$95+ Cheap flights from Puerto Rico to Midway (MDW)
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 3/5. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MDW
Mrz 16 — Mrz 231
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
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
Cheapest
Best
Last-minute
One-way
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 Februar 14, 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 Februar 14, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/10. 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.
Mi 2/254:31 pm
SJU
- MDW
2 stops25h 45m
Multiple Airlines
So 3/16:15 am
MDW
- SJU
1 stop17h 54m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$198
This Frontier deal was found by Cheapflights users on 2/14. 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.
Fr 5/13:18 pm
SJU
- MDW
1 stop8h 01m
Frontier
Mo 5/46:00 am
MDW
- SJU
1 stop7h 08m
Frontier
Deal found 2/14![Frontier logo]()
$202
This Kiwi.com deal was found by Cheapflights users on 2/11. 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.
Do 3/56:00 am
SJU
- MDW
1 stop9h 56m
Frontier
Mo 3/96:00 am
MDW
- SJU
1 stop14h 03m
Frontier
Deal found 2/11![Frontier logo]()
$205
This Kiwi.com deal was found by Cheapflights users on 2/10. 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.
Do 3/56:00 am
SJU
- MDW
1 stop9h 56m
Multiple Airlines
Mo 3/96:00 am
MDW
- SJU
1 stop10h 58m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$206
This Trip.com deal was found by Cheapflights users on 2/12. 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.
Do 2/266:00 am
SJU
- MDW
1 stop9h 56m
Frontier
Mo 3/29:22 pm
MDW
- SJU
1 stop10h 32m
Frontier
Deal found 2/12![Frontier logo]()
$207
This CheapOair deal was found by Cheapflights users on 2/13. 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.
Fr 2/273:53 am
SJU
- MDW
1 stop13h 02m
Frontier
Mo 3/29:22 pm
MDW
- SJU
1 stop10h 32m
Frontier
Deal found 2/13![Frontier logo]()
$214
This OneTravel deal was found by Cheapflights users on 2/11. 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.
Fr 5/83:18 pm
SJU
- MDW
1 stop8h 01m
Frontier
Mo 5/116:00 am
MDW
- SJU
1 stop7h 08m
Frontier
Deal found 2/11![Frontier logo]()
$217
This Kiwi.com deal was found by Cheapflights users on 2/12. 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.
Mi 3/411:52 am
SJU
- MDW
1 stop28h 04m
Multiple Airlines
Mo 3/96:00 am
MDW
- SJU
1 stop18h 21m
Multiple Airlines
Deal found 2/12![Multiple Airlines logo]()
$219
This deal was found by Cheapflights users on 2/11. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mi 4/81:11 pm
SJU
- MDW
1 stop10h 08m
Frontier
Fr 4/102:56 pm
MDW
- SJU
1 stop8h 56m
Frontier
Deal found 2/11![Frontier logo]()
$223
This Kiwi.com deal was found by Cheapflights users on 2/13. 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.
Di 4/76:00 am
SJU
- MDW
1 stop15h 07m
Frontier
Mo 4/136:30 am
MDW
- SJU
1 stop17h 31m
Frontier
Deal found 2/13![Frontier logo]()
$236
This Frontier deal was found by Cheapflights users on 2/12. 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.
Mi 3/43:58 am
BQN
- MDW
1 stop12h 28m
Frontier
Di 3/1011:19 am
MDW
- BQN
1 stop13h 23m
Frontier
Deal found 2/12![Frontier logo]()
$239
This Orbitz deal was found by Cheapflights users on 2/14. 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.
Do 3/53:42 am
BQN
- MDW
1 stop11h 26m
Frontier
Di 3/1011:19 am
MDW
- BQN
1 stop13h 23m
Frontier
Deal found 2/14![Frontier logo]()
$270
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 Februar 14, 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 Februar 14, 2026.
This Expedia deal was found by Cheapflights users on 2/10. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mi 2/255:25 pm
SJU
- MDW
1 stop23h 01m
Frontier
So 3/16:15 am
MDW
- SJU
1 stop17h 54m
Frontier
Deal found 2/10![Frontier logo]()
$202
This Kiwi.com deal was found by Cheapflights users on 2/12. 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.
Mi 3/411:52 am
SJU
- MDW
1 stop28h 04m
Multiple Airlines
Mo 3/96:00 am
MDW
- SJU
1 stop18h 21m
Multiple Airlines
Deal found 2/12![Multiple Airlines logo]()
$219
This Delta deal was found by Cheapflights users on 2/13. 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.
Do 4/166:15 am
SJU
- MDW
1 stop11h 14m
Delta
Mi 4/2212:53 pm
MDW
- SJU
1 stop6h 31m
Delta
Deal found 2/13![Delta logo]()
$246
This Frontier deal was found by Cheapflights users on 2/13. 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.
Fr 5/13:18 pm
SJU
- MDW
1 stop8h 01m
Frontier
Mo 5/46:00 am
MDW
- SJU
1 stop7h 08m
Frontier
Deal found 2/13![Frontier logo]()
$202
This Frontier deal was found by Cheapflights users on 2/10. 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.
Mi 3/43:53 am
SJU
- MDW
1 stop12h 33m
Frontier
Mo 3/99:51 pm
MDW
- SJU
1 stop11h 21m
Frontier
Deal found 2/10![Frontier logo]()
$220
This Delta deal was found by Cheapflights users on 2/13. 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.
Sa 5/27:30 am
SJU
- MDW
1 stop9h 55m
Delta
Mi 5/612:53 pm
MDW
- SJU
1 stop9h 20m
Delta
Deal found 2/13![Delta logo]()
$246
This Frontier deal was found by Cheapflights users on 2/12. 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.
Mi 3/43:58 am
BQN
- MDW
1 stop12h 28m
Frontier
Di 3/1011:19 am
MDW
- BQN
1 stop13h 23m
Frontier
Deal found 2/12![Frontier logo]()
$239
This Kiwi.com deal was found by Cheapflights users on 2/12. 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.
Mi 3/44:06 pm
SJU
- MDW
2 stops23h 50m
Frontier
Mo 3/96:00 am
MDW
- SJU
1 stop18h 21m
Frontier
Deal found 2/12![Frontier logo]()
$242
This CheapOair deal was found by Cheapflights users on 2/13. 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.
Sa 4/253:18 pm
SJU
- MDW
1 stop8h 01m
Frontier
Mo 4/279:14 am
MDW
- SJU
1 stop27h 52m
Frontier
Deal found 2/13![Frontier logo]()
$250
This eDestinos deal was found by Cheapflights users on 2/10. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Di 2/244:11 pm
SJU
- MDW
1 stop28h 56m
Frontier
Fr 2/276:00 am
MDW
- SJU
2 stops42h 25m
Frontier
Deal found 2/10![Frontier logo]()
$254
This Orbitz deal was found by Cheapflights users on 2/14. 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.
Do 3/53:42 am
BQN
- MDW
1 stop11h 26m
Frontier
Di 3/1011:19 am
MDW
- BQN
1 stop13h 23m
Frontier
Deal found 2/14![Frontier logo]()
$270
This eDestinos deal was found by Cheapflights users on 2/11. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mo 4/132:38 am
BQN
- MDW
2 stops20h 41m
Frontier
Di 4/212:20 pm
MDW
- BQN
2 stops34h 23m
Frontier
Deal found 2/11![Frontier logo]()
$383
This eDestinos deal was found by Cheapflights users on 2/12. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mi 3/43:58 am
BQN
- MDW
2 stops14h 18m
Frontier
Fr 3/132:41 pm
MDW
- BQN
2 stops34h 01m
Frontier
Deal found 2/12![Frontier logo]()
$451
Last-minute flights from Puerto Rico to MidwayDiscover last-minute flight deals from Puerto Rico to Midway. Data last updated Februar 14, 2026 and is based on user searches.
Discover last-minute flight deals from Puerto Rico to Midway. Data last updated Februar 14, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 2/10. 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.
Mi 2/254:31 pm
SJU
- MDW
2 stops25h 45m
Multiple Airlines
So 3/16:15 am
MDW
- SJU
1 stop17h 54m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$198
This Orbitz deal was found by Cheapflights users on 2/11. 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.
Do 2/263:53 am
SJU
- MDW
1 stop12h 33m
Frontier
So 3/16:15 am
MDW
- SJU
1 stop28h 24m
Frontier
Deal found 2/11![Frontier logo]()
$202
This Trip.com deal was found by Cheapflights users on 2/12. 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.
Do 2/266:00 am
SJU
- MDW
1 stop9h 56m
Frontier
Mo 3/29:22 pm
MDW
- SJU
1 stop10h 32m
Frontier
Deal found 2/12![Frontier logo]()
$207
This CheapOair deal was found by Cheapflights users on 2/13. 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.
Fr 2/273:53 am
SJU
- MDW
1 stop13h 02m
Frontier
Mo 3/29:22 pm
MDW
- SJU
1 stop10h 32m
Frontier
Deal found 2/13![Frontier logo]()
$214
This Kiwi.com deal was found by Cheapflights users on 2/12. 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.
Mi 3/411:52 am
SJU
- MDW
1 stop28h 04m
Multiple Airlines
Mo 3/96:00 am
MDW
- SJU
1 stop18h 21m
Multiple Airlines
Deal found 2/12![Multiple Airlines logo]()
$219
This Frontier deal was found by Cheapflights users on 2/12. 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.
Mi 3/43:58 am
BQN
- MDW
1 stop12h 28m
Frontier
Di 3/1011:19 am
MDW
- BQN
1 stop13h 23m
Frontier
Deal found 2/12![Frontier logo]()
$239
This Kiwi.com deal was found by Cheapflights users on 2/12. 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.
Mi 3/44:06 pm
SJU
- MDW
2 stops23h 50m
Frontier
Mo 3/96:00 am
MDW
- SJU
1 stop18h 21m
Frontier
Deal found 2/12![Frontier logo]()
$242
This eDestinos deal was found by Cheapflights users on 2/12. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mi 3/43:58 am
BQN
- MDW
2 stops14h 18m
Frontier
Fr 3/132:41 pm
MDW
- BQN
2 stops34h 01m
Frontier
Deal found 2/12![Frontier logo]()
$451
This Kiwi.com deal was found by Cheapflights users on 2/11. 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.
Do 3/56:00 am
SJU
- MDW
1 stop9h 56m
Frontier
Mo 3/96:00 am
MDW
- SJU
1 stop14h 03m
Frontier
Deal found 2/11![Frontier logo]()
$205
This Kiwi.com deal was found by Cheapflights users on 2/10. 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.
Do 3/56:00 am
SJU
- MDW
1 stop9h 56m
Multiple Airlines
Mo 3/96:00 am
MDW
- SJU
1 stop10h 58m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$206
This Orbitz deal was found by Cheapflights users on 2/14. 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.
Do 3/53:42 am
BQN
- MDW
1 stop11h 26m
Frontier
Di 3/1011:19 am
MDW
- BQN
1 stop13h 23m
Frontier
Deal found 2/14![Frontier logo]()
$270
This CheapOair deal was found by Cheapflights users on 2/12. 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.
Fr 3/63:58 am
SJU
- MDW
1 stop19h 47m
Frontier
Di 3/1011:19 am
MDW
- SJU
1 stop13h 44m
Frontier
Deal found 2/12![Frontier logo]()
$238
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 Februar 14, 2026.
Search for one-way flight options from Puerto Rico to Midway. Find affordable one-way fares based on user searches. Data last updated Februar 14, 2026.
This Trip.com deal was found by Cheapflights users on 2/11. 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.
Do 3/56:00 am
SJU
- MDW
1 stop9h 56m
Frontier
Deal found 2/11![Frontier logo]()
$95
This Trip.com deal was found by Cheapflights users on 2/11. 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.
Do 2/266:00 am
SJU
- MDW
1 stop9h 56m
Frontier
Deal found 2/11![Frontier logo]()
$97
This Super.com deal was found by Cheapflights users on 2/10. 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.
Fr 2/274:16 pm
SJU
- MDW
1 stop8h 21m
Frontier
Deal found 2/10![Frontier logo]()
$100
This Priceline deal was found by Cheapflights users on 2/13. 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.
Fr 5/83:18 pm
SJU
- MDW
1 stop8h 01m
Frontier
Deal found 2/13![Frontier logo]()
$101
This Trip.com deal was found by Cheapflights users on 2/10. 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.
Fr 3/139:58 pm
SJU
- MDW
1 stop16h 43m
Frontier
Deal found 2/10![Frontier logo]()
$103
This Kiwi.com deal was found by Cheapflights users on 2/11. 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.
Fr 3/66:50 pm
SJU
- MDW
1 stop20h 51m
Frontier
Deal found 2/11![Frontier logo]()
$106
This Expedia deal was found by Cheapflights users on 2/14. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
So 4/193:18 pm
SJU
- MDW
1 stop8h 01m
Frontier
Deal found 2/14![Frontier logo]()
$107
This Trip.com deal was found by Cheapflights users on 2/12. 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.
Mi 3/1812:05 pm
SJU
- MDW
1 stop11h 14m
Multiple Airlines
Deal found 2/12![Multiple Airlines logo]()
$109
This Expedia deal was found by Cheapflights users on 2/10. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fr 3/63:58 am
SJU
- MDW
1 stop11h 10m
Frontier
Deal found 2/10![Frontier logo]()
$110
This Kiwi.com deal was found by Cheapflights users on 2/11. 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.
Di 5/191:21 am
SJU
- MDW
1 stop12h 39m
Frontier
Deal found 2/11![Frontier logo]()
$117
This Kiwi.com deal was found by Cheapflights users on 2/10. 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.
Mo 3/23:59 am
BQN
- MDW
2 stops17h 08m
Frontier
Deal found 2/10![Frontier logo]()
$167
This Trip.com deal was found by Cheapflights users on 2/14. 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.
Sa 3/142:42 am
BQN
- MDW
1 stop14h 10m
Frontier
Deal found 2/14![Frontier logo]()
$294
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 Februar 14, 2026.
Round-trip from | $198 (Kiwi.com) |
|---|---|
One-way from | $95 (Trip.com) |
Popular in | December |
Cheapest in | February |
Average price | $191 |
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 2,558,603 searches. Data last updated Februar 14, 2026.
Use the filters below to find and compare flights from Puerto Rico to Chicago Midway Airport that are best for you.
Fly from
Puerto Rico
Fly to
Midway
Route
Depart
Return
Price
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Mi 2/25
5:25 pm-2:26 pm
1 stop23h 01m
Chicago Midway
So 3/1
6:15 am-2:09 am
1 stop17h 54m
$202
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Fr 5/1
3:18 pm-10:19 pm
1 stop8h 01m
Chicago Midway
Mo 5/4
6:00 am-2:08 pm
1 stop7h 08m
$202
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Mi 3/4
11:52 am-1:56 pm
1 stop28h 04m
Chicago Midway
Mo 3/9
6:00 am-1:21 am
1 stop18h 21m
$219
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Mi 3/4
3:53 am-2:26 pm
1 stop12h 33m
Chicago Midway
Mo 3/9
9:51 pm-10:12 am
1 stop11h 21m
$220
AguadillaChicago
BQN - MDW
BQNMDW
Aguadilla Borinquen
Mi 3/4
3:58 am-2:26 pm
1 stop12h 28m
Chicago Midway
Di 3/10
11:19 am-1:42 am
1 stop13h 23m
$239
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Mi 3/4
4:06 pm-1:56 pm
2 stops23h 50m
Chicago Midway
Mo 3/9
6:00 am-1:21 am
1 stop18h 21m
$242
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Do 4/16
6:15 am-4:29 pm
1 stop11h 14m
Chicago Midway
Mi 4/22
12:53 pm-8:24 pm
1 stop6h 31m
$246
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Sa 5/2
7:30 am-4:25 pm
1 stop9h 55m
Chicago Midway
Mi 5/6
12:53 pm-11:13 pm
1 stop9h 20m
$246
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Sa 4/25
3:18 pm-10:19 pm
1 stop8h 01m
Chicago Midway
Mo 4/27
9:14 am-2:06 pm
1 stop27h 52m
$250
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Di 2/24
4:11 pm-7:07 pm
1 stop28h 56m
Chicago Midway
Fr 2/27
6:00 am-2:25 am
2 stops42h 25m
$254
Showing 1-10 of 25 results
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, December is the cheapest month in which you can book a flight from Puerto Rico to Chicago Midway Airport (average of $213). Flying from Puerto Rico to Chicago Midway Airport in February is currently the most expensive (average of $427). 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 Februar 14, 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 Februar 14, 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.
Food
7.0
Overall
8.0
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Food
7.0
Overall
8.0
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
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 locationsLansing
Merrillville
Hammond
Porter
Benton Harbor
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
Flights by cabin class
Midway flight routes
Other flight options
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 Februar 14, 2026.
Puerto Rico and Midway flights
Browse other Puerto Rico and Midway flight options. Last updated on Februar 14, 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 2,558,603 searches. Data last updated Februar 14, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$419 | Average$553 | FlexibilityNo cancel fee | On-time63% |