$124+ 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 8/25. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MDW
Sep 18 — Sep 251
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 August 19, 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 August 19, 2026.
This Southwest deal was found by Cheapflights users on 8/17. 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 9/102:35 pm -
1 stop7h 55m
Tue 9/159:40 am -
1 stop10h 20m
Deal found 8/17![Southwest logo]()
$226
This Southwest deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/176:30 am -
1 stop10h 05m
Sat 9/261:55 pm -
1 stop7h 05m
Deal found 8/18![Southwest logo]()
$246
This Faresmojo deal was found by Cheapflights users on 8/18. 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 Faresmojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/296:25 am -
1 stop11h 50m
Thu 10/18:40 pm -
1 stop11h 40m
Deal found 8/18![JetBlue logo]()
$247
This Southwest deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2611:50 am -
1 stop6h 50m
Tue 9/112:20 pm -
1 stop8h 40m
Deal found 8/16![Southwest logo]()
$261
This Southwest deal was found by Cheapflights users on 8/14. 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.
Wed 10/148:15 am -
2 stops12h 05m
Sun 10/185:25 pm -
1 stop7h 00m
Deal found 8/14![Southwest logo]()
$266
This Southwest deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2210:50 pm -
1 stop12h 10m
Mon 10/263:45 pm -
1 stop8h 35m
Deal found 8/18![Southwest logo]()
$281
This Faresmojo deal was found by Cheapflights users on 8/14. 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 Faresmojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/218:15 am -
1 stop12h 35m
Wed 10/284:40 pm -
1 stop6h 05m
Deal found 8/14![JetBlue logo]()
$292
This Kiwi.com deal was found by Cheapflights users on 8/16. 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 9/96:30 am -
1 stop12h 21m
Sat 9/121:06 pm -
2 stops12h 07m
Deal found 8/16![Frontier logo]()
$293
This Southwest deal was found by Cheapflights users on 8/14. 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.
Fri 9/1810:00 am -
1 stop6h 35m
Mon 9/213:15 pm -
1 stop6h 55m
Deal found 8/14![Southwest logo]()
$295
This Southwest deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/28:20 am -
1 stop7h 25m
Sun 9/61:45 pm -
2 stops8h 35m
Deal found 8/18![Southwest logo]()
$296
This Kiwi.com deal was found by Cheapflights users on 8/14. 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.
Sat 9/129:30 am -
2 stops9h 21m
Wed 9/166:25 am -
1 stop7h 54m
Deal found 8/14![Frontier logo]()
$299
This Southwest deal was found by Cheapflights users on 8/17. 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 9/95:15 am -
2 stops7h 50m
Mon 9/213:15 pm -
1 stop6h 55m
Deal found 8/17![Southwest logo]()
$301
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 August 19, 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 August 19, 2026.
This Southwest deal was found by Cheapflights users on 8/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/106:00 am -
2 stops9h 30m
Wed 9/169:40 am -
1 stop10h 20m
Deal found 8/15![Southwest logo]()
$226
This Southwest deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/176:30 am -
1 stop10h 05m
Sat 9/261:55 pm -
1 stop7h 05m
Deal found 8/18![Southwest logo]()
$246
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 11/153:48 am -
2 stops13h 53m
Sun 11/221:29 pm -
1 stop11h 06m
Deal found 8/17![Multiple Airlines logo]()
$599
This Southwest deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/115:00 am -
2 stops8h 25m
Mon 9/145:00 am -
1 stop7h 45m
Deal found 8/16![Southwest logo]()
$281
This Southwest deal was found by Cheapflights users on 8/16. 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 10/225:30 am -
2 stops8h 15m
Mon 10/263:45 pm -
1 stop8h 35m
Deal found 8/16![Southwest logo]()
$281
This Southwest deal was found by Cheapflights users on 8/14. 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.
Fri 9/1810:00 am -
1 stop6h 35m
Mon 9/213:15 pm -
1 stop6h 55m
Deal found 8/14![Southwest logo]()
$295
This Southwest deal was found by Cheapflights users on 8/14. 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.
Wed 9/95:15 am -
2 stops7h 50m
Fri 9/113:15 pm -
1 stop6h 55m
Deal found 8/14![Southwest logo]()
$301
This Southwest deal was found by Cheapflights users on 8/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/25:30 am -
2 stops8h 55m
Wed 10/79:30 am -
2 stops11h 20m
Deal found 8/15![Southwest logo]()
$336
This Southwest deal was found by Cheapflights users on 8/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/72:25 pm -
2 stops8h 45m
Sun 10/111:05 pm -
2 stops9h 10m
Deal found 8/15![Southwest logo]()
$336
This Southwest deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/285:00 am -
2 stops8h 25m
Sat 8/297:50 am -
2 stops9h 15m
Deal found 8/17![Southwest logo]()
$341
This Southwest deal was found by Cheapflights users on 8/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/222:50 pm -
1 stop7h 05m
Sat 8/297:05 am -
1 stop10h 10m
Deal found 8/15![Southwest logo]()
$366
This Southwest deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/85:30 am -
2 stops8h 55m
Mon 10/126:40 pm -
1 stop13h 30m
Deal found 8/18![Southwest logo]()
$376
Last-minute flights from Puerto Rico to MidwayDiscover last-minute flight deals from Puerto Rico to Midway. Data last updated August 19, 2026 and is based on user searches.
Discover last-minute flight deals from Puerto Rico to Midway. Data last updated August 19, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2611:50 am -
1 stop8h 25m
Tue 9/112:45 pm -
2 stops8h 15m
Deal found 8/16![Southwest logo]()
$261
This Southwest deal was found by Cheapflights users on 8/14. 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.
Fri 8/286:30 am -
2 stops8h 15m
Mon 8/317:25 am -
1 stop8h 30m
Deal found 8/14![Southwest logo]()
$266
This Faresmojo deal was found by Cheapflights users on 8/18. 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 Faresmojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/296:25 am -
1 stop11h 50m
Thu 10/18:40 pm -
1 stop11h 40m
Deal found 8/18![JetBlue logo]()
$247
This Southwest deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/28:20 am -
1 stop7h 25m
Sun 9/61:45 pm -
2 stops8h 35m
Deal found 8/18![Southwest logo]()
$296
This Southwest deal was found by Cheapflights users on 8/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/32:35 pm -
1 stop9h 10m
Tue 9/812:45 pm -
1 stop8h 20m
Deal found 8/15![Southwest logo]()
$281
This Kiwi.com deal was found by Cheapflights users on 8/16. 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 9/96:30 am -
1 stop12h 21m
Sat 9/121:06 pm -
2 stops12h 07m
Deal found 8/16![Frontier logo]()
$293
This Southwest deal was found by Cheapflights users on 8/17. 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 9/95:15 am -
2 stops7h 50m
Mon 9/213:15 pm -
1 stop6h 55m
Deal found 8/17![Southwest logo]()
$301
This Kiwi.com deal was found by Cheapflights users on 8/16. 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 9/96:30 am -
1 stop12h 21m
Wed 9/166:25 am -
1 stop7h 54m
Deal found 8/16![Frontier logo]()
$306
This Southwest deal was found by Cheapflights users on 8/17. 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 9/102:35 pm -
1 stop7h 55m
Tue 9/159:40 am -
1 stop10h 20m
Deal found 8/17![Southwest logo]()
$226
This Kiwi.com deal was found by Cheapflights users on 8/14. 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.
Sat 9/129:30 am -
2 stops9h 21m
Wed 9/166:25 am -
1 stop7h 54m
Deal found 8/14![Frontier logo]()
$299
This Southwest deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/176:30 am -
1 stop10h 05m
Sat 9/261:55 pm -
1 stop7h 05m
Deal found 8/18![Southwest logo]()
$246
This Southwest deal was found by Cheapflights users on 8/14. 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.
Fri 9/1810:00 am -
1 stop6h 35m
Mon 9/213:15 pm -
1 stop6h 55m
Deal found 8/14![Southwest logo]()
$295
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 August 19, 2026.
Search for one-way flight options from Puerto Rico to Midway. Find affordable one-way fares based on user searches. Data last updated August 19, 2026.
This Faresmojo deal was found by Cheapflights users on 8/14. 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 Faresmojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/255:15 am -
1 stop7h 50m
Deal found 8/14![JetBlue logo]()
$124
This Kiwi.com deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/148:45 am -
2 stops34h 00m
Deal found 8/17![Frontier logo]()
$125
This Southwest deal was found by Cheapflights users on 8/19. 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 9/12:25 pm -
1 stop7h 20m
Deal found 8/19![Southwest logo]()
$128
This Kiwi.com deal was found by Cheapflights users on 8/16. 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 11/178:24 pm -
2 stops16h 34m
Deal found 8/16![Frontier logo]()
$129
This Kiwi.com deal was found by Cheapflights users on 8/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/168:24 pm -
2 stops16h 34m
Deal found 8/15![Frontier logo]()
$131
This Southwest deal was found by Cheapflights users on 8/17. 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 9/195:55 am -
1 stop11h 45m
Deal found 8/17![Southwest logo]()
$133
This Faresmojo deal was found by Cheapflights users on 8/15. 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 Faresmojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/67:00 am -
1 stop9h 44m
Deal found 8/15![JetBlue logo]()
$138
This Kiwi.com deal was found by Cheapflights users on 8/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/157:00 am -
2 stops11h 45m
Deal found 8/15![Frontier logo]()
$139
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 9/158:45 am -
2 stops34h 06m
Deal found 8/17![Frontier logo]()
$140
This Kiwi.com deal was found by Cheapflights users on 8/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/168:45 am -
2 stops34h 01m
Deal found 8/15![Frontier logo]()
$141
This Kiwi.com deal was found by Cheapflights users on 8/14. 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 9/98:45 am -
2 stops34h 01m
Deal found 8/14![Frontier logo]()
$142
This Kiwi.com deal was found by Cheapflights users on 8/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/43:10 am -
2 stops20h 37m
Deal found 8/15![Frontier logo]()
$184
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 August 19, 2026.
Round-trip from | $226 (Southwest) |
|---|---|
One-way from | $124 (Faresmojo) |
Popular in | June |
Cheapest in | February |
Average price | $302 |
Good round-trip deal | $552 or less |
Good one-way deal | $279 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 7,457,451 searches. Data last updated August 19, 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 San Juan Luis Munoz Marin Intl - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 9/10
6:00 am-2:30 pm
2 stops9h 30m
Chicago Midway
Wed 9/16
9:40 am-9:00 pm
1 stop10h 20m
$226
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 9/17
6:30 am-3:35 pm
1 stop10h 05m
Chicago Midway
Sat 9/26
1:55 pm-10:00 pm
1 stop7h 05m
$246
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Fri 9/11
5:00 am-12:25 pm
2 stops8h 25m
Chicago Midway
Mon 9/14
5:00 am-1:45 pm
1 stop7h 45m
$281
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 10/22
5:30 am-12:45 pm
2 stops8h 15m
Chicago Midway
Mon 10/26
3:45 pm-1:20 am
1 stop8h 35m
$281
Quickest round-trip
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Fri 9/18
10:00 am-3:35 pm
1 stop6h 35m
Chicago Midway
Mon 9/21
3:15 pm-11:10 pm
1 stop6h 55m
$295
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Wed 9/9
5:15 am-12:05 pm
2 stops7h 50m
Chicago Midway
Fri 9/11
3:15 pm-11:10 pm
1 stop6h 55m
$301
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Fri 10/2
5:30 am-1:25 pm
2 stops8h 55m
Chicago Midway
Wed 10/7
9:30 am-9:50 pm
2 stops11h 20m
$336
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Wed 10/7
2:25 pm-10:10 pm
2 stops8h 45m
Chicago Midway
Sun 10/11
1:05 pm-11:15 pm
2 stops9h 10m
$336
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Fri 8/28
5:00 am-12:25 pm
2 stops8h 25m
Chicago Midway
Sat 8/29
7:50 am-6:05 pm
2 stops9h 15m
$341
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Sat 8/22
2:50 pm-8:55 pm
1 stop7h 05m
Chicago Midway
Sat 8/29
7:05 am-6:15 pm
1 stop10h 10m
$366
Showing 1-10 of 27 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
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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 August 19, 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.
Comfort
8.0
Crew
8.6
Boarding
8.1
Overall
8.0
Food
7.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Crew
8.6
Boarding
8.1
Overall
8.0
Food
7.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
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
Valparaiso
Hammond
Saint Joseph
Porter
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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 August 19, 2026.
Puerto Rico and Midway flights
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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 7,457,451 searches. Data last updated August 19, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$266 | Average$540 | FlexibilityNo cancel fee | On-time63% |