$128+ 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 8/20. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJU
Aug 22 — Aug 291
Round-trip
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 July 23, 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 July 23, 2026.
This Southwest deal was found by Cheapflights users on 7/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/319:10 am
MDW
- SJU
1 stop6h 45m
Southwest
Mon 8/318:55 pm
SJU
- MDW
1 stop13h 30m
Southwest
Deal found 7/21![Southwest logo]()
$251
This Southwest deal was found by Cheapflights users on 7/22. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/283:10 pm
MDW
- SJU
2 stops7h 40m
Southwest
Mon 8/318:55 pm
SJU
- MDW
1 stop13h 30m
Southwest
Deal found 7/22![Southwest logo]()
$256
This Southwest deal was found by Cheapflights users on 7/20. 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.
Thu 9/247:50 pm
MDW
- SJU
1 stop12h 20m
Southwest
Mon 9/288:55 pm
SJU
- MDW
1 stop13h 30m
Southwest
Deal found 7/20![Southwest logo]()
$266
This Southwest deal was found by Cheapflights users on 7/20. 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.
Wed 8/1912:20 pm
MDW
- SJU
1 stop8h 40m
Southwest
Mon 8/318:55 pm
SJU
- MDW
1 stop13h 30m
Southwest
Deal found 7/20![Southwest logo]()
$276
This Southwest deal was found by Cheapflights users on 7/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/2512:45 pm
MDW
- SJU
2 stops8h 15m
Southwest
Wed 8/268:20 am
SJU
- MDW
2 stops9h 30m
Southwest
Deal found 7/21![Southwest logo]()
$281
This Southwest deal was found by Cheapflights users on 7/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/47:50 pm
MDW
- SJU
1 stop12h 35m
Southwest
Mon 9/78:55 pm
SJU
- MDW
1 stop13h 30m
Southwest
Deal found 7/21![Southwest logo]()
$286
This Southwest deal was found by Cheapflights users on 7/22. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/37:50 pm
MDW
- SJU
1 stop12h 20m
Southwest
Thu 9/108:55 pm
SJU
- MDW
1 stop12h 50m
Southwest
Deal found 7/22![Southwest logo]()
$296
This Southwest deal was found by Cheapflights users on 7/20. 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.
Fri 9/2511:15 am
MDW
- SJU
1 stop9h 55m
Southwest
Sat 10/37:50 am
SJU
- MDW
2 stops8h 35m
Southwest
Deal found 7/20![Southwest logo]()
$306
This Southwest deal was found by Cheapflights users on 7/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1912:45 pm
MDW
- SJU
2 stops8h 15m
Southwest
Tue 8/2511:50 am
SJU
- MDW
1 stop8h 25m
Southwest
Deal found 7/21![Southwest logo]()
$311
This Southwest deal was found by Cheapflights users on 7/19. 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.
Wed 8/2612:20 pm
MDW
- SJU
1 stop8h 40m
Southwest
Wed 9/210:30 am
SJU
- MDW
1 stop8h 10m
Southwest
Deal found 7/19![Southwest logo]()
$316
This Southwest deal was found by Cheapflights users on 7/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/103:10 pm
MDW
- SJU
2 stops7h 40m
Southwest
Mon 9/146:00 am
SJU
- MDW
2 stops9h 30m
Southwest
Deal found 7/21![Southwest logo]()
$326
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 July 23, 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 July 23, 2026.
This Southwest deal was found by Cheapflights users on 7/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2612:45 pm
MDW
- SJU
2 stops8h 15m
Southwest
Sun 8/309:25 pm
SJU
- MDW
1 stop12h 20m
Southwest
Deal found 7/21![Southwest logo]()
$256
This Southwest deal was found by Cheapflights users on 7/22. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/2511:15 am
MDW
- SJU
1 stop7h 50m
Southwest
Sun 9/279:25 pm
SJU
- MDW
1 stop12h 20m
Southwest
Deal found 7/22![Southwest logo]()
$286
This Southwest deal was found by Cheapflights users on 7/20. 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 8/186:15 am
MDW
- SJU
1 stop9h 10m
Southwest
Mon 8/248:55 pm
SJU
- MDW
1 stop13h 30m
Southwest
Deal found 7/20![Southwest logo]()
$296
This Southwest deal was found by Cheapflights users on 7/22. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/213:10 pm
MDW
- SJU
2 stops7h 40m
Southwest
Mon 8/248:55 pm
SJU
- MDW
1 stop13h 30m
Southwest
Deal found 7/22![Southwest logo]()
$296
This Southwest deal was found by Cheapflights users on 7/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/61:45 pm
MDW
- SJU
2 stops8h 35m
Southwest
Wed 9/92:25 pm
SJU
- MDW
1 stop7h 20m
Southwest
Deal found 7/21![Southwest logo]()
$296
This Southwest deal was found by Cheapflights users on 7/19. 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.
Sun 8/308:05 am
MDW
- SJU
1 stop8h 00m
Southwest
Fri 9/46:30 am
SJU
- MDW
1 stop10h 05m
Southwest
Deal found 7/19![Southwest logo]()
$316
This Southwest deal was found by Cheapflights users on 7/19. 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.
Sat 8/297:45 am
MDW
- SJU
1 stop9h 20m
Southwest
Fri 9/46:30 am
SJU
- MDW
1 stop10h 05m
Southwest
Deal found 7/19![Southwest logo]()
$316
This Southwest deal was found by Cheapflights users on 7/18. 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 10/172:40 pm
MDW
- SJU
1 stop6h 30m
Southwest
Sat 10/245:40 am
SJU
- MDW
2 stops12h 40m
Southwest
Deal found 7/18![Southwest logo]()
$336
This Southwest deal was found by Cheapflights users on 7/19. 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 8/1112:50 pm
MDW
- SJU
2 stops8h 10m
Southwest
Fri 8/148:55 pm
SJU
- MDW
1 stop13h 00m
Southwest
Deal found 7/19![Southwest logo]()
$371
This Southwest deal was found by Cheapflights users on 7/18. 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.
Thu 10/228:40 pm
MDW
- SJU
1 stop11h 40m
Southwest
Sun 10/255:00 am
SJU
- MDW
1 stop8h 00m
Southwest
Deal found 7/18![Southwest logo]()
$381
This Southwest deal was found by Cheapflights users on 7/22. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1212:50 pm
MDW
- SJU
2 stops10h 15m
Southwest
Sun 11/156:05 am
SJU
- MDW
2 stops10h 20m
Southwest
Deal found 7/22![Southwest logo]()
$411
Last-minute flights from Midway to Puerto RicoDiscover last-minute flight deals from Midway to Puerto Rico. Data last updated July 23, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Puerto Rico. Data last updated July 23, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 7/22. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/2910:15 am
MDW
- SJU
2 stops13h 35m
Southwest
Wed 8/261:20 pm
SJU
- MDW
1 stop6h 50m
Southwest
Deal found 7/22![Southwest logo]()
$331
This Southwest deal was found by Cheapflights users on 7/19. 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.
Thu 8/137:50 pm
MDW
- SJU
1 stop12h 20m
Southwest
Thu 9/172:35 pm
SJU
- MDW
1 stop7h 55m
Southwest
Deal found 7/19![Southwest logo]()
$336
This Southwest deal was found by Cheapflights users on 7/22. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/168:20 am
MDW
- SJU
1 stop13h 25m
Southwest
Thu 8/208:55 pm
SJU
- MDW
2 stops15h 30m
Southwest
Deal found 7/22![Southwest logo]()
$296
This Southwest deal was found by Cheapflights users on 7/20. 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 8/1812:45 pm
MDW
- SJU
2 stops8h 15m
Southwest
Tue 8/255:15 am
SJU
- MDW
2 stops7h 50m
Southwest
Deal found 7/20![Southwest logo]()
$326
This Southwest deal was found by Cheapflights users on 7/20. 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.
Wed 8/1912:20 pm
MDW
- SJU
1 stop8h 40m
Southwest
Mon 8/318:55 pm
SJU
- MDW
1 stop13h 30m
Southwest
Deal found 7/20![Southwest logo]()
$276
This Southwest deal was found by Cheapflights users on 7/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1912:45 pm
MDW
- SJU
2 stops8h 15m
Southwest
Tue 8/2511:50 am
SJU
- MDW
1 stop8h 25m
Southwest
Deal found 7/21![Southwest logo]()
$311
This Southwest deal was found by Cheapflights users on 7/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/2512:45 pm
MDW
- SJU
2 stops8h 15m
Southwest
Wed 8/268:20 am
SJU
- MDW
2 stops9h 30m
Southwest
Deal found 7/21![Southwest logo]()
$281
This Southwest deal was found by Cheapflights users on 7/19. 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.
Wed 8/2612:20 pm
MDW
- SJU
1 stop8h 40m
Southwest
Wed 9/210:30 am
SJU
- MDW
1 stop8h 10m
Southwest
Deal found 7/19![Southwest logo]()
$316
This Southwest deal was found by Cheapflights users on 7/22. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2711:15 am
MDW
- SJU
1 stop9h 55m
Southwest
Tue 9/12:25 pm
SJU
- MDW
1 stop7h 20m
Southwest
Deal found 7/22![Southwest logo]()
$286
This Southwest deal was found by Cheapflights users on 7/22. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/283:10 pm
MDW
- SJU
2 stops7h 40m
Southwest
Mon 8/318:55 pm
SJU
- MDW
1 stop13h 30m
Southwest
Deal found 7/22![Southwest logo]()
$256
This Southwest deal was found by Cheapflights users on 7/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/319:10 am
MDW
- SJU
1 stop6h 45m
Southwest
Mon 8/318:55 pm
SJU
- MDW
1 stop13h 30m
Southwest
Deal found 7/21![Southwest logo]()
$251
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 July 23, 2026.
Search for one-way flight options from Midway to Puerto Rico. Find affordable one-way fares based on user searches. Data last updated July 23, 2026.
This Southwest deal was found by Cheapflights users on 7/22. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/201:00 pm
MDW
- SJU
2 stops8h 50m
Southwest
Deal found 7/22![Southwest logo]()
$128
This Southwest deal was found by Cheapflights users on 7/20. 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.
Fri 8/141:00 pm
MDW
- SJU
2 stops8h 50m
Southwest
Deal found 7/20![Southwest logo]()
$158
This Southwest deal was found by Cheapflights users on 7/20. 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 8/173:10 pm
MDW
- SJU
2 stops7h 40m
Southwest
Deal found 7/20![Southwest logo]()
$168
This Southwest deal was found by Cheapflights users on 7/20. 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 7/278:55 pm
MDW
- SJU
1 stop11h 05m
Southwest
Deal found 7/20![Southwest logo]()
$170
This Kiwi.com deal was found by Cheapflights users on 7/22. 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.
Wed 8/1211:06 am
MDW
- SJU
2 stops12h 35m
Frontier
Deal found 7/22![Frontier logo]()
$171
This Kiwi.com deal was found by Cheapflights users on 7/22. 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 8/306:05 am
MDW
- SJU
2 stops41h 51m
Frontier
Deal found 7/22![Frontier logo]()
$173
This Kiwi.com deal was found by Cheapflights users on 7/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/1511:06 am
MDW
- SJU
2 stops12h 35m
Frontier
Deal found 7/21![Frontier logo]()
$174
This Kiwi.com deal was found by Cheapflights users on 7/22. 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.
Thu 9/1712:03 pm
MDW
- SJU
2 stops34h 54m
Frontier
Deal found 7/22![Frontier logo]()
$175
This Southwest deal was found by Cheapflights users on 7/19. 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.
Thu 9/103:10 pm
MDW
- SJU
2 stops7h 40m
Southwest
Deal found 7/19![Southwest logo]()
$178
This Kiwi.com deal was found by Cheapflights users on 7/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/216:40 am
MDW
- SJU
2 stops16h 36m
Frontier
Deal found 7/21![Frontier logo]()
$179
This Kiwi.com deal was found by Cheapflights users on 7/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1512:03 pm
MDW
- SJU
2 stops35h 13m
Frontier
Deal found 7/18![Frontier logo]()
$180
This Kiwi.com deal was found by Cheapflights users on 7/22. 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.
Tue 10/206:40 am
MDW
- SJU
2 stops16h 36m
Frontier
Deal found 7/22![Frontier logo]()
$181
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 July 23, 2026.
Round-trip from | $251 (Southwest) |
|---|---|
One-way from | $128 (Southwest) |
Popular in | December |
Cheapest in | August |
Average price | $384 |
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 July 23, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Puerto Rico that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Wed 8/26
12:45 pm-10:00 pm
2 stops8h 15m
San Juan Luis Munoz Marin Intl
Sun 8/30
9:25 pm-8:45 am
1 stop12h 20m
$256
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Fri 9/25
11:15 am-8:05 pm
1 stop7h 50m
San Juan Luis Munoz Marin Intl
Sun 9/27
9:25 pm-8:45 am
1 stop12h 20m
$286
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Tue 8/18
6:15 am-4:25 pm
1 stop9h 10m
San Juan Luis Munoz Marin Intl
Mon 8/24
8:55 pm-9:25 am
1 stop13h 30m
$296
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Fri 8/21
3:10 pm-11:50 pm
2 stops7h 40m
San Juan Luis Munoz Marin Intl
Mon 8/24
8:55 pm-9:25 am
1 stop13h 30m
$296
Quickest round-trip
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Sun 9/6
1:45 pm-11:20 pm
2 stops8h 35m
San Juan Luis Munoz Marin Intl
Wed 9/9
2:25 pm-8:45 pm
1 stop7h 20m
$296
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Sun 8/30
8:05 am-5:05 pm
1 stop8h 00m
San Juan Luis Munoz Marin Intl
Fri 9/4
6:30 am-3:35 pm
1 stop10h 05m
$316
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Sat 8/29
7:45 am-6:05 pm
1 stop9h 20m
San Juan Luis Munoz Marin Intl
Fri 9/4
6:30 am-3:35 pm
1 stop10h 05m
$316
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Sat 10/17
2:40 pm-10:10 pm
1 stop6h 30m
San Juan Luis Munoz Marin Intl
Sat 10/24
5:40 am-5:20 pm
2 stops12h 40m
$336
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Tue 8/11
12:50 pm-10:00 pm
2 stops8h 10m
San Juan Luis Munoz Marin Intl
Fri 8/14
8:55 pm-8:55 am
1 stop13h 00m
$371
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Thu 10/22
8:40 pm-9:20 am
1 stop11h 40m
San Juan Luis Munoz Marin Intl
Sun 10/25
5:00 am-12:00 pm
1 stop8h 00m
$381
Showing 1-10 of 20 resultsSorted by cheapest first
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, February is the cheapest month in which you can book a flight from Chicago Midway Airport to Puerto Rico (average of $243). Flying from Chicago Midway Airport to Puerto Rico in June is currently the most expensive (average of $556). 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 July 23, 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 28% of weekly flights between Chicago and Puerto Rico have experienced delays in the past year, with the average delay time being 128 minutes.
What is the most punctual flight time for Chicago to Puerto Rico flights?
Historically, flights departing in the early afternoon 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?
Wednesday tends to have the lowest number of delays on this route, whereas Saturday 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.
How far ahead should I book a flight from Chicago Midway Airport to Puerto Rico?
The price you pay for your flight from Chicago Midway Airport to Puerto Rico may vary depending on when you book. For the best chance of a lower fare, look to book 20 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
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 July 23, 2026.
Peruse reviews from past customers who have flown with Southwest,Delta, andFrontier 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
Entertainment
7.5
Food
7.0
Crew
8.6
Overall
8.0
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Boarding
8.1
Entertainment
7.5
Food
7.0
Crew
8.6
Overall
8.0
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Boarding
8.1
Entertainment
7.5
Food
7.0
Crew
8.6
Overall
8.0
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Boarding
8.1
Entertainment
7.5
Food
7.0
Crew
8.6
Overall
8.0
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
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
Complete your trip to Puerto Rico by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Midway to Puerto Rico by cabin class
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 July 23, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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 July 23, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$91 | Average$294 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$132 | Average$531 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$346 | Average$490 | FlexibilityNo cancel fee | On-time63% |