$110+ Cheap flights from Midway (MDW) to Puerto Rico
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/22. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJU
Oct 24 — Oct 311
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 September 24, 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 September 24, 2026.
This CheapOair deal was found by Cheapflights users on 9/22. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/266:15 am -
1 stop8h 51m
Mon 11/23:59 pm -
1 stop9h 48m
Deal found 9/22![Frontier logo]()
$217
This Frontier deal was found by Cheapflights users on 9/23. 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 10/36:25 am -
1 stop8h 41m
Sat 10/175:11 pm -
1 stop7h 32m
Deal found 9/23![Frontier logo]()
$218
This CheapOair deal was found by Cheapflights users on 9/22. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/196:15 am -
1 stop8h 51m
Fri 10/235:11 pm -
1 stop7h 32m
Deal found 9/22![Frontier logo]()
$219
This FlightHub deal was found by Cheapflights users on 9/20. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/208:42 pm -
1 stop27h 42m
Thu 11/266:13 pm -
1 stop15h 10m
Deal found 9/20![Frontier logo]()
$223
This Cheapflightsfares deal was found by Cheapflights users on 9/22. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/36:25 am -
1 stop8h 41m
Thu 10/85:11 pm -
1 stop7h 32m
Deal found 9/22![Frontier logo]()
$226
This Super.com deal was found by Cheapflights users on 9/23. 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.
Wed 9/306:25 am -
1 stop7h 57m
Wed 10/76:30 am -
1 stop12h 21m
Deal found 9/23![Frontier logo]()
$228
This Trip.com deal was found by Cheapflights users on 9/22. 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.
Sun 11/228:42 pm -
1 stop27h 42m
Thu 11/266:13 pm -
1 stop15h 10m
Deal found 9/22![Frontier logo]()
$229
This Cheapflightsfares deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/33:50 pm -
1 stop7h 17m
Tue 12/85:01 am -
1 stop8h 32m
Deal found 9/23![Frontier logo]()
$230
This Cheapflightsfares deal was found by Cheapflights users on 9/20. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/79:37 pm -
1 stop26h 36m
Wed 12/95:01 am -
1 stop8h 32m
Deal found 9/20![Frontier logo]()
$232
This CheapOair deal was found by Cheapflights users on 9/22. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/46:25 am -
1 stop8h 41m
Wed 10/76:30 am -
1 stop12h 21m
Deal found 9/22![Frontier logo]()
$233
This CheapOair deal was found by Cheapflights users on 9/23. 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.
Sat 10/36:25 am -
1 stop8h 41m
Wed 10/76:30 am -
1 stop12h 21m
Deal found 9/23![Frontier logo]()
$237
This Cheapflightsfares deal was found by Cheapflights users on 9/22. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/266:25 am -
1 stop8h 41m
Mon 10/56:30 am -
1 stop12h 21m
Deal found 9/22![Frontier logo]()
$241
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 September 24, 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 September 24, 2026.
This Southwest deal was found by Cheapflights users on 9/21. 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 10/211:35 pm -
2 stops8h 35m
Wed 10/288:15 am -
2 stops12h 05m
Deal found 9/21![Southwest logo]()
$301
This Southwest deal was found by Cheapflights users on 9/19. 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 10/162:15 pm -
1 stop9h 10m
Tue 10/208:15 am -
1 stop7h 30m
Deal found 9/19![Southwest logo]()
$301
This Southwest deal was found by Cheapflights users on 9/19. 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.
Mon 10/52:15 pm -
1 stop9h 10m
Fri 10/91:05 pm -
1 stop8h 30m
Deal found 9/19![Southwest logo]()
$321
This Southwest deal was found by Cheapflights users on 9/18. 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.
Thu 10/224:15 pm -
2 stops8h 10m
Mon 10/2610:50 pm -
1 stop10h 35m
Deal found 9/18![Southwest logo]()
$321
This Southwest deal was found by Cheapflights users on 9/21. 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.
Mon 10/194:30 pm -
2 stops7h 55m
Fri 10/235:30 am -
2 stops8h 55m
Deal found 9/21![Southwest logo]()
$321
This Southwest deal was found by Cheapflights users on 9/21. 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.
Mon 10/192:15 pm -
1 stop9h 10m
Sat 11/71:30 pm -
Nonstop4h 55m
Deal found 9/21![Southwest logo]()
$326
This Southwest deal was found by Cheapflights users on 9/22. 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.
Sat 9/267:15 am -
1 stop9h 55m
Sat 10/35:40 am -
2 stops12h 40m
Deal found 9/22![Southwest logo]()
$356
This Southwest deal was found by Cheapflights users on 9/23. 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 10/912:50 pm -
1 stop6h 10m
Tue 10/136:35 am -
2 stops9h 05m
Deal found 9/23![Southwest logo]()
$385
This Southwest deal was found by Cheapflights users on 9/21. 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 10/255:10 am -
1 stop7h 35m
Sat 10/317:45 am -
1 stop7h 35m
Deal found 9/21![Southwest logo]()
$385
This Southwest deal was found by Cheapflights users on 9/21. 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 10/224:15 pm -
2 stops8h 10m
Sun 10/255:40 pm -
1 stop7h 00m
Deal found 9/21![Southwest logo]()
$396
This Southwest deal was found by Cheapflights users on 9/19. 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.
Wed 11/1112:45 pm -
2 stops10h 05m
Wed 11/2510:30 pm -
2 stops15h 20m
Deal found 9/19![Southwest logo]()
$411
Last-minute flights from Midway to Puerto RicoDiscover last-minute flight deals from Midway to Puerto Rico. Data last updated September 24, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Puerto Rico. Data last updated September 24, 2026 and is based on user searches.
This CheapOair deal was found by Cheapflights users on 9/23. 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 9/286:25 am -
1 stop7h 57m
Wed 10/76:30 am -
1 stop12h 21m
Deal found 9/23![Frontier logo]()
$252
This Trip.com deal was found by Cheapflights users on 9/22. 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.
Mon 9/286:25 am -
1 stop7h 57m
Fri 10/26:30 am -
1 stop12h 21m
Deal found 9/22![Frontier logo]()
$254
This CheapOair deal was found by Cheapflights users on 9/21. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/286:25 am -
1 stop7h 57m
Wed 9/306:33 am -
1 stop12h 18m
Deal found 9/21![Frontier logo]()
$280
This Super.com deal was found by Cheapflights users on 9/23. 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.
Wed 9/306:25 am -
1 stop7h 57m
Wed 10/76:30 am -
1 stop12h 21m
Deal found 9/23![Frontier logo]()
$228
This Cheapflightsfares deal was found by Cheapflights users on 9/19. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/16:25 am -
1 stop8h 41m
Thu 10/85:11 pm -
1 stop7h 32m
Deal found 9/19![Frontier logo]()
$272
This Frontier deal was found by Cheapflights users on 9/23. 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 10/36:25 am -
1 stop8h 41m
Thu 10/225:11 pm -
1 stop7h 32m
Deal found 9/23![Frontier logo]()
$218
This Cheapflightsfares deal was found by Cheapflights users on 9/22. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/36:25 am -
1 stop8h 41m
Thu 10/85:11 pm -
1 stop7h 32m
Deal found 9/22![Frontier logo]()
$226
This CheapOair deal was found by Cheapflights users on 9/23. 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.
Sat 10/36:25 am -
1 stop8h 41m
Wed 10/76:30 am -
1 stop12h 21m
Deal found 9/23![Frontier logo]()
$237
This Frontier deal was found by Cheapflights users on 9/21. 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 10/36:25 am -
1 stop8h 41m
Wed 10/145:11 pm -
1 stop7h 32m
Deal found 9/21![Frontier logo]()
$245
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 September 24, 2026.
Search for one-way flight options from Midway to Puerto Rico. Find affordable one-way fares based on user searches. Data last updated September 24, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 9/19. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/228:42 pm -
1 stop27h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![Frontier logo]()
$110
This Cheapflightsfares deal was found by Cheapflights users on 9/22. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/306:25 am -
1 stop7h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Frontier logo]()
$112
This Trip.com deal was found by Cheapflights users on 9/22. 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.
Mon 10/56:50 am -
1 stop7h 29m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Frontier logo]()
$116
This Trip.com deal was found by Cheapflights users on 9/19. 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.
Mon 11/232:28 pm -
1 stop9h 08m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![Frontier logo]()
$122
This Southwest deal was found by Cheapflights users on 9/21. 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 10/162:15 pm -
1 stop9h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Southwest logo]()
$123
This Delta deal was found by Cheapflights users on 9/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1711:27 am -
1 stop9h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Delta logo]()
$125
This CheapOair deal was found by Cheapflights users on 9/23. 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.
Sat 9/266:25 am -
1 stop8h 41m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![Frontier logo]()
$130
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 September 24, 2026.
Round-trip from | $217 (CheapOair) |
|---|---|
One-way from | $110 (Cheapflightsfares) |
Popular in | December |
Cheapest in | August |
Average price | $357 |
Good round-trip deal | $572 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 September 24, 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
Quickest round-trip
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Tue 11/17
1:15 pm-9:55 pm
1 stop6h 40m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$123
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
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$123
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Tue 10/6
1:40 pm-11:10 pm
2 stops8h 30m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$143
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 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$143
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Fri 10/23
6:15 am-4:06 pm
1 stop8h 51m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$174
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Wed 11/18
9:55 am-9:55 pm
2 stops10h 00m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$178
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Fri 11/13
11:10 am-11:00 pm
2 stops9h 50m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$178
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Tue 11/24
8:35 pm-9:50 am
1 stop11h 15m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$178
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Wed 10/21
1:35 pm-11:10 pm
2 stops8h 35m
San Juan Luis Munoz Marin Intl
Wed 10/28
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
Fri 10/16
2:15 pm-12:25 am
1 stop9h 10m
San Juan Luis Munoz Marin Intl
Tue 10/20
8:15 am-2:45 pm
1 stop7h 30m
$301
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 $156). 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 25% of weekly flights between Chicago and Puerto Rico have experienced delays in the past year, with the average delay time being 123 minutes.
What is the most punctual flight time for Chicago to Puerto Rico 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 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 23 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 September 24, 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.
Boarding
8.1
Overall
8.0
Comfort
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Boarding
8.1
Overall
8.0
Comfort
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Boarding
8.1
Overall
8.0
Comfort
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Boarding
8.1
Overall
8.0
Comfort
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
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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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 September 24, 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$493 | FlexibilityNo cancel fee | On-time63% |