$114+ Cheap flights from Midway (MDW) to Puerto Rico
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/23. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJU
Nov 22 — Nov 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
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 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 October 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 October 23, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/910:40 am -
2 stops12h 27m
Thu 12/177:32 am -
1 stop13h 58m
Deal found 10/20![Frontier logo]()
$236
This Kiwi.com deal was found by Cheapflights users on 10/21. 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.
Fri 12/43:36 pm -
1 stop8h 35m
Mon 12/75:01 am -
1 stop13h 05m
Deal found 10/21![Frontier logo]()
$237
This Kiwi.com deal was found by Cheapflights users on 10/23. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/96:42 pm -
2 stops26h 56m
Thu 11/123:55 pm -
1 stop9h 52m
Deal found 10/23![Frontier logo]()
$238
This CheapOair deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/261:16 pm -
1 stop10h 20m
Tue 12/15:01 am -
1 stop8h 32m
Deal found 10/22![Frontier logo]()
$240
This FlightHub deal was found by Cheapflights users on 10/23. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/261:16 pm -
1 stop10h 20m
Sun 12/68:44 pm -
1 stop22h 32m
Deal found 10/23![Frontier logo]()
$241
This Kiwi.com deal was found by Cheapflights users on 10/18. 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.
Tue 11/176:08 am -
1 stop16h 51m
Thu 11/193:55 pm -
1 stop9h 52m
Deal found 10/18![Frontier logo]()
$243
This Kiwi.com deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/106:42 pm -
2 stops19h 35m
Sat 11/143:55 pm -
1 stop9h 52m
Deal found 10/19![Frontier logo]()
$244
This Kiwi.com deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/261:16 pm -
1 stop10h 20m
Wed 12/22:49 am -
2 stops15h 18m
Deal found 10/19![Frontier logo]()
$245
This Cheapflightsfares deal was found by Cheapflights users on 10/19. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/266:15 am -
1 stop8h 51m
Thu 10/293:59 pm -
1 stop8h 48m
Deal found 10/19![Frontier logo]()
$246
This FlightHub deal was found by Cheapflights users on 10/18. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/147:15 am -
1 stop15h 44m
Thu 11/193:55 pm -
1 stop9h 52m
Deal found 10/18![Frontier logo]()
$247
This Kiwi.com deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/75:02 pm -
2 stops25h 35m
Wed 12/165:01 am -
1 stop8h 32m
Deal found 10/20![Frontier logo]()
$248
This Kiwi.com deal was found by Cheapflights users on 10/22. 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.
Sat 12/512:28 pm -
1 stop10h 39m
Sat 12/123:43 am -
1 stop17h 59m
Deal found 10/22![Frontier logo]()
$249
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 October 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 October 23, 2026.
This Southwest deal was found by Cheapflights users on 10/22. 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 10/2912:45 pm -
1 stop10h 25m
Wed 11/410:45 am -
1 stop7h 50m
Deal found 10/22![Southwest logo]()
$306
This Delta deal was found by Cheapflights users on 10/19. 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 1/610:35 am -
1 stop8h 25m
Thu 1/143:55 pm -
1 stop8h 15m
Deal found 10/19![Delta logo]()
$396
This Kiwi.com deal was found by Cheapflights users on 10/22. 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 12/308:35 pm -
1 stop27h 08m
Fri 1/293:59 am -
2 stops21h 47m
Deal found 10/22![Frontier logo]()
$462
This Southwest deal was found by Cheapflights users on 10/20. 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 1/201:40 pm -
1 stop6h 20m
Wed 1/276:15 am -
2 stops10h 30m
Deal found 10/20![Southwest logo]()
$331
This Southwest deal was found by Cheapflights users on 10/20. 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 12/112:40 pm -
1 stop8h 20m
Sun 12/2010:30 pm -
1 stop13h 25m
Deal found 10/20![Southwest logo]()
$331
This Southwest deal was found by Cheapflights users on 10/20. 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 11/49:55 am -
2 stops10h 00m
Tue 11/107:40 am -
2 stops9h 15m
Deal found 10/20![Southwest logo]()
$346
This Southwest deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals ”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/11:20 pm -
2 stops9h 30m
Fri 12/42:25 pm -
1 stop9h 05m
Deal found 10/18![Southwest logo]()
$358
This Cheapflightsfares deal was found by Cheapflights users on 10/20. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/318:35 pm -
1 stop27h 08m
Wed 1/63:59 am -
1 stop17h 36m
Deal found 10/20![Frontier logo]()
$481
This Southwest deal was found by Cheapflights users on 10/22. 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.
Mon 12/73:00 pm -
1 stop7h 50m
Mon 12/146:10 am -
2 stops10h 20m
Deal found 10/22![Southwest logo]()
$373
This FlightHub deal was found by Cheapflights users on 10/22. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/76:42 pm -
2 stops38h 50m
Sat 11/1412:22 pm -
2 stops13h 25m
Deal found 10/22![Frontier logo]()
$526
This Southwest deal was found by Cheapflights users on 10/19. 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.
Fri 12/118:40 pm -
1 stop11h 20m
Sun 12/136:05 am -
2 stops10h 20m
Deal found 10/19![Southwest logo]()
$388
This Kiwi.com deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/198:35 pm -
1 stop15h 51m
Mon 12/213:13 am -
2 stops10h 57m
Deal found 10/20![Frontier logo]()
$531
This Kiwi.com deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/198:35 pm -
1 stop15h 51m
Thu 12/242:44 pm -
2 stops11h 17m
Deal found 10/20![Frontier logo]()
$541
This Southwest deal was found by Cheapflights users on 10/18. 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.
Fri 11/131:20 pm -
2 stops9h 40m
Mon 11/1610:45 am -
2 stops9h 40m
Deal found 10/18![Southwest logo]()
$433
This FlightHub deal was found by Cheapflights users on 10/22. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/176:52 am -
2 stops28h 57m
Thu 12/242:44 pm -
2 stops11h 17m
Deal found 10/22![Frontier logo]()
$543
This Southwest deal was found by Cheapflights users on 10/18. 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.
Fri 11/131:20 pm -
2 stops9h 40m
Fri 11/207:30 am -
1 stop8h 25m
Deal found 10/18![Southwest logo]()
$436
This Kiwi.com deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/198:35 pm -
1 stop15h 51m
Fri 12/252:44 pm -
2 stops11h 17m
Deal found 10/20![Frontier logo]()
$579
This Southwest deal was found by Cheapflights users on 10/22. 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 12/301:05 pm -
2 stops9h 10m
Sat 1/306:10 am -
2 stops12h 55m
Deal found 10/22![Southwest logo]()
$472
This Cheapflightsfares deal was found by Cheapflights users on 10/21. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/38:35 pm -
1 stop15h 14m
Sat 1/93:59 am -
1 stop17h 36m
Deal found 10/21![Frontier logo]()
$607
This Southwest deal was found by Cheapflights users on 10/20. 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 1/910:05 am -
2 stops9h 55m
Wed 1/1310:45 am -
2 stops9h 50m
Deal found 10/20![Southwest logo]()
$531
Last-minute flights from Midway to Puerto RicoDiscover last-minute flight deals from Midway to Puerto Rico. Data last updated October 23, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Puerto Rico. Data last updated October 23, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 10/19. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/266:15 am -
1 stop8h 51m
Thu 10/293:59 pm -
1 stop8h 48m
Deal found 10/19![Frontier logo]()
$246
This Kiwi.com deal was found by Cheapflights users on 10/23. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/96:42 pm -
2 stops26h 56m
Thu 11/123:55 pm -
1 stop9h 52m
Deal found 10/23![Frontier logo]()
$238
This Kiwi.com deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/96:42 pm -
2 stops17h 56m
Fri 11/133:55 pm -
1 stop9h 52m
Deal found 10/19![Frontier logo]()
$253
This Kiwi.com deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/106:42 pm -
2 stops19h 35m
Sat 11/143:55 pm -
1 stop9h 52m
Deal found 10/19![Frontier logo]()
$244
This Kiwi.com deal was found by Cheapflights users on 10/21. 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.
Thu 11/126:08 am -
2 stops15h 30m
Thu 11/193:55 pm -
1 stop9h 52m
Deal found 10/21![Frontier logo]()
$256
This FlightHub deal was found by Cheapflights users on 10/18. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/147:15 am -
1 stop15h 44m
Thu 11/193:55 pm -
1 stop9h 52m
Deal found 10/18![Frontier logo]()
$247
This Justfly.com deal was found by Cheapflights users on 10/18. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/147:15 am -
1 stop15h 44m
Sat 11/2110:21 pm -
1 stop23h 26m
Deal found 10/18![Frontier logo]()
$254
This Kiwi.com deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/166:08 am -
2 stops15h 30m
Thu 11/193:55 pm -
1 stop9h 52m
Deal found 10/20![Frontier logo]()
$255
This Kiwi.com deal was found by Cheapflights users on 10/18. 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.
Tue 11/176:08 am -
1 stop16h 51m
Thu 11/193:55 pm -
1 stop9h 52m
Deal found 10/18![Frontier logo]()
$243
This CheapOair deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/261:16 pm -
1 stop10h 20m
Tue 12/15:01 am -
1 stop8h 32m
Deal found 10/22![Frontier logo]()
$240
This FlightHub deal was found by Cheapflights users on 10/23. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/261:16 pm -
1 stop10h 20m
Sun 12/68:44 pm -
1 stop22h 32m
Deal found 10/23![Frontier logo]()
$241
This Kiwi.com deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/261:16 pm -
1 stop10h 20m
Wed 12/22:49 am -
2 stops15h 18m
Deal found 10/19![Frontier logo]()
$245
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 October 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 October 23, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 10/21. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/238:42 pm -
1 stop15h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Frontier logo]()
$114
This CheapOair deal was found by Cheapflights users on 10/21. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/228:42 pm -
1 stop15h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Frontier logo]()
$118
This Trip.com deal was found by Cheapflights users on 10/22. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/171:18 pm -
1 stop10h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Frontier logo]()
$121
This Mytrip deal was found by Cheapflights users on 10/22. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/166:42 pm -
2 stops19h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Frontier logo]()
$122
This FlightHub deal was found by Cheapflights users on 10/21. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/212:28 pm -
2 stops12h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Frontier logo]()
$123
This Kiwi.com deal was found by Cheapflights users on 10/22. 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 11/228:42 pm -
1 stop27h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Frontier logo]()
$123
This Kiwi.com deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/106:42 pm -
2 stops19h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![Frontier logo]()
$125
This Kiwi.com deal was found by Cheapflights users on 10/22. 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 11/186:08 am -
2 stops29h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Frontier logo]()
$130
This Southwest deal was found by Cheapflights users on 10/19. 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 11/164:25 pm -
1 stop6h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Southwest logo]()
$133
This Super.com deal was found by Cheapflights users on 10/21. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/248:42 pm -
1 stop28h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Frontier logo]()
$160
This CheapOair deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/308:42 pm -
1 stop28h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Frontier logo]()
$168
This Kiwi.com deal was found by Cheapflights users on 10/18. 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.
Sat 10/317:25 am -
2 stops26h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/18![Frontier logo]()
$211
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 October 23, 2026.
Round-trip from | $236 (Kiwi.com) |
|---|---|
One-way from | $114 (Cheapflightsfares) |
Popular in | December |
Cheapest in | August |
Average price | $406 |
Good round-trip deal | $565 or less |
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 7,457,451 searches. Data last updated October 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
ChicagoAguadilla
MDW Chicago Midway - BQN Aguadilla Borinquen
MDWBQN
Chicago Midway
Wed 12/2
12:28 pm-2:45 am
2 stops12h 17m
Aguadilla Borinquen
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$123
Quickest round-trip
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Mon 11/16
4:25 pm-12:50 am
1 stop6h 25m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$133
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Mon 11/16
6:08 am-3:19 pm
2 stops31h 11m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$135
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Fri 10/30
2:50 pm-12:10 am
2 stops8h 20m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$153
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Thu 10/29
12:45 pm-12:10 am
2 stops10h 25m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$153
ChicagoAguadilla
MDW Chicago Midway - BQN Aguadilla Borinquen
MDWBQN
Chicago Midway
Mon 11/30
8:42 pm-2:45 am
1 stop28h 03m
Aguadilla Borinquen
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$168
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Mon 11/2
12:45 pm-1:05 am
2 stops10h 20m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$173
ChicagoAguadilla
MDW Chicago Midway - BQN Aguadilla Borinquen
MDWBQN
Chicago Midway
Sat 12/19
8:35 pm-1:43 am
1 stop27h 08m
Aguadilla Borinquen
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$262
ChicagoAguadilla
MDW Chicago Midway - BQN Aguadilla Borinquen
MDWBQN
Chicago Midway
Tue 11/24
1:16 pm-2:47 am
2 stops35h 31m
Aguadilla Borinquen
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$271
ChicagoAguadilla
MDW Chicago Midway - BQN Aguadilla Borinquen
MDWBQN
Chicago Midway
Mon 12/28
8:35 pm-1:49 pm
1 stop15h 14m
Aguadilla Borinquen
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$301
Showing 1-10 of 33 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
MDW-BQN
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
MDW-BQN
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 $156). 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.
How often are flights from Chicago to Puerto Rico delayed?
About 25% of weekly flights between Chicago and Puerto Rico have experienced delays in the past year, with the average delay time being 123 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?
Sunday 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 25% 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 22 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 October 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.
Comfort
8.0
Overall
7.9
Boarding
8.1
Entertainment
7.4
Food
7.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Comfort
8.0
Overall
7.9
Boarding
8.1
Entertainment
7.4
Food
7.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Comfort
8.0
Overall
7.9
Boarding
8.1
Entertainment
7.4
Food
7.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Comfort
8.0
Overall
7.9
Boarding
8.1
Entertainment
7.4
Food
7.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Related info for your journey
Find useful and relevant information for your journey from Midway to Puerto Rico. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Midway to Puerto Rico
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Complete your trip
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Find flights from Midway to Puerto Rico, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Midway and Puerto Rico flights
Browse other Midway and Puerto Rico flight options. Last updated on October 23, 2026.
Popular flight searches
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Top 3 airlines flying from Midway to Puerto Rico
Discover the top 3 airlines that operate flights from Midway to Puerto Rico. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated October 23, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$91 | Average$287 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$132 | Average$616 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$276 | Average$496 | FlexibilityNo cancel fee | On-time63% |