$124+ Cheap flights from Midway (MDW) to San Juan
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/13. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJU
Dec 4 — Dec 111
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
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 April, booked 26 days in advance, depart on a Tuesday or Monday and return on a Monday
Cheap flight deals from Midway to San Juan
Cheapest
Best
Last-minute
One-way
Cheapest flights from Midway to San JuanExplore the most affordable flight options available from Midway to San Juan. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 4, 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 November 4, 2026.
This CheapOair deal was found by Cheapflights users on 11/2. 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.
Sun 12/68:37 pm -
1 stop27h 36m
Wed 12/95:01 am -
1 stop8h 32m
Deal found 11/2![Frontier logo]()
$245
This Priceline deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/812:28 pm -
1 stop10h 39m
Mon 1/112:41 am -
1 stop23h 05m
Deal found 10/30![Frontier logo]()
$246
This CheapOair deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/212:28 pm -
1 stop10h 39m
Sun 12/68:44 pm -
1 stop22h 32m
Deal found 11/3![Frontier logo]()
$251
This Cheapflightsfares deal was found by Cheapflights users on 11/2. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/218:42 pm -
1 stop27h 42m
Thu 11/266:31 pm -
1 stop15h 06m
Deal found 11/2![Frontier logo]()
$252
This Frontier deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/228:42 pm -
1 stop11h 17m
Thu 12/35:01 am -
1 stop13h 06m
Deal found 11/3![Frontier logo]()
$254
This Kiwi.com deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/271:29 pm -
1 stop11h 04m
Fri 12/42:36 pm -
1 stop22h 57m
Deal found 10/30![Frontier logo]()
$257
This Kiwi.com deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/1212:28 pm -
1 stop10h 39m
Tue 12/223:53 pm -
1 stop10h 08m
Deal found 11/3![Frontier logo]()
$260
This CheapOair deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/238:42 pm -
1 stop11h 17m
Thu 11/265:19 am -
1 stop9h 02m
Deal found 11/3![Frontier logo]()
$262
This Southwest deal was found by Cheapflights users on 11/1. 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 12/51:25 pm -
1 stop7h 30m
Wed 12/95:40 am -
2 stops11h 10m
Deal found 11/1![Southwest logo]()
$266
This Kiwi.com deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/43:36 pm -
1 stop8h 35m
Tue 12/83:28 am -
2 stops10h 05m
Deal found 11/3![Frontier logo]()
$269
This Kiwi.com deal was found by Cheapflights users on 11/4. 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 12/912:28 pm -
1 stop10h 39m
Fri 12/113:28 am -
2 stops10h 05m
Deal found 11/4![Frontier logo]()
$270
This Kiwi.com deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/238:42 pm -
1 stop11h 17m
Wed 12/25:01 am -
1 stop8h 32m
Deal found 11/3![Frontier logo]()
$271
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 November 4, 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 November 4, 2026.
This Southwest deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/313:40 pm -
1 stop6h 00m
Sat 2/66:05 am -
2 stops13h 10m
Deal found 11/3![Southwest logo]()
$266
This Delta deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/276:00 am -
1 stop9h 25m
Wed 2/107:45 am -
1 stop11h 09m
Deal found 11/3![Delta logo]()
$535
This Southwest deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/98:40 pm -
1 stop13h 00m
Wed 11/116:10 am -
1 stop10h 50m
Deal found 10/31![Southwest logo]()
$306
This Southwest deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/158:40 pm -
1 stop11h 15m
Tue 11/176:10 am -
1 stop8h 50m
Deal found 11/3![Southwest logo]()
$340
This Southwest deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/111:40 pm -
1 stop7h 50m
Thu 1/142:30 pm -
1 stop10h 20m
Deal found 11/3![Southwest logo]()
$348
This Southwest deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/2310:10 am -
2 stops9h 55m
Tue 1/267:25 am -
2 stops9h 20m
Deal found 10/30![Southwest logo]()
$375
This Southwest deal was found by Cheapflights users on 11/1. 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.
Fri 11/1312:50 pm -
1 stop8h 45m
Wed 11/187:40 am -
1 stop9h 15m
Deal found 11/1![Southwest logo]()
$409
This Southwest deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/78:15 am -
Nonstop4h 45m
Sat 11/146:45 am -
1 stop11h 45m
Deal found 10/31![Southwest logo]()
$422
This Southwest deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/57:55 am -
2 stops11h 20m
Sat 12/125:40 am -
2 stops9h 45m
Deal found 10/31![Southwest logo]()
$426
This Southwest deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/137:00 am -
1 stop8h 50m
Sat 12/193:30 pm -
Nonstop5h 10m
Deal found 11/3![Southwest logo]()
$471
This Southwest deal was found by Cheapflights users on 11/2. 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 12/1512:50 pm -
2 stops10h 00m
Wed 12/236:35 am -
2 stops11h 15m
Deal found 11/2![Southwest logo]()
$483
This Southwest deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/146:35 am -
1 stop8h 40m
Mon 11/166:10 am -
1 stop8h 50m
Deal found 11/3![Southwest logo]()
$501
Last-minute flights from Midway to San JuanDiscover last-minute flight deals from Midway to San Juan. Data last updated November 4, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to San Juan. Data last updated November 4, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 11/2. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/218:42 pm -
1 stop27h 42m
Thu 11/266:31 pm -
1 stop15h 06m
Deal found 11/2![Frontier logo]()
$252
This Frontier deal was found by Cheapflights users on 11/2. 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.
Sun 11/228:42 pm -
1 stop11h 17m
Thu 11/265:19 am -
1 stop9h 02m
Deal found 11/2![Frontier logo]()
$254
This CheapOair deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/238:42 pm -
1 stop11h 17m
Thu 11/265:19 am -
1 stop9h 02m
Deal found 11/3![Frontier logo]()
$262
This Kiwi.com deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/238:42 pm -
1 stop11h 17m
Wed 12/25:01 am -
1 stop8h 32m
Deal found 11/3![Frontier logo]()
$271
This Kiwi.com deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/271:29 pm -
1 stop11h 04m
Fri 12/42:36 pm -
1 stop22h 57m
Deal found 10/30![Frontier logo]()
$257
This CheapOair deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/212:28 pm -
1 stop10h 39m
Sun 12/68:44 pm -
1 stop22h 32m
Deal found 11/3![Frontier logo]()
$251
This Kiwi.com deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/43:36 pm -
1 stop8h 35m
Tue 12/83:28 am -
2 stops10h 05m
Deal found 11/3![Frontier logo]()
$269
This Southwest deal was found by Cheapflights users on 11/1. 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 12/51:25 pm -
1 stop7h 30m
Wed 12/95:40 am -
2 stops11h 10m
Deal found 11/1![Southwest logo]()
$266
This CheapOair deal was found by Cheapflights users on 11/2. 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.
Sun 12/68:37 pm -
1 stop27h 36m
Wed 12/95:01 am -
1 stop8h 32m
Deal found 11/2![Frontier logo]()
$245
This Priceline deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/812:28 pm -
1 stop10h 39m
Mon 1/112:41 am -
1 stop23h 05m
Deal found 10/30![Frontier logo]()
$246
This Kiwi.com deal was found by Cheapflights users on 11/4. 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 12/912:28 pm -
1 stop10h 39m
Fri 12/113:28 am -
2 stops10h 05m
Deal found 11/4![Frontier logo]()
$270
This Kiwi.com deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/1212:28 pm -
1 stop10h 39m
Tue 12/223:53 pm -
1 stop10h 08m
Deal found 11/3![Frontier logo]()
$260
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 November 4, 2026.
Search for one-way flight options from Midway to San Juan. Find affordable one-way fares based on user searches. Data last updated November 4, 2026.
This CheapOair deal was found by Cheapflights users on 11/2. 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.
Sun 12/138:37 pm -
1 stop27h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Frontier logo]()
$124
This Trip.com deal was found by Cheapflights users on 10/31. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/238:42 pm -
1 stop27h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/31![Frontier logo]()
$125
This Priceline deal was found by Cheapflights users on 11/2. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/231:18 pm -
1 stop23h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Frontier logo]()
$133
This Frontier deal was found by Cheapflights users on 11/4. 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 11/228:42 pm -
1 stop11h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/4![Frontier logo]()
$138
This Super.com deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/218:42 pm -
1 stop27h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Frontier logo]()
$141
This eDestinos deal was found by Cheapflights users on 10/31. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/126:08 am -
1 stop16h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/31![Frontier logo]()
$144
This Delta deal was found by Cheapflights users on 11/4. 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 1/116:00 am -
1 stop9h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/4![Delta logo]()
$145
This Southwest deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/163:00 pm -
1 stop7h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/30![Southwest logo]()
$153
This Kiwi.com deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/301:11 pm -
1 stop23h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Frontier logo]()
$163
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 November 4, 2026.
Round-trip from | $245 (CheapOair) |
|---|---|
One-way from | $124 (CheapOair) |
Popular in | December |
Cheapest in | February |
Average price | $483 |
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 7,457,451 searches. Data last updated November 4, 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 Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Tue 1/26
3:35 pm-12:35 am
1 stop7h 00m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$133
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Sun 1/31
3:40 pm-1:40 am
1 stop8h 00m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$133
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Mon 11/23
8:42 pm-9:59 am
1 stop11h 17m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$140
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Mon 1/11
6:00 am-5:25 pm
1 stop9h 25m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$145
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Mon 11/16
3:00 pm-12:50 am
1 stop7h 50m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$153
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Sat 1/23
11:25 am-11:15 pm
1 stop9h 50m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$153
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Mon 12/7
6:00 am-2:20 pm
1 stop6h 20m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$173
Quickest round-trip
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Sat 11/7
8:15 am-3:00 pm
Nonstop4h 45m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$183
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Wed 11/18
3:00 pm-12:50 am
1 stop7h 50m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$222
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Sun 1/31
3:40 pm-11:40 pm
1 stop6h 00m
San Juan Luis Munoz Marin Intl
Sat 2/6
6:05 am-5:15 pm
2 stops13h 10m
$266
Showing 1-10 of 21 resultsSorted by cheapest first
Best time to book a flight from Midway to San Juan
Have a flexible travel schedule? Discover the best time to fly to San Juan from Midway with our price prediction graph.
MDW-PR1
MDW-SJU
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago Midway Airport to San Juan
MDW-PR1
MDW-SJU
What is the cheapest month to book a flight from Chicago Midway Airport to San Juan?
Currently, February is the cheapest month in which you can book a flight from Chicago Midway Airport to San Juan (average of $243). Flying from Chicago Midway Airport to San Juan in December is currently the most expensive (average of $560). 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.
How much does it cost to fly round-trip from Chicago Midway Airport to San Juan?
Airfare is below average for this route at the moment.
Chicago Midway Airport to San Juan flights typically cost between $401 and $789 in December.The cheapest round-trip price found within the last 5 days was $245 on Frontier (Dec 6-Dec 9).
How often are flights from Chicago to San Juan delayed?
About 25% of weekly flights between Chicago and San Juan have experienced delays in the past year, with the average delay time being 123 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?
Sunday tends to have the lowest number of delays on this route, whereas Saturday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Chicago to San Juan flights?
Over the last year, Southwest have had the lowest number of delays on this route, with just 25% of flights being delayed.
How far ahead should I book a flight from Chicago Midway Airport to San Juan?
The best time to book flights from Chicago Midway Airport to San Juan is 22 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
Reviews of airlines servicing San Juan
Get insights into the airlines that provide service to San Juan. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to San Juan. Reviews last updated November 4, 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
Food
7.0
Overall
8.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Entertainment
7.5
Food
7.0
Overall
8.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Entertainment
7.5
Food
7.0
Overall
8.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Entertainment
7.5
Food
7.0
Overall
8.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
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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Midway and San Juan flights
Browse other Midway and San Juan flight options. Last updated on November 4, 2026.
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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 7,457,451 searches. Data last updated November 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$91 | Average$301 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$132 | Average$616 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$276 | Average$492 | FlexibilityNo cancel fee | On-time63% |