$119+ 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 8/24. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJU
Sep 11 — Sep 181
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 January, 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 August 12, 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 August 12, 2026.
This Southwest deal was found by Cheapflights users on 8/11. 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 9/812:45 pm -
2 stops8h 20m
Fri 9/115:00 am -
2 stops8h 25m
Deal found 8/11![Southwest logo]()
$256
This Southwest deal was found by Cheapflights users on 8/9. 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.
Wed 9/212:45 pm -
2 stops8h 15m
Thu 9/106:00 am -
2 stops9h 30m
Deal found 8/9![Southwest logo]()
$266
This Southwest deal was found by Cheapflights users on 8/7. 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 9/812:45 pm -
2 stops8h 20m
Tue 9/151:20 pm -
1 stop6h 50m
Deal found 8/7![Southwest logo]()
$276
This Southwest deal was found by Cheapflights users on 8/8. 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 8/243:15 pm -
1 stop6h 50m
Fri 8/285:30 am -
1 stop9h 35m
Deal found 8/8![Southwest logo]()
$286
This Southwest deal was found by Cheapflights users on 8/7. 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 8/2711:15 am -
1 stop7h 50m
Mon 8/318:55 pm -
1 stop13h 30m
Deal found 8/7![Southwest logo]()
$291
This Southwest deal was found by Cheapflights users on 8/10. 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.
Mon 8/2411:15 am -
1 stop9h 55m
Thu 8/275:00 am -
2 stops8h 25m
Deal found 8/10![Southwest logo]()
$296
This Southwest deal was found by Cheapflights users on 8/11. 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.
Fri 10/22:15 pm -
1 stop9h 05m
Mon 10/55:00 am -
1 stop8h 30m
Deal found 8/11![Southwest logo]()
$301
This Southwest deal was found by Cheapflights users on 8/10. 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.
Sun 8/308:05 am -
1 stop8h 00m
Sat 9/55:05 am -
1 stop6h 55m
Deal found 8/10![Southwest logo]()
$306
This Southwest deal was found by Cheapflights users on 8/11. 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.
Mon 8/319:20 am -
2 stops9h 45m
Thu 9/106:00 am -
2 stops9h 30m
Deal found 8/11![Southwest logo]()
$310
This Delta deal was found by Cheapflights users on 8/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/110:54 am -
1 stop10h 35m
Wed 9/92:59 pm -
1 stop8h 45m
Deal found 8/10![Delta logo]()
$316
This Southwest deal was found by Cheapflights users on 8/11. 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 11/1212:45 pm -
2 stops10h 20m
Tue 11/176:10 am -
1 stop8h 50m
Deal found 8/11![Southwest logo]()
$320
This Southwest deal was found by Cheapflights users on 8/11. 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.
Mon 8/249:10 am -
1 stop9h 55m
Sat 8/2910:25 am -
1 stop10h 15m
Deal found 8/11![Southwest logo]()
$321
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 August 12, 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 August 12, 2026.
This Southwest deal was found by Cheapflights users on 8/8. 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 8/315:00 am -
1 stop7h 45m
Sat 9/55:05 am -
1 stop6h 55m
Deal found 8/8![Southwest logo]()
$266
This Southwest deal was found by Cheapflights users on 8/7. 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 9/812:20 pm -
1 stop7h 50m
Tue 9/151:20 pm -
1 stop6h 50m
Deal found 8/7![Southwest logo]()
$276
This Southwest deal was found by Cheapflights users on 8/7. 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 9/112:45 pm -
2 stops8h 15m
Sat 9/125:05 am -
2 stops9h 05m
Deal found 8/7![Southwest logo]()
$276
This Southwest deal was found by Cheapflights users on 8/7. 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 9/113:15 pm -
1 stop6h 55m
Mon 9/218:55 pm -
1 stop13h 30m
Deal found 8/7![Southwest logo]()
$320
This Southwest deal was found by Cheapflights users on 8/8. 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 10/2411:55 am -
1 stop7h 10m
Tue 10/275:05 am -
1 stop10h 35m
Deal found 8/8![Southwest logo]()
$326
This Southwest deal was found by Cheapflights users on 8/9. 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 8/2512:45 pm -
2 stops8h 15m
Sat 8/295:55 am -
2 stops8h 10m
Deal found 8/9![Southwest logo]()
$326
This Southwest deal was found by Cheapflights users on 8/11. 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.
Wed 9/27:30 am -
1 stop10h 30m
Wed 9/96:00 am -
2 stops8h 30m
Deal found 8/11![Southwest logo]()
$336
This Southwest deal was found by Cheapflights users on 8/8. 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 11/62:40 pm -
1 stop8h 15m
Wed 11/116:10 am -
1 stop8h 50m
Deal found 8/8![Southwest logo]()
$351
This Southwest deal was found by Cheapflights users on 8/9. 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.
Sun 8/231:30 pm -
2 stops8h 55m
Sun 8/309:25 pm -
1 stop12h 20m
Deal found 8/9![Southwest logo]()
$361
This Southwest deal was found by Cheapflights users on 8/7. 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 11/179:55 am -
2 stops9h 55m
Sun 11/229:35 pm -
1 stop13h 45m
Deal found 8/7![Southwest logo]()
$376
This Southwest deal was found by Cheapflights users on 8/10. 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 9/247:50 pm -
1 stop12h 20m
Sun 9/279:25 pm -
1 stop12h 20m
Deal found 8/10![Southwest logo]()
$380
Last-minute flights from Midway to San JuanDiscover last-minute flight deals from Midway to San Juan. Data last updated August 12, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to San Juan. Data last updated August 12, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 8/8. 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 8/243:15 pm -
1 stop6h 50m
Fri 8/285:30 am -
1 stop9h 35m
Deal found 8/8![Southwest logo]()
$286
This Southwest deal was found by Cheapflights users on 8/10. 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.
Mon 8/243:10 pm -
2 stops7h 40m
Wed 9/211:50 am -
1 stop6h 50m
Deal found 8/10![Southwest logo]()
$296
This Southwest deal was found by Cheapflights users on 8/11. 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.
Mon 8/249:10 am -
1 stop9h 55m
Sat 8/2910:25 am -
1 stop10h 15m
Deal found 8/11![Southwest logo]()
$321
This Southwest deal was found by Cheapflights users on 8/7. 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 8/2711:15 am -
1 stop7h 50m
Mon 8/318:55 pm -
1 stop13h 30m
Deal found 8/7![Southwest logo]()
$291
This Southwest deal was found by Cheapflights users on 8/10. 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.
Sun 8/308:05 am -
1 stop8h 00m
Sat 9/55:05 am -
1 stop6h 55m
Deal found 8/10![Southwest logo]()
$306
This Southwest deal was found by Cheapflights users on 8/11. 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.
Mon 8/319:20 am -
2 stops9h 45m
Thu 9/106:00 am -
2 stops9h 30m
Deal found 8/11![Southwest logo]()
$310
This Delta deal was found by Cheapflights users on 8/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/110:54 am -
1 stop10h 35m
Wed 9/92:59 pm -
1 stop8h 45m
Deal found 8/10![Delta logo]()
$316
This Southwest deal was found by Cheapflights users on 8/9. 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.
Wed 9/212:45 pm -
2 stops8h 15m
Thu 9/106:00 am -
2 stops9h 30m
Deal found 8/9![Southwest logo]()
$266
This Southwest deal was found by Cheapflights users on 8/10. 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.
Wed 9/212:45 pm -
2 stops8h 15m
Sat 9/125:05 am -
2 stops9h 05m
Deal found 8/10![Southwest logo]()
$301
This Southwest deal was found by Cheapflights users on 8/10. 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.
Wed 9/212:45 pm -
2 stops8h 15m
Wed 9/95:15 am -
2 stops7h 50m
Deal found 8/10![Southwest logo]()
$320
This Southwest deal was found by Cheapflights users on 8/11. 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 9/812:45 pm -
1 stop8h 20m
Fri 9/115:00 am -
2 stops8h 25m
Deal found 8/11![Southwest logo]()
$256
This Southwest deal was found by Cheapflights users on 8/7. 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 9/812:45 pm -
2 stops8h 20m
Thu 9/176:00 am -
2 stops9h 30m
Deal found 8/7![Southwest logo]()
$276
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 August 12, 2026.
Search for one-way flight options from Midway to San Juan. Find affordable one-way fares based on user searches. Data last updated August 12, 2026.
This Faresmojo deal was found by Cheapflights users on 8/10. 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 Faresmojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/2411:15 am -
1 stop9h 55m
Deal found 8/10![JetBlue logo]()
$119
This Kiwi.com deal was found by Cheapflights users on 8/10. 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.
Sat 8/2211:45 am -
2 stops27h 26m
Deal found 8/10![Frontier logo]()
$122
This Southwest deal was found by Cheapflights users on 8/11. 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 9/112:45 pm -
2 stops8h 15m
Deal found 8/11![Southwest logo]()
$128
This Trip.com deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/712:03 pm -
2 stops10h 35m
Deal found 8/8![Frontier logo]()
$135
This Kiwi.com deal was found by Cheapflights users on 8/10. 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.
Sun 8/236:05 am -
2 stops17h 38m
Deal found 8/10![Frontier logo]()
$136
This Southwest deal was found by Cheapflights users on 8/11. 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.
Fri 10/94:15 pm -
2 stops8h 05m
Deal found 8/11![Southwest logo]()
$138
This Kiwi.com deal was found by Cheapflights users on 8/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/86:05 am -
2 stops19h 02m
Deal found 8/11![Frontier logo]()
$141
This Trip.com deal was found by Cheapflights users on 8/7. 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 10/1412:03 pm -
2 stops11h 13m
Deal found 8/7![Frontier logo]()
$143
This Kiwi.com deal was found by Cheapflights users on 8/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1012:54 pm -
2 stops34h 04m
Deal found 8/11![Frontier logo]()
$145
This Kiwi.com deal was found by Cheapflights users on 8/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/76:25 am -
2 stops18h 48m
Deal found 8/11![Frontier logo]()
$146
This Kiwi.com deal was found by Cheapflights users on 8/12. 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 8/3111:50 am -
2 stops14h 09m
Deal found 8/12![Frontier logo]()
$147
This Kiwi.com deal was found by Cheapflights users on 8/8. 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 11/1012:03 pm -
2 stops29h 16m
Deal found 8/8![Frontier logo]()
$148
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 August 12, 2026.
Round-trip from | $256 (Southwest) |
|---|---|
One-way from | $119 (Faresmojo) |
Popular in | June |
Cheapest in | February |
Average price | $366 |
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 August 12, 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 Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Mon 8/31
5:00 am-1:45 pm
1 stop7h 45m
San Juan Luis Munoz Marin Intl
Sat 9/5
5:05 am-11:00 am
1 stop6h 55m
$266
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Tue 9/8
12:20 pm-9:10 pm
1 stop7h 50m
San Juan Luis Munoz Marin Intl
Tue 9/15
1:20 pm-7:10 pm
1 stop6h 50m
$276
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Tue 9/1
12:45 pm-10:00 pm
2 stops8h 15m
San Juan Luis Munoz Marin Intl
Sat 9/12
5:05 am-1:10 pm
2 stops9h 05m
$276
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Fri 9/11
3:15 pm-11:10 pm
1 stop6h 55m
San Juan Luis Munoz Marin Intl
Mon 9/21
8:55 pm-9:25 am
1 stop13h 30m
$320
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Sat 10/24
11:55 am-8:05 pm
1 stop7h 10m
San Juan Luis Munoz Marin Intl
Tue 10/27
5:05 am-2:40 pm
1 stop10h 35m
$326
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Tue 8/25
12:45 pm-10:00 pm
2 stops8h 15m
San Juan Luis Munoz Marin Intl
Sat 8/29
5:55 am-1:05 pm
2 stops8h 10m
$326
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Wed 9/2
7:30 am-7:00 pm
1 stop10h 30m
San Juan Luis Munoz Marin Intl
Wed 9/9
6:00 am-1:30 pm
2 stops8h 30m
$336
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Fri 11/6
2:40 pm-12:55 am
1 stop8h 15m
San Juan Luis Munoz Marin Intl
Wed 11/11
6:10 am-1:00 pm
1 stop8h 50m
$351
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Sun 8/23
1:30 pm-11:25 pm
2 stops8h 55m
San Juan Luis Munoz Marin Intl
Sun 8/30
9:25 pm-8:45 am
1 stop12h 20m
$361
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Tue 11/17
9:55 am-9:50 pm
2 stops9h 55m
San Juan Luis Munoz Marin Intl
Sun 11/22
9:35 pm-9:20 am
1 stop13h 45m
$376
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
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 June is currently the most expensive (average of $556). 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 typical for this route at the moment.
Chicago Midway Airport to San Juan flights typically cost between $246 and $551 in September.The cheapest round-trip price found within the last 5 days was $256 on Southwest (Sep 8-Sep 11).
How often are flights from Chicago to San Juan delayed?
About 28% of weekly flights between Chicago and San Juan have experienced delays in the past year, with the average delay time being 127 minutes.
What is the most punctual flight time for Chicago to San Juan flights?
Historically, flights departing in the early afternoon 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?
Wednesday 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 27% 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 20 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 August 12, 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.
Boarding
8.1
Entertainment
7.5
Overall
8.0
Food
7.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Boarding
8.1
Entertainment
7.5
Overall
8.0
Food
7.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Boarding
8.1
Entertainment
7.5
Overall
8.0
Food
7.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Boarding
8.1
Entertainment
7.5
Overall
8.0
Food
7.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Related info for your journey
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Midway and San Juan flights
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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 August 12, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$91 | Average$301 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$132 | Average$606 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$296 | Average$496 | FlexibilityNo cancel fee | On-time63% |