$118+ 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 8/24. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MDW
Jun 25 — Jul 21
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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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 May 26, 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 May 26, 2026.
This Southwest deal was found by Cheapflights users on 5/23. 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 8/206:30 am
SJU
- MDW
2 stops8h 15m
Southwest
Tue 9/812:20 pm
MDW
- SJU
1 stop7h 45m
Southwest
Deal found 5/23![Southwest logo]()
$236
This Delta deal was found by Cheapflights users on 5/23. 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
Sat 9/56:05 am
MDW
- SJU
1 stop9h 33m
Delta
Deal found 5/23![Delta logo]()
$246
This Southwest deal was found by Cheapflights users on 5/22. 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
1 stop7h 50m
Southwest
Mon 8/242:55 pm
MDW
- SJU
1 stop7h 55m
Southwest
Deal found 5/22![Southwest logo]()
$256
This Delta deal was found by Cheapflights users on 5/22. 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.
Sat 8/226:48 am
SJU
- MDW
1 stop9h 50m
Delta
Wed 8/2612:46 pm
MDW
- SJU
1 stop8h 43m
Delta
Deal found 5/22![Delta logo]()
$266
This Delta deal was found by Cheapflights users on 5/23. 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 8/192:59 pm
SJU
- MDW
1 stop8h 37m
Delta
Wed 9/910:35 am
MDW
- SJU
1 stop10h 48m
Delta
Deal found 5/23![Delta logo]()
$276
This Southwest deal was found by Cheapflights users on 5/23. 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 8/125:15 am
SJU
- MDW
2 stops7h 50m
Southwest
Wed 8/1912:45 pm
MDW
- SJU
2 stops8h 15m
Southwest
Deal found 5/23![Southwest logo]()
$286
This Southwest deal was found by Cheapflights users on 5/22. 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
1 stop9h 30m
Southwest
Sun 8/308:05 pm
MDW
- SJU
1 stop12h 05m
Southwest
Deal found 5/22![Southwest logo]()
$301
This Delta deal was found by Cheapflights users on 5/23. 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.
Sat 8/227:00 am
SJU
- MDW
1 stop9h 38m
Delta
Fri 9/116:00 am
MDW
- SJU
1 stop9h 31m
Delta
Deal found 5/23![Delta logo]()
$306
This Southwest deal was found by Cheapflights users on 5/23. 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.
Tue 8/111:45 pm
SJU
- MDW
1 stop8h 15m
Southwest
Tue 8/187:30 am
MDW
- SJU
1 stop10h 30m
Southwest
Deal found 5/23![Southwest logo]()
$316
This Southwest deal was found by Cheapflights users on 5/22. 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 8/286:00 am
SJU
- MDW
1 stop9h 30m
Southwest
Sun 8/308:05 pm
MDW
- SJU
1 stop12h 05m
Southwest
Deal found 5/22![Southwest logo]()
$321
This Southwest deal was found by Cheapflights users on 5/25. 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 9/25:15 am
SJU
- MDW
2 stops7h 50m
Southwest
Fri 9/41:00 pm
MDW
- SJU
2 stops8h 50m
Southwest
Deal found 5/25![Southwest logo]()
$331
This Southwest deal was found by Cheapflights users on 5/25. 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 8/315:00 am
SJU
- MDW
1 stop7h 45m
Southwest
Mon 9/75:00 am
MDW
- SJU
1 stop7h 45m
Southwest
Deal found 5/25![Southwest logo]()
$336
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 May 26, 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 May 26, 2026.
This Southwest deal was found by Cheapflights users on 5/22. 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
1 stop9h 30m
Southwest
Mon 8/3111:15 am
MDW
- SJU
1 stop9h 55m
Southwest
Deal found 5/22![Southwest logo]()
$256
This Delta deal was found by Cheapflights users on 5/24. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1912:58 pm
SJU
- MDW
1 stop10h 27m
Delta
Fri 9/256:05 am
MDW
- SJU
1 stop9h 26m
Delta
Deal found 5/24![Delta logo]()
$316
This Southwest deal was found by Cheapflights users on 5/24. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1010:00 am
SJU
- MDW
1 stop9h 00m
Southwest
Sun 9/135:00 am
MDW
- SJU
1 stop7h 00m
Southwest
Deal found 5/24![Southwest logo]()
$356
This Southwest deal was found by Cheapflights users on 5/25. 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 9/76:30 am
SJU
- MDW
2 stops8h 15m
Southwest
Mon 9/147:15 am
MDW
- SJU
1 stop8h 40m
Southwest
Deal found 5/25![Southwest logo]()
$356
This Southwest deal was found by Cheapflights users on 5/23. 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.
Mon 8/316:30 am
SJU
- MDW
2 stops8h 15m
Southwest
Mon 9/712:15 pm
MDW
- SJU
2 stops9h 50m
Southwest
Deal found 5/23![Southwest logo]()
$371
This Delta deal was found by Cheapflights users on 5/21. 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.
Sat 8/112:56 pm
SJU
- MDW
1 stop10h 19m
Delta
Sat 8/810:56 am
MDW
- SJU
1 stop10h 33m
Delta
Deal found 5/21![Delta logo]()
$486
This Southwest deal was found by Cheapflights users on 5/25. 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 stop11h 55m
Southwest
Sun 6/2812:00 pm
MDW
- SJU
2 stops9h 35m
Southwest
Deal found 5/25![Southwest logo]()
$446
This Southwest deal was found by Cheapflights users on 5/21. 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 6/1210:20 pm
SJU
- MDW
1 stop11h 30m
Southwest
Sat 7/412:30 pm
MDW
- SJU
1 stop8h 20m
Southwest
Deal found 5/21![Southwest logo]()
$461
This Southwest deal was found by Cheapflights users on 5/22. 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 6/56:30 pm
SJU
- MDW
1 stop7h 10m
Southwest
Sat 6/135:05 pm
MDW
- SJU
1 stop7h 10m
Southwest
Deal found 5/22![Southwest logo]()
$476
This Southwest deal was found by Cheapflights users on 5/21. 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.
Sun 6/75:00 am
SJU
- MDW
2 stops11h 20m
Southwest
Sat 6/135:05 pm
MDW
- SJU
1 stop7h 10m
Southwest
Deal found 5/21![Southwest logo]()
$521
Last-minute flights from Puerto Rico to MidwayDiscover last-minute flight deals from Puerto Rico to Midway. Data last updated May 26, 2026 and is based on user searches.
Discover last-minute flight deals from Puerto Rico to Midway. Data last updated May 26, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 5/23. 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 5/272:00 pm
SJU
- MDW
2 stops9h 15m
Southwest
Fri 5/298:35 pm
MDW
- SJU
1 stop11h 20m
Southwest
Deal found 5/23![Southwest logo]()
$486
This eDestinos deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/312:59 am
BQN
- MDW
2 stops20h 03m
Frontier
Wed 6/36:00 am
MDW
- BQN
2 stops28h 31m
Frontier
Deal found 5/25![Frontier logo]()
$904
This Southwest deal was found by Cheapflights users on 5/24. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/46:00 am
SJU
- MDW
1 stop11h 20m
Southwest
Sat 7/49:35 am
MDW
- SJU
1 stop11h 15m
Southwest
Deal found 5/24![Southwest logo]()
$451
This Southwest deal was found by Cheapflights users on 5/26. 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 6/46:00 am
SJU
- MDW
1 stop11h 20m
Southwest
Sat 6/66:30 am
MDW
- SJU
1 stop7h 30m
Southwest
Deal found 5/26![Southwest logo]()
$491
This Southwest deal was found by Cheapflights users on 5/21. 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.
Sat 6/65:30 am
SJU
- MDW
Nonstop4h 50m
Southwest
Sat 6/135:05 pm
MDW
- SJU
1 stop7h 10m
Southwest
Deal found 5/21![Southwest logo]()
$477
This Southwest deal was found by Cheapflights users on 5/21. 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 6/1210:20 pm
SJU
- MDW
1 stop11h 30m
Southwest
Sat 7/412:30 pm
MDW
- SJU
1 stop8h 20m
Southwest
Deal found 5/21![Southwest logo]()
$476
This Southwest deal was found by Cheapflights users on 5/21. 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.
Mon 6/1510:20 pm
SJU
- MDW
1 stop11h 40m
Southwest
Sat 7/49:35 am
MDW
- SJU
1 stop11h 15m
Southwest
Deal found 5/21![Southwest logo]()
$461
This Southwest deal was found by Cheapflights users on 5/25. 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 6/1810:20 pm
SJU
- MDW
2 stops12h 40m
Southwest
Mon 6/228:55 pm
MDW
- SJU
1 stop11h 05m
Southwest
Deal found 5/25![Southwest logo]()
$496
This Southwest deal was found by Cheapflights users on 5/26. 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 stop11h 55m
Southwest
Sat 7/412:30 pm
MDW
- SJU
1 stop8h 20m
Southwest
Deal found 5/26![Southwest logo]()
$381
This Southwest deal was found by Cheapflights users on 5/25. 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 stop11h 55m
Southwest
Sun 6/2812:00 pm
MDW
- SJU
2 stops9h 35m
Southwest
Deal found 5/25![Southwest logo]()
$446
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 May 26, 2026.
Search for one-way flight options from Puerto Rico to Midway. Find affordable one-way fares based on user searches. Data last updated May 26, 2026.
This Southwest deal was found by Cheapflights users on 5/25. 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 5/25![Southwest logo]()
$118
This Southwest deal was found by Cheapflights users on 5/22. 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.
Tue 8/188:20 am
SJU
- MDW
1 stop7h 25m
Southwest
Deal found 5/22![Southwest logo]()
$138
This Southwest deal was found by Cheapflights users on 5/26. 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 8/225:05 am
SJU
- MDW
1 stop6h 55m
Southwest
Deal found 5/26![Southwest logo]()
$148
This Southwest deal was found by Cheapflights users on 5/22. 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 7/1610:20 pm
SJU
- MDW
1 stop12h 40m
Southwest
Deal found 5/22![Southwest logo]()
$168
This Southwest deal was found by Cheapflights users on 5/25. 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 stop11h 55m
Southwest
Deal found 5/25![Southwest logo]()
$183
This Kiwi.com deal was found by Cheapflights users on 5/23. 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.
Sun 8/166:00 am
SJU
- MDW
2 stops33h 59m
Multiple Airlines
Deal found 5/23![Multiple Airlines logo]()
$200
This Southwest deal was found by Cheapflights users on 5/25. 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 6/1110:20 pm
SJU
- MDW
2 stops12h 40m
Southwest
Deal found 5/25![Southwest logo]()
$203
This Southwest deal was found by Cheapflights users on 5/22. 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 7/910:20 pm
SJU
- MDW
2 stops12h 40m
Southwest
Deal found 5/22![Southwest logo]()
$213
This Kiwi.com deal was found by Cheapflights users on 5/23. 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.
Tue 6/167:30 am
SJU
- MDW
2 stops15h 41m
Frontier
Deal found 5/23![Frontier logo]()
$224
This Kiwi.com deal was found by Cheapflights users on 5/25. 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 8/63:10 am
BQN
- MDW
2 stops12h 49m
Multiple Airlines
Deal found 5/25![Multiple Airlines logo]()
$304
This Kiwi.com deal was found by Cheapflights users on 5/21. 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 6/113:00 am
BQN
- MDW
2 stops17h 30m
Multiple Airlines
Deal found 5/21![Multiple Airlines logo]()
$339
This Trip.com deal was found by Cheapflights users on 5/24. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/12:59 am
BQN
- MDW
2 stops20h 03m
Frontier
Deal found 5/24![Frontier logo]()
$369
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 May 26, 2026.
Round-trip from | $236 (Southwest) |
|---|---|
One-way from | $118 (Southwest) |
Popular in | June |
Cheapest in | February |
Average price | $376 |
Good one-way deal | $278 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 May 26, 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 8/21
6:00 am-2:30 pm
1 stop9h 30m
Chicago Midway
Mon 8/31
11:15 am-10:10 pm
1 stop9h 55m
$256
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Sat 9/19
12:58 pm-10:25 pm
1 stop10h 27m
Chicago Midway
Fri 9/25
6:05 am-4:31 pm
1 stop9h 26m
$316
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 9/10
10:00 am-6:00 pm
1 stop9h 00m
Chicago Midway
Sun 9/13
5:00 am-1:00 pm
1 stop7h 00m
$356
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Mon 9/7
6:30 am-1:45 pm
2 stops8h 15m
Chicago Midway
Mon 9/14
7:15 am-4:55 pm
1 stop8h 40m
$356
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Mon 8/31
6:30 am-1:45 pm
2 stops8h 15m
Chicago Midway
Mon 9/7
12:15 pm-11:05 pm
2 stops9h 50m
$371
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 6/25
10:20 pm-9:15 am
1 stop11h 55m
Chicago Midway
Sun 6/28
12:00 pm-10:35 pm
2 stops9h 35m
$446
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Fri 6/12
10:20 pm-8:50 am
1 stop11h 30m
Chicago Midway
Sat 7/4
12:30 pm-9:50 pm
1 stop8h 20m
$461
Quickest round-trip
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Fri 6/5
6:30 pm-12:40 am
1 stop7h 10m
Chicago Midway
Sat 6/13
5:05 pm-1:15 am
1 stop7h 10m
$476
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Sat 8/1
12:56 pm-10:15 pm
1 stop10h 19m
Chicago Midway
Sat 8/8
10:56 am-10:29 pm
1 stop10h 33m
$486
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Sun 6/7
5:00 am-3:20 pm
2 stops11h 20m
Chicago Midway
Sat 6/13
5:05 pm-1:15 am
1 stop7h 10m
$521
Showing 1-10 of 25 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 May 26, 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 May 26, 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
Overall
8.0
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Overall
8.0
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Related info for your journey
Find useful and relevant information for your journey from Puerto Rico to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago Midway Airport?
Book flights to Chicago Midway Airport if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Hammond
Porter
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Alternative routes for Puerto Rico to Midway
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Complete your trip
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 May 26, 2026.
Puerto Rico and Midway flights
Browse other Puerto Rico and Midway flight options. Last updated on May 26, 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 May 26, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$326 | Average$559 | FlexibilityNo cancel fee | On-time63% |