$94+ 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 3/8. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJU
Mar 5 — Mar 121
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 May or February, booked 25 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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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 February 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 February 3, 2026.
This Frontier deal was found by Cheapflights users on 2/2. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/216:00 am
MDW
- SJU
1 stop8h 21m
Frontier
Fri 2/273:53 am
SJU
- MDW
1 stop13h 02m
Frontier
Deal found 2/2![Frontier logo]()
$187
This Orbitz deal was found by Cheapflights users on 2/2. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/218:00 am
MDW
- SJU
1 stop16h 53m
Frontier
Wed 2/255:25 pm
SJU
- MDW
1 stop23h 01m
Frontier
Deal found 2/2![Frontier logo]()
$188
This Gotogate deal was found by Cheapflights users on 2/2. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/236:00 am
MDW
- SJU
1 stop7h 02m
Frontier
Wed 3/411:07 am
SJU
- MDW
1 stop29h 19m
Frontier
Deal found 2/2![Frontier logo]()
$192
This Frontier deal was found by Cheapflights users on 2/1. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/246:10 am
MDW
- SJU
1 stop6h 56m
Frontier
Thu 3/56:00 am
SJU
- MDW
1 stop9h 56m
Frontier
Deal found 2/1![Frontier logo]()
$197
This Booking.com deal was found by Cheapflights users on 2/2. 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 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
Thu 2/264:11 pm
SJU
- MDW
1 stop8h 18m
Frontier
Deal found 2/2![Frontier logo]()
$201
This Frontier deal was found by Cheapflights users on 2/1. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/246:10 am
MDW
- SJU
1 stop6h 56m
Frontier
Fri 2/273:53 am
SJU
- MDW
1 stop13h 02m
Frontier
Deal found 2/1![Frontier logo]()
$209
This Expedia deal was found by Cheapflights users on 2/2. 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 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
Sun 3/83:08 am
SJU
- MDW
1 stop18h 45m
Frontier
Deal found 2/2![Frontier logo]()
$211
This Kiwi.com deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/239:22 pm
MDW
- SJU
2 stops16h 09m
Multiple Airlines
Thu 2/266:00 am
SJU
- MDW
1 stop9h 56m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$213
This Kiwi.com deal was found by Cheapflights users on 1/31. 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 2/289:15 am
MDW
- SJU
1 stop24h 22m
Multiple Airlines
Fri 3/66:50 pm
SJU
- MDW
1 stop20h 51m
Multiple Airlines
Deal found 1/31![Multiple Airlines logo]()
$215
This CheapOair deal was found by Cheapflights users on 2/2. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/57:30 am
MDW
- SJU
1 stop17h 23m
Frontier
Sun 3/83:08 am
SJU
- MDW
1 stop11h 00m
Frontier
Deal found 2/2![Frontier logo]()
$220
This CheapOair deal was found by Cheapflights users on 2/1. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/126:00 am
MDW
- SJU
1 stop18h 21m
Frontier
Wed 3/186:39 pm
SJU
- MDW
1 stop20h 02m
Frontier
Deal found 2/1![Frontier logo]()
$221
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 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 February 3, 2026.
This Delta deal was found by Cheapflights users on 2/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/2112:53 pm
MDW
- SJU
1 stop9h 19m
Delta
Wed 4/292:34 pm
SJU
- MDW
1 stop8h 54m
Delta
Deal found 2/2![Delta logo]()
$246
This Frontier deal was found by Cheapflights users on 2/2. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/239:14 am
MDW
- SJU
1 stop12h 34m
Frontier
Sat 4/253:18 pm
SJU
- MDW
1 stop8h 01m
Frontier
Deal found 2/2![Frontier logo]()
$258
This Southwest deal was found by Cheapflights users on 2/2. 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.
Tue 3/33:15 pm
MDW
- SJU
1 stop7h 20m
Southwest
Tue 3/106:40 am
SJU
- MDW
1 stop9h 25m
Southwest
Deal found 2/2![Southwest logo]()
$331
This Delta deal was found by Cheapflights users on 2/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/2010:43 am
MDW
- SJU
1 stop8h 41m
Delta
Wed 4/296:15 am
SJU
- MDW
1 stop11h 10m
Delta
Deal found 2/2![Delta logo]()
$246
This Delta deal was found by Cheapflights users on 2/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/2210:43 am
MDW
- SJU
1 stop8h 41m
Delta
Sat 4/251:00 pm
SJU
- MDW
1 stop10h 28m
Delta
Deal found 2/2![Delta logo]()
$284
This Southwest deal was found by Cheapflights users on 2/2. 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.
Tue 4/712:50 pm
MDW
- SJU
2 stops8h 50m
Southwest
Tue 4/142:00 pm
SJU
- MDW
2 stops9h 15m
Southwest
Deal found 2/2![Southwest logo]()
$346
This Southwest deal was found by Cheapflights users on 2/1. 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 5/27:50 am
MDW
- SJU
2 stops8h 45m
Southwest
Wed 5/68:10 am
SJU
- MDW
2 stops9h 35m
Southwest
Deal found 2/1![Southwest logo]()
$390
This Delta deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/410:49 am
MDW
- SJU
1 stop8h 23m
Delta
Tue 3/106:15 am
SJU
- MDW
1 stop6h 47m
Delta
Deal found 2/1![Delta logo]()
$374
This Southwest deal was found by Cheapflights users on 2/1. 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 2/242:20 pm
MDW
- SJU
2 stops8h 15m
Southwest
Tue 3/105:55 am
SJU
- MDW
1 stop8h 55m
Southwest
Deal found 2/1![Southwest logo]()
$390
This Southwest deal was found by Cheapflights users on 2/2. 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 4/309:00 am
MDW
- SJU
2 stops10h 00m
Southwest
Wed 5/68:10 am
SJU
- MDW
2 stops9h 35m
Southwest
Deal found 2/2![Southwest logo]()
$395
This Southwest deal was found by Cheapflights users on 2/1. 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.
Sun 2/222:20 pm
MDW
- SJU
2 stops8h 45m
Southwest
Wed 2/255:40 am
SJU
- MDW
2 stops9h 30m
Southwest
Deal found 2/1![Southwest logo]()
$404
This Southwest deal was found by Cheapflights users on 2/2. 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.
Tue 4/215:55 am
MDW
- SJU
1 stop7h 55m
Southwest
Mon 4/275:35 am
SJU
- MDW
1 stop7h 30m
Southwest
Deal found 2/2![Southwest logo]()
$409
Last-minute flights from Midway to San JuanDiscover last-minute flight deals from Midway to San Juan. Data last updated February 3, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to San Juan. Data last updated February 3, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 2/2. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/216:00 am
MDW
- SJU
1 stop8h 21m
Frontier
Fri 2/273:53 am
SJU
- MDW
1 stop13h 02m
Frontier
Deal found 2/2![Frontier logo]()
$187
This Orbitz deal was found by Cheapflights users on 2/2. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/218:00 am
MDW
- SJU
1 stop16h 53m
Frontier
Wed 2/255:25 pm
SJU
- MDW
1 stop23h 01m
Frontier
Deal found 2/2![Frontier logo]()
$188
This Booking.com deal was found by Cheapflights users on 2/2. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/236:00 am
MDW
- SJU
1 stop7h 02m
Frontier
Wed 3/45:25 pm
SJU
- MDW
1 stop23h 01m
Frontier
Deal found 2/2![Frontier logo]()
$192
This Booking.com deal was found by Cheapflights users on 2/2. 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 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
Thu 2/264:11 pm
SJU
- MDW
1 stop8h 18m
Frontier
Deal found 2/2![Frontier logo]()
$201
This Kiwi.com deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/239:22 pm
MDW
- SJU
2 stops16h 09m
Multiple Airlines
Thu 2/266:00 am
SJU
- MDW
1 stop9h 56m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$213
This Frontier deal was found by Cheapflights users on 2/1. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/246:10 am
MDW
- SJU
1 stop6h 56m
Frontier
Thu 3/56:00 am
SJU
- MDW
1 stop9h 56m
Frontier
Deal found 2/1![Frontier logo]()
$197
This Frontier deal was found by Cheapflights users on 2/1. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/246:10 am
MDW
- SJU
1 stop6h 56m
Frontier
Fri 2/273:53 am
SJU
- MDW
1 stop13h 02m
Frontier
Deal found 2/1![Frontier logo]()
$209
This Kiwi.com deal was found by Cheapflights users on 1/31. 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 2/289:15 am
MDW
- SJU
1 stop24h 22m
Multiple Airlines
Fri 3/66:50 pm
SJU
- MDW
1 stop20h 51m
Multiple Airlines
Deal found 1/31![Multiple Airlines logo]()
$215
This Expedia deal was found by Cheapflights users on 2/2. 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 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
Sun 3/83:08 am
SJU
- MDW
1 stop18h 45m
Frontier
Deal found 2/2![Frontier logo]()
$211
This CheapOair deal was found by Cheapflights users on 2/2. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/57:30 am
MDW
- SJU
1 stop17h 23m
Frontier
Sun 3/83:08 am
SJU
- MDW
1 stop11h 00m
Frontier
Deal found 2/2![Frontier logo]()
$220
This Orbitz deal was found by Cheapflights users on 2/1. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/126:00 am
MDW
- SJU
1 stop18h 21m
Frontier
Mon 3/163:08 am
SJU
- MDW
1 stop16h 05m
Frontier
Deal found 2/1![Frontier logo]()
$221
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 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 February 3, 2026.
This Trip.com deal was found by Cheapflights users on 2/1. 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 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 stop10h 58m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$94
This Kiwi.com deal was found by Cheapflights users on 2/1. 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.
Sun 2/226:15 am
MDW
- SJU
1 stop28h 24m
Frontier
Deal found 2/1![Frontier logo]()
$96
This Super.com deal was found by Cheapflights users on 2/1. 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 Super.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
Deal found 2/1![Frontier logo]()
$99
This CheapOair deal was found by Cheapflights users on 2/2. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/218:00 am
MDW
- SJU
1 stop8h 59m
Frontier
Deal found 2/2![Frontier logo]()
$101
This Trip.com deal was found by Cheapflights users on 2/1. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/156:00 am
MDW
- SJU
1 stop16h 58m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$102
This Kiwi.com deal was found by Cheapflights users on 2/1. 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.
Tue 2/246:10 am
MDW
- SJU
2 stops34h 48m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$104
This Kiwi.com deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/309:42 pm
MDW
- SJU
1 stop26h 37m
Frontier
Deal found 2/2![Frontier logo]()
$105
This Mytrip deal was found by Cheapflights users on 2/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/57:30 am
MDW
- SJU
1 stop17h 23m
Frontier
Deal found 2/2![Frontier logo]()
$110
This Kiwi.com deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/232:19 pm
MDW
- SJU
2 stops26h 39m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$111
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 3, 2026.
Round-trip from | $187 (Frontier) |
|---|---|
One-way from | $94 (Trip.com) |
Popular in | June |
Cheapest in | May |
Average price | $331 |
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 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
Midway
Fly to
San Juan
Route
Depart
Return
Price
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Tue 4/21
12:53 pm-11:12 pm
1 stop9h 19m
San Juan Luis Munoz Marin Intl
Wed 4/29
2:34 pm-10:28 pm
1 stop8h 54m
$246
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Mon 4/20
10:43 am-8:24 pm
1 stop8h 41m
San Juan Luis Munoz Marin Intl
Wed 4/29
6:15 am-4:25 pm
1 stop11h 10m
$246
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Thu 4/23
9:14 am-10:48 pm
1 stop12h 34m
San Juan Luis Munoz Marin Intl
Sat 4/25
3:18 pm-10:19 pm
1 stop8h 01m
$258
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Wed 4/22
10:43 am-8:24 pm
1 stop8h 41m
San Juan Luis Munoz Marin Intl
Sat 4/25
1:00 pm-10:28 pm
1 stop10h 28m
$284
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Tue 3/3
3:15 pm-12:35 am
1 stop7h 20m
San Juan Luis Munoz Marin Intl
Tue 3/10
6:40 am-3:05 pm
1 stop9h 25m
$331
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Tue 4/7
12:50 pm-10:40 pm
2 stops8h 50m
San Juan Luis Munoz Marin Intl
Tue 4/14
2:00 pm-10:15 pm
2 stops9h 15m
$346
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Wed 3/4
10:49 am-9:12 pm
1 stop8h 23m
San Juan Luis Munoz Marin Intl
Tue 3/10
6:15 am-12:02 pm
1 stop6h 47m
$374
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Sat 5/2
7:50 am-5:35 pm
2 stops8h 45m
San Juan Luis Munoz Marin Intl
Wed 5/6
8:10 am-4:45 pm
2 stops9h 35m
$390
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Tue 2/24
2:20 pm-12:35 am
2 stops8h 15m
San Juan Luis Munoz Marin Intl
Tue 3/10
5:55 am-1:50 pm
1 stop8h 55m
$390
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Thu 4/30
9:00 am-8:00 pm
2 stops10h 00m
San Juan Luis Munoz Marin Intl
Wed 5/6
8:10 am-4:45 pm
2 stops9h 35m
$395
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 January 30, 2026.
The best time to book flights from Chicago Midway Airport to San Juan is 25 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 May 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 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 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 96 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 Tuesday 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 February 3, 2026.
Read through reviews of airlines operating flights from Chicago Midway Airport to San Juan, such as Southwest, Delta, and Spirit Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Overall
8.0
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Food
7.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Overall
8.0
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Food
7.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Overall
8.0
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Food
7.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Overall
8.0
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Food
7.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Overall
8.0
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Food
7.0
Crew
8.6
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
See prices for flight routes from nearby airports that may be better suited for you.
Top 4 airlines flying from Midway to San Juan
Discover the top 4 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 3, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$130 | Average$295 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$149 | Average$235 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$196 | Average$405 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$379 | Average$489 | FlexibilityNo cancel fee | On-time63% |