$113+ Cheap flights from Midway (MDW) to Puerto Rico
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 9/15. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJU
Sep 21 — Sep 281
Round-trip
1 adult, Economy
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Find cheap flights from Midway to Puerto Rico 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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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Midway to Puerto Rico
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Cheapest flights from Midway to Puerto RicoExplore the most affordable flight options available from Midway to Puerto Rico. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 22, 2026.
Explore the most affordable flight options available from Midway to Puerto Rico. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 22, 2026.
This Southwest deal was found by Cheapflights users on 8/18. 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.
Sun 9/138:05 pm -
1 stop12h 05m
Tue 9/225:15 am -
1 stop7h 50m
Deal found 8/18![Southwest logo]()
$226
This Southwest deal was found by Cheapflights users on 8/18. 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.
Tue 9/297:30 am -
1 stop10h 35m
Tue 10/65:05 am -
2 stops10h 35m
Deal found 8/18![Southwest logo]()
$246
This Faresmojo deal was found by Cheapflights users on 8/18. 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 Faresmojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/279:10 am -
1 stop9h 55m
Sat 8/296:25 am -
1 stop11h 50m
Deal found 8/18![JetBlue logo]()
$247
This Southwest deal was found by Cheapflights users on 8/17. 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.
Tue 9/18:30 am -
1 stop6h 55m
Sat 9/55:05 am -
1 stop8h 30m
Deal found 8/17![Southwest logo]()
$261
This Southwest deal was found by Cheapflights users on 8/18. 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.
Tue 8/2512:45 pm -
2 stops8h 15m
Sat 8/296:25 am -
2 stops11h 40m
Deal found 8/18![Southwest logo]()
$266
This Southwest deal was found by Cheapflights users on 8/18. 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.
Sun 9/61:35 pm -
1 stop8h 35m
Fri 9/115:00 am -
2 stops8h 25m
Deal found 8/18![Southwest logo]()
$281
This Southwest deal was found by Cheapflights users on 8/22. 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.
Tue 10/63:20 pm -
1 stop6h 45m
Tue 10/135:05 am -
2 stops10h 35m
Deal found 8/22![Southwest logo]()
$286
This Southwest deal was found by Cheapflights users on 8/17. 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 8/227:50 am -
2 stops9h 15m
Tue 8/255:15 am -
2 stops7h 50m
Deal found 8/17![Southwest logo]()
$291
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/136:15 am -
1 stop8h 51m
Tue 10/208:45 am -
2 stops15h 58m
Deal found 8/17![Frontier logo]()
$292
This Southwest deal was found by Cheapflights users on 8/17. 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.
Mon 8/3111:15 am -
1 stop9h 55m
Thu 9/36:30 am -
1 stop10h 05m
Deal found 8/17![Southwest logo]()
$296
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 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
Tue 10/135:11 pm -
1 stop7h 32m
Deal found 8/17![Frontier logo]()
$299
This Southwest deal was found by Cheapflights users on 8/18. 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.
Sat 9/127:50 am -
2 stops9h 20m
Tue 9/151:45 pm -
1 stop8h 15m
Deal found 8/18![Southwest logo]()
$301
Best flights from Midway to Puerto RicoDiscover carefully curated flight deals from Midway to Puerto Rico that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 22, 2026.
Discover carefully curated flight deals from Midway to Puerto Rico that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 22, 2026.
This Southwest deal was found by Cheapflights users on 8/17. 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.
Thu 10/294:15 pm -
2 stops8h 05m
Thu 11/55:50 pm -
1 stop7h 15m
Deal found 8/17![Southwest logo]()
$281
This Southwest deal was found by Cheapflights users on 8/21. 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 10/91:20 pm -
2 stops8h 45m
Tue 10/135:50 am -
1 stop11h 15m
Deal found 8/21![Southwest logo]()
$286
This Southwest deal was found by Cheapflights users on 8/17. 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.
Wed 9/3012:45 pm -
2 stops8h 20m
Wed 10/78:15 am -
2 stops12h 05m
Deal found 8/17![Southwest logo]()
$301
This Southwest deal was found by Cheapflights users on 8/21. 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.
Sat 9/1911:00 am -
1 stop6h 20m
Fri 9/256:30 am -
2 stops8h 15m
Deal found 8/21![Southwest logo]()
$326
This Southwest deal was found by Cheapflights users on 8/17. 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.
Tue 9/17:30 am -
1 stop10h 30m
Fri 9/46:30 am -
2 stops8h 15m
Deal found 8/17![Southwest logo]()
$326
This Southwest deal was found by Cheapflights users on 8/17. 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.
Tue 9/112:45 pm -
2 stops8h 15m
Sat 9/56:25 am -
2 stops11h 20m
Deal found 8/17![Southwest logo]()
$336
This Southwest deal was found by Cheapflights users on 8/18. 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.
Sat 9/1911:00 am -
1 stop6h 20m
Wed 9/236:00 am -
2 stops8h 05m
Deal found 8/18![Southwest logo]()
$336
This Southwest deal was found by Cheapflights users on 8/17. 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.
Tue 10/201:40 pm -
2 stops8h 25m
Sun 10/255:30 am -
2 stops9h 25m
Deal found 8/17![Southwest logo]()
$341
This Southwest deal was found by Cheapflights users on 8/18. 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.
Fri 10/94:15 pm -
2 stops8h 05m
Sun 10/115:30 am -
2 stops9h 25m
Deal found 8/18![Southwest logo]()
$341
This Southwest deal was found by Cheapflights users on 8/19. 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.
Sat 9/191:55 pm -
1 stop7h 05m
Tue 9/225:15 am -
2 stops7h 50m
Deal found 8/19![Southwest logo]()
$341
This Southwest deal was found by Cheapflights users on 8/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/104:25 pm -
1 stop6h 20m
Sat 11/146:45 am -
1 stop11h 45m
Deal found 8/20![Southwest logo]()
$346
Last-minute flights from Midway to Puerto RicoDiscover last-minute flight deals from Midway to Puerto Rico. Data last updated August 22, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Puerto Rico. Data last updated August 22, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 8/17. 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 8/227:05 am -
1 stop10h 10m
Tue 8/255:15 am -
1 stop7h 50m
Deal found 8/17![Southwest logo]()
$291
This Southwest deal was found by Cheapflights users on 8/18. 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.
Tue 8/2512:20 pm -
1 stop7h 45m
Sat 8/296:25 am -
2 stops11h 40m
Deal found 8/18![Southwest logo]()
$266
This Faresmojo deal was found by Cheapflights users on 8/18. 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 Faresmojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/279:10 am -
1 stop9h 55m
Sat 8/296:25 am -
1 stop11h 50m
Deal found 8/18![JetBlue logo]()
$247
This Southwest deal was found by Cheapflights users on 8/17. 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.
Mon 8/317:25 am -
1 stop8h 30m
Thu 9/36:00 am -
2 stops9h 30m
Deal found 8/17![Southwest logo]()
$296
This Southwest deal was found by Cheapflights users on 8/17. 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.
Tue 9/18:30 am -
1 stop6h 55m
Sat 9/55:05 am -
1 stop8h 30m
Deal found 8/17![Southwest logo]()
$261
This Southwest deal was found by Cheapflights users on 8/18. 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.
Sun 9/61:45 pm -
2 stops8h 35m
Fri 9/115:00 am -
2 stops8h 25m
Deal found 8/18![Southwest logo]()
$281
This Southwest deal was found by Cheapflights users on 8/18. 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.
Sat 9/127:50 am -
2 stops9h 20m
Tue 9/151:45 pm -
1 stop8h 15m
Deal found 8/18![Southwest logo]()
$301
This Southwest deal was found by Cheapflights users on 8/18. 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.
Sun 9/138:05 pm -
1 stop12h 05m
Tue 9/225:15 am -
2 stops7h 50m
Deal found 8/18![Southwest logo]()
$226
This Southwest deal was found by Cheapflights users on 8/21. 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.
Tue 9/159:40 am -
1 stop10h 20m
Fri 9/186:30 am -
2 stops8h 15m
Deal found 8/21![Southwest logo]()
$286
This Trip.com deal was found by Cheapflights users on 8/19. 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.
Wed 9/236:25 am -
1 stop7h 54m
Thu 10/17:00 am -
2 stops17h 44m
Deal found 8/19![Frontier logo]()
$303
This Southwest deal was found by Cheapflights users on 8/18. 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.
Tue 9/297:30 am -
1 stop10h 35m
Tue 10/65:05 am -
2 stops10h 35m
Deal found 8/18![Southwest logo]()
$246
One-way flights from Midway to Puerto RicoSearch for one-way flight options from Midway to Puerto Rico. Find affordable one-way fares based on user searches. Data last updated August 22, 2026.
Search for one-way flight options from Midway to Puerto Rico. Find affordable one-way fares based on user searches. Data last updated August 22, 2026.
This Southwest deal was found by Cheapflights users on 8/17. 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.
Tue 9/156:15 am -
1 stop9h 10m
Deal found 8/17![Southwest logo]()
$113
This Southwest deal was found by Cheapflights users on 8/18. 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 9/212:45 pm -
2 stops8h 15m
Deal found 8/18![Southwest logo]()
$128
This Southwest deal was found by Cheapflights users on 8/19. 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.
Tue 9/112:20 pm -
1 stop7h 45m
Deal found 8/19![Southwest logo]()
$133
This Kiwi.com deal was found by Cheapflights users on 8/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/112:54 pm -
2 stops12h 19m
Deal found 8/21![Frontier logo]()
$135
This Kiwi.com deal was found by Cheapflights users on 8/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/216:15 am -
2 stops18h 54m
Deal found 8/22![Frontier logo]()
$136
This Kiwi.com deal was found by Cheapflights users on 8/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/226:15 am -
2 stops18h 54m
Deal found 8/21![Frontier logo]()
$146
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/166:25 am -
2 stops18h 48m
Deal found 8/17![Frontier logo]()
$148
This Super.com deal was found by Cheapflights users on 8/18. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/256:25 am -
1 stop7h 54m
Deal found 8/18![Frontier logo]()
$151
This Super.com deal was found by Cheapflights users on 8/18. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/126:25 am -
1 stop8h 41m
Deal found 8/18![Frontier logo]()
$152
This Frontier deal was found by Cheapflights users on 8/18. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/206:25 am -
1 stop8h 41m
Deal found 8/18![Frontier logo]()
$154
Find flight deals from Midway to Puerto Rico
Keep the following information in mind while searching for Midway to Puerto Rico flight deals. Data was last updated August 22, 2026.
Round-trip from | $226 (Southwest) |
|---|---|
One-way from | $113 (Southwest) |
Popular in | December |
Cheapest in | August |
Average price | $320 |
Good round-trip deal | $542 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Midway to Puerto Rico 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 22, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Puerto Rico 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
Thu 10/29
4:15 pm-1:20 am
2 stops8h 05m
San Juan Luis Munoz Marin Intl
Thu 11/5
5:50 pm-11:05 pm
1 stop7h 15m
$281
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Fri 10/9
1:20 pm-11:05 pm
2 stops8h 45m
San Juan Luis Munoz Marin Intl
Tue 10/13
5:50 am-4:05 pm
1 stop11h 15m
$286
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Wed 9/30
12:45 pm-10:05 pm
2 stops8h 20m
San Juan Luis Munoz Marin Intl
Wed 10/7
8:15 am-7:20 pm
2 stops12h 05m
$301
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Sat 9/19
11:00 am-6:20 pm
1 stop6h 20m
San Juan Luis Munoz Marin Intl
Fri 9/25
6:30 am-1:45 pm
2 stops8h 15m
$326
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Tue 9/1
7:30 am-7:00 pm
1 stop10h 30m
San Juan Luis Munoz Marin Intl
Fri 9/4
6:30 am-1:45 pm
2 stops8h 15m
$326
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 9/5
6:25 am-4:45 pm
2 stops11h 20m
$336
Quickest round-trip
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Sat 9/19
11:00 am-6:20 pm
1 stop6h 20m
San Juan Luis Munoz Marin Intl
Wed 9/23
6:00 am-1:05 pm
2 stops8h 05m
$336
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Tue 10/20
1:40 pm-11:05 pm
2 stops8h 25m
San Juan Luis Munoz Marin Intl
Sun 10/25
5:30 am-1:55 pm
2 stops9h 25m
$341
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Fri 10/9
4:15 pm-1:20 am
2 stops8h 05m
San Juan Luis Munoz Marin Intl
Sun 10/11
5:30 am-1:55 pm
2 stops9h 25m
$341
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Sat 9/19
1:55 pm-10:00 pm
1 stop7h 05m
San Juan Luis Munoz Marin Intl
Tue 9/22
5:15 am-12:05 pm
2 stops7h 50m
$341
Showing 1-10 of 19 resultsSorted by cheapest first
Best time to book a flight from Midway to Puerto Rico
Have a flexible travel schedule? Discover the best time to fly to Puerto Rico from Midway with our price prediction graph.
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 Puerto Rico
MDW-PR0
MDW-SJU
What is the cheapest month to book a flight from Chicago Midway Airport to Puerto Rico?
Currently, February is the cheapest month in which you can book a flight from Chicago Midway Airport to Puerto Rico (average of $243). Flying from Chicago Midway Airport to Puerto Rico 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 often are flights from Chicago to Puerto Rico delayed?
About 26% of weekly flights between Chicago and Puerto Rico have experienced delays in the past year, with the average delay time being 117 minutes.
What is the most punctual flight time for Chicago to Puerto Rico 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 Puerto Rico 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 Puerto Rico?
The price you pay for your flight from Chicago Midway Airport to Puerto Rico may vary depending on when you book. For the best chance of a lower fare, look to book 20 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
Reviews of airlines servicing Puerto Rico
Get insights into the airlines that provide service to Puerto Rico. 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 Puerto Rico. Reviews last updated August 22, 2026.
Peruse reviews from past customers who have flown with Southwest,Delta, andFrontier from Chicago Midway Airport to Puerto Rico to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
8.0
Crew
8.6
Food
7.0
Boarding
8.1
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Comfort
8.0
Crew
8.6
Food
7.0
Boarding
8.1
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Comfort
8.0
Crew
8.6
Food
7.0
Boarding
8.1
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Comfort
8.0
Crew
8.6
Food
7.0
Boarding
8.1
Overall
8.0
Entertainment
7.5
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 Puerto Rico. 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 Puerto Rico
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Midway and Puerto Rico flights
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Top 3 airlines flying from Midway to Puerto Rico
Discover the top 3 airlines that operate flights from Midway to Puerto Rico. 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 22, 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% |