$120+ 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 4/25. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJU
May 9 — May 161
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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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 April 9, 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 April 9, 2026.
This Frontier deal was found by Cheapflights users on 4/4. 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 4/206:00 am
MDW
- SJU
1 stop7h 13m
Frontier
Thu 4/233:03 pm
SJU
- MDW
1 stop8h 16m
Frontier
Deal found 4/4![Frontier logo]()
$226
This Frontier deal was found by Cheapflights users on 4/6. 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.
Thu 4/166:00 am
MDW
- SJU
1 stop7h 08m
Frontier
Thu 4/303:03 pm
SJU
- MDW
1 stop8h 16m
Frontier
Deal found 4/6![Frontier logo]()
$230
This Frontier deal was found by Cheapflights users on 4/4. 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 5/36:00 am
MDW
- SJU
1 stop7h 08m
Frontier
Sat 5/306:25 am
SJU
- MDW
1 stop8h 47m
Frontier
Deal found 4/4![Frontier logo]()
$231
This CheapOair deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/206:00 am
MDW
- SJU
1 stop7h 13m
Frontier
Tue 4/283:08 am
SJU
- MDW
1 stop29h 13m
Frontier
Deal found 4/7![Frontier logo]()
$235
This Frontier deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/179:14 am
MDW
- SJU
1 stop12h 34m
Frontier
Sat 4/258:00 am
SJU
- MDW
1 stop9h 13m
Frontier
Deal found 4/8![Frontier logo]()
$236
This Booking.com deal was found by Cheapflights users on 4/4. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/169:14 am
MDW
- SJU
1 stop15h 47m
Frontier
Sat 4/188:00 am
SJU
- MDW
1 stop24h 59m
Frontier
Deal found 4/4![Frontier logo]()
$237
This Priceline deal was found by Cheapflights users on 4/6. 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 4/196:00 am
MDW
- SJU
1 stop7h 08m
Frontier
Fri 4/243:23 pm
SJU
- MDW
1 stop8h 03m
Frontier
Deal found 4/6![Frontier logo]()
$240
This CheapOair deal was found by Cheapflights users on 4/4. 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.
Fri 4/179:14 am
MDW
- SJU
1 stop12h 34m
Frontier
Sat 4/188:00 am
SJU
- MDW
1 stop24h 59m
Frontier
Deal found 4/4![Frontier logo]()
$245
This Frontier deal was found by Cheapflights users on 4/6. 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 4/196:00 am
MDW
- SJU
1 stop7h 08m
Frontier
Sun 4/263:18 pm
SJU
- MDW
1 stop8h 01m
Frontier
Deal found 4/6![Frontier logo]()
$260
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 April 9, 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 April 9, 2026.
This Southwest deal was found by Cheapflights users on 4/5. 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 4/2012:50 pm
MDW
- SJU
2 stops10h 05m
Southwest
Wed 4/295:35 am
SJU
- MDW
1 stop9h 10m
Southwest
Deal found 4/5![Southwest logo]()
$346
This Delta deal was found by Cheapflights users on 4/5. 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 5/266:23 am
MDW
- SJU
1 stop9h 10m
Delta
Tue 6/21:14 pm
SJU
- MDW
1 stop8h 55m
Delta
Deal found 4/5![Delta logo]()
$366
This Southwest deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/259:20 am
MDW
- SJU
1 stop7h 15m
Southwest
Sat 5/21:10 pm
SJU
- MDW
Nonstop5h 10m
Southwest
Deal found 4/8![Southwest logo]()
$352
This Southwest deal was found by Cheapflights users on 4/5. 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 5/32:40 pm
MDW
- SJU
2 stops7h 55m
Southwest
Wed 5/205:35 am
SJU
- MDW
1 stop7h 35m
Southwest
Deal found 4/5![Southwest logo]()
$356
This Delta deal was found by Cheapflights users on 4/5. 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.
Fri 5/112:52 pm
MDW
- SJU
1 stop6h 32m
Delta
Tue 5/56:15 am
SJU
- MDW
1 stop11h 11m
Delta
Deal found 4/5![Delta logo]()
$416
This Southwest deal was found by Cheapflights users on 4/4. 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 5/191:25 pm
MDW
- SJU
1 stop6h 40m
Southwest
Sat 5/235:15 am
SJU
- MDW
1 stop14h 00m
Southwest
Deal found 4/4![Southwest logo]()
$356
This Delta deal was found by Cheapflights users on 4/4. 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.
Mon 6/156:05 am
MDW
- SJU
1 stop9h 41m
Delta
Sun 6/216:00 am
SJU
- MDW
1 stop7h 00m
Delta
Deal found 4/4![Delta logo]()
$416
This Southwest deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/2712:00 pm
MDW
- SJU
2 stops10h 25m
Southwest
Fri 5/153:45 pm
SJU
- MDW
1 stop9h 30m
Southwest
Deal found 4/7![Southwest logo]()
$376
This Southwest deal was found by Cheapflights users on 4/4. 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
Tue 5/125:05 am
SJU
- MDW
2 stops11h 45m
Southwest
Deal found 4/4![Southwest logo]()
$376
This Southwest deal was found by Cheapflights users on 4/5. 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 4/189:20 am
MDW
- SJU
1 stop7h 15m
Southwest
Fri 5/1510:00 am
SJU
- MDW
2 stops9h 15m
Southwest
Deal found 4/5![Southwest logo]()
$396
This Southwest deal was found by Cheapflights users on 4/4. 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 6/51:00 pm
MDW
- SJU
2 stops10h 15m
Southwest
Tue 6/97:00 am
SJU
- MDW
2 stops8h 30m
Southwest
Deal found 4/4![Southwest logo]()
$436
Last-minute flights from Midway to Puerto RicoDiscover last-minute flight deals from Midway to Puerto Rico. Data last updated April 9, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Puerto Rico. Data last updated April 9, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 4/6. 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.
Thu 4/166:00 am
MDW
- SJU
1 stop7h 08m
Frontier
Thu 4/303:03 pm
SJU
- MDW
1 stop8h 16m
Frontier
Deal found 4/6![Frontier logo]()
$230
This Booking.com deal was found by Cheapflights users on 4/4. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/169:14 am
MDW
- SJU
1 stop15h 47m
Frontier
Sat 4/188:00 am
SJU
- MDW
1 stop24h 59m
Frontier
Deal found 4/4![Frontier logo]()
$237
This Frontier deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/179:14 am
MDW
- SJU
1 stop12h 34m
Frontier
Sat 4/258:00 am
SJU
- MDW
1 stop9h 13m
Frontier
Deal found 4/8![Frontier logo]()
$236
This CheapOair deal was found by Cheapflights users on 4/4. 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.
Fri 4/179:14 am
MDW
- SJU
1 stop12h 34m
Frontier
Sat 4/188:00 am
SJU
- MDW
1 stop24h 59m
Frontier
Deal found 4/4![Frontier logo]()
$245
This Priceline deal was found by Cheapflights users on 4/6. 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 4/196:00 am
MDW
- SJU
1 stop7h 08m
Frontier
Fri 4/243:23 pm
SJU
- MDW
1 stop8h 03m
Frontier
Deal found 4/6![Frontier logo]()
$240
This Frontier deal was found by Cheapflights users on 4/6. 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 4/196:00 am
MDW
- SJU
1 stop7h 08m
Frontier
Sun 4/263:18 pm
SJU
- MDW
1 stop8h 01m
Frontier
Deal found 4/6![Frontier logo]()
$260
This Frontier deal was found by Cheapflights users on 4/4. 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 4/206:00 am
MDW
- SJU
1 stop7h 13m
Frontier
Thu 4/233:03 pm
SJU
- MDW
1 stop8h 16m
Frontier
Deal found 4/4![Frontier logo]()
$226
This CheapOair deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/206:00 am
MDW
- SJU
1 stop7h 13m
Frontier
Tue 4/283:08 am
SJU
- MDW
1 stop29h 13m
Frontier
Deal found 4/7![Frontier logo]()
$235
This Frontier deal was found by Cheapflights users on 4/4. 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 5/36:00 am
MDW
- SJU
1 stop7h 08m
Frontier
Sat 5/306:25 am
SJU
- MDW
1 stop8h 47m
Frontier
Deal found 4/4![Frontier logo]()
$231
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 April 9, 2026.
Search for one-way flight options from Midway to Puerto Rico. Find affordable one-way fares based on user searches. Data last updated April 9, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/6. 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 4/257:34 pm
MDW
- SJU
2 stops21h 25m
Frontier
Deal found 4/6![Frontier logo]()
$120
This Super.com deal was found by Cheapflights users on 4/5. 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 5/56:00 am
MDW
- SJU
1 stop7h 07m
Frontier
Deal found 4/5![Frontier logo]()
$122
This Orbitz deal was found by Cheapflights users on 4/6. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/36:00 am
MDW
- SJU
1 stop7h 08m
Frontier
Deal found 4/6![Frontier logo]()
$123
This Kiwi.com deal was found by Cheapflights users on 4/6. 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 5/26:00 am
MDW
- SJU
2 stops29h 23m
Frontier
Deal found 4/6![Frontier logo]()
$125
This Kiwi.com deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/12:15 pm
MDW
- SJU
2 stops28h 07m
Multiple Airlines
Deal found 4/8![Multiple Airlines logo]()
$126
This Kiwi.com deal was found by Cheapflights users on 4/5. 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 5/93:07 pm
MDW
- SJU
2 stops15h 57m
Frontier
Deal found 4/5![Frontier logo]()
$127
This Kiwi.com deal was found by Cheapflights users on 4/6. 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 4/232:15 pm
MDW
- SJU
2 stops21h 08m
Frontier
Deal found 4/6![Frontier logo]()
$129
This Kiwi.com deal was found by Cheapflights users on 4/6. 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 4/296:10 am
MDW
- SJU
2 stops29h 40m
Frontier
Deal found 4/6![Frontier logo]()
$130
This Kiwi.com deal was found by Cheapflights users on 4/6. 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 4/222:15 pm
MDW
- SJU
2 stops22h 51m
Frontier
Deal found 4/6![Frontier logo]()
$131
This Orbitz deal was found by Cheapflights users on 4/5. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/63:07 pm
MDW
- SJU
1 stop12h 42m
Frontier
Deal found 4/5![Frontier logo]()
$132
This Kiwi.com deal was found by Cheapflights users on 4/6. 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 4/279:14 am
MDW
- SJU
2 stops13h 29m
Frontier
Deal found 4/6![Frontier logo]()
$134
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 April 9, 2026.
Round-trip from | $226 (Frontier) |
|---|---|
One-way from | $120 (Kiwi.com) |
Popular in | December |
Cheapest in | January |
Average price | $381 |
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 2,558,603 searches. Data last updated April 9, 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 - SJU
MDWSJU
Chicago Midway
Mon 4/20
12:50 pm-11:55 pm
2 stops10h 05m
San Juan Luis Munoz Marin Intl
Wed 4/29
5:35 am-1:45 pm
1 stop9h 10m
$346
Quickest round-trip
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Sat 4/25
9:20 am-5:35 pm
1 stop7h 15m
San Juan Luis Munoz Marin Intl
Sat 5/2
1:10 pm-5:20 pm
Nonstop5h 10m
$352
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Sun 5/3
2:40 pm-11:35 pm
2 stops7h 55m
San Juan Luis Munoz Marin Intl
Wed 5/20
5:35 am-12:10 pm
1 stop7h 35m
$356
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Tue 5/19
1:25 pm-9:05 pm
1 stop6h 40m
San Juan Luis Munoz Marin Intl
Sat 5/23
5:15 am-6:15 pm
1 stop14h 00m
$356
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Tue 5/26
6:23 am-4:33 pm
1 stop9h 10m
San Juan Luis Munoz Marin Intl
Tue 6/2
1:14 pm-9:09 pm
1 stop8h 55m
$366
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Mon 4/27
12:00 pm-11:25 pm
2 stops10h 25m
San Juan Luis Munoz Marin Intl
Fri 5/15
3:45 pm-12:15 am
1 stop9h 30m
$376
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
Tue 5/12
5:05 am-3:50 pm
2 stops11h 45m
$376
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Sat 4/18
9:20 am-5:35 pm
1 stop7h 15m
San Juan Luis Munoz Marin Intl
Fri 5/15
10:00 am-6:15 pm
2 stops9h 15m
$396
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Fri 5/1
12:52 pm-8:24 pm
1 stop6h 32m
San Juan Luis Munoz Marin Intl
Tue 5/5
6:15 am-4:26 pm
1 stop11h 11m
$416
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Mon 6/15
6:05 am-4:46 pm
1 stop9h 41m
San Juan Luis Munoz Marin Intl
Sun 6/21
6:00 am-12:00 pm
1 stop7h 00m
$416
Showing 1-10 of 21 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, April is the cheapest month in which you can book a flight from Chicago Midway Airport to Puerto Rico (average of $91). Flying from Chicago Midway Airport to Puerto Rico in June is currently the most expensive (average of $314). 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 PR?
Find hourly flight availability from Midway to Puerto Rico. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 9, 2026.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago Midway Airport to Puerto Rico as you normally would.
How often are flights from Chicago to Puerto Rico delayed?
About 31% of weekly flights between Chicago and Puerto Rico have experienced delays in the past year, with the average delay time being 110 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?
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 Puerto Rico flights?
Over the last year, Southwest have had the lowest number of delays on this route, with just 31% of flights being delayed.
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 April 9, 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
Crew
8.6
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Crew
8.6
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Crew
8.6
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Crew
8.6
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
8.0
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 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 2,558,603 searches. Data last updated April 9, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$132 | Average$573 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$138 | Average$289 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$377 | Average$491 | FlexibilityNo cancel fee | On-time63% |