$124+ Cheap flights from Puerto Rico to Midway (MDW)
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 12/2. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MDW
Dec 9 — Dec 161
Round-trip
1 adult, Economy
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Find cheap flights from Puerto Rico to Midway 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.Cheap flight deals from Puerto Rico to Midway
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Cheapest flights from Puerto Rico to MidwayExplore the most affordable flight options available from Puerto Rico to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 9, 2026.
Explore the most affordable flight options available from Puerto Rico to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 9, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 11/9. 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 12/34:07 pm -
1 stop24h 34m
Sun 12/68:37 pm -
1 stop24h 52m
Deal found 11/9![Frontier logo]()
$240
This FlightHub deal was found by Cheapflights users on 11/5. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/35:01 am -
1 stop13h 06m
Mon 12/76:11 pm -
1 stop14h 26m
Deal found 11/5![Frontier logo]()
$245
This Trip.com deal was found by Cheapflights users on 11/9. 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.
Sat 12/55:01 am -
1 stop8h 32m
Tue 12/812:28 pm -
1 stop10h 39m
Deal found 11/9![Frontier logo]()
$246
This Trip.com deal was found by Cheapflights users on 11/9. 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.
Tue 12/85:01 am -
1 stop8h 32m
Sat 12/1212:28 pm -
1 stop10h 39m
Deal found 11/9![Frontier logo]()
$247
This Cheapflightsfares deal was found by Cheapflights users on 11/5. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/33:09 pm -
1 stop25h 32m
Sun 12/68:37 pm -
1 stop28h 15m
Deal found 11/5![Frontier logo]()
$250
This OneTravel deal was found by Cheapflights users on 11/6. 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 OneTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/33:43 am -
1 stop12h 58m
Mon 12/76:11 pm -
1 stop14h 26m
Deal found 11/6![Frontier logo]()
$250
This Trip.com deal was found by Cheapflights users on 11/5. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/24:07 pm -
1 stop24h 34m
Sat 12/1212:28 pm -
1 stop10h 39m
Deal found 11/5![Frontier logo]()
$252
This Cheapflightsfares deal was found by Cheapflights users on 11/5. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/193:55 pm -
1 stop9h 52m
Thu 11/261:16 pm -
1 stop10h 20m
Deal found 11/5![Frontier logo]()
$253
This CheapOair deal was found by Cheapflights users on 11/6. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/193:55 pm -
1 stop9h 52m
Thu 12/33:36 pm -
1 stop8h 35m
Deal found 11/6![Frontier logo]()
$262
This Cheapflightsfares deal was found by Cheapflights users on 11/5. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/193:55 pm -
1 stop9h 52m
Sat 11/218:42 pm -
1 stop24h 36m
Deal found 11/5![Frontier logo]()
$266
This Trip.com deal was found by Cheapflights users on 11/6. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/33:09 pm -
1 stop25h 32m
Thu 12/108:37 pm -
1 stop28h 15m
Deal found 11/6![Frontier logo]()
$317
This Cheapflightsfares deal was found by Cheapflights users on 11/8. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/223:47 am -
1 stop18h 00m
Fri 11/278:42 pm -
1 stop28h 05m
Deal found 11/8![Frontier logo]()
$476
Best flights from Puerto Rico to MidwayDiscover carefully curated flight deals from Puerto Rico to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated November 9, 2026.
Discover carefully curated flight deals from Puerto Rico to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated November 9, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 11/5. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/33:09 pm -
1 stop25h 32m
Sun 12/68:37 pm -
1 stop28h 15m
Deal found 11/5![Frontier logo]()
$250
This Southwest deal was found by Cheapflights users on 11/8. 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.
Fri 1/1510:05 pm -
1 stop11h 55m
Sun 1/173:35 pm -
1 stop7h 05m
Deal found 11/8![Southwest logo]()
$276
This Southwest deal was found by Cheapflights users on 11/4. 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.
Wed 12/96:10 am -
1 stop8h 50m
Mon 12/143:00 pm -
1 stop7h 50m
Deal found 11/4![Southwest logo]()
$296
This Southwest deal was found by Cheapflights users on 11/8. 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.
Thu 12/37:40 am -
2 stops9h 15m
Sun 12/68:40 pm -
1 stop11h 15m
Deal found 11/8![Southwest logo]()
$330
This Southwest deal was found by Cheapflights users on 11/8. 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.
Fri 11/205:50 pm -
1 stop7h 20m
Mon 11/308:35 pm -
1 stop11h 20m
Deal found 11/8![Southwest logo]()
$330
This Southwest deal was found by Cheapflights users on 11/6. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/116:35 am -
1 stop11h 25m
Tue 12/153:00 pm -
1 stop7h 50m
Deal found 11/6![Southwest logo]()
$346
This Cheapflightsfares deal was found by Cheapflights users on 11/8. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/223:47 am -
1 stop18h 00m
Fri 11/278:42 pm -
1 stop28h 05m
Deal found 11/8![Frontier logo]()
$476
This Southwest deal was found by Cheapflights users on 11/8. 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.
Thu 12/102:25 pm -
1 stop9h 05m
Sun 12/1312:50 pm -
2 stops10h 20m
Deal found 11/8![Southwest logo]()
$361
This Kiwi.com deal was found by Cheapflights users on 11/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/173:13 am -
1 stop18h 17m
Thu 1/75:41 pm -
2 stops30h 44m
Deal found 11/7![Frontier logo]()
$486
This Southwest deal was found by Cheapflights users on 11/9. 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 12/102:25 pm -
1 stop9h 05m
Tue 12/154:25 pm -
1 stop6h 25m
Deal found 11/9![Southwest logo]()
$361
This Cheapflightsfares deal was found by Cheapflights users on 11/5. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/253:13 am -
1 stop18h 27m
Wed 12/308:35 pm -
1 stop27h 08m
Deal found 11/5![Frontier logo]()
$491
This Kiwi.com deal was found by Cheapflights users on 11/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/163:19 am -
1 stop18h 11m
Wed 1/65:41 pm -
2 stops17h 50m
Deal found 11/7![Frontier logo]()
$512
This Southwest deal was found by Cheapflights users on 11/6. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/66:05 am -
2 stops10h 20m
Sun 12/132:40 pm -
1 stop6h 20m
Deal found 11/6![Southwest logo]()
$400
This Cheapflightsfares deal was found by Cheapflights users on 11/6. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/62:54 pm -
1 stop28h 22m
Sun 12/208:35 pm -
1 stop27h 08m
Deal found 11/6![Frontier logo]()
$519
This Cheapflightsfares deal was found by Cheapflights users on 11/9. 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 12/173:13 am -
1 stop18h 17m
Tue 12/228:35 pm -
1 stop15h 14m
Deal found 11/9![Frontier logo]()
$587
Last-minute flights from Puerto Rico to MidwayDiscover last-minute flight deals from Puerto Rico to Midway. Data last updated November 9, 2026 and is based on user searches.
Discover last-minute flight deals from Puerto Rico to Midway. Data last updated November 9, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 11/5. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/193:55 pm -
1 stop9h 52m
Thu 11/261:16 pm -
1 stop10h 20m
Deal found 11/5![Frontier logo]()
$253
This CheapOair deal was found by Cheapflights users on 11/6. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/193:55 pm -
1 stop9h 52m
Thu 12/33:36 pm -
1 stop8h 35m
Deal found 11/6![Frontier logo]()
$262
This Cheapflightsfares deal was found by Cheapflights users on 11/5. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/193:55 pm -
1 stop9h 52m
Sat 11/218:42 pm -
1 stop24h 36m
Deal found 11/5![Frontier logo]()
$266
This Cheapflightsfares deal was found by Cheapflights users on 11/8. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/223:47 am -
1 stop18h 00m
Fri 11/278:42 pm -
1 stop28h 05m
Deal found 11/8![Frontier logo]()
$476
This Trip.com deal was found by Cheapflights users on 11/5. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/24:07 pm -
1 stop24h 34m
Sat 12/1212:28 pm -
1 stop10h 39m
Deal found 11/5![Frontier logo]()
$252
This Cheapflightsfares deal was found by Cheapflights users on 11/9. 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 12/34:07 pm -
1 stop24h 34m
Sun 12/68:37 pm -
1 stop24h 52m
Deal found 11/9![Frontier logo]()
$240
This FlightHub deal was found by Cheapflights users on 11/5. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/35:01 am -
1 stop13h 06m
Mon 12/76:11 pm -
1 stop14h 26m
Deal found 11/5![Frontier logo]()
$245
This Cheapflightsfares deal was found by Cheapflights users on 11/5. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/33:09 pm -
1 stop25h 32m
Sun 12/68:37 pm -
1 stop28h 15m
Deal found 11/5![Frontier logo]()
$250
This OneTravel deal was found by Cheapflights users on 11/6. 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 OneTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/33:43 am -
1 stop12h 58m
Mon 12/76:11 pm -
1 stop14h 26m
Deal found 11/6![Frontier logo]()
$250
This Trip.com deal was found by Cheapflights users on 11/6. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/33:09 pm -
1 stop25h 32m
Thu 12/108:37 pm -
1 stop28h 15m
Deal found 11/6![Frontier logo]()
$317
This Trip.com deal was found by Cheapflights users on 11/9. 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.
Sat 12/55:01 am -
1 stop8h 32m
Tue 12/812:28 pm -
1 stop10h 39m
Deal found 11/9![Frontier logo]()
$246
This Trip.com deal was found by Cheapflights users on 11/9. 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.
Tue 12/85:01 am -
1 stop8h 32m
Sat 12/1212:28 pm -
1 stop10h 39m
Deal found 11/9![Frontier logo]()
$247
One-way flights from Puerto Rico to MidwaySearch for one-way flight options from Puerto Rico to Midway. Find affordable one-way fares based on user searches. Data last updated November 9, 2026.
Search for one-way flight options from Puerto Rico to Midway. Find affordable one-way fares based on user searches. Data last updated November 9, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 11/6. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/23:47 am -
1 stop12h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/6![Frontier logo]()
$124
This CheapOair deal was found by Cheapflights users on 11/4. 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.
Tue 12/85:01 am -
1 stop8h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/4![Frontier logo]()
$124
This Super.com deal was found by Cheapflights users on 11/8. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/134:04 pm -
1 stop27h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/8![Frontier logo]()
$125
This Kiwi.com deal was found by Cheapflights users on 11/9. 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 1/1212:46 pm -
1 stop13h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/9![Frontier logo]()
$127
This OneTravel deal was found by Cheapflights users on 11/7. 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 OneTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/94:04 pm -
1 stop29h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/7![Frontier logo]()
$129
This Cheapflightsfares deal was found by Cheapflights users on 11/9. 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.
Tue 11/173:55 pm -
1 stop9h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/9![Frontier logo]()
$132
This Frontier deal was found by Cheapflights users on 11/8. 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.
Wed 11/183:55 pm -
1 stop9h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/8![Frontier logo]()
$134
This Trip.com deal was found by Cheapflights users on 11/9. 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.
Thu 11/193:55 pm -
1 stop9h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/9![Frontier logo]()
$136
This Cheapflightsfares deal was found by Cheapflights users on 11/9. 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.
Fri 11/2010:21 pm -
1 stop23h 26m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/9![Frontier logo]()
$138
This Frontier deal was found by Cheapflights users on 11/7. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/53:59 am -
2 stops14h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/7![Frontier logo]()
$289
This Trip.com deal was found by Cheapflights users on 11/9. 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 12/273:13 am -
1 stop18h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/9![Frontier logo]()
$330
This Super.com deal was found by Cheapflights users on 11/8. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/283:47 am -
1 stop18h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/8![Frontier logo]()
$478
Find flight deals from Puerto Rico to Midway
Keep the following information in mind while searching for Puerto Rico to Midway flight deals. Data was last updated November 9, 2026.
Round-trip from | $240 (Cheapflightsfares) |
|---|---|
One-way from | $124 (Cheapflightsfares) |
Popular in | June |
Cheapest in | February |
Average price | $383 |
Cheapflights Fare Finder
Customize your flight search to find flights from Puerto Rico to Midway 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 November 9, 2026.
Use the filters below to find and compare flights from Puerto Rico to Chicago Midway Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Wed 11/18
3:55 pm-11:47 pm
1 stop9h 52m
Chicago Midway
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$136
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Wed 12/9
5:40 am-2:50 pm
2 stops11h 10m
Chicago Midway
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$138
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 12/17
2:20 pm-10:45 pm
1 stop10h 25m
Chicago Midway
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$138
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Fri 1/22
5:35 am-12:35 pm
2 stops9h 00m
Chicago Midway
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$158
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Sun 12/20
6:30 am-4:19 pm
1 stop11h 49m
Chicago Midway
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$163
Quickest round-trip
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Sat 11/21
3:30 pm-6:40 pm
Nonstop5h 10m
Chicago Midway
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$188
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Tue 11/17
6:10 am-12:55 pm
2 stops8h 45m
Chicago Midway
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$192
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Wed 12/23
5:35 am-12:05 pm
2 stops8h 30m
Chicago Midway
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$238
AguadillaChicago
BQN Aguadilla Borinquen - MDW Chicago Midway
BQNMDW
Aguadilla Borinquen
Thu 12/3
3:09 pm-2:41 pm
1 stop25h 32m
Chicago Midway
Sun 12/6
8:37 pm-2:52 am
1 stop28h 15m
$250
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 11/26
5:19 am-12:21 pm
1 stop9h 02m
Chicago Midway
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$251
Showing 1-10 of 31 resultsSorted by cheapest first
Best time to book a flight from Puerto Rico to Midway
Have a flexible travel schedule? Discover the best time to fly to Midway from Puerto Rico with our price prediction graph.
SJU-MDW
BQN-MDW
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 Puerto Rico to Chicago Midway Airport
PR0-MDW
SJU-MDW
BQN-MDW
What is the cheapest month to book a flight from Puerto Rico to Chicago Midway Airport?
Currently, September is the cheapest month in which you can book a flight from Puerto Rico to Chicago Midway Airport (average of $276). Flying from Puerto Rico to Chicago Midway Airport in February is currently the most expensive (average of $726). 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 PR to MDW?
Find hourly flight availability from Puerto Rico to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 9, 2026.
When flying from Puerto Rico to Chicago Midway Airport, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
Reviews of airlines servicing Midway
Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated November 9, 2026.
Read reviews from past customers who have flown Southwest from Puerto Rico to Chicago Midway Airport. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
Find useful and relevant information for your journey from Puerto Rico to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago Midway Airport?
Book flights to Chicago Midway Airport if you plan to visit one of these locationsBenton Harbor
Merrillville
Lansing
Valparaiso
Hammond
Saint Joseph
Porter
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
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Midway flight routes
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Popular flights
Alternative routes for Puerto Rico to Midway
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Midway by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Puerto Rico to Midway by cabin class
Find flights from Puerto Rico to Midway, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Other flights to Midway
Explore flights to Midway departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on November 9, 2026.
Puerto Rico and Midway flights
Browse other Puerto Rico and Midway flight options. Last updated on November 9, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top airline flying from Puerto Rico to Midway
Discover the top airline that operate flights from Puerto Rico to Midway. 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 November 9, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$266 | Average$476 | FlexibilityNo cancel fee | On-time63% |