$113+ 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 8/28. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJU
May 24 — May 311
Round-trip
1 adult, Economy
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Find cheap flights from Midway to Puerto Rico with Cheapflights
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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 April 24, 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 April 24, 2026.
This Delta deal was found by Cheapflights users on 4/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/196:00 am
MDW
- SJU
1 stop9h 35m
Delta
Wed 9/22:40 pm
SJU
- MDW
1 stop8h 06m
Delta
Deal found 4/20![Delta logo]()
$226
This Trip.com deal was found by Cheapflights users on 4/23. 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 5/114:52 pm
MDW
- SJU
1 stop8h 16m
Frontier
Mon 5/186:00 am
SJU
- MDW
1 stop10h 57m
Frontier
Deal found 4/23![Frontier logo]()
$228
This Southwest deal was found by Cheapflights users on 4/20. 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 8/227:50 am
MDW
- SJU
2 stops7h 50m
Southwest
Sun 8/305:00 am
SJU
- MDW
2 stops8h 55m
Southwest
Deal found 4/20![Southwest logo]()
$236
This Trip.com deal was found by Cheapflights users on 4/21. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/56:00 am
MDW
- SJU
1 stop7h 07m
Frontier
Thu 5/143:33 pm
SJU
- MDW
1 stop25h 24m
Frontier
Deal found 4/21![Frontier logo]()
$242
This Southwest deal was found by Cheapflights users on 4/20. 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 8/172:55 pm
MDW
- SJU
1 stop7h 55m
Southwest
Fri 8/216:30 am
SJU
- MDW
2 stops8h 15m
Southwest
Deal found 4/20![Southwest logo]()
$246
This Frontier deal was found by Cheapflights users on 4/23. 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.
Fri 5/84:52 pm
MDW
- SJU
1 stop8h 16m
Frontier
Fri 5/156:00 am
SJU
- MDW
1 stop10h 57m
Frontier
Deal found 4/23![Frontier logo]()
$251
This Delta deal was found by Cheapflights users on 4/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/411:05 am
MDW
- SJU
1 stop10h 24m
Delta
Mon 8/172:40 pm
SJU
- MDW
1 stop8h 06m
Delta
Deal found 4/20![Delta logo]()
$256
This Priceline deal was found by Cheapflights users on 4/21. 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.
Mon 4/279:14 am
MDW
- SJU
1 stop23h 40m
Frontier
Thu 4/303:03 pm
SJU
- MDW
1 stop8h 16m
Frontier
Deal found 4/21![Frontier logo]()
$261
This Delta deal was found by Cheapflights users on 4/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/2812:52 pm
MDW
- SJU
1 stop6h 32m
Delta
Fri 5/12:45 pm
SJU
- MDW
1 stop8h 43m
Delta
Deal found 4/21![Delta logo]()
$266
This Mytrip deal was found by Cheapflights users on 4/19. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/246:49 pm
MDW
- SJU
1 stop26h 59m
Frontier
Fri 5/13:23 pm
SJU
- MDW
1 stop8h 03m
Frontier
Deal found 4/19![Frontier logo]()
$267
This Kiwi.com deal was found by Cheapflights users on 4/21. 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.
Tue 5/56:00 am
MDW
- SJU
1 stop7h 07m
Frontier
Wed 5/66:00 am
SJU
- MDW
2 stops17h 02m
Frontier
Deal found 4/21![Frontier logo]()
$269
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 April 24, 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 April 24, 2026.
This Delta deal was found by Cheapflights users on 4/23. 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.
Wed 8/266:00 am
MDW
- SJU
1 stop9h 35m
Delta
Tue 9/11:06 pm
SJU
- MDW
1 stop9h 40m
Delta
Deal found 4/23![Delta logo]()
$288
This Southwest deal was found by Cheapflights users on 4/23. 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 9/1012:15 pm
MDW
- SJU
2 stops9h 50m
Southwest
Sun 9/136:00 am
SJU
- MDW
1 stop7h 40m
Southwest
Deal found 4/23![Southwest logo]()
$388
This Delta deal was found by Cheapflights users on 4/19. 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.
Wed 5/66:00 am
MDW
- SJU
1 stop9h 23m
Delta
Sat 5/161:14 pm
SJU
- MDW
1 stop8h 55m
Delta
Deal found 4/19![Delta logo]()
$401
This Southwest deal was found by Cheapflights users on 4/20. 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 7/185:05 pm
MDW
- SJU
1 stop6h 40m
Southwest
Wed 7/2210:00 am
SJU
- MDW
1 stop8h 55m
Southwest
Deal found 4/20![Southwest logo]()
$416
This Southwest deal was found by Cheapflights users on 4/22. 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.
Sat 5/97:45 am
MDW
- SJU
Nonstop4h 35m
Southwest
Tue 5/125:05 am
SJU
- MDW
1 stop12h 10m
Southwest
Deal found 4/22![Southwest logo]()
$422
This Southwest deal was found by Cheapflights users on 4/21. 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 8/32:45 pm
MDW
- SJU
2 stops8h 20m
Southwest
Mon 8/106:30 am
SJU
- MDW
2 stops8h 15m
Southwest
Deal found 4/21![Southwest logo]()
$431
This Delta deal was found by Cheapflights users on 4/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/512:52 pm
MDW
- SJU
1 stop9h 21m
Delta
Sun 5/107:30 am
SJU
- MDW
1 stop9h 42m
Delta
Deal found 4/21![Delta logo]()
$476
This Southwest deal was found by Cheapflights users on 4/19. 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 7/2810:15 am
MDW
- SJU
2 stops13h 30m
Southwest
Mon 8/310:20 pm
SJU
- MDW
2 stops14h 45m
Southwest
Deal found 4/19![Southwest logo]()
$436
This Delta deal was found by Cheapflights users on 4/23. 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 7/286:05 am
MDW
- SJU
1 stop9h 40m
Delta
Fri 7/3112:56 pm
SJU
- MDW
1 stop10h 19m
Delta
Deal found 4/23![Delta logo]()
$491
This Southwest deal was found by Cheapflights users on 4/22. 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.
Sat 10/35:05 am
MDW
- SJU
1 stop6h 35m
Southwest
Mon 10/53:20 pm
SJU
- MDW
1 stop10h 20m
Southwest
Deal found 4/22![Southwest logo]()
$466
This Southwest deal was found by Cheapflights users on 4/20. 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 5/1612:05 pm
MDW
- SJU
1 stop10h 10m
Southwest
Sun 5/179:45 pm
SJU
- MDW
2 stops15h 05m
Southwest
Deal found 4/20![Southwest logo]()
$471
Last-minute flights from Midway to Puerto RicoDiscover last-minute flight deals from Midway to Puerto Rico. Data last updated April 24, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Puerto Rico. Data last updated April 24, 2026 and is based on user searches.
This Mytrip deal was found by Cheapflights users on 4/19. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/246:49 pm
MDW
- SJU
1 stop26h 59m
Frontier
Fri 5/13:23 pm
SJU
- MDW
1 stop8h 03m
Frontier
Deal found 4/19![Frontier logo]()
$267
This Priceline deal was found by Cheapflights users on 4/19. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/266:00 am
MDW
- SJU
1 stop7h 08m
Frontier
Sat 5/29:58 am
SJU
- MDW
1 stop22h 43m
Frontier
Deal found 4/19![Frontier logo]()
$256
This Southwest deal was found by Cheapflights users on 4/19. 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 4/268:55 am
MDW
- SJU
1 stop6h 35m
Southwest
Sat 5/21:10 pm
SJU
- MDW
Nonstop5h 10m
Southwest
Deal found 4/19![Southwest logo]()
$272
This Priceline deal was found by Cheapflights users on 4/21. 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.
Mon 4/279:14 am
MDW
- SJU
1 stop23h 40m
Frontier
Thu 4/303:03 pm
SJU
- MDW
1 stop8h 16m
Frontier
Deal found 4/21![Frontier logo]()
$261
This Delta deal was found by Cheapflights users on 4/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/2812:52 pm
MDW
- SJU
1 stop6h 32m
Delta
Fri 5/12:45 pm
SJU
- MDW
1 stop8h 43m
Delta
Deal found 4/21![Delta logo]()
$266
This Kiwi.com deal was found by Cheapflights users on 4/22. 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 4/282:15 pm
MDW
- SJU
2 stops26h 44m
Multiple Airlines
Thu 4/303:03 pm
SJU
- MDW
1 stop8h 16m
Multiple Airlines
Deal found 4/22![Multiple Airlines logo]()
$276
This Trip.com deal was found by Cheapflights users on 4/21. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/56:00 am
MDW
- SJU
1 stop7h 07m
Frontier
Thu 5/143:33 pm
SJU
- MDW
1 stop25h 24m
Frontier
Deal found 4/21![Frontier logo]()
$242
This Kiwi.com deal was found by Cheapflights users on 4/21. 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.
Tue 5/56:00 am
MDW
- SJU
1 stop7h 07m
Frontier
Wed 5/66:00 am
SJU
- MDW
2 stops17h 02m
Frontier
Deal found 4/21![Frontier logo]()
$269
This Frontier deal was found by Cheapflights users on 4/23. 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.
Fri 5/84:52 pm
MDW
- SJU
1 stop8h 16m
Frontier
Fri 5/156:00 am
SJU
- MDW
1 stop10h 57m
Frontier
Deal found 4/23![Frontier logo]()
$251
This Trip.com deal was found by Cheapflights users on 4/23. 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 5/114:52 pm
MDW
- SJU
1 stop8h 16m
Frontier
Mon 5/186:00 am
SJU
- MDW
1 stop10h 57m
Frontier
Deal found 4/23![Frontier logo]()
$228
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 April 24, 2026.
Search for one-way flight options from Midway to Puerto Rico. Find affordable one-way fares based on user searches. Data last updated April 24, 2026.
This Southwest deal was found by Cheapflights users on 4/19. 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.
Mon 5/117:55 am
MDW
- SJU
1 stop6h 40m
Southwest
Deal found 4/19![Southwest logo]()
$113
This Frontier deal was found by Cheapflights users on 4/21. 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.
Sat 7/186:00 am
MDW
- SJU
1 stop7h 15m
Frontier
Deal found 4/21![Frontier logo]()
$120
This Super.com deal was found by Cheapflights users on 4/20. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/176:00 am
MDW
- SJU
1 stop7h 07m
Frontier
Deal found 4/20![Frontier logo]()
$122
This Expedia deal was found by Cheapflights users on 4/21. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/184:52 pm
MDW
- SJU
1 stop8h 16m
Frontier
Deal found 4/21![Frontier logo]()
$123
This Kiwi.com deal was found by Cheapflights users on 4/21. 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 5/911:59 am
MDW
- SJU
2 stops28h 17m
Multiple Airlines
Deal found 4/21![Multiple Airlines logo]()
$126
This Super.com deal was found by Cheapflights users on 4/23. 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.
Fri 5/84:52 pm
MDW
- SJU
1 stop8h 16m
Frontier
Deal found 4/23![Frontier logo]()
$127
This Travelocity deal was found by Cheapflights users on 4/22. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/114:52 pm
MDW
- SJU
1 stop8h 16m
Frontier
Deal found 4/22![Frontier logo]()
$128
This Trip.com deal was found by Cheapflights users on 4/20. 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.
Thu 5/146:00 am
MDW
- SJU
2 stops16h 57m
Frontier
Deal found 4/20![Frontier logo]()
$130
This Trip.com deal was found by Cheapflights users on 4/21. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/111:33 am
MDW
- SJU
1 stop13h 28m
Frontier
Deal found 4/21![Frontier logo]()
$131
This Mytrip deal was found by Cheapflights users on 4/20. 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.
Thu 4/308:21 am
MDW
- SJU
1 stop13h 35m
Frontier
Deal found 4/20![Frontier logo]()
$132
This Delta deal was found by Cheapflights users on 4/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/1010:59 am
MDW
- SJU
1 stop10h 18m
Delta
Deal found 4/22![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 April 24, 2026.
Round-trip from | $226 (Delta) |
|---|---|
One-way from | $113 (Southwest) |
Popular in | December |
Cheapest in | January |
Average price | $381 |
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 April 24, 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
6:00 am-4:35 pm
1 stop9h 35m
San Juan Luis Munoz Marin Intl
Tue 9/1
1:06 pm-9:46 pm
1 stop9h 40m
$288
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Thu 9/10
12:15 pm-11:05 pm
2 stops9h 50m
San Juan Luis Munoz Marin Intl
Sun 9/13
6:00 am-12:40 pm
1 stop7h 40m
$388
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Wed 5/6
6:00 am-4:23 pm
1 stop9h 23m
San Juan Luis Munoz Marin Intl
Sat 5/16
1:14 pm-9:09 pm
1 stop8h 55m
$401
Quickest round-trip
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Sat 7/18
5:05 pm-12:45 am
1 stop6h 40m
San Juan Luis Munoz Marin Intl
Wed 7/22
10:00 am-5:55 pm
1 stop8h 55m
$416
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Sat 5/9
7:45 am-1:20 pm
Nonstop4h 35m
San Juan Luis Munoz Marin Intl
Tue 5/12
5:05 am-4:15 pm
1 stop12h 10m
$422
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Mon 8/3
2:45 pm-12:05 am
2 stops8h 20m
San Juan Luis Munoz Marin Intl
Mon 8/10
6:30 am-1:45 pm
2 stops8h 15m
$431
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Tue 7/28
10:15 am-12:45 am
2 stops13h 30m
San Juan Luis Munoz Marin Intl
Mon 8/3
10:20 pm-12:05 pm
2 stops14h 45m
$436
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Sat 10/3
5:05 am-12:40 pm
1 stop6h 35m
San Juan Luis Munoz Marin Intl
Mon 10/5
3:20 pm-12:40 am
1 stop10h 20m
$466
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Sat 5/16
12:05 pm-11:15 pm
1 stop10h 10m
San Juan Luis Munoz Marin Intl
Sun 5/17
9:45 pm-11:50 am
2 stops15h 05m
$471
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Tue 5/5
12:52 pm-11:13 pm
1 stop9h 21m
San Juan Luis Munoz Marin Intl
Sun 5/10
7:30 am-4:12 pm
1 stop9h 42m
$476
Showing 1-10 of 22 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
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 42 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
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 $284). 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 April 24, 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 31% of weekly flights between Chicago and Puerto Rico have experienced delays in the past year, with the average delay time being 113 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 31% 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 April 24, 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.
Food
7.0
Overall
8.0
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Overall
8.0
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Overall
8.0
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Overall
8.0
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
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
See prices for flight routes from nearby airports that may be better suited for you.
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 April 24, 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 April 24, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$132 | Average$428 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$138 | Average$286 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$355 | Average$495 | FlexibilityNo cancel fee | On-time63% |