$158+ 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 10/21. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MDW
Aug 22 — Aug 291
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
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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 July 23, 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 July 23, 2026.
This Southwest deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/276:30 am
SJU
- MDW
2 stops8h 15m
Southwest
Mon 8/315:00 am
MDW
- SJU
1 stop7h 45m
Southwest
Deal found 7/22![Southwest logo]()
$256
This Southwest deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/216:00 am
SJU
- MDW
2 stops9h 30m
Southwest
Fri 8/283:15 pm
MDW
- SJU
1 stop6h 50m
Southwest
Deal found 7/22![Southwest logo]()
$296
This Southwest deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/265:55 am
SJU
- MDW
2 stops8h 10m
Southwest
Sat 10/311:25 am
MDW
- SJU
2 stops9h 05m
Southwest
Deal found 7/22![Southwest logo]()
$306
This Southwest deal was found by Cheapflights users on 7/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/285:00 am
SJU
- MDW
2 stops8h 25m
Southwest
Fri 8/282:55 pm
MDW
- SJU
1 stop6h 15m
Southwest
Deal found 7/18![Southwest logo]()
$311
This Southwest deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/175:00 am
SJU
- MDW
2 stops8h 25m
Southwest
Wed 9/2312:45 pm
MDW
- SJU
1 stop8h 20m
Southwest
Deal found 7/23![Southwest logo]()
$316
This Southwest deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/68:55 pm
SJU
- MDW
1 stop12h 50m
Southwest
Tue 8/1812:45 pm
MDW
- SJU
2 stops8h 15m
Southwest
Deal found 7/22![Southwest logo]()
$318
This Southwest deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/2511:50 am
SJU
- MDW
1 stop8h 25m
Southwest
Sat 8/297:50 am
MDW
- SJU
2 stops7h 50m
Southwest
Deal found 7/21![Southwest logo]()
$328
This Southwest deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/278:55 pm
SJU
- MDW
2 stops15h 30m
Southwest
Sun 8/303:00 pm
MDW
- SJU
2 stops8h 30m
Southwest
Deal found 7/22![Southwest logo]()
$331
This Southwest deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/208:55 pm
SJU
- MDW
2 stops15h 30m
Southwest
Mon 8/241:00 pm
MDW
- SJU
2 stops8h 50m
Southwest
Deal found 7/19![Southwest logo]()
$336
This Southwest deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/2310:20 pm
SJU
- MDW
1 stop11h 55m
Southwest
Mon 7/275:10 pm
MDW
- SJU
1 stop7h 15m
Southwest
Deal found 7/19![Southwest logo]()
$340
This Southwest deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/218:55 pm
SJU
- MDW
1 stop13h 00m
Southwest
Mon 8/243:15 pm
MDW
- SJU
1 stop6h 50m
Southwest
Deal found 7/20![Southwest logo]()
$341
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 July 23, 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 July 23, 2026.
This Southwest deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/282:35 pm
SJU
- MDW
1 stop9h 05m
Southwest
Mon 8/3111:15 am
MDW
- SJU
1 stop7h 50m
Southwest
Deal found 7/22![Southwest logo]()
$256
This Southwest deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/148:55 pm
SJU
- MDW
1 stop13h 00m
Southwest
Tue 8/189:40 am
MDW
- SJU
1 stop10h 25m
Southwest
Deal found 7/22![Southwest logo]()
$311
This Southwest deal was found by Cheapflights users on 7/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/266:00 am
SJU
- MDW
2 stops8h 30m
Southwest
Tue 9/16:15 am
MDW
- SJU
1 stop6h 20m
Southwest
Deal found 7/18![Southwest logo]()
$316
This Southwest deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/2511:35 am
SJU
- MDW
1 stop11h 00m
Southwest
Sat 10/32:40 pm
MDW
- SJU
1 stop6h 30m
Southwest
Deal found 7/23![Southwest logo]()
$316
This Southwest deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/176:30 am
SJU
- MDW
2 stops8h 15m
Southwest
Tue 9/2212:45 pm
MDW
- SJU
2 stops8h 15m
Southwest
Deal found 7/20![Southwest logo]()
$316
This Southwest deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/278:55 pm
SJU
- MDW
2 stops15h 30m
Southwest
Sun 8/303:00 pm
MDW
- SJU
2 stops8h 30m
Southwest
Deal found 7/22![Southwest logo]()
$331
This Southwest deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/178:55 pm
SJU
- MDW
1 stop12h 50m
Southwest
Mon 9/211:00 pm
MDW
- SJU
2 stops8h 50m
Southwest
Deal found 7/20![Southwest logo]()
$336
This Southwest deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/148:55 pm
SJU
- MDW
1 stop13h 00m
Southwest
Thu 8/201:00 pm
MDW
- SJU
1 stop8h 50m
Southwest
Deal found 7/23![Southwest logo]()
$371
This Southwest deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/46:00 am
SJU
- MDW
2 stops9h 30m
Southwest
Mon 9/77:25 am
MDW
- SJU
1 stop8h 30m
Southwest
Deal found 7/21![Southwest logo]()
$391
This Southwest deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/38:55 pm
SJU
- MDW
2 stops15h 30m
Southwest
Mon 9/711:15 am
MDW
- SJU
1 stop10h 00m
Southwest
Deal found 7/23![Southwest logo]()
$391
Last-minute flights from Puerto Rico to MidwayDiscover last-minute flight deals from Puerto Rico to Midway. Data last updated July 23, 2026 and is based on user searches.
Discover last-minute flight deals from Puerto Rico to Midway. Data last updated July 23, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/2310:20 pm
SJU
- MDW
1 stop11h 55m
Southwest
Mon 7/275:10 pm
MDW
- SJU
1 stop7h 15m
Southwest
Deal found 7/19![Southwest logo]()
$340
This Southwest deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/68:55 pm
SJU
- MDW
1 stop12h 50m
Southwest
Tue 8/1812:45 pm
MDW
- SJU
1 stop8h 15m
Southwest
Deal found 7/22![Southwest logo]()
$318
This Southwest deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/68:55 pm
SJU
- MDW
1 stop12h 50m
Southwest
Wed 8/129:40 am
MDW
- SJU
1 stop10h 25m
Southwest
Deal found 7/21![Southwest logo]()
$351
This Southwest deal was found by Cheapflights users on 7/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/208:55 pm
SJU
- MDW
1 stop12h 50m
Southwest
Sun 8/238:05 pm
MDW
- SJU
1 stop12h 05m
Southwest
Deal found 7/18![Southwest logo]()
$336
This Southwest deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/216:00 am
SJU
- MDW
2 stops9h 30m
Southwest
Fri 8/283:15 pm
MDW
- SJU
1 stop6h 50m
Southwest
Deal found 7/22![Southwest logo]()
$296
This Southwest deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/218:55 pm
SJU
- MDW
1 stop13h 00m
Southwest
Mon 8/243:15 pm
MDW
- SJU
1 stop6h 50m
Southwest
Deal found 7/20![Southwest logo]()
$341
This Southwest deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/2511:50 am
SJU
- MDW
1 stop6h 50m
Southwest
Sat 8/297:45 am
MDW
- SJU
1 stop9h 20m
Southwest
Deal found 7/21![Southwest logo]()
$328
This Southwest deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/268:20 am
SJU
- MDW
1 stop7h 25m
Southwest
Sun 8/308:05 pm
MDW
- SJU
1 stop12h 05m
Southwest
Deal found 7/19![Southwest logo]()
$316
This Southwest deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/276:00 am
SJU
- MDW
2 stops9h 30m
Southwest
Sun 8/308:20 am
MDW
- SJU
1 stop13h 25m
Southwest
Deal found 7/22![Southwest logo]()
$256
This Southwest deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/278:55 pm
SJU
- MDW
2 stops15h 30m
Southwest
Mon 8/313:10 pm
MDW
- SJU
2 stops7h 40m
Southwest
Deal found 7/22![Southwest logo]()
$286
This Southwest deal was found by Cheapflights users on 7/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/285:00 am
SJU
- MDW
2 stops8h 25m
Southwest
Fri 8/282:55 pm
MDW
- SJU
1 stop6h 15m
Southwest
Deal found 7/18![Southwest logo]()
$311
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 July 23, 2026.
Search for one-way flight options from Puerto Rico to Midway. Find affordable one-way fares based on user searches. Data last updated July 23, 2026.
This Southwest deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/266:00 am
SJU
- MDW
2 stops8h 30m
Southwest
Deal found 7/21![Southwest logo]()
$158
This Kiwi.com deal was found by Cheapflights users on 7/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/118:24 pm
SJU
- MDW
2 stops27h 29m
Frontier
Deal found 7/18![Frontier logo]()
$166
This Southwest deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/208:55 pm
SJU
- MDW
1 stop12h 50m
Southwest
Deal found 7/22![Southwest logo]()
$168
This Kiwi.com deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/125:22 pm
SJU
- MDW
2 stops29h 41m
Frontier
Deal found 7/22![Frontier logo]()
$173
This Kiwi.com deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/185:37 pm
SJU
- MDW
2 stops30h 10m
Frontier
Deal found 7/22![Frontier logo]()
$174
This Kiwi.com deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/234:39 pm
SJU
- MDW
2 stops30h 19m
Frontier
Deal found 7/22![Frontier logo]()
$175
This Kiwi.com deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/204:39 pm
SJU
- MDW
2 stops43h 19m
Frontier
Deal found 7/22![Frontier logo]()
$176
This Kiwi.com deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/224:39 pm
SJU
- MDW
2 stops30h 19m
Frontier
Deal found 7/22![Frontier logo]()
$177
This Southwest deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/188:25 pm
SJU
- MDW
1 stop13h 20m
Southwest
Deal found 7/19![Southwest logo]()
$178
This Kiwi.com deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/205:12 pm
SJU
- MDW
2 stops29h 46m
Frontier
Deal found 7/20![Frontier logo]()
$179
This Kiwi.com deal was found by Cheapflights users on 7/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/106:12 pm
SJU
- MDW
2 stops18h 46m
Frontier
Deal found 7/18![Frontier logo]()
$180
This Kiwi.com deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/216:00 am
SJU
- MDW
2 stops29h 58m
Frontier
Deal found 7/20![Frontier logo]()
$181
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 July 23, 2026.
Round-trip from | $256 (Southwest) |
|---|---|
One-way from | $158 (Southwest) |
Popular in | June |
Cheapest in | February |
Average price | $331 |
Good one-way deal | $295 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 July 23, 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
Fri 8/28
2:35 pm-10:40 pm
1 stop9h 05m
Chicago Midway
Mon 8/31
11:15 am-8:05 pm
1 stop7h 50m
$256
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Fri 8/14
8:55 pm-8:55 am
1 stop13h 00m
Chicago Midway
Tue 8/18
9:40 am-9:05 pm
1 stop10h 25m
$311
Quickest round-trip
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Wed 8/26
6:00 am-1:30 pm
2 stops8h 30m
Chicago Midway
Tue 9/1
6:15 am-1:35 pm
1 stop6h 20m
$316
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Fri 9/25
11:35 am-9:35 pm
1 stop11h 00m
Chicago Midway
Sat 10/3
2:40 pm-10:10 pm
1 stop6h 30m
$316
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 9/17
6:30 am-1:45 pm
2 stops8h 15m
Chicago Midway
Tue 9/22
12:45 pm-10:00 pm
2 stops8h 15m
$316
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 8/27
8:55 pm-11:25 am
2 stops15h 30m
Chicago Midway
Sun 8/30
3:00 pm-12:30 am
2 stops8h 30m
$331
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 9/17
8:55 pm-8:45 am
1 stop12h 50m
Chicago Midway
Mon 9/21
1:00 pm-10:50 pm
2 stops8h 50m
$336
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Fri 8/14
8:55 pm-8:55 am
1 stop13h 00m
Chicago Midway
Thu 8/20
1:00 pm-10:50 pm
1 stop8h 50m
$371
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Fri 9/4
6:00 am-2:30 pm
2 stops9h 30m
Chicago Midway
Mon 9/7
7:25 am-4:55 pm
1 stop8h 30m
$391
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 9/3
8:55 pm-11:25 am
2 stops15h 30m
Chicago Midway
Mon 9/7
11:15 am-10:15 pm
1 stop10h 00m
$391
Showing 1-10 of 20 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
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
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 July 23, 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 July 23, 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.
Food
7.0
Boarding
8.1
Overall
8.0
Comfort
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Boarding
8.1
Overall
8.0
Comfort
8.0
Crew
8.6
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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Alternative routes for Puerto Rico to Midway
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Complete your trip
Complete your trip to Midway by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Puerto Rico to Midway by cabin class
Find flights from Puerto Rico to Midway, based on your preferred cabin class, be it economy, premium economy, business, or first class.
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 July 23, 2026.
Puerto Rico and Midway flights
Browse other Puerto Rico and Midway flight options. Last updated on July 23, 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 July 23, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$266 | Average$540 | FlexibilityNo cancel fee | On-time63% |