$133+ 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 8/15. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJU
Aug 6 — Aug 131
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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
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 April, booked 26 days in advance, depart on a Tuesday or Monday and return on a Monday
Cheap flight deals from Midway to San Juan
Cheapest
Best
Last-minute
One-way
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 July 7, 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 July 7, 2026.
This Southwest deal was found by Cheapflights users on 7/3. 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 8/227:50 am
MDW
- SJU
2 stops9h 15m
Southwest
Sat 8/295:05 am
SJU
- MDW
1 stop6h 55m
Southwest
Deal found 7/3![Southwest logo]()
$266
This Southwest deal was found by Cheapflights users on 7/6. 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.
Fri 8/211:00 pm
MDW
- SJU
2 stops8h 50m
Southwest
Mon 8/245:30 am
SJU
- MDW
2 stops10h 25m
Southwest
Deal found 7/6![Southwest logo]()
$291
This Southwest deal was found by Cheapflights users on 7/6. 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 9/1010:30 am
MDW
- SJU
2 stops8h 35m
Southwest
Mon 9/145:00 am
SJU
- MDW
2 stops8h 25m
Southwest
Deal found 7/6![Southwest logo]()
$296
This Delta deal was found by Cheapflights users on 7/3. 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 8/186:05 am
MDW
- SJU
1 stop9h 33m
Delta
Mon 8/317:00 am
SJU
- MDW
1 stop9h 44m
Delta
Deal found 7/3![Delta logo]()
$301
This Southwest deal was found by Cheapflights users on 7/6. 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.
Wed 8/1912:20 pm
MDW
- SJU
1 stop8h 40m
Southwest
Sat 8/222:00 pm
SJU
- MDW
1 stop7h 30m
Southwest
Deal found 7/6![Southwest logo]()
$306
This Southwest deal was found by Cheapflights users on 7/6. 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.
Sat 8/227:50 am
MDW
- SJU
2 stops7h 50m
Southwest
Mon 8/245:30 am
SJU
- MDW
1 stop9h 35m
Southwest
Deal found 7/6![Southwest logo]()
$311
This Southwest deal was found by Cheapflights users on 7/3. 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 8/231:10 pm
MDW
- SJU
2 stops8h 35m
Southwest
Wed 8/265:15 am
SJU
- MDW
2 stops7h 50m
Southwest
Deal found 7/3![Southwest logo]()
$316
This Southwest deal was found by Cheapflights users on 7/4. 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 8/1812:20 pm
MDW
- SJU
1 stop7h 45m
Southwest
Tue 8/255:15 am
SJU
- MDW
2 stops7h 50m
Southwest
Deal found 7/4![Southwest logo]()
$320
This Southwest deal was found by Cheapflights users on 7/6. 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.
Mon 7/208:55 pm
MDW
- SJU
1 stop11h 05m
Southwest
Thu 7/2310:20 pm
SJU
- MDW
1 stop11h 55m
Southwest
Deal found 7/6![Southwest logo]()
$321
This Southwest deal was found by Cheapflights users on 7/2. 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 8/168:20 am
MDW
- SJU
1 stop13h 25m
Southwest
Sun 8/235:00 am
SJU
- MDW
2 stops8h 55m
Southwest
Deal found 7/2![Southwest logo]()
$323
This Southwest deal was found by Cheapflights users on 7/1. 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 8/186:15 am
MDW
- SJU
1 stop6h 20m
Southwest
Sat 8/2210:25 am
SJU
- MDW
1 stop10h 15m
Southwest
Deal found 7/1![Southwest logo]()
$326
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 July 7, 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 July 7, 2026.
This Southwest deal was found by Cheapflights users on 7/3. 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 8/172:55 pm
MDW
- SJU
1 stop7h 55m
Southwest
Mon 8/245:30 am
SJU
- MDW
2 stops10h 25m
Southwest
Deal found 7/3![Southwest logo]()
$301
This Delta deal was found by Cheapflights users on 7/1. 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 8/1110:54 am
MDW
- SJU
1 stop10h 35m
Delta
Mon 8/1712:56 pm
SJU
- MDW
1 stop10h 40m
Delta
Deal found 7/1![Delta logo]()
$361
This Southwest deal was found by Cheapflights users on 7/2. 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 8/1012:20 pm
MDW
- SJU
2 stops9h 45m
Southwest
Thu 8/138:55 pm
SJU
- MDW
2 stops15h 30m
Southwest
Deal found 7/2![Southwest logo]()
$306
This Southwest deal was found by Cheapflights users on 7/5. 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 8/1511:00 am
MDW
- SJU
1 stop6h 15m
Southwest
Mon 8/245:30 am
SJU
- MDW
1 stop9h 35m
Southwest
Deal found 7/5![Southwest logo]()
$311
This Southwest deal was found by Cheapflights users on 7/3. 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 8/173:10 pm
MDW
- SJU
2 stops7h 40m
Southwest
Sat 8/228:20 am
SJU
- MDW
2 stops9h 25m
Southwest
Deal found 7/3![Southwest logo]()
$311
This Southwest deal was found by Cheapflights users on 7/1. 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 9/43:15 pm
MDW
- SJU
1 stop6h 50m
Southwest
Sun 9/66:30 am
SJU
- MDW
2 stops10h 00m
Southwest
Deal found 7/1![Southwest logo]()
$311
This Southwest deal was found by Cheapflights users on 7/2. 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 8/161:10 pm
MDW
- SJU
2 stops8h 35m
Southwest
Sun 8/235:00 am
SJU
- MDW
2 stops8h 55m
Southwest
Deal found 7/2![Southwest logo]()
$383
This Southwest deal was found by Cheapflights users on 7/4. 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 7/113:50 pm
MDW
- SJU
1 stop8h 30m
Southwest
Sat 7/185:30 am
SJU
- MDW
Nonstop4h 50m
Southwest
Deal found 7/4![Southwest logo]()
$392
This Southwest deal was found by Cheapflights users on 7/2. 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 8/512:45 pm
MDW
- SJU
2 stops8h 15m
Southwest
Tue 8/118:20 am
SJU
- MDW
2 stops9h 35m
Southwest
Deal found 7/2![Southwest logo]()
$416
This Southwest deal was found by Cheapflights users on 7/5. 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 7/305:10 pm
MDW
- SJU
1 stop7h 15m
Southwest
Thu 8/65:30 am
SJU
- MDW
1 stop9h 35m
Southwest
Deal found 7/5![Southwest logo]()
$421
Last-minute flights from Midway to San JuanDiscover last-minute flight deals from Midway to San Juan. Data last updated July 7, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to San Juan. Data last updated July 7, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 7/6. 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.
Mon 7/208:55 pm
MDW
- SJU
1 stop11h 05m
Southwest
Thu 7/2310:20 pm
SJU
- MDW
1 stop11h 55m
Southwest
Deal found 7/6![Southwest logo]()
$321
This Southwest deal was found by Cheapflights users on 7/2. 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 7/278:55 pm
MDW
- SJU
1 stop11h 05m
Southwest
Thu 7/3010:20 pm
SJU
- MDW
1 stop11h 55m
Southwest
Deal found 7/2![Southwest logo]()
$336
This Southwest deal was found by Cheapflights users on 7/2. 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 8/168:20 am
MDW
- SJU
1 stop13h 25m
Southwest
Sun 8/235:00 am
SJU
- MDW
2 stops8h 55m
Southwest
Deal found 7/2![Southwest logo]()
$323
This Delta deal was found by Cheapflights users on 7/3. 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 8/186:05 am
MDW
- SJU
1 stop9h 33m
Delta
Mon 8/317:00 am
SJU
- MDW
1 stop9h 44m
Delta
Deal found 7/3![Delta logo]()
$301
This Southwest deal was found by Cheapflights users on 7/4. 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 8/1812:20 pm
MDW
- SJU
1 stop7h 45m
Southwest
Tue 8/255:15 am
SJU
- MDW
2 stops7h 50m
Southwest
Deal found 7/4![Southwest logo]()
$320
This Southwest deal was found by Cheapflights users on 7/1. 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 8/186:15 am
MDW
- SJU
1 stop6h 20m
Southwest
Sat 8/2210:25 am
SJU
- MDW
1 stop10h 15m
Southwest
Deal found 7/1![Southwest logo]()
$326
This Southwest deal was found by Cheapflights users on 7/6. 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.
Wed 8/1912:20 pm
MDW
- SJU
1 stop8h 40m
Southwest
Sat 8/222:00 pm
SJU
- MDW
1 stop7h 30m
Southwest
Deal found 7/6![Southwest logo]()
$306
This Southwest deal was found by Cheapflights users on 7/6. 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.
Fri 8/217:50 pm
MDW
- SJU
1 stop12h 35m
Southwest
Mon 8/246:00 am
SJU
- MDW
2 stops9h 30m
Southwest
Deal found 7/6![Southwest logo]()
$291
This Southwest deal was found by Cheapflights users on 7/3. 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 8/227:50 am
MDW
- SJU
2 stops9h 15m
Southwest
Sat 8/295:05 am
SJU
- MDW
1 stop6h 55m
Southwest
Deal found 7/3![Southwest logo]()
$266
This Southwest deal was found by Cheapflights users on 7/6. 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.
Sat 8/227:05 am
MDW
- SJU
1 stop10h 10m
Southwest
Mon 8/245:30 am
SJU
- MDW
1 stop9h 35m
Southwest
Deal found 7/6![Southwest logo]()
$311
This Southwest deal was found by Cheapflights users on 7/3. 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 8/231:10 pm
MDW
- SJU
2 stops8h 35m
Southwest
Wed 8/265:15 am
SJU
- MDW
2 stops7h 50m
Southwest
Deal found 7/3![Southwest logo]()
$316
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 July 7, 2026.
Search for one-way flight options from Midway to San Juan. Find affordable one-way fares based on user searches. Data last updated July 7, 2026.
This Delta deal was found by Cheapflights users on 7/3. 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 9/412:46 pm
MDW
- SJU
1 stop8h 43m
Delta
Deal found 7/3![Delta logo]()
$133
This Southwest deal was found by Cheapflights users on 7/5. 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 7/138:55 pm
MDW
- SJU
1 stop11h 05m
Southwest
Deal found 7/5![Southwest logo]()
$143
This Kiwi.com deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/97:25 am
MDW
- SJU
2 stops15h 32m
Frontier
Deal found 7/2![Frontier logo]()
$157
This Kiwi.com deal was found by Cheapflights users on 7/2. 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 9/811:50 am
MDW
- SJU
2 stops12h 06m
Frontier
Deal found 7/2![Frontier logo]()
$158
This Kiwi.com deal was found by Cheapflights users on 7/2. 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 9/111:50 am
MDW
- SJU
2 stops12h 06m
Frontier
Deal found 7/2![Frontier logo]()
$166
This Kiwi.com deal was found by Cheapflights users on 7/6. 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.
Wed 8/511:06 am
MDW
- SJU
2 stops12h 35m
Frontier
Deal found 7/6![Frontier logo]()
$167
This Southwest deal was found by Cheapflights users on 7/6. 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.
Fri 9/43:10 pm
MDW
- SJU
2 stops7h 40m
Southwest
Deal found 7/6![Southwest logo]()
$168
This Kiwi.com deal was found by Cheapflights users on 7/3. 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 8/412:11 pm
MDW
- SJU
2 stops11h 30m
Frontier
Deal found 7/3![Frontier logo]()
$170
This Kiwi.com deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/211:50 am
MDW
- SJU
2 stops12h 06m
Frontier
Deal found 7/5![Frontier logo]()
$171
This Kiwi.com deal was found by Cheapflights users on 7/2. 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 9/287:25 am
MDW
- SJU
2 stops15h 32m
Frontier
Deal found 7/2![Frontier logo]()
$172
This Kiwi.com deal was found by Cheapflights users on 7/3. 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 9/2912:03 pm
MDW
- SJU
2 stops34h 54m
Frontier
Deal found 7/3![Frontier logo]()
$173
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 July 7, 2026.
Round-trip from | $266 (Southwest) |
|---|---|
One-way from | $133 (Delta) |
Popular in | June |
Cheapest in | February |
Average price | $413 |
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 July 7, 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
Mon 8/17
2:55 pm-11:50 pm
1 stop7h 55m
San Juan Luis Munoz Marin Intl
Mon 8/24
5:30 am-2:55 pm
2 stops10h 25m
$301
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Mon 8/10
12:20 pm-11:05 pm
2 stops9h 45m
San Juan Luis Munoz Marin Intl
Thu 8/13
8:55 pm-11:25 am
2 stops15h 30m
$306
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Sat 8/15
11:00 am-6:15 pm
1 stop6h 15m
San Juan Luis Munoz Marin Intl
Mon 8/24
5:30 am-2:05 pm
1 stop9h 35m
$311
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Mon 8/17
3:10 pm-11:50 pm
2 stops7h 40m
San Juan Luis Munoz Marin Intl
Sat 8/22
8:20 am-4:45 pm
2 stops9h 25m
$311
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Fri 9/4
3:15 pm-11:05 pm
1 stop6h 50m
San Juan Luis Munoz Marin Intl
Sun 9/6
6:30 am-3:30 pm
2 stops10h 00m
$311
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Tue 8/11
10:54 am-10:29 pm
1 stop10h 35m
San Juan Luis Munoz Marin Intl
Mon 8/17
12:56 pm-10:36 pm
1 stop10h 40m
$361
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Sun 8/16
1:10 pm-10:45 pm
2 stops8h 35m
San Juan Luis Munoz Marin Intl
Sun 8/23
5:00 am-12:55 pm
2 stops8h 55m
$383
Quickest round-trip
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Sat 7/11
3:50 pm-1:20 am
1 stop8h 30m
San Juan Luis Munoz Marin Intl
Sat 7/18
5:30 am-9:20 am
Nonstop4h 50m
$392
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Wed 8/5
12:45 pm-10:00 pm
2 stops8h 15m
San Juan Luis Munoz Marin Intl
Tue 8/11
8:20 am-4:55 pm
2 stops9h 35m
$416
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Thu 7/30
5:10 pm-1:25 am
1 stop7h 15m
San Juan Luis Munoz Marin Intl
Thu 8/6
5:30 am-2:05 pm
1 stop9h 35m
$421
Showing 1-10 of 21 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
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 November is currently the most expensive (average of $279). 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 July 7, 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 30% of weekly flights between Chicago and San Juan have experienced delays in the past year, with the average delay time being 128 minutes.
What is the most punctual flight time for Chicago to San Juan flights?
Historically, flights departing in the early afternoon 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?
Wednesday 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 29% of flights being delayed.
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 19 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.
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 July 7, 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.
Entertainment
7.5
Overall
7.9
Comfort
8.0
Food
7.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Entertainment
7.5
Overall
7.9
Comfort
8.0
Food
7.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Entertainment
7.5
Overall
7.9
Comfort
8.0
Food
7.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Entertainment
7.5
Overall
7.9
Comfort
8.0
Food
7.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
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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Midway and San Juan flights
Browse other Midway and San Juan flight options. Last updated on July 7, 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 July 7, 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 July 7, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$91 | Average$288 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$132 | Average$531 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$352 | Average$492 | FlexibilityNo cancel fee | On-time63% |