$123+ 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 8/13. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MDW
Jul 24 — Jul 311
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 June 24, 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 June 24, 2026.
This Delta deal was found by Cheapflights users on 6/19. 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 8/1912:56 pm
SJU
- MDW
1 stop10h 40m
Delta
Wed 8/2612:46 pm
MDW
- SJU
1 stop8h 43m
Delta
Deal found 6/19![Delta logo]()
$246
This Delta deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2612:56 pm
SJU
- MDW
1 stop10h 40m
Delta
Sat 8/296:05 am
MDW
- SJU
1 stop9h 33m
Delta
Deal found 6/23![Delta logo]()
$256
This Delta deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1912:56 pm
SJU
- MDW
1 stop10h 40m
Delta
Mon 8/246:05 am
MDW
- SJU
1 stop6h 37m
Delta
Deal found 6/23![Delta logo]()
$266
This Delta deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1912:56 pm
SJU
- MDW
1 stop10h 40m
Delta
Fri 8/2112:46 pm
MDW
- SJU
1 stop8h 43m
Delta
Deal found 6/22![Delta logo]()
$276
This Southwest deal was found by Cheapflights users on 6/22. 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 8/195:15 am
SJU
- MDW
2 stops7h 50m
Southwest
Fri 8/211:00 pm
MDW
- SJU
1 stop8h 50m
Southwest
Deal found 6/22![Southwest logo]()
$286
This Southwest deal was found by Cheapflights users on 6/23. 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 9/178:55 pm
SJU
- MDW
2 stops15h 30m
Southwest
Mon 9/211:00 pm
MDW
- SJU
2 stops9h 50m
Southwest
Deal found 6/23![Southwest logo]()
$291
This Southwest deal was found by Cheapflights users on 6/21. 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 9/178:55 pm
SJU
- MDW
2 stops15h 30m
Southwest
Wed 9/2312:50 pm
MDW
- SJU
2 stops8h 10m
Southwest
Deal found 6/21![Southwest logo]()
$296
This Southwest deal was found by Cheapflights users on 6/19. 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 8/145:00 am
SJU
- MDW
1 stop7h 45m
Southwest
Sun 8/168:05 pm
MDW
- SJU
1 stop12h 05m
Southwest
Deal found 6/19![Southwest logo]()
$306
This Southwest deal was found by Cheapflights users on 6/23. 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 7/1710:20 pm
SJU
- MDW
1 stop11h 30m
Southwest
Fri 8/72:55 pm
MDW
- SJU
1 stop7h 55m
Southwest
Deal found 6/23![Southwest logo]()
$316
This Southwest deal was found by Cheapflights users on 6/21. 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 8/138:55 pm
SJU
- MDW
2 stops15h 30m
Southwest
Sun 8/161:10 pm
MDW
- SJU
2 stops8h 35m
Southwest
Deal found 6/21![Southwest logo]()
$326
This Delta deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/127:00 am
SJU
- MDW
1 stop10h 15m
Delta
Tue 8/186:05 am
MDW
- SJU
1 stop9h 33m
Delta
Deal found 6/22![Delta logo]()
$336
This Southwest deal was found by Cheapflights users on 6/22. 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 9/246:30 am
SJU
- MDW
2 stops8h 15m
Southwest
Sun 9/272:45 pm
MDW
- SJU
2 stops8h 45m
Southwest
Deal found 6/22![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 June 24, 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 June 24, 2026.
This Southwest deal was found by Cheapflights users on 6/23. 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.
Wed 8/265:15 am
SJU
- MDW
2 stops7h 50m
Southwest
Sun 8/308:05 pm
MDW
- SJU
1 stop12h 05m
Southwest
Deal found 6/23![Southwest logo]()
$246
This Delta deal was found by Cheapflights users on 6/19. 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 8/1912:56 pm
SJU
- MDW
1 stop10h 40m
Delta
Fri 8/2812:46 pm
MDW
- SJU
1 stop8h 43m
Delta
Deal found 6/19![Delta logo]()
$256
This Southwest deal was found by Cheapflights users on 6/18. 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 9/46:30 am
SJU
- MDW
1 stop10h 05m
Southwest
Mon 9/73:15 pm
MDW
- SJU
1 stop6h 50m
Southwest
Deal found 6/18![Southwest logo]()
$256
This Delta deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/127:00 am
SJU
- MDW
1 stop10h 15m
Delta
Tue 8/186:05 am
MDW
- SJU
1 stop9h 33m
Delta
Deal found 6/21![Delta logo]()
$336
This Delta deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/272:59 pm
SJU
- MDW
1 stop8h 37m
Delta
Sat 8/296:05 am
MDW
- SJU
1 stop9h 33m
Delta
Deal found 6/21![Delta logo]()
$346
This Southwest deal was found by Cheapflights users on 6/23. 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.
Sat 8/156:25 am
SJU
- MDW
2 stops11h 40m
Southwest
Mon 8/243:15 pm
MDW
- SJU
1 stop6h 50m
Southwest
Deal found 6/23![Southwest logo]()
$371
This Delta deal was found by Cheapflights users on 6/19. 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.
Tue 8/187:00 am
SJU
- MDW
1 stop10h 15m
Delta
Thu 8/2710:54 am
MDW
- SJU
1 stop10h 35m
Delta
Deal found 6/19![Delta logo]()
$358
This Delta deal was found by Cheapflights users on 6/19. 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 8/1912:56 pm
SJU
- MDW
1 stop10h 40m
Delta
Sun 8/236:05 am
MDW
- SJU
1 stop6h 37m
Delta
Deal found 6/19![Delta logo]()
$391
This Delta deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/22:59 pm
SJU
- MDW
1 stop8h 37m
Delta
Mon 9/76:05 am
MDW
- SJU
1 stop9h 33m
Delta
Deal found 6/23![Delta logo]()
$401
This Delta deal was found by Cheapflights users on 6/19. 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.
Mon 8/1712:56 pm
SJU
- MDW
1 stop10h 40m
Delta
Tue 8/2512:46 pm
MDW
- SJU
1 stop8h 43m
Delta
Deal found 6/19![Delta logo]()
$406
This Delta deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/142:59 pm
SJU
- MDW
1 stop8h 37m
Delta
Sun 8/166:05 am
MDW
- SJU
1 stop6h 37m
Delta
Deal found 6/22![Delta logo]()
$426
Last-minute flights from Puerto Rico to MidwayDiscover last-minute flight deals from Puerto Rico to Midway. Data last updated June 24, 2026 and is based on user searches.
Discover last-minute flight deals from Puerto Rico to Midway. Data last updated June 24, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 6/19. 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 6/2510:20 pm
SJU
- MDW
1 stop12h 40m
Southwest
Thu 7/91:40 pm
MDW
- SJU
1 stop6h 50m
Southwest
Deal found 6/19![Southwest logo]()
$379
This Southwest deal was found by Cheapflights users on 6/21. 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 7/26:30 pm
SJU
- MDW
1 stop7h 10m
Southwest
Tue 7/74:40 pm
MDW
- SJU
1 stop6h 40m
Southwest
Deal found 6/21![Southwest logo]()
$356
This Southwest deal was found by Cheapflights users on 6/19. 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 7/1610:20 pm
SJU
- MDW
2 stops12h 40m
Southwest
Mon 7/205:10 pm
MDW
- SJU
1 stop7h 15m
Southwest
Deal found 6/19![Southwest logo]()
$401
This Southwest deal was found by Cheapflights users on 6/23. 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 7/1710:20 pm
SJU
- MDW
1 stop11h 30m
Southwest
Fri 8/72:55 pm
MDW
- SJU
1 stop7h 55m
Southwest
Deal found 6/23![Southwest logo]()
$316
This Southwest deal was found by Cheapflights users on 6/19. 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 7/1710:20 pm
SJU
- MDW
1 stop11h 30m
Southwest
Mon 7/205:10 pm
MDW
- SJU
1 stop7h 15m
Southwest
Deal found 6/19![Southwest logo]()
$346
This Southwest deal was found by Cheapflights users on 6/23. 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 7/2310:20 pm
SJU
- MDW
1 stop11h 55m
Southwest
Tue 7/284:40 pm
MDW
- SJU
1 stop6h 40m
Southwest
Deal found 6/23![Southwest logo]()
$366
This Frontier deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/256:32 am
SJU
- MDW
1 stop11h 54m
Frontier
Tue 7/285:46 pm
MDW
- SJU
1 stop10h 16m
Frontier
Deal found 6/23![Frontier logo]()
$396
This Travelocity deal was found by Cheapflights users on 6/23. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/256:32 am
SJU
- MDW
1 stop11h 54m
Frontier
Mon 8/36:05 am
MDW
- SJU
1 stop7h 11m
Frontier
Deal found 6/23![Frontier logo]()
$416
This Southwest deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/2710:20 pm
SJU
- MDW
1 stop11h 40m
Southwest
Tue 8/1112:20 pm
MDW
- SJU
1 stop7h 45m
Southwest
Deal found 6/20![Southwest logo]()
$391
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 June 24, 2026.
Search for one-way flight options from Puerto Rico to Midway. Find affordable one-way fares based on user searches. Data last updated June 24, 2026.
This Southwest deal was found by Cheapflights users on 6/19. 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 8/138:55 pm
SJU
- MDW
1 stop12h 50m
Southwest
Deal found 6/19![Southwest logo]()
$123
This Southwest deal was found by Cheapflights users on 6/20. 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.
Sun 9/139:25 pm
SJU
- MDW
1 stop13h 35m
Southwest
Deal found 6/20![Southwest logo]()
$128
This Southwest deal was found by Cheapflights users on 6/23. 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.
Sat 8/295:55 am
SJU
- MDW
1 stop11h 45m
Southwest
Deal found 6/23![Southwest logo]()
$133
This Delta deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1912:56 pm
SJU
- MDW
1 stop10h 40m
Delta
Deal found 6/23![Delta logo]()
$143
This Southwest deal was found by Cheapflights users on 6/23. 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.
Wed 8/195:15 am
SJU
- MDW
2 stops7h 50m
Southwest
Deal found 6/23![Southwest logo]()
$163
This Kiwi.com deal was found by Cheapflights users on 6/24. 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 9/184:39 pm
SJU
- MDW
2 stops30h 19m
Frontier
Deal found 6/24![Frontier logo]()
$165
This Southwest deal was found by Cheapflights users on 6/20. 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
2 stops15h 30m
Southwest
Deal found 6/20![Southwest logo]()
$168
This Kiwi.com deal was found by Cheapflights users on 6/22. 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 stops19h 19m
Frontier
Deal found 6/22![Frontier logo]()
$174
This Kiwi.com deal was found by Cheapflights users on 6/20. 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 9/216:31 pm
SJU
- MDW
2 stops28h 27m
Frontier
Deal found 6/20![Frontier logo]()
$181
This Southwest deal was found by Cheapflights users on 6/19. 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.
Sat 7/411:30 am
SJU
- MDW
1 stop7h 00m
Southwest
Deal found 6/19![Southwest logo]()
$183
This Kiwi.com deal was found by Cheapflights users on 6/19. 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.
Sun 8/166:00 am
SJU
- MDW
2 stops33h 59m
Multiple Airlines
Deal found 6/19![Multiple Airlines logo]()
$184
This Super.com deal was found by Cheapflights users on 6/19. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/56:32 am
SJU
- MDW
1 stop10h 18m
Frontier
Deal found 6/19![Frontier logo]()
$185
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 June 24, 2026.
Round-trip from | $246 (Delta) |
|---|---|
One-way from | $123 (Southwest) |
Popular in | June |
Cheapest in | February |
Average price | $443 |
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 June 24, 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
Wed 8/26
5:15 am-12:05 pm
2 stops7h 50m
Chicago Midway
Sun 8/30
8:05 pm-9:10 am
1 stop12h 05m
$246
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Wed 8/19
12:56 pm-10:36 pm
1 stop10h 40m
Chicago Midway
Fri 8/28
12:46 pm-10:29 pm
1 stop8h 43m
$256
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Fri 9/4
6:30 am-3:35 pm
1 stop10h 05m
Chicago Midway
Mon 9/7
3:15 pm-11:05 pm
1 stop6h 50m
$256
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Wed 8/12
7:00 am-4:15 pm
1 stop10h 15m
Chicago Midway
Tue 8/18
6:05 am-4:38 pm
1 stop9h 33m
$336
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 8/27
2:59 pm-10:36 pm
1 stop8h 37m
Chicago Midway
Sat 8/29
6:05 am-4:38 pm
1 stop9h 33m
$346
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Tue 8/18
7:00 am-4:15 pm
1 stop10h 15m
Chicago Midway
Thu 8/27
10:54 am-10:29 pm
1 stop10h 35m
$358
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Sat 8/15
6:25 am-5:05 pm
2 stops11h 40m
Chicago Midway
Mon 8/24
3:15 pm-11:05 pm
1 stop6h 50m
$371
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Wed 8/19
12:56 pm-10:36 pm
1 stop10h 40m
Chicago Midway
Sun 8/23
6:05 am-1:42 pm
1 stop6h 37m
$391
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Wed 9/2
2:59 pm-10:36 pm
1 stop8h 37m
Chicago Midway
Mon 9/7
6:05 am-4:38 pm
1 stop9h 33m
$401
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Mon 8/17
12:56 pm-10:36 pm
1 stop10h 40m
Chicago Midway
Tue 8/25
12:46 pm-10:29 pm
1 stop8h 43m
$406
Showing 1-10 of 23 resultsSorted by cheapest first
Best time to book a flight from Puerto Rico to Midway
Have a flexible travel schedule? Discover the best time to fly to Midway from Puerto Rico with our price prediction graph.
SJU-MDW
BQN-MDW
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Puerto Rico to Chicago Midway Airport
PR0-MDW
SJU-MDW
BQN-MDW
What is the cheapest time of day to fly from PR to MDW?
Find hourly flight availability from Puerto Rico to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 24, 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 June 24, 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.
Overall
7.9
Crew
8.6
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
7.9
Crew
8.6
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Food
7.0
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
Hammond
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 June 24, 2026.
Puerto Rico and Midway flights
Browse other Puerto Rico and Midway flight options. Last updated on June 24, 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 June 24, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$326 | Average$559 | FlexibilityNo cancel fee | On-time63% |