$119+ 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 11/18. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MDW
Nov 29 — Dec 61
Round-trip
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 October 30, 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 October 30, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/25. 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 11/193:55 pm -
1 stop9h 52m
Mon 11/231:16 pm -
1 stop10h 20m
Deal found 10/25![Frontier logo]()
$229
This Cheapflightsfares deal was found by Cheapflights users on 10/27. 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 10/27![Frontier logo]()
$230
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 11/215:19 am -
1 stop10h 26m
Thu 11/261:16 pm -
1 stop10h 20m
Deal found 10/27![Frontier logo]()
$231
This Frontier deal was found by Cheapflights users on 10/28. 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 12/23:43 am -
1 stop12h 58m
Sat 12/512:28 pm -
1 stop10h 39m
Deal found 10/28![Frontier logo]()
$232
This Kiwi.com deal was found by Cheapflights users on 10/27. 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.
Sun 11/227:17 am -
1 stop14h 30m
Thu 11/261:16 pm -
1 stop10h 20m
Deal found 10/27![Frontier logo]()
$233
This FlightHub deal was found by Cheapflights users on 10/27. 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.
Sun 11/223:55 am -
1 stop17h 52m
Thu 11/261:16 pm -
1 stop10h 20m
Deal found 10/27![Frontier logo]()
$235
This Trip.com deal was found by Cheapflights users on 10/28. 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.
Fri 11/205:19 am -
1 stop8h 36m
Thu 11/261:16 pm -
1 stop10h 20m
Deal found 10/28![Frontier logo]()
$236
This OneTravel deal was found by Cheapflights users on 10/29. 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 11/193:55 pm -
1 stop9h 52m
Sun 11/228:42 pm -
1 stop11h 17m
Deal found 10/29![Frontier logo]()
$238
This Kiwi.com deal was found by Cheapflights users on 10/25. 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 11/108:45 am -
2 stops17h 02m
Mon 11/166:08 am -
1 stop16h 51m
Deal found 10/25![Frontier logo]()
$245
This Cheapflightsfares deal was found by Cheapflights users on 10/25. 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 11/123:55 pm -
1 stop9h 52m
Thu 11/261:16 pm -
1 stop10h 20m
Deal found 10/25![Frontier logo]()
$248
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 October 30, 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 October 30, 2026.
This Southwest deal was found by Cheapflights users on 10/29. 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 1/147:25 am -
2 stops9h 20m
Sun 1/173:35 pm -
1 stop7h 00m
Deal found 10/29![Southwest logo]()
$286
This Southwest deal was found by Cheapflights users on 10/27. 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 11/135:50 pm -
1 stop7h 25m
Tue 11/174:25 pm -
1 stop6h 25m
Deal found 10/27![Southwest logo]()
$298
This Southwest deal was found by Cheapflights users on 10/27. 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 11/54:00 pm -
1 stop9h 00m
Tue 11/101:20 pm -
1 stop7h 05m
Deal found 10/27![Southwest logo]()
$306
This Southwest deal was found by Cheapflights users on 10/29. 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 11/710:55 am -
1 stop8h 30m
Mon 11/163:00 pm -
1 stop7h 50m
Deal found 10/29![Southwest logo]()
$340
This Southwest deal was found by Cheapflights users on 10/28. 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 1/207:25 am -
2 stops9h 20m
Sun 1/242:25 pm -
2 stops8h 10m
Deal found 10/28![Southwest logo]()
$343
This Southwest deal was found by Cheapflights users on 10/25. 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 12/412:30 pm -
2 stops8h 35m
Mon 12/71:15 pm -
2 stops8h 10m
Deal found 10/25![Southwest logo]()
$346
This Southwest deal was found by Cheapflights users on 10/27. 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 11/1311:20 am -
2 stops9h 00m
Mon 11/161:20 pm -
2 stops9h 30m
Deal found 10/27![Southwest logo]()
$346
This Southwest deal was found by Cheapflights users on 10/26. 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 12/312:30 pm -
2 stops8h 35m
Tue 12/81:15 pm -
2 stops8h 10m
Deal found 10/26![Southwest logo]()
$346
This Southwest deal was found by Cheapflights users on 10/28. 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 11/64:00 pm -
2 stops9h 15m
Mon 11/98:40 pm -
1 stop11h 15m
Deal found 10/28![Southwest logo]()
$375
This Southwest deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/410:45 am -
2 stops10h 20m
Wed 11/119:55 am -
2 stops10h 00m
Deal found 10/26![Southwest logo]()
$401
This Southwest deal was found by Cheapflights users on 10/27. 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 11/78:45 am -
2 stops9h 45m
Wed 11/1111:45 am -
2 stops8h 40m
Deal found 10/27![Southwest logo]()
$411
Last-minute flights from Puerto Rico to MidwayDiscover last-minute flight deals from Puerto Rico to Midway. Data last updated October 30, 2026 and is based on user searches.
Discover last-minute flight deals from Puerto Rico to Midway. Data last updated October 30, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 10/25. 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 11/33:59 pm -
1 stop9h 48m
Tue 11/106:08 am -
1 stop16h 51m
Deal found 10/25![Frontier logo]()
$256
This Kiwi.com deal was found by Cheapflights users on 10/25. 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 11/108:45 am -
2 stops17h 02m
Mon 11/166:08 am -
1 stop16h 51m
Deal found 10/25![Frontier logo]()
$245
This Cheapflightsfares deal was found by Cheapflights users on 10/25. 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 11/123:55 pm -
1 stop9h 52m
Thu 11/261:16 pm -
1 stop10h 20m
Deal found 10/25![Frontier logo]()
$248
This Kiwi.com deal was found by Cheapflights users on 10/25. 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 11/193:55 pm -
1 stop9h 52m
Mon 11/231:16 pm -
1 stop10h 20m
Deal found 10/25![Frontier logo]()
$229
This Cheapflightsfares deal was found by Cheapflights users on 10/27. 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 10/27![Frontier logo]()
$230
This OneTravel deal was found by Cheapflights users on 10/29. 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 11/193:55 pm -
1 stop9h 52m
Sun 11/228:42 pm -
1 stop11h 17m
Deal found 10/29![Frontier logo]()
$238
This Trip.com deal was found by Cheapflights users on 10/28. 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.
Fri 11/205:19 am -
1 stop8h 36m
Thu 11/261:16 pm -
1 stop10h 20m
Deal found 10/28![Frontier logo]()
$236
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 11/215:19 am -
1 stop10h 26m
Thu 11/261:16 pm -
1 stop10h 20m
Deal found 10/27![Frontier logo]()
$231
This Kiwi.com deal was found by Cheapflights users on 10/27. 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.
Sun 11/227:17 am -
1 stop14h 30m
Thu 11/261:16 pm -
1 stop10h 20m
Deal found 10/27![Frontier logo]()
$233
This FlightHub deal was found by Cheapflights users on 10/27. 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.
Sun 11/223:55 am -
1 stop17h 52m
Thu 11/261:16 pm -
1 stop10h 20m
Deal found 10/27![Frontier logo]()
$235
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 October 30, 2026.
Search for one-way flight options from Puerto Rico to Midway. Find affordable one-way fares based on user searches. Data last updated October 30, 2026.
This OneTravel deal was found by Cheapflights users on 10/25. 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 11/183:55 pm -
1 stop9h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![Frontier logo]()
$119
This Cheapflightsfares deal was found by Cheapflights users on 10/27. 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 1/1310:53 pm -
1 stop22h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Frontier logo]()
$120
This Trip.com deal was found by Cheapflights users on 10/27. 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 12/134:04 pm -
1 stop27h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Frontier logo]()
$124
This Trip.com deal was found by Cheapflights users on 10/27. 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.
Fri 11/2010:21 pm -
1 stop23h 26m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Frontier logo]()
$125
This Super.com deal was found by Cheapflights users on 10/26. 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 11/143:55 pm -
1 stop9h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Frontier logo]()
$132
This Cheapflightsfares deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/73:55 pm -
1 stop9h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Frontier logo]()
$136
This OneTravel deal was found by Cheapflights users on 10/26. 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 11/123:55 pm -
1 stop9h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Frontier logo]()
$137
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 12/82:49 am -
2 stops39h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Frontier logo]()
$139
This FlightHub deal was found by Cheapflights users on 10/28. 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.
Tue 11/103:55 pm -
1 stop9h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Frontier logo]()
$140
This OneTravel deal was found by Cheapflights users on 10/29. 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 11/113:55 pm -
1 stop9h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![Frontier logo]()
$141
This OneTravel deal was found by Cheapflights users on 10/27. 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.
Tue 11/33:59 pm -
1 stop9h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Frontier logo]()
$142
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 October 30, 2026.
Round-trip from | $229 (Kiwi.com) |
|---|---|
One-way from | $119 (OneTravel) |
Popular in | June |
Cheapest in | February |
Average price | $405 |
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 October 30, 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 1/13
7:25 am-2:45 pm
2 stops9h 20m
Chicago Midway
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$145
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Sat 1/23
7:45 am-4:22 pm
1 stop10h 37m
Chicago Midway
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$145
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Wed 1/20
7:25 am-2:45 pm
2 stops9h 20m
Chicago Midway
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$145
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 1/14
4:10 pm-10:17 pm
1 stop8h 07m
Chicago Midway
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$145
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Sat 1/16
7:45 am-4:22 pm
1 stop10h 37m
Chicago Midway
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$145
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Mon 12/21
2:29 am-12:10 pm
1 stop11h 41m
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
$169
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Fri 11/20
5:50 pm-11:10 pm
1 stop7h 20m
Chicago Midway
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$185
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 12/3
7:40 am-2:55 pm
2 stops9h 15m
Chicago Midway
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$185
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Tue 11/10
5:40 am-12:55 pm
2 stops9h 15m
Chicago Midway
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$187
Showing 1-10 of 21 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
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
No data available for this route at this time. Please check back soon.
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 October 30, 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.
Overall
7.9
Crew
8.6
Boarding
8.1
Food
7.0
Entertainment
7.4
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
7.9
Crew
8.6
Boarding
8.1
Food
7.0
Entertainment
7.4
Comfort
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
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 October 30, 2026.
Puerto Rico and Midway flights
Browse other Puerto Rico and Midway flight options. Last updated on October 30, 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 October 30, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$266 | Average$425 | FlexibilityNo cancel fee | On-time63% |