$100+ 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 3/1. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJU
Mar 20 — Mar 271
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 January, booked 55 days in advance, depart on a Monday or Tuesday and return on a Monday
Cheap flight deals from Midway to San Juan
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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 February 18, 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 February 18, 2026.
This Frontier deal was found by Cheapflights users on 2/14. 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.
Tue 3/1011:19 am
MDW
- SJU
1 stop10h 26m
Frontier
Wed 3/116:30 am
SJU
- MDW
1 stop12h 43m
Frontier
Deal found 2/14![Frontier logo]()
$197
This Priceline deal was found by Cheapflights users on 2/17. 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.
Sat 4/116:30 am
MDW
- SJU
1 stop14h 03m
Frontier
Wed 4/153:19 pm
SJU
- MDW
1 stop17h 45m
Frontier
Deal found 2/17![Frontier logo]()
$202
This Booking.com deal was found by Cheapflights users on 2/17. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/92:56 pm
MDW
- SJU
1 stop8h 56m
Frontier
Mon 4/135:45 am
SJU
- MDW
1 stop15h 24m
Frontier
Deal found 2/17![Frontier logo]()
$203
This Frontier deal was found by Cheapflights users on 2/14. 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.
Mon 3/99:51 pm
MDW
- SJU
1 stop11h 21m
Frontier
Wed 3/116:30 am
SJU
- MDW
1 stop12h 43m
Frontier
Deal found 2/14![Frontier logo]()
$211
This CheapOair deal was found by Cheapflights users on 2/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/106:30 am
MDW
- SJU
1 stop17h 31m
Frontier
Fri 4/173:08 am
SJU
- MDW
1 stop14h 05m
Frontier
Deal found 2/14![Frontier logo]()
$213
This Frontier deal was found by Cheapflights users on 2/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/92:56 pm
MDW
- SJU
1 stop8h 56m
Frontier
Fri 4/106:00 am
SJU
- MDW
1 stop9h 01m
Frontier
Deal found 2/16![Frontier logo]()
$218
This CheapOair deal was found by Cheapflights users on 2/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/29:22 pm
MDW
- SJU
1 stop10h 32m
Frontier
Wed 3/45:25 pm
SJU
- MDW
1 stop23h 01m
Frontier
Deal found 2/16![Frontier logo]()
$221
This Kiwi.com deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/16:15 am
MDW
- SJU
1 stop17h 54m
Frontier
Thu 3/56:00 am
SJU
- MDW
1 stop9h 56m
Frontier
Deal found 2/13![Frontier logo]()
$222
This Orbitz deal was found by Cheapflights users on 2/14. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/82:56 pm
MDW
- SJU
1 stop8h 56m
Frontier
Wed 4/156:30 am
SJU
- MDW
1 stop26h 34m
Frontier
Deal found 2/14![Frontier logo]()
$223
This Frontier deal was found by Cheapflights users on 2/16. 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.
Tue 3/314:33 pm
MDW
- SJU
1 stop8h 30m
Frontier
Thu 4/233:18 pm
SJU
- MDW
1 stop8h 01m
Frontier
Deal found 2/16![Frontier logo]()
$224
This Booking.com deal was found by Cheapflights users on 2/16. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/106:00 am
MDW
- SJU
1 stop7h 17m
Frontier
Tue 3/176:30 am
SJU
- MDW
1 stop12h 43m
Frontier
Deal found 2/16![Frontier logo]()
$225
This Booking.com deal was found by Cheapflights users on 2/15. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/239:22 pm
MDW
- SJU
1 stop10h 32m
Frontier
Wed 3/45:25 pm
SJU
- MDW
1 stop23h 01m
Frontier
Deal found 2/15![Frontier logo]()
$229
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 February 18, 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 February 18, 2026.
This Priceline deal was found by Cheapflights users on 2/17. 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.
Fri 5/89:14 am
MDW
- SJU
1 stop15h 47m
Frontier
Mon 5/113:18 pm
SJU
- MDW
1 stop8h 01m
Frontier
Deal found 2/17![Frontier logo]()
$202
This Delta deal was found by Cheapflights users on 2/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/1512:52 pm
MDW
- SJU
1 stop9h 20m
Delta
Tue 4/2112:55 pm
SJU
- MDW
1 stop10h 33m
Delta
Deal found 2/15![Delta logo]()
$246
This Southwest deal was found by Cheapflights users on 2/15. 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 5/158:35 pm
MDW
- SJU
1 stop11h 20m
Southwest
Wed 5/203:45 pm
SJU
- MDW
1 stop6h 40m
Southwest
Deal found 2/15![Southwest logo]()
$296
This Priceline deal was found by Cheapflights users on 2/17. 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.
Thu 4/99:20 am
MDW
- SJU
1 stop15h 41m
Frontier
Mon 4/135:45 am
SJU
- MDW
1 stop15h 24m
Frontier
Deal found 2/17![Frontier logo]()
$233
This Southwest deal was found by Cheapflights users on 2/15. 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 5/25:00 am
MDW
- SJU
1 stop9h 35m
Southwest
Wed 5/611:25 am
SJU
- MDW
2 stops9h 20m
Southwest
Deal found 2/15![Southwest logo]()
$296
This Delta deal was found by Cheapflights users on 2/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/912:47 pm
MDW
- SJU
1 stop6h 31m
Delta
Wed 4/152:45 pm
SJU
- MDW
1 stop8h 43m
Delta
Deal found 2/15![Delta logo]()
$296
This Expedia deal was found by Cheapflights users on 2/17. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/26:00 am
MDW
- SJU
1 stop7h 37m
Frontier
Sun 5/103:19 pm
SJU
- MDW
1 stop17h 45m
Frontier
Deal found 2/17![Frontier logo]()
$280
This Southwest deal was found by Cheapflights users on 2/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/101:25 pm
MDW
- SJU
1 stop9h 10m
Southwest
Thu 5/1410:00 am
SJU
- MDW
2 stops8h 45m
Southwest
Deal found 2/17![Southwest logo]()
$296
This Southwest deal was found by Cheapflights users on 2/15. 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 5/118:35 pm
MDW
- SJU
1 stop13h 00m
Southwest
Sun 5/179:45 pm
SJU
- MDW
2 stops15h 05m
Southwest
Deal found 2/15![Southwest logo]()
$296
This Priceline deal was found by Cheapflights users on 2/17. 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.
Thu 5/149:14 am
MDW
- SJU
1 stop12h 34m
Frontier
Mon 5/183:18 pm
SJU
- MDW
1 stop8h 01m
Frontier
Deal found 2/17![Frontier logo]()
$316
This Southwest deal was found by Cheapflights users on 2/15. 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 5/25:00 am
MDW
- SJU
1 stop9h 35m
Southwest
Sat 5/95:45 am
SJU
- MDW
2 stops9h 10m
Southwest
Deal found 2/15![Southwest logo]()
$310
This Southwest deal was found by Cheapflights users on 2/15. 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 2/2311:50 am
MDW
- SJU
1 stop8h 35m
Southwest
Wed 3/45:40 am
SJU
- MDW
2 stops8h 50m
Southwest
Deal found 2/15![Southwest logo]()
$316
Last-minute flights from Midway to San JuanDiscover last-minute flight deals from Midway to San Juan. Data last updated February 18, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to San Juan. Data last updated February 18, 2026 and is based on user searches.
This Booking.com deal was found by Cheapflights users on 2/15. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/239:22 pm
MDW
- SJU
1 stop10h 32m
Frontier
Wed 3/45:25 pm
SJU
- MDW
1 stop23h 01m
Frontier
Deal found 2/15![Frontier logo]()
$229
This Kiwi.com deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/16:15 am
MDW
- SJU
1 stop17h 54m
Frontier
Thu 3/56:00 am
SJU
- MDW
1 stop9h 56m
Frontier
Deal found 2/13![Frontier logo]()
$222
This Expedia deal was found by Cheapflights users on 2/14. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/29:22 pm
MDW
- SJU
1 stop10h 32m
Frontier
Wed 3/45:25 pm
SJU
- MDW
1 stop23h 01m
Frontier
Deal found 2/14![Frontier logo]()
$202
This WAYA deal was found by Cheapflights users on 2/17. 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 WAYA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/37:30 am
MDW
- SJU
1 stop8h 02m
Multiple Airlines
Thu 3/56:00 am
SJU
- MDW
1 stop9h 56m
Multiple Airlines
Deal found 2/17![Multiple Airlines logo]()
$232
This Priceline deal was found by Cheapflights users on 2/15. 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.
Mon 3/99:51 pm
MDW
- SJU
1 stop11h 21m
Frontier
Wed 3/1110:04 am
SJU
- MDW
1 stop9h 09m
Frontier
Deal found 2/15![Frontier logo]()
$211
This Frontier deal was found by Cheapflights users on 2/14. 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.
Tue 3/1011:19 am
MDW
- SJU
1 stop10h 26m
Frontier
Wed 3/116:30 am
SJU
- MDW
1 stop12h 43m
Frontier
Deal found 2/14![Frontier logo]()
$197
This Booking.com deal was found by Cheapflights users on 2/16. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/106:00 am
MDW
- SJU
1 stop7h 17m
Frontier
Tue 3/176:30 am
SJU
- MDW
1 stop12h 43m
Frontier
Deal found 2/16![Frontier logo]()
$225
This Frontier deal was found by Cheapflights users on 2/14. 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.
Tue 3/314:33 pm
MDW
- SJU
1 stop8h 30m
Frontier
Wed 4/81:11 pm
SJU
- MDW
1 stop10h 08m
Frontier
Deal found 2/14![Frontier logo]()
$223
This Frontier deal was found by Cheapflights users on 2/16. 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.
Tue 3/314:33 pm
MDW
- SJU
1 stop8h 30m
Frontier
Thu 4/233:18 pm
SJU
- MDW
1 stop8h 01m
Frontier
Deal found 2/16![Frontier logo]()
$224
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 February 18, 2026.
Search for one-way flight options from Midway to San Juan. Find affordable one-way fares based on user searches. Data last updated February 18, 2026.
This Super.com deal was found by Cheapflights users on 2/15. 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.
Sun 3/17:30 am
MDW
- SJU
1 stop17h 23m
Frontier
Deal found 2/15![Frontier logo]()
$100
This Priceline deal was found by Cheapflights users on 2/17. 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.
Mon 4/132:56 pm
MDW
- SJU
1 stop8h 56m
Frontier
Deal found 2/17![Frontier logo]()
$101
This Frontier deal was found by Cheapflights users on 2/17. 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.
Tue 3/314:33 pm
MDW
- SJU
1 stop8h 30m
Frontier
Deal found 2/17![Frontier logo]()
$102
This Trip.com deal was found by Cheapflights users on 2/16. 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.
Sat 4/116:30 am
MDW
- SJU
1 stop14h 03m
Frontier
Deal found 2/16![Frontier logo]()
$104
This Trip.com deal was found by Cheapflights users on 2/16. 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.
Sat 4/189:14 am
MDW
- SJU
1 stop12h 34m
Frontier
Deal found 2/16![Frontier logo]()
$106
This Trip.com deal was found by Cheapflights users on 2/14. 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.
Sun 3/86:00 am
MDW
- SJU
1 stop18h 21m
Frontier
Deal found 2/14![Frontier logo]()
$107
This Super.com deal was found by Cheapflights users on 2/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/99:51 pm
MDW
- SJU
1 stop11h 21m
Frontier
Deal found 2/15![Frontier logo]()
$108
This Trip.com deal was found by Cheapflights users on 2/15. 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.
Sat 3/76:00 am
MDW
- SJU
1 stop10h 58m
Multiple Airlines
Deal found 2/15![Multiple Airlines logo]()
$110
This Kiwi.com deal was found by Cheapflights users on 2/16. 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 3/309:42 pm
MDW
- SJU
1 stop26h 37m
Frontier
Deal found 2/16![Frontier logo]()
$113
This Kiwi.com deal was found by Cheapflights users on 2/16. 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 3/166:00 am
MDW
- SJU
1 stop18h 21m
Frontier
Deal found 2/16![Frontier logo]()
$118
This Kiwi.com deal was found by Cheapflights users on 2/16. 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 3/166:00 am
MDW
- SJU
1 stop16h 58m
Multiple Airlines
Deal found 2/16![Multiple Airlines logo]()
$119
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 February 18, 2026.
Round-trip from | $197 (Frontier) |
|---|---|
One-way from | $100 (Super.com) |
Popular in | March |
Cheapest in | February |
Average price | $289 |
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 February 18, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to San Juan that are best for you.
Fly from
Midway
Fly to
San Juan
Route
Depart
Return
Price
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Fri 5/8
9:14 am-2:01 am
1 stop15h 47m
San Juan Luis Munoz Marin Intl
Mon 5/11
3:18 pm-10:19 pm
1 stop8h 01m
$202
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Thu 4/9
9:20 am-2:01 am
1 stop15h 41m
San Juan Luis Munoz Marin Intl
Mon 4/13
5:45 am-8:09 pm
1 stop15h 24m
$233
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Wed 4/15
12:52 pm-11:12 pm
1 stop9h 20m
San Juan Luis Munoz Marin Intl
Tue 4/21
12:55 pm-10:28 pm
1 stop10h 33m
$246
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Sat 5/2
6:00 am-2:37 pm
1 stop7h 37m
San Juan Luis Munoz Marin Intl
Sun 5/10
3:19 pm-8:04 am
1 stop17h 45m
$280
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Fri 5/15
8:35 pm-8:55 am
1 stop11h 20m
San Juan Luis Munoz Marin Intl
Wed 5/20
3:45 pm-9:25 pm
1 stop6h 40m
$296
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Sat 5/2
5:00 am-3:35 pm
1 stop9h 35m
San Juan Luis Munoz Marin Intl
Wed 5/6
11:25 am-7:45 pm
2 stops9h 20m
$296
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Thu 4/9
12:47 pm-8:18 pm
1 stop6h 31m
San Juan Luis Munoz Marin Intl
Wed 4/15
2:45 pm-10:28 pm
1 stop8h 43m
$296
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Sun 5/10
1:25 pm-11:35 pm
1 stop9h 10m
San Juan Luis Munoz Marin Intl
Thu 5/14
10:00 am-5:45 pm
2 stops8h 45m
$296
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Mon 5/11
8:35 pm-10:35 am
1 stop13h 00m
San Juan Luis Munoz Marin Intl
Sun 5/17
9:45 pm-11:50 am
2 stops15h 05m
$296
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Sat 5/2
5:00 am-3:35 pm
1 stop9h 35m
San Juan Luis Munoz Marin Intl
Sat 5/9
5:45 am-1:55 pm
2 stops9h 10m
$310
Showing 1-10 of 21 results
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?
Use this chart to determine the optimal time to book a round-trip flight from Midway to San Juan. Price data was last updated on February 13, 2026.
The best time to book flights from Chicago Midway Airport to San Juan is 55 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 $298). 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 February 18, 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 often are flights from Chicago to San Juan delayed?
About 27% of weekly flights between Chicago and San Juan have experienced delays in the past year, with the average delay time being 100 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 27% 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 February 18, 2026.
Read through reviews of airlines operating flights from Chicago Midway Airport to San Juan, such as Southwest, Delta, and Frontier. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Overall
8.0
Comfort
8.0
Crew
8.6
Food
7.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Overall
8.0
Comfort
8.0
Crew
8.6
Food
7.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Overall
8.0
Comfort
8.0
Crew
8.6
Food
7.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Overall
8.0
Comfort
8.0
Crew
8.6
Food
7.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
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
Complete your trip to San Juan by adding a car rental and/or hotel reservation to your travel itinerary.
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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 February 18, 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 February 18, 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 February 18, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$132 | Average$500 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$138 | Average$290 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$379 | Average$487 | FlexibilityNo cancel fee | On-time63% |