$98+ Cheap flights from Midway (MDW) to San Juan
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/3. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJU
Apr 21 — Apr 281
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
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Cheapest flights from Midway to San JuanExplore the most affordable flight options available from Midway to San Juan. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 22, 2026.
Explore the most affordable flight options available from Midway to San Juan. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 22, 2026.
This CheapOair deal was found by Cheapflights users on 3/20. 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 4/279:14 am
MDW
- SJU
1 stop23h 40m
Frontier
Thu 4/303:03 pm
SJU
- MDW
1 stop8h 16m
Frontier
Deal found 3/20![Frontier logo]()
$205
This Priceline deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/125:05 am
MDW
- SJU
1 stop29h 13m
Frontier
Sat 4/183:21 am
SJU
- MDW
1 stop29h 43m
Frontier
Deal found 3/21![Frontier logo]()
$211
This Priceline deal was found by Cheapflights users on 3/19. 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.
Fri 4/179:14 am
MDW
- SJU
1 stop23h 40m
Frontier
Fri 4/243:23 pm
SJU
- MDW
1 stop8h 03m
Frontier
Deal found 3/19![Frontier logo]()
$214
This Frontier deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/116:00 am
MDW
- SJU
1 stop11h 49m
Frontier
Sat 4/188:00 am
SJU
- MDW
1 stop9h 00m
Frontier
Deal found 3/21![Frontier logo]()
$221
This Priceline deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/125:05 am
MDW
- SJU
1 stop29h 13m
Frontier
Tue 4/143:08 am
SJU
- MDW
1 stop29h 56m
Frontier
Deal found 3/17![Frontier logo]()
$222
This Frontier deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/35:30 am
MDW
- SJU
1 stop6h 56m
Frontier
Thu 4/99:01 am
SJU
- MDW
1 stop13h 20m
Frontier
Deal found 3/20![Frontier logo]()
$226
This Priceline deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/238:26 am
MDW
- SJU
1 stop16h 35m
Frontier
Tue 4/283:08 am
SJU
- MDW
1 stop29h 13m
Frontier
Deal found 3/19![Frontier logo]()
$229
This Frontier deal was found by Cheapflights users on 3/21. 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.
Wed 4/82:56 pm
MDW
- SJU
1 stop8h 56m
Frontier
Sat 4/188:00 am
SJU
- MDW
1 stop9h 00m
Frontier
Deal found 3/21![Frontier logo]()
$231
This Priceline deal was found by Cheapflights users on 3/22. 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 4/72:56 pm
MDW
- SJU
1 stop8h 56m
Frontier
Fri 4/103:16 am
SJU
- MDW
1 stop20h 49m
Frontier
Deal found 3/22![Frontier logo]()
$236
This Priceline deal was found by Cheapflights users on 3/19. 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.
Fri 5/84:52 pm
MDW
- SJU
1 stop28h 51m
Frontier
Sun 5/103:03 am
SJU
- MDW
1 stop13h 54m
Frontier
Deal found 3/19![Frontier logo]()
$239
Best flights from Midway to San JuanDiscover carefully curated flight deals from Midway to San Juan that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated March 22, 2026.
Discover carefully curated flight deals from Midway to San Juan that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated March 22, 2026.
This Southwest deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/222:35 pm
MDW
- SJU
2 stops8h 05m
Southwest
Tue 4/285:35 am
SJU
- MDW
1 stop9h 10m
Southwest
Deal found 3/18![Southwest logo]()
$379
This Southwest deal was found by Cheapflights users on 3/17. 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 4/125:15 am
MDW
- SJU
2 stops10h 50m
Southwest
Wed 4/155:05 am
SJU
- MDW
2 stops11h 45m
Southwest
Deal found 3/17![Southwest logo]()
$399
This Southwest deal was found by Cheapflights users on 3/17. 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 4/257:45 am
MDW
- SJU
Nonstop4h 35m
Southwest
Tue 4/285:35 am
SJU
- MDW
1 stop9h 10m
Southwest
Deal found 3/17![Southwest logo]()
$412
This Southwest deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/177:45 am
MDW
- SJU
2 stops7h 45m
Southwest
Thu 5/215:35 am
SJU
- MDW
2 stops8h 35m
Southwest
Deal found 3/17![Southwest logo]()
$416
This Southwest deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/115:10 pm
MDW
- SJU
1 stop7h 10m
Southwest
Wed 6/177:00 am
SJU
- MDW
1 stop6h 45m
Southwest
Deal found 3/21![Southwest logo]()
$421
This Southwest deal was found by Cheapflights users on 3/22. 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 4/1312:00 pm
MDW
- SJU
2 stops10h 25m
Southwest
Wed 4/155:05 am
SJU
- MDW
2 stops11h 45m
Southwest
Deal found 3/22![Southwest logo]()
$431
This Southwest deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/81:55 pm
MDW
- SJU
2 stops8h 45m
Southwest
Sat 4/115:45 am
SJU
- MDW
2 stops9h 10m
Southwest
Deal found 3/21![Southwest logo]()
$476
This Southwest deal was found by Cheapflights users on 3/19. 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 4/307:55 am
MDW
- SJU
1 stop6h 40m
Southwest
Mon 5/48:40 pm
SJU
- MDW
1 stop13h 30m
Southwest
Deal found 3/19![Southwest logo]()
$479
This Southwest deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/812:50 pm
MDW
- SJU
2 stops10h 05m
Southwest
Mon 5/116:50 am
SJU
- MDW
2 stops14h 45m
Southwest
Deal found 3/21![Southwest logo]()
$481
This Southwest deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/39:40 pm
MDW
- SJU
1 stop11h 50m
Southwest
Thu 4/96:50 am
SJU
- MDW
2 stops8h 50m
Southwest
Deal found 3/19![Southwest logo]()
$521
This Southwest deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/201:55 pm
MDW
- SJU
2 stops8h 45m
Southwest
Wed 5/272:00 pm
SJU
- MDW
2 stops9h 15m
Southwest
Deal found 3/21![Southwest logo]()
$526
This Southwest deal was found by Cheapflights users on 3/21. 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 4/512:55 pm
MDW
- SJU
2 stops10h 10m
Southwest
Thu 4/96:50 am
SJU
- MDW
2 stops8h 50m
Southwest
Deal found 3/21![Southwest logo]()
$536
Last-minute flights from Midway to San JuanDiscover last-minute flight deals from Midway to San Juan. Data last updated March 22, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to San Juan. Data last updated March 22, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/35:30 am
MDW
- SJU
1 stop6h 56m
Frontier
Thu 4/99:01 am
SJU
- MDW
1 stop13h 20m
Frontier
Deal found 3/20![Frontier logo]()
$226
This Priceline deal was found by Cheapflights users on 3/22. 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 4/72:56 pm
MDW
- SJU
1 stop8h 56m
Frontier
Fri 4/103:16 am
SJU
- MDW
1 stop20h 49m
Frontier
Deal found 3/22![Frontier logo]()
$236
This Frontier deal was found by Cheapflights users on 3/21. 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.
Wed 4/82:56 pm
MDW
- SJU
1 stop8h 56m
Frontier
Sat 4/188:00 am
SJU
- MDW
1 stop9h 00m
Frontier
Deal found 3/21![Frontier logo]()
$231
This Frontier deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/116:00 am
MDW
- SJU
1 stop11h 49m
Frontier
Sat 4/188:00 am
SJU
- MDW
1 stop9h 00m
Frontier
Deal found 3/21![Frontier logo]()
$221
This Priceline deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/125:05 am
MDW
- SJU
1 stop29h 13m
Frontier
Sat 4/183:21 am
SJU
- MDW
1 stop29h 43m
Frontier
Deal found 3/21![Frontier logo]()
$211
This Priceline deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/125:05 am
MDW
- SJU
1 stop29h 13m
Frontier
Tue 4/143:08 am
SJU
- MDW
1 stop29h 56m
Frontier
Deal found 3/17![Frontier logo]()
$222
This Priceline deal was found by Cheapflights users on 3/19. 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.
Fri 4/179:14 am
MDW
- SJU
1 stop23h 40m
Frontier
Fri 4/243:23 pm
SJU
- MDW
1 stop8h 03m
Frontier
Deal found 3/19![Frontier logo]()
$214
This Priceline deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/238:26 am
MDW
- SJU
1 stop16h 35m
Frontier
Tue 4/283:08 am
SJU
- MDW
1 stop29h 13m
Frontier
Deal found 3/19![Frontier logo]()
$229
This Priceline deal was found by Cheapflights users on 3/17. 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.
Fri 4/246:49 pm
MDW
- SJU
1 stop14h 05m
Frontier
Tue 4/283:08 am
SJU
- MDW
1 stop29h 13m
Frontier
Deal found 3/17![Frontier logo]()
$243
This CheapOair deal was found by Cheapflights users on 3/20. 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 4/279:14 am
MDW
- SJU
1 stop23h 40m
Frontier
Thu 4/303:03 pm
SJU
- MDW
1 stop8h 16m
Frontier
Deal found 3/20![Frontier logo]()
$205
One-way flights from Midway to San JuanSearch for one-way flight options from Midway to San Juan. Find affordable one-way fares based on user searches. Data last updated March 22, 2026.
Search for one-way flight options from Midway to San Juan. Find affordable one-way fares based on user searches. Data last updated March 22, 2026.
This Frontier deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/35:30 am
MDW
- SJU
1 stop6h 56m
Frontier
Deal found 3/20![Frontier logo]()
$98
This Priceline deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/95:01 am
MDW
- SJU
1 stop29h 17m
Frontier
Deal found 3/21![Frontier logo]()
$104
This Super.com deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/72:56 pm
MDW
- SJU
1 stop8h 56m
Frontier
Deal found 3/22![Frontier logo]()
$107
This Frontier deal was found by Cheapflights users on 3/20. 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.
Wed 4/82:56 pm
MDW
- SJU
1 stop8h 56m
Frontier
Deal found 3/20![Frontier logo]()
$108
This Kiwi.com deal was found by Cheapflights users on 3/18. 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 3/256:48 pm
MDW
- SJU
1 stop29h 33m
Frontier
Deal found 3/18![Frontier logo]()
$112
This Trip.com deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/246:49 pm
MDW
- SJU
1 stop14h 05m
Frontier
Deal found 3/22![Frontier logo]()
$113
This Super.com deal was found by Cheapflights users on 3/19. 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.
Fri 4/105:30 am
MDW
- SJU
1 stop19h 31m
Frontier
Deal found 3/19![Frontier logo]()
$116
This Trip.com deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/84:52 pm
MDW
- SJU
1 stop28h 51m
Frontier
Deal found 3/19![Frontier logo]()
$120
This Super.com deal was found by Cheapflights users on 3/22. 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.
Sun 4/266:00 am
MDW
- SJU
1 stop7h 08m
Frontier
Deal found 3/22![Frontier logo]()
$122
Find flight deals from Midway to San Juan
Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to San Juan (PR1). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated March 22, 2026.
Round-trip from | $205 (CheapOair) |
|---|---|
One-way from | $98 (Frontier) |
Popular in | June |
Cheapest in | February |
Average price | $415 |
Cheapflights Fare Finder
Customize your flight search to find flights from Midway to San Juan that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated March 22, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to San Juan that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Wed 4/22
2:35 pm-11:40 pm
2 stops8h 05m
San Juan Luis Munoz Marin Intl
Tue 4/28
5:35 am-1:45 pm
1 stop9h 10m
$379
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Sun 4/12
5:15 am-5:05 pm
2 stops10h 50m
San Juan Luis Munoz Marin Intl
Wed 4/15
5:05 am-3:50 pm
2 stops11h 45m
$399
Quickest round-trip
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Sat 4/25
7:45 am-1:20 pm
Nonstop4h 35m
San Juan Luis Munoz Marin Intl
Tue 4/28
5:35 am-1:45 pm
1 stop9h 10m
$412
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Sun 5/17
7:45 am-4:30 pm
2 stops7h 45m
San Juan Luis Munoz Marin Intl
Thu 5/21
5:35 am-1:10 pm
2 stops8h 35m
$416
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Thu 6/11
5:10 pm-1:20 am
1 stop7h 10m
San Juan Luis Munoz Marin Intl
Wed 6/17
7:00 am-12:45 pm
1 stop6h 45m
$421
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Mon 4/13
12:00 pm-11:25 pm
2 stops10h 25m
San Juan Luis Munoz Marin Intl
Wed 4/15
5:05 am-3:50 pm
2 stops11h 45m
$431
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Wed 4/8
1:55 pm-11:40 pm
2 stops8h 45m
San Juan Luis Munoz Marin Intl
Sat 4/11
5:45 am-1:55 pm
2 stops9h 10m
$476
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Thu 4/30
7:55 am-3:35 pm
1 stop6h 40m
San Juan Luis Munoz Marin Intl
Mon 5/4
8:40 pm-9:10 am
1 stop13h 30m
$479
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Fri 5/8
12:50 pm-11:55 pm
2 stops10h 05m
San Juan Luis Munoz Marin Intl
Mon 5/11
6:50 am-8:35 pm
2 stops14h 45m
$481
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Fri 4/3
9:40 pm-10:30 am
1 stop11h 50m
San Juan Luis Munoz Marin Intl
Thu 4/9
6:50 am-2:40 pm
2 stops8h 50m
$521
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
How far ahead should I book a flight from Chicago Midway Airport to San Juan?
Use this chart to determine the optimal time to book a round-trip flight from Midway to San Juan. Price data was last updated on March 13, 2026.
The best time to book flights from Chicago Midway Airport to San Juan is 55 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
What is the cheapest month to book a flight from Chicago Midway Airport to San Juan?
Currently, April is the cheapest month in which you can book a flight from Chicago Midway Airport to San Juan (average of $91). Flying from Chicago Midway Airport to San Juan in June is currently the most expensive (average of $298). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from MDW to SJU?
Find hourly flight availability from Midway to San Juan. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated March 22, 2026.
When flying from Chicago Midway Airport to San Juan, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
How much does it cost to fly round-trip from Chicago Midway Airport to San Juan?
How often are flights from Chicago to San Juan delayed?
About 29% of weekly flights between Chicago and San Juan have experienced delays in the past year, with the average delay time being 103 minutes.
What is the most punctual flight time for Chicago to San Juan flights?
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the morning tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Saturday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Chicago to San Juan flights?
Over the last year, Southwest have had the lowest number of delays on this route, with just 29% of flights being delayed.
Reviews of airlines servicing San Juan
Get insights into the airlines that provide service to San Juan. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to San Juan. Reviews last updated March 22, 2026.
Read through reviews of airlines operating flights from Chicago Midway Airport to San Juan, such as Southwest,Delta, andFrontier. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Food
7.0
Overall
8.0
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Overall
8.0
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Overall
8.0
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Overall
8.0
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Related info for your journey
Find useful and relevant information for your journey from Midway to San Juan. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Midway and San Juan flights
Browse other Midway and San Juan flight options. Last updated on March 22, 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 2,558,603 searches. Data last updated March 22, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$132 | Average$494 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$142 | Average$296 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$377 | Average$493 | FlexibilityNo cancel fee | On-time63% |