$113+ 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 7/31. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MDW
Jun 10 — Jun 171
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 May 11, 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 11, 2026.
This Delta deal was found by Cheapflights users on 5/10. 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
Tue 9/810:35 am
MDW
- SJU
1 stop10h 48m
Delta
Deal found 5/10![Delta logo]()
$226
This Frontier deal was found by Cheapflights users on 5/10. 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.
Wed 10/213:51 pm
SJU
- MDW
1 stop7h 07m
Frontier
Wed 10/287:25 am
MDW
- SJU
1 stop7h 00m
Frontier
Deal found 5/10![Frontier logo]()
$276
This Southwest deal was found by Cheapflights users on 5/7. 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
Sat 8/297:50 am
MDW
- SJU
2 stops9h 15m
Southwest
Deal found 5/7![Southwest logo]()
$296
This Southwest deal was found by Cheapflights users on 5/10. 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
Wed 9/912:45 pm
MDW
- SJU
2 stops8h 15m
Southwest
Deal found 5/10![Southwest logo]()
$316
This Frontier deal was found by Cheapflights users on 5/6. 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.
Sun 8/96:32 am
SJU
- MDW
1 stop8h 55m
Frontier
Sat 8/156:00 am
MDW
- SJU
1 stop7h 16m
Frontier
Deal found 5/6![Frontier logo]()
$321
This Delta deal was found by Cheapflights users on 5/8. 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 8/242:59 pm
SJU
- MDW
1 stop8h 37m
Delta
Mon 8/316:00 am
MDW
- SJU
1 stop6h 30m
Delta
Deal found 5/8![Delta logo]()
$326
This eDestinos deal was found by Cheapflights users on 5/10. 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.
Tue 8/47:30 am
SJU
- MDW
2 stops15h 38m
Frontier
Tue 8/1112:11 pm
MDW
- SJU
2 stops28h 25m
Frontier
Deal found 5/10![Frontier logo]()
$331
This Frontier deal was found by Cheapflights users on 5/8. 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.
Fri 8/76:32 am
SJU
- MDW
1 stop8h 55m
Frontier
Mon 8/106:00 am
MDW
- SJU
1 stop7h 16m
Frontier
Deal found 5/8![Frontier logo]()
$343
This Delta deal was found by Cheapflights users on 5/10. 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
Fri 9/116:00 am
MDW
- SJU
1 stop6h 16m
Delta
Deal found 5/10![Delta logo]()
$346
This Delta deal was found by Cheapflights users on 5/10. 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 9/22:40 pm
SJU
- MDW
1 stop8h 06m
Delta
Mon 9/76:00 am
MDW
- SJU
1 stop6h 30m
Delta
Deal found 5/10![Delta logo]()
$356
This Frontier deal was found by Cheapflights users on 5/10. 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.
Thu 8/276:25 am
SJU
- MDW
1 stop8h 42m
Frontier
Sun 8/306:00 am
MDW
- SJU
1 stop7h 15m
Frontier
Deal found 5/10![Frontier logo]()
$361
This Southwest deal was found by Cheapflights users on 5/6. 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
1 stop12h 40m
Southwest
Tue 6/232:40 pm
MDW
- SJU
1 stop6h 20m
Southwest
Deal found 5/6![Southwest logo]()
$366
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 11, 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 11, 2026.
This Southwest deal was found by Cheapflights users on 5/10. 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 9/205:00 am
SJU
- MDW
2 stops8h 55m
Southwest
Sat 10/1710:30 am
MDW
- SJU
2 stops10h 35m
Southwest
Deal found 5/10![Southwest logo]()
$396
This Delta deal was found by Cheapflights users on 5/7. 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 7/146:00 am
SJU
- MDW
1 stop11h 15m
Delta
Tue 7/216:00 am
MDW
- SJU
1 stop9h 45m
Delta
Deal found 5/7![Delta logo]()
$426
This eDestinos deal was found by Cheapflights users on 5/7. 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.
Thu 5/212:59 am
BQN
- MDW
2 stops33h 05m
Frontier
Fri 5/296:00 am
MDW
- BQN
2 stops43h 02m
Frontier
Deal found 5/7![Frontier logo]()
$589
This Southwest deal was found by Cheapflights users on 5/9. 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 6/238:35 pm
SJU
- MDW
1 stop13h 25m
Southwest
Thu 7/161:00 pm
MDW
- SJU
2 stops10h 15m
Southwest
Deal found 5/9![Southwest logo]()
$446
This Southwest deal was found by Cheapflights users on 5/7. 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 7/18:35 pm
SJU
- MDW
1 stop13h 40m
Southwest
Tue 7/74:40 pm
MDW
- SJU
1 stop6h 35m
Southwest
Deal found 5/7![Southwest logo]()
$460
This Southwest deal was found by Cheapflights users on 5/8. 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 6/209:25 pm
SJU
- MDW
1 stop12h 05m
Southwest
Sat 6/275:05 pm
MDW
- SJU
1 stop7h 10m
Southwest
Deal found 5/8![Southwest logo]()
$466
This Southwest deal was found by Cheapflights users on 5/7. 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 6/166:00 am
SJU
- MDW
1 stop7h 20m
Southwest
Mon 6/2911:35 am
MDW
- SJU
1 stop11h 50m
Southwest
Deal found 5/7![Southwest logo]()
$476
This Southwest deal was found by Cheapflights users on 5/9. 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
Sat 6/272:10 pm
MDW
- SJU
2 stops8h 30m
Southwest
Deal found 5/9![Southwest logo]()
$495
This Southwest deal was found by Cheapflights users on 5/10. 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 6/410:20 pm
SJU
- MDW
1 stop12h 40m
Southwest
Fri 6/1210:10 am
MDW
- SJU
1 stop13h 15m
Southwest
Deal found 5/10![Southwest logo]()
$495
This Southwest deal was found by Cheapflights users on 5/9. 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
2 stops12h 40m
Southwest
Fri 7/311:00 pm
MDW
- SJU
2 stops10h 15m
Southwest
Deal found 5/9![Southwest logo]()
$510
Last-minute flights from Puerto Rico to MidwayDiscover last-minute flight deals from Puerto Rico to Midway. Data last updated May 11, 2026 and is based on user searches.
Discover last-minute flight deals from Puerto Rico to Midway. Data last updated May 11, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 5/6. 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 5/91:14 pm
SJU
- MDW
1 stop8h 55m
Delta
Tue 5/126:23 am
MDW
- SJU
1 stop9h 10m
Delta
Deal found 5/6![Delta logo]()
$423
This Southwest deal was found by Cheapflights users on 5/6. 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 5/105:00 am
SJU
- MDW
2 stops9h 05m
Southwest
Tue 5/121:25 pm
MDW
- SJU
1 stop9h 15m
Southwest
Deal found 5/6![Southwest logo]()
$401
This Delta deal was found by Cheapflights users on 5/6. 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 5/146:15 am
SJU
- MDW
1 stop10h 57m
Delta
Mon 5/186:23 am
MDW
- SJU
1 stop9h 10m
Delta
Deal found 5/6![Delta logo]()
$415
This Faresmojo deal was found by Cheapflights users on 5/6. 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.
Fri 5/156:15 am
SJU
- MDW
1 stop6h 41m
JetBlue
Wed 5/206:23 am
MDW
- SJU
1 stop9h 10m
JetBlue
Deal found 5/6![JetBlue logo]()
$416
This Faresmojo deal was found by Cheapflights users on 5/6. 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.
Thu 5/217:30 am
SJU
- MDW
1 stop9h 42m
JetBlue
Fri 5/2210:59 am
MDW
- SJU
1 stop8h 31m
JetBlue
Deal found 5/6![JetBlue logo]()
$386
This eDestinos deal was found by Cheapflights users on 5/7. 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.
Thu 5/212:59 am
BQN
- MDW
2 stops33h 05m
Frontier
Fri 5/296:00 am
MDW
- BQN
2 stops43h 02m
Frontier
Deal found 5/7![Frontier logo]()
$589
This eDestinos deal was found by Cheapflights users on 5/6. 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.
Sat 6/69:45 pm
SJU
- MDW
2 stops38h 24m
Frontier
Wed 6/106:00 am
MDW
- SJU
2 stops17h 37m
Frontier
Deal found 5/6![Frontier logo]()
$412
This Southwest deal was found by Cheapflights users on 5/6. 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
1 stop12h 40m
Southwest
Tue 6/232:40 pm
MDW
- SJU
1 stop6h 20m
Southwest
Deal found 5/6![Southwest logo]()
$366
This Southwest deal was found by Cheapflights users on 5/9. 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
1 stop12h 40m
Southwest
Sun 6/148:35 pm
MDW
- SJU
1 stop11h 25m
Southwest
Deal found 5/9![Southwest logo]()
$445
This Kiwi.com deal was found by Cheapflights users on 5/6. 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 6/125:15 pm
SJU
- MDW
1 stop18h 49m
Frontier
Wed 6/2412:04 pm
MDW
- SJU
2 stops11h 33m
Frontier
Deal found 5/6![Frontier logo]()
$422
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 11, 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 11, 2026.
This Delta deal was found by Cheapflights users on 5/7. 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 7/312:42 pm
SJU
- MDW
1 stop8h 33m
Delta
Deal found 5/7![Delta logo]()
$113
This Super.com deal was found by Cheapflights users on 5/6. 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.
Mon 8/176:32 am
SJU
- MDW
1 stop8h 55m
Frontier
Deal found 5/6![Frontier logo]()
$137
This CheapOair deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/306:25 am
SJU
- MDW
1 stop8h 42m
Frontier
Deal found 5/8![Frontier logo]()
$138
This Delta deal was found by Cheapflights users on 5/7. 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 8/52:59 pm
SJU
- MDW
1 stop8h 37m
Delta
Deal found 5/7![Delta logo]()
$143
This Kiwi.com deal was found by Cheapflights users on 5/10. 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 6/27:00 am
SJU
- MDW
2 stops29h 09m
Frontier
Deal found 5/10![Frontier logo]()
$154
This Southwest deal was found by Cheapflights users on 5/10. 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 8/55:15 am
SJU
- MDW
2 stops7h 50m
Southwest
Deal found 5/10![Southwest logo]()
$163
This Kiwi.com deal was found by Cheapflights users on 5/10. 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 8/47:30 am
SJU
- MDW
2 stops15h 38m
Frontier
Deal found 5/10![Frontier logo]()
$166
This Kiwi.com deal was found by Cheapflights users on 5/9. 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 6/307:00 am
SJU
- MDW
2 stops29h 09m
Frontier
Deal found 5/9![Frontier logo]()
$167
This Kiwi.com deal was found by Cheapflights users on 5/7. 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 6/86:41 pm
SJU
- MDW
2 stops28h 30m
Frontier
Deal found 5/7![Frontier logo]()
$168
This Kiwi.com deal was found by Cheapflights users on 5/10. 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 6/37:00 am
SJU
- MDW
2 stops29h 12m
Frontier
Deal found 5/10![Frontier logo]()
$170
This Kiwi.com deal was found by Cheapflights users on 5/6. 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 7/33:00 am
BQN
- MDW
2 stops20h 11m
Frontier
Deal found 5/6![Frontier logo]()
$302
This Kiwi.com deal was found by Cheapflights users on 5/6. 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 7/53:00 am
BQN
- MDW
2 stops33h 07m
Frontier
Deal found 5/6![Frontier logo]()
$304
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 11, 2026.
Round-trip from | $226 (Delta) |
|---|---|
One-way from | $113 (Delta) |
Popular in | December |
Cheapest in | February |
Average price | $327 |
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 11, 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
Sun 9/20
5:00 am-12:55 pm
2 stops8h 55m
Chicago Midway
Sat 10/17
10:30 am-10:05 pm
2 stops10h 35m
$396
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Tue 7/14
6:00 am-4:15 pm
1 stop11h 15m
Chicago Midway
Tue 7/21
6:00 am-4:45 pm
1 stop9h 45m
$426
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Tue 6/23
8:35 pm-9:00 am
1 stop13h 25m
Chicago Midway
Thu 7/16
1:00 pm-12:15 am
2 stops10h 15m
$446
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Wed 7/1
8:35 pm-9:15 am
1 stop13h 40m
Chicago Midway
Tue 7/7
4:40 pm-12:15 am
1 stop6h 35m
$460
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Sat 6/20
9:25 pm-8:30 am
1 stop12h 05m
Chicago Midway
Sat 6/27
5:05 pm-1:15 am
1 stop7h 10m
$466
Quickest round-trip
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Tue 6/16
6:00 am-12:20 pm
1 stop7h 20m
Chicago Midway
Mon 6/29
11:35 am-12:25 am
1 stop11h 50m
$476
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 6/18
10:20 pm-10:00 am
2 stops12h 40m
Chicago Midway
Sat 6/27
2:10 pm-11:40 pm
2 stops8h 30m
$495
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 6/4
10:20 pm-10:00 am
1 stop12h 40m
Chicago Midway
Fri 6/12
10:10 am-12:25 am
1 stop13h 15m
$495
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 7/23
10:20 pm-10:00 am
2 stops12h 40m
Chicago Midway
Fri 7/31
1:00 pm-12:15 am
2 stops10h 15m
$510
AguadillaChicago
BQN - MDW
BQNMDW
Aguadilla Borinquen
Thu 5/21
2:59 am-11:04 am
2 stops33h 05m
Chicago Midway
Fri 5/29
6:00 am-2:02 am
2 stops43h 02m
$589
Showing 1-10 of 24 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 11, 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 11, 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
Overall
8.0
Food
7.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Overall
8.0
Food
7.0
Entertainment
7.5
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
Browse thousands of different options on Cheapflights for your next trip
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Alternative routes for Puerto Rico to Midway
See prices for flight routes from nearby airports that may be better suited for you.
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 11, 2026.
Puerto Rico and Midway flights
Browse other Puerto Rico and Midway flight options. Last updated on May 11, 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 11, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$326 | Average$566 | FlexibilityNo cancel fee | On-time63% |