$115+ 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 10/1. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MDW
Oct 5 — Oct 121
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
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 September 5, 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 September 5, 2026.
This Travelocity deal was found by Cheapflights users on 9/2. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/15:11 pm -
1 stop7h 33m
Sun 10/46:25 am -
1 stop8h 41m
Deal found 9/2![Frontier logo]()
$232
This Trip.com deal was found by Cheapflights users on 8/31. 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 9/256:33 am -
1 stop12h 18m
Sun 10/46:25 am -
1 stop8h 41m
Deal found 8/31![Frontier logo]()
$236
This CheapOair deal was found by Cheapflights users on 9/3. 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.
Wed 10/145:11 pm -
1 stop7h 32m
Wed 10/216:21 am -
1 stop8h 45m
Deal found 9/3![Frontier logo]()
$238
This OneTravel deal was found by Cheapflights users on 9/2. 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.
Fri 9/256:33 am -
1 stop12h 18m
Sun 9/276:25 am -
1 stop8h 41m
Deal found 9/2![Frontier logo]()
$240
This Southwest deal was found by Cheapflights users on 9/2. 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 9/2510:00 am -
1 stop6h 35m
Tue 9/2912:45 pm -
2 stops8h 20m
Deal found 9/2![Southwest logo]()
$246
This Travelocity deal was found by Cheapflights users on 9/1. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/105:11 pm -
1 stop7h 32m
Tue 10/136:21 am -
1 stop8h 45m
Deal found 9/1![Frontier logo]()
$247
This Expedia deal was found by Cheapflights users on 9/3. 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.
Sun 10/45:11 pm -
1 stop7h 32m
Wed 10/76:25 am -
1 stop7h 54m
Deal found 9/3![Frontier logo]()
$257
This Southwest deal was found by Cheapflights users on 8/31. 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 9/116:30 am -
2 stops8h 15m
Wed 9/167:30 am -
1 stop10h 35m
Deal found 8/31![Southwest logo]()
$261
This Southwest deal was found by Cheapflights users on 9/3. 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 9/102:35 pm -
1 stop7h 55m
Sun 9/138:05 pm -
1 stop12h 05m
Deal found 9/3![Southwest logo]()
$266
This Frontier deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/105:11 pm -
1 stop7h 32m
Sun 10/256:24 am -
1 stop8h 42m
Deal found 9/1![Frontier logo]()
$275
This Southwest deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/28:50 pm -
1 stop13h 45m
Fri 10/92:50 pm -
2 stops8h 20m
Deal found 9/4![Southwest logo]()
$281
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 September 5, 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 September 5, 2026.
This Southwest deal was found by Cheapflights users on 9/1. 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 9/106:00 am -
2 stops9h 30m
Thu 9/173:15 pm -
1 stop6h 55m
Deal found 9/1![Southwest logo]()
$266
This Southwest deal was found by Cheapflights users on 9/3. 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 10/245:00 am -
2 stops9h 55m
Fri 10/302:50 pm -
2 stops8h 20m
Deal found 9/3![Southwest logo]()
$281
This Southwest deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/45:40 pm -
1 stop7h 00m
Wed 10/79:30 am -
2 stops11h 25m
Deal found 9/3![Southwest logo]()
$301
This Southwest deal was found by Cheapflights users on 9/4. 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.
Thu 10/14:10 pm -
2 stops8h 00m
Mon 10/52:15 pm -
1 stop9h 10m
Deal found 9/4![Southwest logo]()
$301
This Southwest deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/294:10 pm -
1 stop9h 15m
Fri 11/64:00 pm -
1 stop7h 05m
Deal found 9/2![Southwest logo]()
$320
This Southwest deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/910:50 pm -
1 stop11h 45m
Mon 10/128:40 pm -
1 stop11h 30m
Deal found 9/4![Southwest logo]()
$336
This Southwest deal was found by Cheapflights users on 9/4. 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.
Thu 10/225:30 am -
2 stops8h 15m
Mon 10/261:20 pm -
2 stops8h 50m
Deal found 9/4![Southwest logo]()
$336
This Southwest deal was found by Cheapflights users on 9/3. 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 10/317:45 am -
2 stops10h 00m
Sat 11/71:05 pm -
2 stops8h 25m
Deal found 9/3![Southwest logo]()
$351
This Southwest deal was found by Cheapflights users on 9/1. 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 10/37:50 am -
1 stop7h 25m
Thu 10/82:50 pm -
2 stops8h 20m
Deal found 9/1![Southwest logo]()
$360
Last-minute flights from Puerto Rico to MidwayDiscover last-minute flight deals from Puerto Rico to Midway. Data last updated September 5, 2026 and is based on user searches.
Discover last-minute flight deals from Puerto Rico to Midway. Data last updated September 5, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 9/3. 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 9/106:00 am -
2 stops9h 30m
Sun 9/138:05 pm -
1 stop12h 05m
Deal found 9/3![Southwest logo]()
$266
This Southwest deal was found by Cheapflights users on 8/31. 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 9/116:30 am -
2 stops8h 15m
Wed 9/167:30 am -
1 stop10h 35m
Deal found 8/31![Southwest logo]()
$261
This Trip.com deal was found by Cheapflights users on 8/31. 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 9/256:33 am -
1 stop12h 18m
Sun 10/46:25 am -
1 stop8h 41m
Deal found 8/31![Frontier logo]()
$236
This OneTravel deal was found by Cheapflights users on 9/2. 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.
Fri 9/256:33 am -
1 stop12h 18m
Sun 9/276:25 am -
1 stop8h 41m
Deal found 9/2![Frontier logo]()
$240
This Southwest deal was found by Cheapflights users on 9/2. 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 9/2510:00 am -
1 stop6h 35m
Tue 9/2912:45 pm -
2 stops8h 20m
Deal found 9/2![Southwest logo]()
$246
This Frontier deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/15:11 pm -
1 stop7h 33m
Mon 10/56:50 am -
1 stop7h 29m
Deal found 9/2![Frontier logo]()
$232
This Southwest deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/28:50 pm -
1 stop13h 45m
Fri 10/92:50 pm -
2 stops8h 20m
Deal found 9/4![Southwest logo]()
$281
This Expedia deal was found by Cheapflights users on 9/3. 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.
Sun 10/45:11 pm -
1 stop7h 32m
Wed 10/76:25 am -
1 stop7h 54m
Deal found 9/3![Frontier logo]()
$257
This Travelocity deal was found by Cheapflights users on 9/1. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/105:11 pm -
1 stop7h 32m
Tue 10/136:21 am -
1 stop8h 45m
Deal found 9/1![Frontier logo]()
$247
This Frontier deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/105:11 pm -
1 stop7h 32m
Sun 10/256:24 am -
1 stop8h 42m
Deal found 9/1![Frontier logo]()
$275
This CheapOair deal was found by Cheapflights users on 9/3. 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.
Wed 10/145:11 pm -
1 stop7h 32m
Wed 10/216:21 am -
1 stop8h 45m
Deal found 9/3![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 September 5, 2026.
Search for one-way flight options from Puerto Rico to Midway. Find affordable one-way fares based on user searches. Data last updated September 5, 2026.
This Super.com deal was found by Cheapflights users on 9/2. 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.
Thu 10/15:11 pm -
1 stop7h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Frontier logo]()
$115
This Frontier deal was found by Cheapflights users on 9/2. 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 9/306:33 am -
1 stop12h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Frontier logo]()
$116
This Trip.com deal was found by Cheapflights users on 9/2. 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 10/76:30 am -
1 stop12h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Frontier logo]()
$118
This Trip.com deal was found by Cheapflights users on 9/2. 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 11/103:59 pm -
1 stop9h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Frontier logo]()
$119
This Southwest deal was found by Cheapflights users on 9/2. 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 9/186:30 am -
2 stops8h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Southwest logo]()
$128
This Frontier deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/23:59 pm -
1 stop9h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Frontier logo]()
$131
This Southwest deal was found by Cheapflights users on 9/3. 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 9/165:15 am -
2 stops7h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Southwest logo]()
$133
This Frontier deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/45:11 pm -
1 stop7h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Frontier logo]()
$141
This Southwest deal was found by Cheapflights users on 9/1. 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 9/116:30 am -
2 stops8h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/1![Southwest logo]()
$143
This Kiwi.com deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/27:15 am -
2 stops35h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 8/31![Frontier logo]()
$151
This Frontier deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/233:30 am -
1 stop10h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Frontier logo]()
$212
This Kiwi.com deal was found by Cheapflights users on 9/2. 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 9/1611:12 am -
2 stops25h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Frontier logo]()
$235
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 September 5, 2026.
Round-trip from | $232 (Frontier) |
|---|---|
One-way from | $115 (Super.com) |
Popular in | June |
Cheapest in | February |
Average price | $276 |
Good one-way deal | $342 or less |
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 September 5, 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
Fri 9/18
6:30 am-1:45 pm
2 stops8h 15m
Chicago Midway
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$128
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Wed 12/2
6:40 am-6:55 pm
1 stop14h 15m
Chicago Midway
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$133
Quickest round-trip
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Wed 9/30
11:50 am-5:40 pm
1 stop6h 50m
Chicago Midway
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$133
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Sun 9/27
9:25 pm-8:45 am
1 stop12h 20m
Chicago Midway
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$133
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Tue 9/15
2:25 pm-8:50 pm
1 stop7h 25m
Chicago Midway
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$133
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Sat 9/19
2:00 pm-8:35 pm
1 stop7h 35m
Chicago Midway
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$133
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Mon 9/21
8:55 pm-9:25 am
1 stop13h 30m
Chicago Midway
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$133
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Tue 9/22
5:15 am-12:05 pm
2 stops7h 50m
Chicago Midway
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$133
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Mon 11/2
5:50 pm-11:05 pm
1 stop7h 15m
Chicago Midway
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$133
AguadillaChicago
BQN Aguadilla Borinquen - MDW Chicago Midway
BQNMDW
Aguadilla Borinquen
Mon 11/23
3:30 am-12:24 pm
1 stop10h 54m
Chicago Midway
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$212
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
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
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 September 5, 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.
Boarding
8.1
Entertainment
7.5
Food
7.0
Overall
8.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Entertainment
7.5
Food
7.0
Overall
8.0
Comfort
8.0
Crew
8.6
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
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
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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 September 5, 2026.
Puerto Rico and Midway flights
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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 September 5, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$266 | Average$540 | FlexibilityNo cancel fee | On-time63% |