$113+ 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 9/29. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJU
Sep 29 — Oct 61
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 30, 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 30, 2026.
This Southwest deal was found by Cheapflights users on 8/29. 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 9/2212:20 pm -
1 stop8h 45m
Fri 9/2510:00 am -
1 stop6h 35m
Deal found 8/29![Southwest logo]()
$226
This Southwest deal was found by Cheapflights users on 8/30. 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.
Tue 9/1512:20 pm -
1 stop8h 45m
Wed 9/305:15 am -
2 stops7h 50m
Deal found 8/30![Southwest logo]()
$241
This Southwest deal was found by Cheapflights users on 8/25. 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 9/239:40 am -
1 stop10h 30m
Wed 9/305:15 am -
2 stops7h 50m
Deal found 8/25![Southwest logo]()
$246
This Southwest deal was found by Cheapflights users on 8/28. 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 9/159:40 am -
1 stop10h 20m
Wed 9/168:20 am -
1 stop7h 25m
Deal found 8/28![Southwest logo]()
$251
This Southwest deal was found by Cheapflights users on 8/26. 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 9/912:45 pm -
2 stops8h 20m
Sat 9/126:25 am -
2 stops11h 40m
Deal found 8/26![Southwest logo]()
$256
This Southwest deal was found by Cheapflights users on 8/28. 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 9/112:35 pm -
1 stop9h 10m
Deal found 8/28![Southwest logo]()
$261
This Southwest deal was found by Cheapflights users on 8/26. 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 9/252:55 pm -
1 stop6h 20m
Wed 9/305:15 am -
2 stops7h 50m
Deal found 8/26![Southwest logo]()
$276
This Frontier deal was found by Cheapflights users on 8/26. 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 10/216:15 am -
1 stop8h 51m
Wed 10/288:45 am -
2 stops16h 02m
Deal found 8/26![Frontier logo]()
$284
This Southwest deal was found by Cheapflights users on 8/25. 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 10/92:50 pm -
2 stops8h 15m
Mon 10/1210:50 pm -
1 stop10h 35m
Deal found 8/25![Southwest logo]()
$286
This Southwest deal was found by Cheapflights users on 8/27. 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 9/17:30 am -
1 stop10h 30m
Fri 9/46:30 am -
2 stops8h 15m
Deal found 8/27![Southwest logo]()
$291
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 30, 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 30, 2026.
This Southwest deal was found by Cheapflights users on 8/29. 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 10/302:50 pm -
2 stops8h 20m
Tue 11/35:40 am -
2 stops11h 15m
Deal found 8/29![Southwest logo]()
$246
This Southwest deal was found by Cheapflights users on 8/25. 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 9/87:30 am -
1 stop10h 35m
Sat 9/126:25 am -
2 stops11h 40m
Deal found 8/25![Southwest logo]()
$261
This Southwest deal was found by Cheapflights users on 8/26. 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 9/912:45 pm -
1 stop8h 20m
Sat 9/1211:45 am -
1 stop10h 15m
Deal found 8/26![Southwest logo]()
$291
This Southwest deal was found by Cheapflights users on 8/25. 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 10/91:25 pm -
1 stop8h 40m
Fri 10/168:50 pm -
1 stop12h 20m
Deal found 8/25![Southwest logo]()
$306
This Southwest deal was found by Cheapflights users on 8/26. 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 9/197:50 am -
2 stops9h 20m
Wed 9/305:15 am -
1 stop7h 50m
Deal found 8/26![Southwest logo]()
$306
This Southwest deal was found by Cheapflights users on 8/27. 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 10/172:40 pm -
1 stop6h 35m
Sat 11/213:30 pm -
Nonstop5h 05m
Deal found 8/27![Southwest logo]()
$322
This Southwest deal was found by Cheapflights users on 8/28. 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 11/161:15 pm -
1 stop7h 05m
Mon 11/232:20 pm -
1 stop10h 20m
Deal found 8/28![Southwest logo]()
$331
This Southwest deal was found by Cheapflights users on 8/25. 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 9/119:20 am -
2 stops9h 45m
Sun 9/139:25 pm -
1 stop12h 20m
Deal found 8/25![Southwest logo]()
$361
This Southwest deal was found by Cheapflights users on 8/29. 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 -
1 stop10h 20m
Fri 11/205:35 am -
2 stops8h 45m
Deal found 8/29![Southwest logo]()
$381
This Southwest deal was found by Cheapflights users on 8/29. 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 11/812:50 pm -
2 stops8h 05m
Fri 11/135:50 pm -
1 stop7h 15m
Deal found 8/29![Southwest logo]()
$381
Last-minute flights from Midway to San JuanDiscover last-minute flight deals from Midway to San Juan. Data last updated August 30, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to San Juan. Data last updated August 30, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 8/27. 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 9/17:30 am -
1 stop10h 30m
Fri 9/46:30 am -
2 stops8h 15m
Deal found 8/27![Southwest logo]()
$291
This Southwest deal was found by Cheapflights users on 8/28. 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 9/112:35 pm -
1 stop9h 10m
Deal found 8/28![Southwest logo]()
$261
This Southwest deal was found by Cheapflights users on 8/26. 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 9/912:45 pm -
2 stops8h 20m
Sat 9/126:25 am -
2 stops11h 40m
Deal found 8/26![Southwest logo]()
$256
This Southwest deal was found by Cheapflights users on 8/30. 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.
Tue 9/1512:20 pm -
1 stop8h 45m
Wed 9/305:15 am -
2 stops7h 50m
Deal found 8/30![Southwest logo]()
$241
This Southwest deal was found by Cheapflights users on 8/28. 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 9/159:40 am -
1 stop10h 20m
Wed 9/168:20 am -
1 stop7h 25m
Deal found 8/28![Southwest logo]()
$251
This Southwest deal was found by Cheapflights users on 8/26. 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 9/173:15 pm -
1 stop6h 55m
Wed 9/235:15 am -
2 stops7h 50m
Deal found 8/26![Southwest logo]()
$296
This Southwest deal was found by Cheapflights users on 8/29. 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 9/2212:20 pm -
1 stop8h 45m
Fri 9/2510:00 am -
1 stop6h 35m
Deal found 8/29![Southwest logo]()
$226
This Southwest deal was found by Cheapflights users on 8/25. 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 9/239:40 am -
1 stop10h 30m
Wed 9/305:15 am -
2 stops7h 50m
Deal found 8/25![Southwest logo]()
$246
This Southwest deal was found by Cheapflights users on 8/26. 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 9/252:55 pm -
1 stop6h 20m
Wed 9/305:15 am -
2 stops7h 50m
Deal found 8/26![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 30, 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 30, 2026.
This Southwest deal was found by Cheapflights users on 8/30. 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.
Tue 9/298:30 am -
1 stop6h 55m
Deal found 8/30![Southwest logo]()
$113
This Southwest deal was found by Cheapflights users on 8/25. 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 9/912:45 pm -
2 stops8h 20m
Deal found 8/25![Southwest logo]()
$128
This Southwest deal was found by Cheapflights users on 8/26. 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 10/91:25 pm -
1 stop8h 40m
Deal found 8/26![Southwest logo]()
$133
This Kiwi.com deal was found by Cheapflights users on 8/27. 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 9/511:45 am -
2 stops27h 26m
Deal found 8/27![Frontier logo]()
$147
This Super.com deal was found by Cheapflights users on 8/28. 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 10/26:25 am -
1 stop7h 54m
Deal found 8/28![Frontier logo]()
$157
This Southwest deal was found by Cheapflights users on 8/28. 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 9/28:30 am -
1 stop8h 40m
Deal found 8/28![Southwest logo]()
$158
This Frontier deal was found by Cheapflights users on 8/26. 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.
Mon 9/286:25 am -
1 stop7h 57m
Deal found 8/26![Frontier logo]()
$159
This CheapOair deal was found by Cheapflights users on 8/27. 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 9/306:25 am -
1 stop7h 57m
Deal found 8/27![Frontier logo]()
$160
This Kiwi.com deal was found by Cheapflights users on 8/25. 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 9/246:25 am -
2 stops18h 48m
Deal found 8/25![Frontier logo]()
$161
This Kiwi.com deal was found by Cheapflights users on 8/25. 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 9/191:06 pm -
2 stops12h 07m
Deal found 8/25![Frontier logo]()
$162
This Southwest deal was found by Cheapflights users on 8/25. 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
Deal found 8/25![Southwest logo]()
$163
This Kiwi.com deal was found by Cheapflights users on 8/25. 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 11/26:16 am -
2 stops15h 22m
Deal found 8/25![Frontier logo]()
$170
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 30, 2026.
Round-trip from | $226 (Southwest) |
|---|---|
One-way from | $113 (Southwest) |
Popular in | June |
Cheapest in | February |
Average price | $361 |
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 August 30, 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
Fri 10/30
2:50 pm-12:10 am
2 stops8h 20m
San Juan Luis Munoz Marin Intl
Tue 11/3
5:40 am-2:55 pm
2 stops11h 15m
$246
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Tue 9/8
7:30 am-7:05 pm
1 stop10h 35m
San Juan Luis Munoz Marin Intl
Sat 9/12
6:25 am-5:05 pm
2 stops11h 40m
$261
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Wed 9/9
12:45 pm-10:05 pm
1 stop8h 20m
San Juan Luis Munoz Marin Intl
Sat 9/12
11:45 am-9:00 pm
1 stop10h 15m
$291
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Fri 10/9
1:25 pm-11:05 pm
1 stop8h 40m
San Juan Luis Munoz Marin Intl
Fri 10/16
8:50 pm-8:10 am
1 stop12h 20m
$306
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Sat 9/19
7:50 am-6:10 pm
2 stops9h 20m
San Juan Luis Munoz Marin Intl
Wed 9/30
5:15 am-12:05 pm
1 stop7h 50m
$306
Quickest round-trip
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Sat 10/17
2:40 pm-10:15 pm
1 stop6h 35m
San Juan Luis Munoz Marin Intl
Sat 11/21
3:30 pm-6:35 pm
Nonstop5h 05m
$322
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Mon 11/16
1:15 pm-10:20 pm
1 stop7h 05m
San Juan Luis Munoz Marin Intl
Mon 11/23
2:20 pm-10:40 pm
1 stop10h 20m
$331
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Fri 9/11
9:20 am-8:05 pm
2 stops9h 45m
San Juan Luis Munoz Marin Intl
Sun 9/13
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
Thu 11/12
12:45 pm-1:05 am
1 stop10h 20m
San Juan Luis Munoz Marin Intl
Fri 11/20
5:35 am-12:20 pm
2 stops8h 45m
$381
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Sun 11/8
12:50 pm-10:55 pm
2 stops8h 05m
San Juan Luis Munoz Marin Intl
Fri 11/13
5:50 pm-11:05 pm
1 stop7h 15m
$381
Showing 1-10 of 19 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 below average for this route at the moment.
Chicago Midway Airport to San Juan flights typically cost between $276 and $401 in September.The cheapest round-trip price found within the last 5 days was $226 on Southwest (Sep 22-Sep 25).
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 120 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 24 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 30, 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
Overall
8.0
Food
7.0
Entertainment
7.5
Comfort
8.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Boarding
8.1
Overall
8.0
Food
7.0
Entertainment
7.5
Comfort
8.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Boarding
8.1
Overall
8.0
Food
7.0
Entertainment
7.5
Comfort
8.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Boarding
8.1
Overall
8.0
Food
7.0
Entertainment
7.5
Comfort
8.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
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
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Midway and San Juan flights
Browse other Midway and San Juan flight options. Last updated on August 30, 2026.
Other flights from Midway
Browse through other flights departing from Midway. Flights are based on user searches made on Cheapflights and were last updated on August 30, 2026.
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Check out other popular destinations found by fellow travelers in 2026
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 August 30, 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% |