$101+ 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 4/19. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJU
Apr 14 — Apr 211
Round-trip
1 adult, Economy
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Find cheap flights from Midway to San Juan with Cheapflights
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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 March 15, 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 March 15, 2026.
This Priceline deal was found by Cheapflights users on 3/9. 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.
Wed 4/82:56 pm
MDW
- SJU
1 stop8h 56m
Frontier
Tue 4/143:08 am
SJU
- MDW
1 stop29h 56m
Frontier
Deal found 3/9![Frontier logo]()
$202
This Mytrip deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/106:30 am
MDW
- SJU
1 stop17h 31m
Frontier
Tue 4/143:08 am
SJU
- MDW
1 stop29h 56m
Frontier
Deal found 3/10![Frontier logo]()
$218
This Frontier deal was found by Cheapflights users on 3/13. 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.
Thu 4/92:56 pm
MDW
- SJU
1 stop8h 56m
Frontier
Thu 4/166:30 am
SJU
- MDW
1 stop26h 29m
Frontier
Deal found 3/13![Frontier logo]()
$222
This Booking.com deal was found by Cheapflights users on 3/11. 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.
Fri 4/106:30 am
MDW
- SJU
1 stop17h 31m
Frontier
Fri 4/173:23 pm
SJU
- MDW
1 stop8h 03m
Frontier
Deal found 3/11![Frontier logo]()
$224
This Priceline deal was found by Cheapflights users on 3/10. 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 4/25:01 am
MDW
- SJU
1 stop20h 00m
Frontier
Thu 4/163:19 pm
SJU
- MDW
1 stop17h 40m
Frontier
Deal found 3/10![Frontier logo]()
$231
This CheapOair deal was found by Cheapflights users on 3/10. 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.
Sat 4/116:00 am
MDW
- SJU
1 stop13h 49m
Frontier
Fri 4/243:23 pm
SJU
- MDW
1 stop8h 03m
Frontier
Deal found 3/10![Frontier logo]()
$233
This Mytrip deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/199:04 am
MDW
- SJU
1 stop15h 57m
Frontier
Tue 4/283:08 am
SJU
- MDW
1 stop29h 13m
Frontier
Deal found 3/10![Frontier logo]()
$234
This Kiwi.com deal was found by Cheapflights users on 3/10. 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 4/146:10 am
MDW
- SJU
1 stop12h 40m
Multiple Airlines
Tue 4/143:08 am
SJU
- MDW
2 stops17h 23m
Multiple Airlines
Deal found 3/10![Multiple Airlines logo]()
$235
This Trip.com deal was found by Cheapflights users on 3/10. 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.
Wed 5/66:00 am
MDW
- SJU
2 stops19h 08m
Frontier
Tue 5/123:03 am
SJU
- MDW
1 stop30h 01m
Frontier
Deal found 3/10![Frontier logo]()
$236
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 March 15, 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 March 15, 2026.
This Southwest deal was found by Cheapflights users on 3/12. 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.
Tue 5/121:25 pm
MDW
- SJU
1 stop9h 15m
Southwest
Sat 5/162:10 pm
SJU
- MDW
1 stop7h 05m
Southwest
Deal found 3/12![Southwest logo]()
$356
This Southwest deal was found by Cheapflights users on 3/13. 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.
Mon 5/412:50 pm
MDW
- SJU
2 stops10h 05m
Southwest
Sun 5/105:00 am
SJU
- MDW
2 stops9h 05m
Southwest
Deal found 3/13![Southwest logo]()
$362
This Southwest deal was found by Cheapflights users on 3/12. 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.
Wed 5/612:55 pm
MDW
- SJU
2 stops9h 45m
Southwest
Sun 5/105:00 am
SJU
- MDW
2 stops9h 05m
Southwest
Deal found 3/12![Southwest logo]()
$406
This Southwest deal was found by Cheapflights users on 3/11. 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 5/1411:45 am
MDW
- SJU
2 stops10h 40m
Southwest
Sun 5/179:45 pm
SJU
- MDW
2 stops15h 05m
Southwest
Deal found 3/11![Southwest logo]()
$406
This Southwest deal was found by Cheapflights users on 3/10. 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 4/241:25 pm
MDW
- SJU
2 stops9h 30m
Southwest
Wed 4/295:05 am
SJU
- MDW
2 stops11h 45m
Southwest
Deal found 3/10![Southwest logo]()
$427
This Southwest deal was found by Cheapflights users on 3/14. 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.
Wed 4/2212:55 pm
MDW
- SJU
2 stops9h 45m
Southwest
Mon 4/275:35 am
SJU
- MDW
2 stops8h 35m
Southwest
Deal found 3/14![Southwest logo]()
$490
This Southwest deal was found by Cheapflights users on 3/11. 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 6/93:00 pm
MDW
- SJU
2 stops8h 15m
Southwest
Tue 6/168:35 pm
SJU
- MDW
1 stop13h 25m
Southwest
Deal found 3/11![Southwest logo]()
$496
This Southwest deal was found by Cheapflights users on 3/9. 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 3/318:55 am
MDW
- SJU
1 stop9h 35m
Southwest
Wed 4/82:00 pm
SJU
- MDW
2 stops9h 15m
Southwest
Deal found 3/9![Southwest logo]()
$532
This Southwest deal was found by Cheapflights users on 3/10. 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 4/911:45 am
MDW
- SJU
2 stops10h 40m
Southwest
Tue 4/142:00 pm
SJU
- MDW
2 stops9h 15m
Southwest
Deal found 3/10![Southwest logo]()
$536
This Southwest deal was found by Cheapflights users on 3/12. 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 5/218:35 pm
MDW
- SJU
1 stop11h 35m
Southwest
Sun 5/241:45 pm
SJU
- MDW
2 stops10h 10m
Southwest
Deal found 3/12![Southwest logo]()
$581
This Southwest deal was found by Cheapflights users on 3/12. 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 4/231:25 pm
MDW
- SJU
2 stops9h 30m
Southwest
Sun 4/269:45 pm
SJU
- MDW
2 stops15h 05m
Southwest
Deal found 3/12![Southwest logo]()
$582
Last-minute flights from Midway to San JuanDiscover last-minute flight deals from Midway to San Juan. Data last updated March 15, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to San Juan. Data last updated March 15, 2026 and is based on user searches.
This Priceline deal was found by Cheapflights users on 3/10. 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 4/25:01 am
MDW
- SJU
1 stop20h 00m
Frontier
Thu 4/163:19 pm
SJU
- MDW
1 stop17h 40m
Frontier
Deal found 3/10![Frontier logo]()
$231
This Priceline deal was found by Cheapflights users on 3/9. 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.
Wed 4/82:56 pm
MDW
- SJU
1 stop8h 56m
Frontier
Tue 4/143:08 am
SJU
- MDW
1 stop29h 56m
Frontier
Deal found 3/9![Frontier logo]()
$202
This Frontier deal was found by Cheapflights users on 3/13. 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.
Thu 4/92:56 pm
MDW
- SJU
1 stop8h 56m
Frontier
Thu 4/166:30 am
SJU
- MDW
1 stop26h 29m
Frontier
Deal found 3/13![Frontier logo]()
$222
This Mytrip deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/106:30 am
MDW
- SJU
1 stop17h 31m
Frontier
Tue 4/143:08 am
SJU
- MDW
1 stop29h 56m
Frontier
Deal found 3/10![Frontier logo]()
$218
This Booking.com deal was found by Cheapflights users on 3/11. 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.
Fri 4/106:30 am
MDW
- SJU
1 stop17h 31m
Frontier
Fri 4/173:23 pm
SJU
- MDW
1 stop8h 03m
Frontier
Deal found 3/11![Frontier logo]()
$224
This CheapOair deal was found by Cheapflights users on 3/10. 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.
Sat 4/116:00 am
MDW
- SJU
1 stop13h 49m
Frontier
Fri 4/243:23 pm
SJU
- MDW
1 stop8h 03m
Frontier
Deal found 3/10![Frontier logo]()
$233
This Kiwi.com deal was found by Cheapflights users on 3/10. 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 4/136:30 am
MDW
- SJU
1 stop16h 23m
Frontier
Tue 4/143:08 am
SJU
- MDW
2 stops17h 23m
Frontier
Deal found 3/10![Frontier logo]()
$238
This Kiwi.com deal was found by Cheapflights users on 3/10. 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 4/146:10 am
MDW
- SJU
1 stop12h 40m
Multiple Airlines
Tue 4/143:08 am
SJU
- MDW
2 stops17h 23m
Multiple Airlines
Deal found 3/10![Multiple Airlines logo]()
$235
This Mytrip deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/199:04 am
MDW
- SJU
1 stop15h 57m
Frontier
Tue 4/283:08 am
SJU
- MDW
1 stop29h 13m
Frontier
Deal found 3/10![Frontier logo]()
$234
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 March 15, 2026.
Search for one-way flight options from Midway to San Juan. Find affordable one-way fares based on user searches. Data last updated March 15, 2026.
This Booking.com deal was found by Cheapflights users on 3/10. 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.
Sun 4/199:04 am
MDW
- SJU
1 stop15h 57m
Frontier
Deal found 3/10![Frontier logo]()
$101
This Trip.com deal was found by Cheapflights users on 3/12. 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 4/136:30 am
MDW
- SJU
1 stop16h 23m
Frontier
Deal found 3/12![Frontier logo]()
$104
This Orbitz deal was found by Cheapflights users on 3/10. 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
Deal found 3/10![Frontier logo]()
$111
This Trip.com deal was found by Cheapflights users on 3/13. 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 Trip.com 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 3/13![Frontier logo]()
$114
This Kiwi.com deal was found by Cheapflights users on 3/10. 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 4/146:10 am
MDW
- SJU
1 stop12h 40m
Multiple Airlines
Deal found 3/10![Multiple Airlines logo]()
$115
This CheapOair deal was found by Cheapflights users on 3/13. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/116:00 am
MDW
- SJU
1 stop13h 49m
Frontier
Deal found 3/13![Frontier logo]()
$117
This Kiwi.com deal was found by Cheapflights users on 3/13. 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.
Fri 4/106:30 am
MDW
- SJU
1 stop17h 31m
Frontier
Deal found 3/13![Frontier logo]()
$123
This Kiwi.com deal was found by Cheapflights users on 3/10. 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 4/216:10 am
MDW
- SJU
2 stops17h 19m
Frontier
Deal found 3/10![Frontier logo]()
$125
This Kiwi.com deal was found by Cheapflights users on 3/10. 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 5/126:00 am
MDW
- SJU
2 stops19h 01m
Frontier
Deal found 3/10![Frontier logo]()
$127
This Kiwi.com deal was found by Cheapflights users on 3/13. 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.
Tue 4/142:15 pm
MDW
- SJU
2 stops26h 44m
Frontier
Deal found 3/13![Frontier logo]()
$129
This Kiwi.com deal was found by Cheapflights users on 3/10. 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 5/192:20 pm
MDW
- SJU
2 stops26h 10m
Frontier
Deal found 3/10![Frontier logo]()
$130
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 March 15, 2026.
Round-trip from | $202 (Priceline) |
|---|---|
One-way from | $101 (Booking.com) |
Popular in | June |
Cheapest in | February |
Average price | $415 |
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 March 15, 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
Quickest round-trip
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Tue 5/12
1:25 pm-11:40 pm
1 stop9h 15m
San Juan Luis Munoz Marin Intl
Sat 5/16
2:10 pm-8:15 pm
1 stop7h 05m
$356
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Mon 5/4
12:50 pm-11:55 pm
2 stops10h 05m
San Juan Luis Munoz Marin Intl
Sun 5/10
5:00 am-1:05 pm
2 stops9h 05m
$362
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Wed 5/6
12:55 pm-11:40 pm
2 stops9h 45m
San Juan Luis Munoz Marin Intl
Sun 5/10
5:00 am-1:05 pm
2 stops9h 05m
$406
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Thu 5/14
11:45 am-11:25 pm
2 stops10h 40m
San Juan Luis Munoz Marin Intl
Sun 5/17
9:45 pm-11:50 am
2 stops15h 05m
$406
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Fri 4/24
1:25 pm-11:55 pm
2 stops9h 30m
San Juan Luis Munoz Marin Intl
Wed 4/29
5:05 am-3:50 pm
2 stops11h 45m
$427
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Wed 4/22
12:55 pm-11:40 pm
2 stops9h 45m
San Juan Luis Munoz Marin Intl
Mon 4/27
5:35 am-1:10 pm
2 stops8h 35m
$490
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Tue 6/9
3:00 pm-12:15 am
2 stops8h 15m
San Juan Luis Munoz Marin Intl
Tue 6/16
8:35 pm-9:00 am
1 stop13h 25m
$496
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Tue 3/31
8:55 am-7:30 pm
1 stop9h 35m
San Juan Luis Munoz Marin Intl
Wed 4/8
2:00 pm-10:15 pm
2 stops9h 15m
$532
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Thu 4/9
11:45 am-11:25 pm
2 stops10h 40m
San Juan Luis Munoz Marin Intl
Tue 4/14
2:00 pm-10:15 pm
2 stops9h 15m
$536
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Thu 5/21
8:35 pm-9:10 am
1 stop11h 35m
San Juan Luis Munoz Marin Intl
Sun 5/24
1:45 pm-10:55 pm
2 stops10h 10m
$581
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 March 6, 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 March 15, 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 29% of weekly flights between Chicago and San Juan have experienced delays in the past year, with the average delay time being 103 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 29% 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 March 15, 2026.
Read through reviews of airlines operating flights from Chicago Midway Airport to San Juan, such as Southwest,Delta, andFrontier. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.5
Crew
8.6
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Entertainment
7.5
Crew
8.6
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Entertainment
7.5
Crew
8.6
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Entertainment
7.5
Crew
8.6
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
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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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 March 15, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$132 | Average$494 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$142 | Average$295 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$379 | Average$491 | FlexibilityNo cancel fee | On-time63% |