$137+ 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 8/27. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJU
Sep 2 — Sep 91
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
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 January, 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 August 3, 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 August 3, 2026.
This Southwest deal was found by Cheapflights users on 7/29. 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 9/812:45 pm
MDW
- SJU
2 stops8h 20m
Southwest
Wed 9/95:15 am
SJU
- MDW
1 stop7h 50m
Southwest
Deal found 7/29![Southwest logo]()
$269
This Southwest deal was found by Cheapflights users on 7/31. 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 9/17:30 am
MDW
- SJU
1 stop10h 30m
Southwest
Wed 9/25:15 am
SJU
- MDW
1 stop7h 50m
Southwest
Deal found 7/31![Southwest logo]()
$271
This Southwest deal was found by Cheapflights users on 7/29. 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 8/2711:15 am
MDW
- SJU
1 stop7h 50m
Southwest
Mon 8/318:55 pm
SJU
- MDW
1 stop13h 30m
Southwest
Deal found 7/29![Southwest logo]()
$274
This Southwest deal was found by Cheapflights users on 7/29. 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 9/127:50 am
MDW
- SJU
2 stops7h 50m
Southwest
Tue 9/155:15 am
SJU
- MDW
1 stop7h 50m
Southwest
Deal found 7/29![Southwest logo]()
$275
This Southwest deal was found by Cheapflights users on 7/30. 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 9/1612:45 pm
MDW
- SJU
1 stop8h 20m
Southwest
Wed 9/3010:30 am
SJU
- MDW
1 stop8h 10m
Southwest
Deal found 7/30![Southwest logo]()
$276
This Southwest deal was found by Cheapflights users on 7/29. 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 9/47:50 pm
MDW
- SJU
1 stop12h 35m
Southwest
Sat 9/52:50 pm
SJU
- MDW
1 stop7h 10m
Southwest
Deal found 7/29![Southwest logo]()
$295
This Southwest deal was found by Cheapflights users on 7/29. 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 9/259:20 am
MDW
- SJU
2 stops9h 45m
Southwest
Mon 9/285:00 am
SJU
- MDW
1 stop7h 45m
Southwest
Deal found 7/29![Southwest logo]()
$300
This Southwest deal was found by Cheapflights users on 7/31. 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 9/1612:45 pm
MDW
- SJU
1 stop8h 20m
Southwest
Wed 9/232:25 pm
SJU
- MDW
1 stop7h 25m
Southwest
Deal found 7/31![Southwest logo]()
$301
This Southwest deal was found by Cheapflights users on 7/29. 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 10/172:40 pm
MDW
- SJU
1 stop6h 30m
Southwest
Sat 10/245:40 am
SJU
- MDW
1 stop11h 30m
Southwest
Deal found 7/29![Southwest logo]()
$311
This Southwest deal was found by Cheapflights users on 7/29. 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 9/183:10 pm
MDW
- SJU
2 stops7h 45m
Southwest
Sun 9/209:25 pm
SJU
- MDW
1 stop12h 20m
Southwest
Deal found 7/29![Southwest logo]()
$319
This Southwest deal was found by Cheapflights users on 7/30. 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 9/138:05 pm
MDW
- SJU
1 stop12h 05m
Southwest
Sun 9/209:25 pm
SJU
- MDW
1 stop12h 20m
Southwest
Deal found 7/30![Southwest logo]()
$320
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 August 3, 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 August 3, 2026.
This Southwest deal was found by Cheapflights users on 8/1. 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 9/159:40 am
MDW
- SJU
1 stop7h 30m
Southwest
Tue 9/2211:50 am
SJU
- MDW
1 stop8h 25m
Southwest
Deal found 8/1![Southwest logo]()
$276
This Southwest deal was found by Cheapflights users on 7/29. 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 10/61:40 pm
MDW
- SJU
2 stops8h 25m
Southwest
Wed 10/145:50 am
SJU
- MDW
1 stop11h 15m
Southwest
Deal found 7/29![Southwest logo]()
$276
This Southwest deal was found by Cheapflights users on 8/2. 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 9/167:30 am
MDW
- SJU
1 stop10h 35m
Southwest
Wed 9/238:20 am
SJU
- MDW
2 stops9h 30m
Southwest
Deal found 8/2![Southwest logo]()
$301
This Southwest deal was found by Cheapflights users on 7/29. 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 9/112:45 pm
MDW
- SJU
2 stops8h 15m
Southwest
Sun 9/65:20 am
SJU
- MDW
1 stop6h 55m
Southwest
Deal found 7/29![Southwest logo]()
$335
This Southwest deal was found by Cheapflights users on 7/29. 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 10/912:45 pm
MDW
- SJU
1 stop10h 20m
Southwest
Mon 10/1210:50 pm
SJU
- MDW
1 stop10h 35m
Southwest
Deal found 7/29![Southwest logo]()
$345
This Southwest deal was found by Cheapflights users on 7/31. 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 8/281:00 pm
MDW
- SJU
2 stops8h 50m
Southwest
Tue 9/15:15 am
SJU
- MDW
2 stops7h 50m
Southwest
Deal found 7/31![Southwest logo]()
$351
This Southwest deal was found by Cheapflights users on 7/31. 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 10/178:40 am
MDW
- SJU
2 stops10h 25m
Southwest
Mon 10/1910:50 pm
SJU
- MDW
1 stop12h 00m
Southwest
Deal found 7/31![Southwest logo]()
$364
This Southwest deal was found by Cheapflights users on 7/30. 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 7/30![Southwest logo]()
$380
This Southwest deal was found by Cheapflights users on 8/2. 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.
Thu 8/203:10 pm
MDW
- SJU
2 stops7h 40m
Southwest
Mon 8/248:55 pm
SJU
- MDW
1 stop13h 30m
Southwest
Deal found 8/2![Southwest logo]()
$396
This Southwest deal was found by Cheapflights users on 8/2. 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.
Fri 8/211:20 pm
MDW
- SJU
2 stops9h 30m
Southwest
Mon 8/248:55 pm
SJU
- MDW
1 stop13h 30m
Southwest
Deal found 8/2![Southwest logo]()
$396
This Southwest deal was found by Cheapflights users on 7/30. 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 8/189:40 am
MDW
- SJU
1 stop10h 25m
Southwest
Sat 8/222:00 pm
SJU
- MDW
1 stop7h 30m
Southwest
Deal found 7/30![Southwest logo]()
$411
Last-minute flights from Midway to San JuanDiscover last-minute flight deals from Midway to San Juan. Data last updated August 3, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to San Juan. Data last updated August 3, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 7/30. 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 8/2210:56 am
MDW
- SJU
1 stop10h 33m
Delta
Sat 8/297:00 am
SJU
- MDW
1 stop9h 38m
Delta
Deal found 7/30![Delta logo]()
$346
This Southwest deal was found by Cheapflights users on 7/29. 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 8/238:20 am
MDW
- SJU
1 stop13h 25m
Southwest
Thu 8/2710:00 am
SJU
- MDW
1 stop6h 35m
Southwest
Deal found 7/29![Southwest logo]()
$300
This Southwest deal was found by Cheapflights users on 7/29. 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
Fri 8/286:30 am
SJU
- MDW
2 stops8h 15m
Southwest
Deal found 7/29![Southwest logo]()
$335
This Southwest deal was found by Cheapflights users on 8/1. 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.
Mon 8/249:20 am
MDW
- SJU
2 stops9h 45m
Southwest
Sat 8/295:55 am
SJU
- MDW
2 stops8h 10m
Southwest
Deal found 8/1![Southwest logo]()
$320
This Southwest deal was found by Cheapflights users on 7/31. 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 8/2512:20 pm
MDW
- SJU
1 stop7h 45m
Southwest
Sat 8/296:25 am
SJU
- MDW
2 stops11h 40m
Southwest
Deal found 7/31![Southwest logo]()
$276
This Southwest deal was found by Cheapflights users on 7/29. 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 8/2711:15 am
MDW
- SJU
1 stop7h 50m
Southwest
Mon 8/318:55 pm
SJU
- MDW
1 stop13h 30m
Southwest
Deal found 7/29![Southwest logo]()
$274
This Southwest deal was found by Cheapflights users on 8/1. 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.
Sat 8/297:50 am
MDW
- SJU
2 stops7h 50m
Southwest
Sun 8/309:25 pm
SJU
- MDW
1 stop13h 35m
Southwest
Deal found 8/1![Southwest logo]()
$301
This Southwest deal was found by Cheapflights users on 7/29. 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 8/308:05 pm
MDW
- SJU
1 stop12h 05m
Southwest
Sat 9/56:25 am
SJU
- MDW
2 stops11h 20m
Southwest
Deal found 7/29![Southwest logo]()
$326
This Southwest deal was found by Cheapflights users on 7/29. 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 8/313:10 pm
MDW
- SJU
2 stops7h 40m
Southwest
Sat 9/55:05 am
SJU
- MDW
1 stop6h 55m
Southwest
Deal found 7/29![Southwest logo]()
$275
This Southwest deal was found by Cheapflights users on 7/30. 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 8/313:10 pm
MDW
- SJU
2 stops7h 40m
Southwest
Sun 9/65:20 am
SJU
- MDW
2 stops9h 40m
Southwest
Deal found 7/30![Southwest logo]()
$336
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 August 3, 2026.
Search for one-way flight options from Midway to San Juan. Find affordable one-way fares based on user searches. Data last updated August 3, 2026.
This Southwest deal was found by Cheapflights users on 7/29. 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 8/2711:15 am
MDW
- SJU
1 stop7h 50m
Southwest
Deal found 7/29![Southwest logo]()
$137
This Southwest deal was found by Cheapflights users on 8/2. 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.
Sat 8/297:50 am
MDW
- SJU
2 stops9h 15m
Southwest
Deal found 8/2![Southwest logo]()
$138
This Kiwi.com deal was found by Cheapflights users on 8/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/112:54 pm
MDW
- SJU
2 stops12h 19m
Frontier
Deal found 8/1![Frontier logo]()
$143
This Kiwi.com deal was found by Cheapflights users on 7/31. 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 9/246:25 am
MDW
- SJU
2 stops18h 48m
Frontier
Deal found 7/31![Frontier logo]()
$145
This Kiwi.com deal was found by Cheapflights users on 7/31. 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 8/3111:50 am
MDW
- SJU
2 stops12h 06m
Frontier
Deal found 7/31![Frontier logo]()
$146
This Kiwi.com deal was found by Cheapflights users on 8/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/286:25 am
MDW
- SJU
2 stops18h 48m
Frontier
Deal found 8/1![Frontier logo]()
$153
This Kiwi.com deal was found by Cheapflights users on 7/31. 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.
Sat 8/2911:45 am
MDW
- SJU
2 stops12h 11m
Frontier
Deal found 7/31![Frontier logo]()
$155
This Kiwi.com deal was found by Cheapflights users on 7/31. 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 7/31![Frontier logo]()
$156
This Kiwi.com deal was found by Cheapflights users on 8/3. 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 9/811:50 am
MDW
- SJU
2 stops25h 03m
Frontier
Deal found 8/3![Frontier logo]()
$158
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 August 3, 2026.
Round-trip from | $269 (Southwest) |
|---|---|
One-way from | $137 (Southwest) |
Popular in | June |
Cheapest in | February |
Average price | $375 |
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 August 3, 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
Tue 9/15
9:40 am-6:10 pm
1 stop7h 30m
San Juan Luis Munoz Marin Intl
Tue 9/22
11:50 am-7:15 pm
1 stop8h 25m
$276
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Tue 10/6
1:40 pm-11:05 pm
2 stops8h 25m
San Juan Luis Munoz Marin Intl
Wed 10/14
5:50 am-4:05 pm
1 stop11h 15m
$276
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Wed 9/16
7:30 am-7:05 pm
1 stop10h 35m
San Juan Luis Munoz Marin Intl
Wed 9/23
8:20 am-4:50 pm
2 stops9h 30m
$301
Quickest round-trip
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Tue 9/1
12:45 pm-10:00 pm
2 stops8h 15m
San Juan Luis Munoz Marin Intl
Sun 9/6
5:20 am-11:15 am
1 stop6h 55m
$335
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Fri 10/9
12:45 pm-12:05 am
1 stop10h 20m
San Juan Luis Munoz Marin Intl
Mon 10/12
10:50 pm-8:25 am
1 stop10h 35m
$345
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Fri 8/28
1:00 pm-10:50 pm
2 stops8h 50m
San Juan Luis Munoz Marin Intl
Tue 9/1
5:15 am-12:05 pm
2 stops7h 50m
$351
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Sat 10/17
8:40 am-8:05 pm
2 stops10h 25m
San Juan Luis Munoz Marin Intl
Mon 10/19
10:50 pm-9:50 am
1 stop12h 00m
$364
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Sun 8/23
1:10 pm-10:45 pm
2 stops8h 35m
San Juan Luis Munoz Marin Intl
Wed 8/26
5:15 am-12:05 pm
2 stops7h 50m
$380
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Thu 8/20
3:10 pm-11:50 pm
2 stops7h 40m
San Juan Luis Munoz Marin Intl
Mon 8/24
8:55 pm-9:25 am
1 stop13h 30m
$396
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Fri 8/21
1:20 pm-11:50 pm
2 stops9h 30m
San Juan Luis Munoz Marin Intl
Mon 8/24
8:55 pm-9:25 am
1 stop13h 30m
$396
Showing 1-10 of 22 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, February is the cheapest month in which you can book a flight from Chicago Midway Airport to San Juan (average of $243). Flying from Chicago Midway Airport to San Juan in June is currently the most expensive (average of $556). 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 August 3, 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?
Airfare is typical for this route at the moment.
Chicago Midway Airport to San Juan flights typically cost between $256 and $551 in September.The cheapest round-trip price found within the last 5 days was $269 on Southwest (Sep 8-Sep 9).
How often are flights from Chicago to San Juan delayed?
About 28% 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 Saturday 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 27% 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 20 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 August 3, 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.
Comfort
8.0
Overall
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Food
7.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Comfort
8.0
Overall
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Food
7.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Comfort
8.0
Overall
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Food
7.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Comfort
8.0
Overall
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Food
7.0
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.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Other flight options
Other flights from Midway
Popular flights
Alternative routes for Midway to San Juan
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to San Juan by adding a car rental and/or hotel reservation to your travel itinerary.
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 August 3, 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 August 3, 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 August 3, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$91 | Average$296 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$132 | Average$606 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$346 | Average$495 | FlexibilityNo cancel fee | On-time63% |