$113+ Cheap flights from Midway (MDW) to San Juan
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 5/11. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJU
Mai 23 — Mai 301
Round-trip
1 adult, Economy
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Find cheap flights from Midway to San Juan 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.Cheapflights Tip: The best prices from Chicago Midway to San Juan are usually found in February or January, booked 55 days in advance, depart on a Tuesday or Monday and return on a Monday
Cheap flight deals from Midway to San Juan
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Cheapest flights from Midway to San JuanExplore the most affordable flight options available from Midway to San Juan. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 23, 2026.
Explore the most affordable flight options available from Midway to San Juan. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 23, 2026.
This Delta deal was found by Cheapflights users on 4/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mi 8/196:00 am
MDW
- SJU
1 stop9h 35m
Delta
Mi 9/22:40 pm
SJU
- MDW
1 stop8h 06m
Delta
Deal found 4/20![Delta logo]()
$226
This Southwest deal was found by Cheapflights users on 4/20. 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.
Sa 8/226:05 am
MDW
- SJU
1 stop11h 10m
Southwest
So 8/305:00 am
SJU
- MDW
2 stops8h 55m
Southwest
Deal found 4/20![Southwest logo]()
$236
This Trip.com deal was found by Cheapflights users on 4/21. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Di 5/56:00 am
MDW
- SJU
1 stop7h 07m
Frontier
Do 5/143:33 pm
SJU
- MDW
1 stop25h 24m
Frontier
Deal found 4/21![Frontier logo]()
$242
This Southwest deal was found by Cheapflights users on 4/21. 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.
Fr 8/2111:15 am
MDW
- SJU
1 stop7h 50m
Southwest
So 8/305:00 am
SJU
- MDW
1 stop9h 45m
Southwest
Deal found 4/21![Southwest logo]()
$246
This Frontier deal was found by Cheapflights users on 4/23. 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.
Mo 5/114:52 pm
MDW
- SJU
1 stop8h 16m
Frontier
Do 5/143:03 am
SJU
- MDW
1 stop13h 54m
Frontier
Deal found 4/23![Frontier logo]()
$251
This Southwest deal was found by Cheapflights users on 4/18. 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.
Mo 5/188:35 pm
MDW
- SJU
1 stop13h 00m
Southwest
Sa 5/231:10 pm
SJU
- MDW
Nonstop5h 10m
Southwest
Deal found 4/18![Southwest logo]()
$252
This Frontier deal was found by Cheapflights users on 4/18. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
So 4/266:00 am
MDW
- SJU
1 stop7h 08m
Frontier
Do 4/303:03 pm
SJU
- MDW
1 stop8h 16m
Frontier
Deal found 4/18![Frontier logo]()
$256
This Priceline deal was found by Cheapflights users on 4/22. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Do 4/238:26 am
MDW
- SJU
1 stop16h 35m
Frontier
Di 4/283:08 am
SJU
- MDW
1 stop29h 13m
Frontier
Deal found 4/22![Frontier logo]()
$261
This Delta deal was found by Cheapflights users on 4/21. 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.
Di 4/2812:52 pm
MDW
- SJU
1 stop6h 32m
Delta
Fr 5/12:45 pm
SJU
- MDW
1 stop8h 43m
Delta
Deal found 4/21![Delta logo]()
$266
This Mytrip deal was found by Cheapflights users on 4/19. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fr 4/246:49 pm
MDW
- SJU
1 stop26h 59m
Frontier
Fr 5/13:23 pm
SJU
- MDW
1 stop8h 03m
Frontier
Deal found 4/19![Frontier logo]()
$267
This Kiwi.com deal was found by Cheapflights users on 4/21. 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.
Di 5/56:00 am
MDW
- SJU
1 stop7h 07m
Frontier
Mi 5/66:00 am
SJU
- MDW
2 stops17h 02m
Frontier
Deal found 4/21![Frontier logo]()
$269
Best flights from Midway to San JuanDiscover carefully curated flight deals from Midway to San Juan that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 23, 2026.
Discover carefully curated flight deals from Midway to San Juan that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 23, 2026.
This Southwest deal was found by Cheapflights users on 4/21. 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.
Di 5/512:50 pm
MDW
- SJU
2 stops8h 50m
Southwest
Fr 5/85:05 am
SJU
- MDW
1 stop7h 55m
Southwest
Deal found 4/21![Southwest logo]()
$326
This Delta deal was found by Cheapflights users on 4/23. 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.
Do 7/911:05 am
MDW
- SJU
1 stop8h 40m
Delta
Do 7/2312:56 pm
SJU
- MDW
1 stop10h 19m
Delta
Deal found 4/23![Delta logo]()
$461
This Southwest deal was found by Cheapflights users on 4/19. 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.
Di 5/59:25 am
MDW
- SJU
1 stop10h 40m
Southwest
Sa 5/99:40 am
SJU
- MDW
1 stop8h 25m
Southwest
Deal found 4/19![Southwest logo]()
$361
This Southwest deal was found by Cheapflights users on 4/23. 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.
Sa 5/99:05 am
MDW
- SJU
1 stop13h 10m
Southwest
Mi 5/135:05 am
SJU
- MDW
2 stops11h 45m
Southwest
Deal found 4/23![Southwest logo]()
$361
This Southwest deal was found by Cheapflights users on 4/22. 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.
So 5/38:50 pm
MDW
- SJU
1 stop11h 20m
Southwest
Sa 5/95:45 am
SJU
- MDW
2 stops9h 10m
Southwest
Deal found 4/22![Southwest logo]()
$361
This Southwest deal was found by Cheapflights users on 4/18. 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.
Di 6/308:10 pm
MDW
- SJU
1 stop11h 50m
Southwest
Sa 7/46:00 am
SJU
- MDW
1 stop12h 30m
Southwest
Deal found 4/18![Southwest logo]()
$416
This Southwest deal was found by Cheapflights users on 4/21. 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.
Di 6/239:10 am
MDW
- SJU
2 stops11h 50m
Southwest
Do 6/256:30 am
SJU
- MDW
1 stop10h 50m
Southwest
Deal found 4/21![Southwest logo]()
$466
This Southwest deal was found by Cheapflights users on 4/20. 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.
Sa 5/1612:05 pm
MDW
- SJU
1 stop10h 10m
Southwest
So 5/179:45 pm
SJU
- MDW
2 stops15h 05m
Southwest
Deal found 4/20![Southwest logo]()
$471
This Southwest deal was found by Cheapflights users on 4/20. 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.
Sa 5/92:15 pm
MDW
- SJU
2 stops8h 25m
Southwest
Di 5/1211:25 am
SJU
- MDW
2 stops9h 20m
Southwest
Deal found 4/20![Southwest logo]()
$476
This Southwest deal was found by Cheapflights users on 4/22. 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.
Di 5/191:25 pm
MDW
- SJU
1 stop6h 40m
Southwest
Fr 6/55:30 am
SJU
- MDW
2 stops9h 35m
Southwest
Deal found 4/22![Southwest logo]()
$481
This Southwest deal was found by Cheapflights users on 4/22. 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.
Do 6/42:45 pm
MDW
- SJU
2 stops8h 20m
Southwest
Di 6/95:00 am
SJU
- MDW
1 stop7h 00m
Southwest
Deal found 4/22![Southwest logo]()
$486
This Southwest deal was found by Cheapflights users on 4/20. 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.
Sa 7/183:50 pm
MDW
- SJU
1 stop7h 55m
Southwest
Mi 7/227:00 am
SJU
- MDW
2 stops8h 30m
Southwest
Deal found 4/20![Southwest logo]()
$491
Last-minute flights from Midway to San JuanDiscover last-minute flight deals from Midway to San Juan. Data last updated April 23, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to San Juan. Data last updated April 23, 2026 and is based on user searches.
This Priceline deal was found by Cheapflights users on 4/22. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Do 4/238:26 am
MDW
- SJU
1 stop16h 35m
Frontier
Di 4/283:08 am
SJU
- MDW
1 stop29h 13m
Frontier
Deal found 4/22![Frontier logo]()
$261
This Mytrip deal was found by Cheapflights users on 4/19. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fr 4/246:49 pm
MDW
- SJU
1 stop26h 59m
Frontier
Fr 5/13:23 pm
SJU
- MDW
1 stop8h 03m
Frontier
Deal found 4/19![Frontier logo]()
$267
This Frontier deal was found by Cheapflights users on 4/18. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sa 4/259:14 am
MDW
- SJU
1 stop12h 34m
Frontier
Sa 5/23:43 pm
SJU
- MDW
1 stop7h 31m
Frontier
Deal found 4/18![Frontier logo]()
$226
This Frontier deal was found by Cheapflights users on 4/18. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
So 4/266:00 am
MDW
- SJU
1 stop7h 08m
Frontier
Do 4/303:03 pm
SJU
- MDW
1 stop8h 16m
Frontier
Deal found 4/18![Frontier logo]()
$256
This Southwest deal was found by Cheapflights users on 4/19. 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.
So 4/268:55 am
MDW
- SJU
1 stop6h 35m
Southwest
Sa 5/21:10 pm
SJU
- MDW
Nonstop5h 10m
Southwest
Deal found 4/19![Southwest logo]()
$272
This Delta deal was found by Cheapflights users on 4/21. 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.
Di 4/2812:52 pm
MDW
- SJU
1 stop6h 32m
Delta
Fr 5/12:45 pm
SJU
- MDW
1 stop8h 43m
Delta
Deal found 4/21![Delta logo]()
$266
This Kiwi.com deal was found by Cheapflights users on 4/22. 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.
Di 4/282:15 pm
MDW
- SJU
2 stops26h 44m
Multiple Airlines
Do 4/303:03 pm
SJU
- MDW
1 stop8h 16m
Multiple Airlines
Deal found 4/22![Multiple Airlines logo]()
$276
This Trip.com deal was found by Cheapflights users on 4/21. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Di 5/56:00 am
MDW
- SJU
1 stop7h 07m
Frontier
Do 5/143:33 pm
SJU
- MDW
1 stop25h 24m
Frontier
Deal found 4/21![Frontier logo]()
$242
This Kiwi.com deal was found by Cheapflights users on 4/21. 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.
Di 5/56:00 am
MDW
- SJU
1 stop7h 07m
Frontier
Mi 5/66:00 am
SJU
- MDW
2 stops17h 02m
Frontier
Deal found 4/21![Frontier logo]()
$269
This Frontier deal was found by Cheapflights users on 4/23. 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.
Mo 5/114:52 pm
MDW
- SJU
1 stop8h 16m
Frontier
Do 5/143:03 am
SJU
- MDW
1 stop13h 54m
Frontier
Deal found 4/23![Frontier logo]()
$251
This Southwest deal was found by Cheapflights users on 4/18. 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.
Mo 5/188:35 pm
MDW
- SJU
1 stop13h 00m
Southwest
Sa 5/231:10 pm
SJU
- MDW
Nonstop5h 10m
Southwest
Deal found 4/18![Southwest logo]()
$252
One-way flights from Midway to San JuanSearch for one-way flight options from Midway to San Juan. Find affordable one-way fares based on user searches. Data last updated April 23, 2026.
Search for one-way flight options from Midway to San Juan. Find affordable one-way fares based on user searches. Data last updated April 23, 2026.
This Southwest deal was found by Cheapflights users on 4/19. 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.
Mo 5/117:55 am
MDW
- SJU
1 stop6h 40m
Southwest
Deal found 4/19![Southwest logo]()
$113
This Frontier deal was found by Cheapflights users on 4/21. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sa 7/186:00 am
MDW
- SJU
1 stop7h 15m
Frontier
Deal found 4/21![Frontier logo]()
$120
This Super.com deal was found by Cheapflights users on 4/20. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
So 5/176:00 am
MDW
- SJU
1 stop7h 07m
Frontier
Deal found 4/20![Frontier logo]()
$122
This Frontier deal was found by Cheapflights users on 4/20. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sa 5/166:00 am
MDW
- SJU
1 stop7h 07m
Frontier
Deal found 4/20![Frontier logo]()
$123
This Kiwi.com deal was found by Cheapflights users on 4/21. 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.
Sa 5/911:59 am
MDW
- SJU
2 stops28h 17m
Multiple Airlines
Deal found 4/21![Multiple Airlines logo]()
$126
This Super.com deal was found by Cheapflights users on 4/23. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fr 5/84:52 pm
MDW
- SJU
1 stop8h 16m
Frontier
Deal found 4/23![Frontier logo]()
$127
This Travelocity deal was found by Cheapflights users on 4/22. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mo 5/114:52 pm
MDW
- SJU
1 stop8h 16m
Frontier
Deal found 4/22![Frontier logo]()
$128
This Trip.com deal was found by Cheapflights users on 4/20. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Do 5/146:00 am
MDW
- SJU
2 stops16h 57m
Frontier
Deal found 4/20![Frontier logo]()
$130
This Trip.com deal was found by Cheapflights users on 4/21. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fr 5/111:33 am
MDW
- SJU
1 stop13h 28m
Frontier
Deal found 4/21![Frontier logo]()
$131
This Mytrip deal was found by Cheapflights users on 4/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Do 4/308:21 am
MDW
- SJU
1 stop13h 35m
Frontier
Deal found 4/20![Frontier logo]()
$132
This Delta deal was found by Cheapflights users on 4/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Di 4/2812:52 pm
MDW
- SJU
1 stop9h 21m
Delta
Deal found 4/20![Delta logo]()
$133
Find flight deals from Midway to San Juan
Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to San Juan (PR1). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated April 23, 2026.
Round-trip from | $242 (Trip.com) |
|---|---|
One-way from | $113 (Southwest) |
Popular in | June |
Cheapest in | February |
Average price | $328 |
Cheapflights Fare Finder
Customize your flight search to find flights from Midway to San Juan 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 April 23, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to San Juan that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Di 5/5
12:50 pm-10:40 pm
2 stops8h 50m
San Juan Luis Munoz Marin Intl
Fr 5/8
5:05 am-12:00 pm
1 stop7h 55m
$326
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Di 5/5
9:25 am-9:05 pm
1 stop10h 40m
San Juan Luis Munoz Marin Intl
Sa 5/9
9:40 am-5:05 pm
1 stop8h 25m
$361
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Sa 5/9
9:05 am-11:15 pm
1 stop13h 10m
San Juan Luis Munoz Marin Intl
Mi 5/13
5:05 am-3:50 pm
2 stops11h 45m
$361
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
So 5/3
8:50 pm-9:10 am
1 stop11h 20m
San Juan Luis Munoz Marin Intl
Sa 5/9
5:45 am-1:55 pm
2 stops9h 10m
$361
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Di 6/30
8:10 pm-9:00 am
1 stop11h 50m
San Juan Luis Munoz Marin Intl
Sa 7/4
6:00 am-5:30 pm
1 stop12h 30m
$416
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Do 7/9
11:05 am-8:45 pm
1 stop8h 40m
San Juan Luis Munoz Marin Intl
Do 7/23
12:56 pm-10:15 pm
1 stop10h 19m
$461
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Di 6/23
9:10 am-10:00 pm
2 stops11h 50m
San Juan Luis Munoz Marin Intl
Do 6/25
6:30 am-4:20 pm
1 stop10h 50m
$466
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Sa 5/16
12:05 pm-11:15 pm
1 stop10h 10m
San Juan Luis Munoz Marin Intl
So 5/17
9:45 pm-11:50 am
2 stops15h 05m
$471
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Sa 5/9
2:15 pm-11:40 pm
2 stops8h 25m
San Juan Luis Munoz Marin Intl
Di 5/12
11:25 am-7:45 pm
2 stops9h 20m
$476
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Di 5/19
1:25 pm-9:05 pm
1 stop6h 40m
San Juan Luis Munoz Marin Intl
Fr 6/5
5:30 am-2:05 pm
2 stops9h 35m
$481
Showing 1-10 of 24 resultsSorted by cheapest first
Best time to book a flight from Midway to San Juan
Have a flexible travel schedule? Discover the best time to fly to San Juan from Midway with our price prediction graph.
MDW-PR1
MDW-SJU
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 Chicago Midway Airport to San Juan
MDW-PR1
MDW-SJU
How far ahead should I book a flight from Chicago Midway Airport to San Juan?
The best time to book flights from Chicago Midway Airport to San Juan is 42 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
What is the cheapest month to book a flight from Chicago Midway Airport to San Juan?
Currently, April is the cheapest month in which you can book a flight from Chicago Midway Airport to San Juan (average of $91). Flying from Chicago Midway Airport to San Juan in June is currently the most expensive (average of $284). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from MDW to SJU?
Find hourly flight availability from Midway to San Juan. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 23, 2026.
When flying from Chicago Midway Airport to San Juan, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
How much does it cost to fly round-trip from Chicago Midway Airport to San Juan?
How often are flights from Chicago to San Juan delayed?
About 31% of weekly flights between Chicago and San Juan have experienced delays in the past year, with the average delay time being 124 minutes.
What is the most punctual flight time for Chicago to San Juan flights?
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the morning tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Saturday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Chicago to San Juan flights?
Over the last year, Southwest have had the lowest number of delays on this route, with just 31% of flights being delayed.
Reviews of airlines servicing San Juan
Get insights into the airlines that provide service to San Juan. 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 San Juan. Reviews last updated April 23, 2026.
Read through reviews of airlines operating flights from Chicago Midway Airport to San Juan, such as Southwest,Delta, andFrontier. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Overall
8.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Overall
8.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Overall
8.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Overall
8.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Related info for your journey
Find useful and relevant information for your journey from Midway to San Juan. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Midway to San Juan
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Complete your trip
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Search flights from Midway to San Juan by cabin class
Find flights from Midway to San Juan, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Midway and San Juan flights
Browse other Midway and San Juan flight options. Last updated on April 23, 2026.
Other flights from Midway
Browse through other flights departing from Midway. Flights are based on user searches made on Cheapflights and were last updated on April 23, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 3 airlines flying from Midway to San Juan
Discover the top 3 airlines that operate flights from Midway to San Juan. 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 April 23, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$132 | Average$428 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$138 | Average$286 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$355 | Average$495 | FlexibilityNo cancel fee | On-time63% |