h 14m
$266
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Sat 4/11
11:25 am-9:25 pm
1 stop9h 00m
San Juan Luis Munoz Marin Intl
Tue 4/14
5:35 am-1:45 pm
1 stop9h 10m
$266
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Mon 5/4
1:00 pm-11:25 pm
1 stop9h 25m
San Juan Luis Munoz Marin Intl
Sat 5/9
5:45 am-1:55 pm
2 stops9h 10m
$311
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Tue 5/12
10:46 am-10:17 pm
1 stop10h 31m
San Juan Luis Munoz Marin Intl
Tue 5/19
6:15 am-4:17 pm
1 stop11h 02m
$316
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Tue 4/28
1:25 pm-9:05 pm
1 stop6h 40m
San Juan Luis Munoz Marin Intl
Sun 5/3
5:00 am-1:45 pm
1 stop9h 45m
$316
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Sat 4/4
2:56 pm-12:14 am
1 stop8h 18m
San Juan Luis Munoz Marin Intl
Fri 4/10
3:16 am-9:40 am
1 stop7h 24m
$336
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Wed 3/11
11:19 am-10:45 pm
1 stop10h 26m
San Juan Luis Munoz Marin Intl
Sun 3/15
6:30 am-3:52 pm
1 stop10h 22m
$336
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Wed 2/25
1:50 pm-12:35 am
2 stops8h 45m
San Juan Luis Munoz Marin Intl
Wed 3/4
6:10 am-1:55 pm
2 stops9h 45m
$336
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Tue 3/3
1:15 pm-11:10 pm
1 stop7h 55m
San Juan Luis Munoz Marin Intl
Thu 3/5
6:00 am-8:25 pm
2 stops16h 25m
$336
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Sat 4/18
9:05 am-11:15 pm
1 stop13h 10m
San Juan Luis Munoz Marin Intl
Wed 4/22
5:05 am-3:50 pm
2 stops11h 45m
$366
Showing 1-10 of 20 results
Best time to book a flight from Midway to Puerto Rico
Have a flexible travel schedule? Discover the best time to fly to Puerto Rico from Midway with our price prediction graph.
MDW-SJU
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago Midway Airport to Puerto Rico
MDW-PR0
MDW-SJU
What is the cheapest month to book a flight from Chicago Midway Airport to Puerto Rico?
Currently, April is the cheapest month in which you can book a flight from Chicago Midway Airport to Puerto Rico (average of $91). Flying from Chicago Midway Airport to Puerto Rico in June is currently the most expensive (average of $298). 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.
What is the cheapest time of day to fly from MDW to PR?
Find hourly flight availability from Midway to Puerto Rico. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated February 22, 2026.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago Midway Airport to Puerto Rico as you normally would.
How often are flights from Chicago to Puerto Rico delayed?
About 27% of weekly flights between Chicago and Puerto Rico have experienced delays in the past year, with the average delay time being 100 minutes.
What is the most punctual flight time for Chicago to Puerto Rico flights?
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the morning tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Saturday 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.
Which airline has the best punctuality record on Chicago to Puerto Rico flights?
Over the last year, Southwest have had the lowest number of delays on this route, with just 27% of flights being delayed.
Reviews of airlines servicing Puerto Rico
Get insights into the airlines that provide service to Puerto Rico. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Puerto Rico. Reviews last updated February 22, 2026.
Peruse reviews from past customers who have flown with Southwest, Delta, and Frontier from Chicago Midway Airport to Puerto Rico to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Comfort
8.0
Crew
8.6
Entertainment
7.5
Overall
8.0
Food
7.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Boarding
8.1
Comfort
8.0
Crew
8.6
Entertainment
7.5
Overall
8.0
Food
7.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Boarding
8.1
Comfort
8.0
Crew
8.6
Entertainment
7.5
Overall
8.0
Food
7.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Boarding
8.1
Comfort
8.0
Crew
8.6
Entertainment
7.5
Overall
8.0
Food
7.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Related info for your journey
Find useful and relevant information for your journey from Midway to Puerto Rico. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Midway to Puerto Rico
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Complete your trip
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Find flights from Midway to Puerto Rico, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Midway and Puerto Rico flights
Browse other Midway and Puerto Rico flight options. Last updated on February 22, 2026.
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Top 3 airlines flying from Midway to Puerto Rico
Discover the top 3 airlines that operate flights from Midway to Puerto Rico. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 22, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$132 | Average$500 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$138 | Average$291 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$379 | Average$487 | FlexibilityNo cancel fee | On-time63% |