$113+ Cheap flights from Puerto Rico to Midway (MDW)
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 5/6. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MDW
May 15 — May 221
Round-trip
1 adult, Economy
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Find cheap flights from Puerto Rico to Midway 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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
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 Puerto Rico to Midway
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Cheapest flights from Puerto Rico to MidwayExplore the most affordable flight options available from Puerto Rico to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 15, 2026.
Explore the most affordable flight options available from Puerto Rico to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 15, 2026.
This Frontier deal was found by Cheapflights users on 4/14. 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.
Thu 5/73:03 am
SJU
- MDW
1 stop13h 54m
Frontier
Mon 5/114:52 pm
MDW
- SJU
1 stop8h 16m
Frontier
Deal found 4/14![Frontier logo]()
$176
This Frontier deal was found by Cheapflights users on 4/13. 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 5/13:23 pm
SJU
- MDW
1 stop8h 03m
Frontier
Mon 5/46:00 am
MDW
- SJU
1 stop7h 13m
Frontier
Deal found 4/13![Frontier logo]()
$186
This Frontier deal was found by Cheapflights users on 4/14. 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 5/27:00 am
SJU
- MDW
1 stop10h 13m
Frontier
Tue 5/56:00 am
MDW
- SJU
1 stop7h 07m
Frontier
Deal found 4/14![Frontier logo]()
$196
This Priceline deal was found by Cheapflights users on 4/15. 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.
Thu 4/303:03 pm
SJU
- MDW
1 stop8h 16m
Frontier
Mon 5/48:41 am
MDW
- SJU
1 stop16h 20m
Frontier
Deal found 4/15![Frontier logo]()
$206
This CheapOair deal was found by Cheapflights users on 4/14. 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 5/73:33 pm
SJU
- MDW
1 stop25h 24m
Frontier
Sun 5/106:00 am
MDW
- SJU
1 stop7h 07m
Frontier
Deal found 4/14![Frontier logo]()
$211
This Priceline deal was found by Cheapflights users on 4/13. 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 4/243:23 pm
SJU
- MDW
1 stop8h 03m
Frontier
Mon 4/279:14 am
MDW
- SJU
1 stop23h 40m
Frontier
Deal found 4/13![Frontier logo]()
$226
This Delta deal was found by Cheapflights users on 4/11. 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.
Sat 5/27:30 am
SJU
- MDW
1 stop9h 56m
Delta
Wed 5/66:00 am
MDW
- SJU
1 stop9h 23m
Delta
Deal found 4/11![Delta logo]()
$236
This Expedia deal was found by Cheapflights users on 4/14. 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.
Tue 4/282:38 am
BQN
- MDW
1 stop29h 43m
Frontier
Sun 5/38:39 am
MDW
- BQN
1 stop16h 04m
Frontier
Deal found 4/14![Frontier logo]()
$301
This Orbitz deal was found by Cheapflights users on 4/13. 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.
Fri 5/12:38 am
BQN
- MDW
1 stop14h 35m
Frontier
Mon 5/48:41 am
MDW
- BQN
1 stop16h 02m
Frontier
Deal found 4/13![Frontier logo]()
$311
This Kiwi.com deal was found by Cheapflights users on 4/13. 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.
Fri 5/12:38 am
BQN
- MDW
2 stops16h 59m
Multiple Airlines
Mon 5/48:41 am
MDW
- BQN
1 stop16h 02m
Multiple Airlines
Deal found 4/13![Multiple Airlines logo]()
$399
This Kiwi.com deal was found by Cheapflights users on 4/13. 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.
Mon 4/272:38 am
BQN
- MDW
2 stops17h 53m
Frontier
Sat 5/29:14 am
MDW
- BQN
1 stop15h 29m
Frontier
Deal found 4/13![Frontier logo]()
$456
This eDestinos deal was found by Cheapflights users on 4/12. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2112:26 pm
BQN
- MDW
2 stops47h 38m
Frontier
Mon 5/256:00 am
MDW
- BQN
2 stops28h 31m
Frontier
Deal found 4/12![Frontier logo]()
$639
Best flights from Puerto Rico to MidwayDiscover carefully curated flight deals from Puerto Rico to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 15, 2026.
Discover carefully curated flight deals from Puerto Rico to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 15, 2026.
This Delta deal was found by Cheapflights users on 4/13. 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.
Sat 5/27:30 am
SJU
- MDW
1 stop9h 56m
Delta
Wed 5/612:52 pm
MDW
- SJU
1 stop6h 34m
Delta
Deal found 4/13![Delta logo]()
$256
This Southwest deal was found by Cheapflights users on 4/14. 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 4/215:35 am
SJU
- MDW
1 stop7h 35m
Southwest
Sat 4/2511:25 am
MDW
- SJU
1 stop9h 00m
Southwest
Deal found 4/14![Southwest logo]()
$276
This Expedia deal was found by Cheapflights users on 4/14. 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.
Tue 4/282:38 am
BQN
- MDW
1 stop29h 43m
Frontier
Sun 5/38:39 am
MDW
- BQN
1 stop16h 04m
Frontier
Deal found 4/14![Frontier logo]()
$301
This Kiwi.com deal was found by Cheapflights users on 4/13. 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.
Fri 5/12:38 am
BQN
- MDW
2 stops16h 59m
Multiple Airlines
Mon 5/48:41 am
MDW
- BQN
1 stop16h 02m
Multiple Airlines
Deal found 4/13![Multiple Airlines logo]()
$399
This Southwest deal was found by Cheapflights users on 4/11. 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 4/306:50 am
SJU
- MDW
2 stops14h 45m
Southwest
Mon 5/48:35 pm
MDW
- SJU
1 stop13h 00m
Southwest
Deal found 4/11![Southwest logo]()
$296
This Orbitz deal was found by Cheapflights users on 4/13. 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.
Fri 5/12:38 am
BQN
- MDW
1 stop14h 35m
Frontier
Mon 5/48:41 am
MDW
- BQN
1 stop16h 02m
Frontier
Deal found 4/13![Frontier logo]()
$311
This Delta deal was found by Cheapflights users on 4/10. 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.
Sat 4/186:15 am
SJU
- MDW
1 stop11h 11m
Delta
Tue 4/2112:52 pm
MDW
- SJU
1 stop9h 20m
Delta
Deal found 4/10![Delta logo]()
$366
This Southwest deal was found by Cheapflights users on 4/13. 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 5/21:10 pm
SJU
- MDW
Nonstop5h 10m
Southwest
Tue 5/59:25 am
MDW
- SJU
1 stop10h 40m
Southwest
Deal found 4/13![Southwest logo]()
$337
This Delta deal was found by Cheapflights users on 4/13. 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.
Sat 4/182:45 pm
SJU
- MDW
1 stop8h 43m
Delta
Mon 4/2012:52 pm
MDW
- SJU
1 stop6h 32m
Delta
Deal found 4/13![Delta logo]()
$376
This Southwest deal was found by Cheapflights users on 4/14. 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 7/146:00 am
SJU
- MDW
1 stop7h 20m
Southwest
Tue 7/214:35 pm
MDW
- SJU
1 stop6h 40m
Southwest
Deal found 4/14![Southwest logo]()
$376
This Delta deal was found by Cheapflights users on 4/12. 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.
Thu 6/112:41 pm
SJU
- MDW
1 stop8h 36m
Delta
Mon 6/1511:05 am
MDW
- SJU
1 stop10h 22m
Delta
Deal found 4/12![Delta logo]()
$406
This Kiwi.com deal was found by Cheapflights users on 4/13. 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.
Mon 4/272:38 am
BQN
- MDW
2 stops17h 53m
Frontier
Sat 5/29:14 am
MDW
- BQN
1 stop15h 29m
Frontier
Deal found 4/13![Frontier logo]()
$456
This Southwest deal was found by Cheapflights users on 4/13. 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 4/185:45 am
SJU
- MDW
2 stops9h 00m
Southwest
Mon 4/208:35 pm
MDW
- SJU
1 stop13h 00m
Southwest
Deal found 4/13![Southwest logo]()
$386
This Delta deal was found by Cheapflights users on 4/11. 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 6/247:30 am
SJU
- MDW
1 stop9h 46m
Delta
Tue 6/306:05 am
MDW
- SJU
1 stop9h 41m
Delta
Deal found 4/11![Delta logo]()
$426
This eDestinos deal was found by Cheapflights users on 4/12. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2112:26 pm
BQN
- MDW
2 stops47h 38m
Frontier
Mon 5/256:00 am
MDW
- BQN
2 stops28h 31m
Frontier
Deal found 4/12![Frontier logo]()
$639
Last-minute flights from Puerto Rico to MidwayDiscover last-minute flight deals from Puerto Rico to Midway. Data last updated April 15, 2026 and is based on user searches.
Discover last-minute flight deals from Puerto Rico to Midway. Data last updated April 15, 2026 and is based on user searches.
This Priceline deal was found by Cheapflights users on 4/13. 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 4/243:23 pm
SJU
- MDW
1 stop8h 03m
Frontier
Mon 4/279:14 am
MDW
- SJU
1 stop23h 40m
Frontier
Deal found 4/13![Frontier logo]()
$226
This Kiwi.com deal was found by Cheapflights users on 4/13. 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.
Mon 4/272:38 am
BQN
- MDW
2 stops17h 53m
Frontier
Sat 5/29:14 am
MDW
- BQN
1 stop15h 29m
Frontier
Deal found 4/13![Frontier logo]()
$456
This Expedia deal was found by Cheapflights users on 4/14. 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.
Tue 4/282:38 am
BQN
- MDW
1 stop29h 43m
Frontier
Sun 5/38:39 am
MDW
- BQN
1 stop16h 04m
Frontier
Deal found 4/14![Frontier logo]()
$301
This Priceline deal was found by Cheapflights users on 4/15. 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.
Thu 4/303:03 pm
SJU
- MDW
1 stop8h 16m
Frontier
Mon 5/48:41 am
MDW
- SJU
1 stop16h 20m
Frontier
Deal found 4/15![Frontier logo]()
$206
This Frontier deal was found by Cheapflights users on 4/13. 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 5/13:23 pm
SJU
- MDW
1 stop8h 03m
Frontier
Mon 5/46:00 am
MDW
- SJU
1 stop7h 13m
Frontier
Deal found 4/13![Frontier logo]()
$186
This Orbitz deal was found by Cheapflights users on 4/13. 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.
Fri 5/12:38 am
BQN
- MDW
1 stop14h 35m
Frontier
Mon 5/48:41 am
MDW
- BQN
1 stop16h 02m
Frontier
Deal found 4/13![Frontier logo]()
$311
This Kiwi.com deal was found by Cheapflights users on 4/13. 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.
Fri 5/12:38 am
BQN
- MDW
2 stops16h 59m
Multiple Airlines
Mon 5/48:41 am
MDW
- BQN
1 stop16h 02m
Multiple Airlines
Deal found 4/13![Multiple Airlines logo]()
$399
This Frontier deal was found by Cheapflights users on 4/14. 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 5/27:00 am
SJU
- MDW
1 stop10h 13m
Frontier
Tue 5/56:00 am
MDW
- SJU
1 stop7h 07m
Frontier
Deal found 4/14![Frontier logo]()
$196
This Delta deal was found by Cheapflights users on 4/11. 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.
Sat 5/27:30 am
SJU
- MDW
1 stop9h 56m
Delta
Wed 5/66:00 am
MDW
- SJU
1 stop9h 23m
Delta
Deal found 4/11![Delta logo]()
$236
This Frontier deal was found by Cheapflights users on 4/14. 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.
Thu 5/73:03 am
SJU
- MDW
1 stop13h 54m
Frontier
Mon 5/114:52 pm
MDW
- SJU
1 stop8h 16m
Frontier
Deal found 4/14![Frontier logo]()
$176
This CheapOair deal was found by Cheapflights users on 4/14. 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 5/73:33 pm
SJU
- MDW
1 stop25h 24m
Frontier
Sun 5/106:00 am
MDW
- SJU
1 stop7h 07m
Frontier
Deal found 4/14![Frontier logo]()
$211
This eDestinos deal was found by Cheapflights users on 4/12. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2112:26 pm
BQN
- MDW
2 stops47h 38m
Frontier
Mon 5/256:00 am
MDW
- BQN
2 stops28h 31m
Frontier
Deal found 4/12![Frontier logo]()
$639
One-way flights from Puerto Rico to MidwaySearch for one-way flight options from Puerto Rico to Midway. Find affordable one-way fares based on user searches. Data last updated April 15, 2026.
Search for one-way flight options from Puerto Rico to Midway. Find affordable one-way fares based on user searches. Data last updated April 15, 2026.
This Delta deal was found by Cheapflights users on 4/13. 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 5/66:15 am
SJU
- MDW
1 stop6h 52m
Delta
Deal found 4/13![Delta logo]()
$113
This Kiwi.com deal was found by Cheapflights users on 4/13. 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.
Fri 5/112:57 pm
SJU
- MDW
2 stops10h 29m
Multiple Airlines
Deal found 4/13![Multiple Airlines logo]()
$119
This Kiwi.com deal was found by Cheapflights users on 4/14. 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 4/293:21 am
SJU
- MDW
2 stops19h 58m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$120
This Kiwi.com deal was found by Cheapflights users on 4/12. 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.
Fri 5/86:41 pm
SJU
- MDW
2 stops28h 21m
Frontier
Deal found 4/12![Frontier logo]()
$121
This Super.com deal was found by Cheapflights users on 4/14. 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.
Thu 5/216:25 am
SJU
- MDW
1 stop8h 47m
Frontier
Deal found 4/14![Frontier logo]()
$122
This Frontier deal was found by Cheapflights users on 4/14. 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.
Thu 5/143:03 am
SJU
- MDW
1 stop13h 54m
Frontier
Deal found 4/14![Frontier logo]()
$123
This Orbitz deal was found by Cheapflights users on 4/13. 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 4/258:00 am
SJU
- MDW
1 stop9h 13m
Frontier
Deal found 4/13![Frontier logo]()
$128
This Kiwi.com deal was found by Cheapflights users on 4/12. 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 5/123:03 am
SJU
- MDW
2 stops19h 59m
Frontier
Deal found 4/12![Frontier logo]()
$129
This Kiwi.com deal was found by Cheapflights users on 4/13. 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 5/126:41 pm
SJU
- MDW
2 stops28h 21m
Frontier
Deal found 4/13![Frontier logo]()
$130
This Mytrip deal was found by Cheapflights users on 4/12. 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 5/143:33 pm
SJU
- MDW
1 stop25h 24m
Frontier
Deal found 4/12![Frontier logo]()
$131
This Delta deal was found by Cheapflights users on 4/13. 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 4/2212:55 pm
SJU
- MDW
1 stop10h 33m
Delta
Deal found 4/13![Delta logo]()
$133
This Kiwi.com deal was found by Cheapflights users on 4/13. 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 5/96:00 am
SJU
- MDW
2 stops17h 02m
Frontier
Deal found 4/13![Frontier logo]()
$134
Find flight deals from Puerto Rico to Midway
Keep the following information in mind while searching for Puerto Rico to Midway flight deals. Data was last updated April 15, 2026.
Round-trip from | $176 (Frontier) |
|---|---|
One-way from | $113 (Delta) |
Popular in | December |
Cheapest in | February |
Average price | $324 |
Good one-way deal | $494 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Puerto Rico to Midway 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 15, 2026.
Use the filters below to find and compare flights from Puerto Rico to Chicago Midway Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Sat 5/2
7:30 am-4:26 pm
1 stop9h 56m
Chicago Midway
Wed 5/6
12:52 pm-8:26 pm
1 stop6h 34m
$256
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Tue 4/21
5:35 am-12:10 pm
1 stop7h 35m
Chicago Midway
Sat 4/25
11:25 am-9:25 pm
1 stop9h 00m
$276
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 4/30
6:50 am-8:35 pm
2 stops14h 45m
Chicago Midway
Mon 5/4
8:35 pm-10:35 am
1 stop13h 00m
$296
AguadillaChicago
BQN - MDW
BQNMDW
Aguadilla Borinquen
Tue 4/28
2:38 am-7:21 am
1 stop29h 43m
Chicago Midway
Sun 5/3
8:39 am-1:43 am
1 stop16h 04m
$301
AguadillaChicago
BQN - MDW
BQNMDW
Aguadilla Borinquen
Fri 5/1
2:38 am-4:13 pm
1 stop14h 35m
Chicago Midway
Mon 5/4
8:41 am-1:43 am
1 stop16h 02m
$311
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Sat 5/2
1:10 pm-5:20 pm
Nonstop5h 10m
Chicago Midway
Tue 5/5
9:25 am-9:05 pm
1 stop10h 40m
$337
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Sat 4/18
6:15 am-4:26 pm
1 stop11h 11m
Chicago Midway
Tue 4/21
12:52 pm-11:12 pm
1 stop9h 20m
$366
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Sat 4/18
2:45 pm-10:28 pm
1 stop8h 43m
Chicago Midway
Mon 4/20
12:52 pm-8:24 pm
1 stop6h 32m
$376
Quickest round-trip
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Tue 7/14
6:00 am-12:20 pm
1 stop7h 20m
Chicago Midway
Tue 7/21
4:35 pm-12:15 am
1 stop6h 40m
$376
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Sat 4/18
5:45 am-1:45 pm
2 stops9h 00m
Chicago Midway
Mon 4/20
8:35 pm-10:35 am
1 stop13h 00m
$386
Showing 1-10 of 26 resultsSorted by cheapest first
Best time to book a flight from Puerto Rico to Midway
Have a flexible travel schedule? Discover the best time to fly to Midway from Puerto Rico with our price prediction graph.
SJU-MDW
BQN-MDW
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 Puerto Rico to Chicago Midway Airport
PR0-MDW
SJU-MDW
BQN-MDW
What is the cheapest time of day to fly from PR to MDW?
Find hourly flight availability from Puerto Rico to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 15, 2026.
When flying from Puerto Rico to Chicago Midway Airport, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
Reviews of airlines servicing Midway
Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated April 15, 2026.
Read reviews from past customers who have flown Southwest from Puerto Rico to Chicago Midway Airport. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.5
Boarding
8.1
Crew
8.6
Food
7.0
Comfort
8.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Boarding
8.1
Crew
8.6
Food
7.0
Comfort
8.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Related info for your journey
Find useful and relevant information for your journey from Puerto Rico to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago Midway Airport?
Book flights to Chicago Midway Airport if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Hammond
Porter
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Alternative routes for Puerto Rico to Midway
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Complete your trip
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Search flights from Puerto Rico to Midway by cabin class
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Other flights to Midway
Explore flights to Midway departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on April 15, 2026.
Puerto Rico and Midway flights
Browse other Puerto Rico and Midway flight options. Last updated on April 15, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top airline flying from Puerto Rico to Midway
Discover the top airline that operate flights from Puerto Rico to Midway. 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 15, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$394 | Average$559 | FlexibilityNo cancel fee | On-time63% |