$113+ Cheap flights from Midway (MDW) to San Juan
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/21. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJU
May 17 — May 241
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
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Cheapest flights from Midway to San JuanExplore the most affordable flight options available from Midway to San Juan. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 17, 2026.
Explore the most affordable flight options available from Midway to San Juan. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 17, 2026.
This Priceline deal was found by Cheapflights users on 4/16. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/259:14 am
MDW
- SJU
1 stop15h 47m
Frontier
Sun 5/36:30 am
SJU
- MDW
1 stop26h 16m
Frontier
Deal found 4/16![Frontier logo]()
$226
This Booking.com deal was found by Cheapflights users on 4/14. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/259:14 am
MDW
- SJU
1 stop12h 34m
Frontier
Thu 4/303:21 am
SJU
- MDW
1 stop8h 07m
Frontier
Deal found 4/14![Frontier logo]()
$227
This Frontier deal was found by Cheapflights users on 4/15. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/276:00 am
MDW
- SJU
1 stop7h 08m
Frontier
Fri 5/13:23 pm
SJU
- MDW
1 stop8h 03m
Frontier
Deal found 4/15![Frontier logo]()
$230
This Priceline deal was found by Cheapflights users on 4/15. 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.
Sun 5/38:39 am
MDW
- SJU
1 stop16h 22m
Frontier
Thu 5/143:03 am
SJU
- MDW
1 stop13h 54m
Frontier
Deal found 4/15![Frontier logo]()
$231
This Frontier deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/266:00 am
MDW
- SJU
1 stop7h 08m
Frontier
Thu 4/303:03 pm
SJU
- MDW
1 stop8h 16m
Frontier
Deal found 4/12![Frontier logo]()
$236
This Frontier deal was found by Cheapflights users on 4/15. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/276:00 am
MDW
- SJU
1 stop7h 08m
Frontier
Sat 5/23:43 pm
SJU
- MDW
1 stop7h 31m
Frontier
Deal found 4/15![Frontier logo]()
$240
This Delta deal was found by Cheapflights users on 4/15. 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.
Mon 4/276:00 am
MDW
- SJU
1 stop9h 23m
Delta
Wed 5/612:55 pm
SJU
- MDW
1 stop10h 33m
Delta
Deal found 4/15![Delta logo]()
$246
This Frontier deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/111:33 am
MDW
- SJU
1 stop10h 15m
Frontier
Fri 5/86:00 am
SJU
- MDW
1 stop10h 57m
Frontier
Deal found 4/12![Frontier logo]()
$251
This Delta deal was found by Cheapflights users on 4/15. 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 4/2912:52 pm
MDW
- SJU
1 stop9h 21m
Delta
Wed 5/612:55 pm
SJU
- MDW
1 stop10h 33m
Delta
Deal found 4/15![Delta logo]()
$256
This Trip.com deal was found by Cheapflights users on 4/12. 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.
Mon 4/276:00 am
MDW
- SJU
1 stop7h 08m
Frontier
Fri 5/88:59 am
SJU
- MDW
1 stop7h 58m
Frontier
Deal found 4/12![Frontier logo]()
$257
This Kiwi.com deal was found by Cheapflights users on 4/12. 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 4/276:00 am
MDW
- SJU
1 stop12h 14m
Multiple Airlines
Wed 4/293:21 am
SJU
- MDW
2 stops17h 10m
Multiple Airlines
Deal found 4/12![Multiple Airlines logo]()
$258
This Priceline deal was found by Cheapflights users on 4/13. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/206:00 am
MDW
- SJU
1 stop7h 13m
Frontier
Fri 4/243:23 pm
SJU
- MDW
1 stop8h 03m
Frontier
Deal found 4/13![Frontier logo]()
$260
Best flights from Midway to San JuanDiscover carefully curated flight deals from Midway to San Juan that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 17, 2026.
Discover carefully curated flight deals from Midway to San Juan that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 17, 2026.
This Delta deal was found by Cheapflights users on 4/15. 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 7/166:05 am
MDW
- SJU
1 stop9h 40m
Delta
Thu 7/232:42 pm
SJU
- MDW
1 stop8h 33m
Delta
Deal found 4/15![Delta logo]()
$326
This Southwest deal was found by Cheapflights users on 4/12. 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 8/296:05 am
MDW
- SJU
1 stop11h 10m
Southwest
Sat 9/125:05 am
SJU
- MDW
1 stop6h 55m
Southwest
Deal found 4/12![Southwest logo]()
$386
This Southwest deal was found by Cheapflights users on 4/15. 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 5/188:35 pm
MDW
- SJU
1 stop13h 00m
Southwest
Fri 5/225:35 am
SJU
- MDW
2 stops8h 35m
Southwest
Deal found 4/15![Southwest logo]()
$396
This Delta deal was found by Cheapflights users on 4/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/266:00 am
MDW
- SJU
1 stop9h 35m
Delta
Tue 9/11:06 pm
SJU
- MDW
1 stop9h 40m
Delta
Deal found 4/13![Delta logo]()
$406
This Southwest deal was found by Cheapflights users on 4/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/18:35 pm
MDW
- SJU
1 stop11h 20m
Southwest
Fri 5/82:00 pm
SJU
- MDW
2 stops9h 20m
Southwest
Deal found 4/16![Southwest logo]()
$426
This Southwest deal was found by Cheapflights users on 4/12. 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 5/77:55 am
MDW
- SJU
1 stop6h 40m
Southwest
Thu 5/145:05 am
SJU
- MDW
1 stop7h 55m
Southwest
Deal found 4/12![Southwest logo]()
$426
This Southwest deal was found by Cheapflights users on 4/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/178:50 pm
MDW
- SJU
1 stop11h 20m
Southwest
Wed 5/205:35 am
SJU
- MDW
1 stop9h 10m
Southwest
Deal found 4/13![Southwest logo]()
$426
This Southwest deal was found by Cheapflights users on 4/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/1612:05 pm
MDW
- SJU
1 stop10h 10m
Southwest
Tue 5/198:10 am
SJU
- MDW
2 stops9h 35m
Southwest
Deal found 4/13![Southwest logo]()
$426
This Southwest deal was found by Cheapflights users on 4/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/2110:10 am
MDW
- SJU
2 stops8h 35m
Southwest
Mon 7/275:00 am
SJU
- MDW
1 stop6h 55m
Southwest
Deal found 4/16![Southwest logo]()
$446
This Southwest deal was found by Cheapflights users on 4/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/42:45 pm
MDW
- SJU
2 stops8h 20m
Southwest
Thu 6/115:30 am
SJU
- MDW
2 stops9h 35m
Southwest
Deal found 4/16![Southwest logo]()
$446
This Southwest deal was found by Cheapflights users on 4/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/101:40 pm
MDW
- SJU
1 stop6h 50m
Southwest
Tue 7/146:00 am
SJU
- MDW
1 stop7h 20m
Southwest
Deal found 4/14![Southwest logo]()
$461
Last-minute flights from Midway to San JuanDiscover last-minute flight deals from Midway to San Juan. Data last updated April 17, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to San Juan. Data last updated April 17, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 4/13. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/206:00 am
MDW
- SJU
1 stop7h 13m
Frontier
Sat 4/253:43 pm
SJU
- MDW
1 stop7h 31m
Frontier
Deal found 4/13![Frontier logo]()
$260
This Frontier deal was found by Cheapflights users on 4/15. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/259:14 am
MDW
- SJU
1 stop12h 34m
Frontier
Thu 4/303:03 pm
SJU
- MDW
1 stop8h 16m
Frontier
Deal found 4/15![Frontier logo]()
$226
This Booking.com deal was found by Cheapflights users on 4/14. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/259:14 am
MDW
- SJU
1 stop12h 34m
Frontier
Thu 4/303:21 am
SJU
- MDW
1 stop8h 07m
Frontier
Deal found 4/14![Frontier logo]()
$227
This Frontier deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/266:00 am
MDW
- SJU
1 stop7h 08m
Frontier
Thu 4/303:03 pm
SJU
- MDW
1 stop8h 16m
Frontier
Deal found 4/12![Frontier logo]()
$236
This Frontier deal was found by Cheapflights users on 4/15. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/276:00 am
MDW
- SJU
1 stop7h 08m
Frontier
Fri 5/13:23 pm
SJU
- MDW
1 stop8h 03m
Frontier
Deal found 4/15![Frontier logo]()
$230
This Frontier deal was found by Cheapflights users on 4/15. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/276:00 am
MDW
- SJU
1 stop7h 08m
Frontier
Sat 5/23:43 pm
SJU
- MDW
1 stop7h 31m
Frontier
Deal found 4/15![Frontier logo]()
$240
This Delta deal was found by Cheapflights users on 4/15. 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.
Mon 4/276:00 am
MDW
- SJU
1 stop9h 23m
Delta
Wed 5/612:55 pm
SJU
- MDW
1 stop10h 33m
Delta
Deal found 4/15![Delta logo]()
$246
This Trip.com deal was found by Cheapflights users on 4/12. 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.
Mon 4/276:00 am
MDW
- SJU
1 stop7h 08m
Frontier
Fri 5/88:59 am
SJU
- MDW
1 stop7h 58m
Frontier
Deal found 4/12![Frontier logo]()
$257
This Kiwi.com deal was found by Cheapflights users on 4/12. 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 4/276:00 am
MDW
- SJU
1 stop12h 14m
Multiple Airlines
Wed 4/293:21 am
SJU
- MDW
2 stops17h 10m
Multiple Airlines
Deal found 4/12![Multiple Airlines logo]()
$258
This Delta deal was found by Cheapflights users on 4/15. 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 4/2912:52 pm
MDW
- SJU
1 stop9h 21m
Delta
Wed 5/612:55 pm
SJU
- MDW
1 stop10h 33m
Delta
Deal found 4/15![Delta logo]()
$256
This Frontier deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/111:33 am
MDW
- SJU
1 stop10h 15m
Frontier
Fri 5/86:00 am
SJU
- MDW
1 stop10h 57m
Frontier
Deal found 4/12![Frontier logo]()
$251
This Priceline deal was found by Cheapflights users on 4/15. 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.
Sun 5/38:39 am
MDW
- SJU
1 stop16h 22m
Frontier
Thu 5/143:03 am
SJU
- MDW
1 stop13h 54m
Frontier
Deal found 4/15![Frontier logo]()
$231
One-way flights from Midway to San JuanSearch for one-way flight options from Midway to San Juan. Find affordable one-way fares based on user searches. Data last updated April 17, 2026.
Search for one-way flight options from Midway to San Juan. Find affordable one-way fares based on user searches. Data last updated April 17, 2026.
This Southwest deal was found by Cheapflights users on 4/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/117:55 am
MDW
- SJU
1 stop6h 40m
Southwest
Deal found 4/16![Southwest logo]()
$113
This Frontier deal was found by Cheapflights users on 4/16. 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.
Sat 7/186:00 am
MDW
- SJU
1 stop7h 15m
Frontier
Deal found 4/16![Frontier logo]()
$120
This Kiwi.com deal was found by Cheapflights users on 4/12. 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 5/911:59 am
MDW
- SJU
2 stops28h 27m
Frontier
Deal found 4/12![Frontier logo]()
$121
This Super.com deal was found by Cheapflights users on 4/12. 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.
Tue 5/126:00 am
MDW
- SJU
1 stop7h 07m
Frontier
Deal found 4/12![Frontier logo]()
$122
This Delta deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/1610:45 am
MDW
- SJU
1 stop10h 32m
Delta
Deal found 4/12![Delta logo]()
$123
This Kiwi.com deal was found by Cheapflights users on 4/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/296:10 am
MDW
- SJU
2 stops12h 12m
Multiple Airlines
Deal found 4/15![Multiple Airlines logo]()
$126
This Frontier deal was found by Cheapflights users on 4/15. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/29:14 am
MDW
- SJU
1 stop12h 34m
Frontier
Deal found 4/15![Frontier logo]()
$128
This Kiwi.com deal was found by Cheapflights users on 4/12. 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 5/1312:04 pm
MDW
- SJU
2 stops13h 04m
Frontier
Deal found 4/12![Frontier logo]()
$130
This Trip.com deal was found by Cheapflights users on 4/14. 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.
Fri 4/246:49 pm
MDW
- SJU
1 stop14h 05m
Frontier
Deal found 4/14![Frontier logo]()
$132
This Delta deal was found by Cheapflights users on 4/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/2812:52 pm
MDW
- SJU
1 stop9h 21m
Delta
Deal found 4/16![Delta logo]()
$133
This Kiwi.com deal was found by Cheapflights users on 4/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/1512:04 pm
MDW
- SJU
2 stops14h 57m
Frontier
Deal found 4/14![Frontier logo]()
$134
Find flight deals from Midway to San Juan
Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to San Juan (PR1). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated April 17, 2026.
Round-trip from | $226 (Southwest) |
|---|---|
One-way from | $113 (Southwest) |
Popular in | June |
Cheapest in | February |
Average price | $328 |
Cheapflights Fare Finder
Customize your flight search to find flights from Midway to San Juan that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 17, 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
Thu 7/16
6:05 am-4:45 pm
1 stop9h 40m
San Juan Luis Munoz Marin Intl
Thu 7/23
2:42 pm-10:15 pm
1 stop8h 33m
$326
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Sat 8/29
6:05 am-6:15 pm
1 stop11h 10m
San Juan Luis Munoz Marin Intl
Sat 9/12
5:05 am-11:00 am
1 stop6h 55m
$386
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Mon 5/18
8:35 pm-10:35 am
1 stop13h 00m
San Juan Luis Munoz Marin Intl
Fri 5/22
5:35 am-1:10 pm
2 stops8h 35m
$396
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Wed 8/26
6:00 am-4:35 pm
1 stop9h 35m
San Juan Luis Munoz Marin Intl
Tue 9/1
1:06 pm-9:46 pm
1 stop9h 40m
$406
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Fri 5/1
8:35 pm-8:55 am
1 stop11h 20m
San Juan Luis Munoz Marin Intl
Fri 5/8
2:00 pm-10:20 pm
2 stops9h 20m
$426
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Thu 5/7
7:55 am-3:35 pm
1 stop6h 40m
San Juan Luis Munoz Marin Intl
Thu 5/14
5:05 am-12:00 pm
1 stop7h 55m
$426
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Sun 5/17
8:50 pm-9:10 am
1 stop11h 20m
San Juan Luis Munoz Marin Intl
Wed 5/20
5:35 am-1:45 pm
1 stop9h 10m
$426
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Sat 5/16
12:05 pm-11:15 pm
1 stop10h 10m
San Juan Luis Munoz Marin Intl
Tue 5/19
8:10 am-4:45 pm
2 stops9h 35m
$426
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Tue 7/21
10:10 am-7:45 pm
2 stops8h 35m
San Juan Luis Munoz Marin Intl
Mon 7/27
5:00 am-10:55 am
1 stop6h 55m
$446
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Thu 6/4
2:45 pm-12:05 am
2 stops8h 20m
San Juan Luis Munoz Marin Intl
Thu 6/11
5:30 am-2:05 pm
2 stops9h 35m
$446
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
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 April 10, 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 $284). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from MDW to SJU?
Find hourly flight availability from Midway to San Juan. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 17, 2026.
When flying from Chicago Midway Airport to San Juan, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
How much does it cost to fly round-trip from Chicago Midway Airport to San Juan?
How often are flights from Chicago to San Juan delayed?
About 31% of weekly flights between Chicago and San Juan have experienced delays in the past year, with the average delay time being 113 minutes.
What is the most punctual flight time for Chicago to San Juan flights?
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the morning tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Saturday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Chicago to San Juan flights?
Over the last year, Southwest have had the lowest number of delays on this route, with just 31% of flights being delayed.
Reviews of airlines servicing San Juan
Get insights into the airlines that provide service to San Juan. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to San Juan. Reviews last updated April 17, 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.
Food
7.0
Entertainment
7.5
Boarding
8.1
Overall
8.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Entertainment
7.5
Boarding
8.1
Overall
8.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Entertainment
7.5
Boarding
8.1
Overall
8.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Entertainment
7.5
Boarding
8.1
Overall
8.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Related info for your journey
Find useful and relevant information for your journey from 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.
Search flights from Midway to San Juan by cabin class
Find flights from Midway to San Juan, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Midway and San Juan flights
Browse other Midway and San Juan flight options. Last updated on April 17, 2026.
Other flights from Midway
Browse through other flights departing from Midway. Flights are based on user searches made on Cheapflights and were last updated on April 17, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 3 airlines flying from Midway to San Juan
Discover the top 3 airlines that operate flights from Midway to San Juan. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 17, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$132 | Average$428 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$138 | Average$286 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$355 | Average$488 | FlexibilityNo cancel fee | On-time63% |