$127+ 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 8/15. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MDW
Sep 7 — Sep 141
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 August 8, 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 August 8, 2026.
This Southwest deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/112:35 pm -
1 stop9h 10m
Sun 9/138:05 pm -
1 stop12h 05m
Deal found 8/5![Southwest logo]()
$256
This Southwest deal was found by Cheapflights users on 8/4. 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.
Sat 9/510:25 am -
1 stop10h 20m
Tue 9/159:40 am -
1 stop7h 30m
Deal found 8/4![Southwest logo]()
$266
This Southwest deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/286:30 am -
2 stops8h 15m
Sat 8/2911:00 am -
1 stop6h 15m
Deal found 8/5![Southwest logo]()
$276
This Southwest deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/276:00 am -
2 stops9h 30m
Tue 9/112:45 pm -
2 stops8h 15m
Deal found 8/5![Southwest logo]()
$291
This Southwest deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/225:30 am -
2 stops8h 15m
Mon 10/263:45 pm -
1 stop8h 35m
Deal found 8/7![Southwest logo]()
$301
This Southwest deal was found by Cheapflights users on 8/4. 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 9/98:20 am -
1 stop7h 25m
Tue 9/159:40 am -
1 stop10h 20m
Deal found 8/4![Southwest logo]()
$310
This Southwest deal was found by Cheapflights users on 8/4. 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 9/98:20 am -
1 stop7h 25m
Sun 9/138:05 pm -
1 stop12h 05m
Deal found 8/4![Southwest logo]()
$320
This Southwest deal was found by Cheapflights users on 8/6. 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.
Wed 8/261:45 pm -
1 stop6h 30m
Tue 9/18:30 am -
1 stop8h 40m
Deal found 8/6![Southwest logo]()
$336
This Southwest deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/810:50 pm -
1 stop10h 55m
Fri 10/912:45 pm -
1 stop10h 20m
Deal found 8/7![Southwest logo]()
$340
This Southwest deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/255:15 am -
2 stops7h 50m
Wed 9/912:45 pm -
2 stops8h 20m
Deal found 8/4![Southwest logo]()
$341
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 August 8, 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 August 8, 2026.
This Southwest deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/161:20 pm -
1 stop6h 50m
Sat 9/197:40 am -
2 stops8h 00m
Deal found 8/5![Southwest logo]()
$310
This Southwest deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/151:20 pm -
1 stop6h 50m
Sat 9/1911:45 am -
2 stops9h 15m
Deal found 8/4![Southwest logo]()
$320
This Southwest deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/186:00 am -
2 stops9h 30m
Sun 9/208:05 pm -
1 stop12h 05m
Deal found 8/7![Southwest logo]()
$320
This Southwest deal was found by Cheapflights users on 8/6. 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.
Thu 10/225:30 am -
2 stops8h 55m
Mon 10/261:20 pm -
2 stops8h 45m
Deal found 8/6![Southwest logo]()
$326
This Southwest deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/255:15 am -
2 stops7h 50m
Wed 9/912:45 pm -
1 stop8h 20m
Deal found 8/4![Southwest logo]()
$341
This Southwest deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/186:00 am -
2 stops9h 30m
Mon 9/211:20 pm -
2 stops9h 35m
Deal found 8/7![Southwest logo]()
$351
This Southwest deal was found by Cheapflights users on 8/4. 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.
Sun 10/46:35 am -
2 stops8h 40m
Fri 10/94:15 pm -
2 stops8h 05m
Deal found 8/4![Southwest logo]()
$351
This Southwest deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/196:25 am -
2 stops11h 20m
Mon 9/213:10 pm -
2 stops7h 45m
Deal found 8/7![Southwest logo]()
$376
This Southwest deal was found by Cheapflights users on 8/4. 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 9/36:00 am -
2 stops9h 30m
Mon 9/73:15 pm -
1 stop6h 55m
Deal found 8/4![Southwest logo]()
$411
This Southwest deal was found by Cheapflights users on 8/3. 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.
Mon 8/176:30 am -
2 stops8h 40m
Mon 8/243:10 pm -
2 stops7h 40m
Deal found 8/3![Southwest logo]()
$445
This Southwest deal was found by Cheapflights users on 8/4. 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 9/46:00 am -
2 stops9h 30m
Mon 9/73:15 pm -
1 stop6h 55m
Deal found 8/4![Southwest logo]()
$446
Last-minute flights from Puerto Rico to MidwayDiscover last-minute flight deals from Puerto Rico to Midway. Data last updated August 8, 2026 and is based on user searches.
Discover last-minute flight deals from Puerto Rico to Midway. Data last updated August 8, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/255:15 am -
2 stops7h 50m
Wed 9/912:45 pm -
1 stop8h 20m
Deal found 8/4![Southwest logo]()
$341
This Southwest deal was found by Cheapflights users on 8/6. 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.
Wed 8/266:00 am -
2 stops8h 30m
Tue 9/16:15 am -
1 stop6h 20m
Deal found 8/6![Southwest logo]()
$336
This Southwest deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/276:00 am -
2 stops9h 30m
Tue 9/112:45 pm -
2 stops8h 15m
Deal found 8/5![Southwest logo]()
$291
This Southwest deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/286:30 am -
2 stops8h 15m
Sat 8/2911:00 am -
1 stop6h 15m
Deal found 8/5![Southwest logo]()
$276
This Southwest deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/285:00 am -
1 stop7h 45m
Sun 8/308:05 am -
1 stop8h 00m
Deal found 8/5![Southwest logo]()
$301
This Southwest deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/15:15 am -
2 stops7h 50m
Tue 9/812:45 pm -
2 stops8h 20m
Deal found 8/4![Southwest logo]()
$326
This Southwest deal was found by Cheapflights users on 8/4. 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.
Sat 9/510:25 am -
1 stop10h 20m
Tue 9/159:40 am -
1 stop7h 30m
Deal found 8/4![Southwest logo]()
$266
This Southwest deal was found by Cheapflights users on 8/4. 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 9/98:20 am -
1 stop7h 25m
Tue 9/159:40 am -
1 stop10h 20m
Deal found 8/4![Southwest logo]()
$310
This Southwest deal was found by Cheapflights users on 8/4. 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 9/98:20 am -
1 stop7h 25m
Sun 9/138:05 pm -
1 stop12h 05m
Deal found 8/4![Southwest logo]()
$320
This Southwest deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/112:35 pm -
1 stop9h 10m
Sun 9/138:05 pm -
1 stop12h 05m
Deal found 8/5![Southwest logo]()
$256
This Delta deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/172:59 pm -
1 stop8h 46m
Wed 9/236:05 am -
1 stop6h 40m
Deal found 8/4![Delta logo]()
$348
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 August 8, 2026.
Search for one-way flight options from Puerto Rico to Midway. Find affordable one-way fares based on user searches. Data last updated August 8, 2026.
This Trip.com deal was found by Cheapflights users on 8/7. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/156:00 am -
2 stops17h 03m
Deal found 8/7![Frontier logo]()
$127
This Southwest deal was found by Cheapflights users on 8/4. 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 9/106:30 am -
2 stops8h 15m
Deal found 8/4![Southwest logo]()
$128
This Kiwi.com deal was found by Cheapflights users on 8/7. 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.
Tue 10/68:45 am -
2 stops34h 06m
Deal found 8/7![Frontier logo]()
$129
This Kiwi.com deal was found by Cheapflights users on 8/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/27:00 am -
2 stops35h 51m
Deal found 8/4![Frontier logo]()
$135
This Kiwi.com deal was found by Cheapflights users on 8/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/298:45 am -
2 stops34h 06m
Deal found 8/3![Frontier logo]()
$136
This Southwest deal was found by Cheapflights users on 8/4. 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 8/286:30 am -
2 stops8h 15m
Deal found 8/4![Southwest logo]()
$138
This Kiwi.com deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/228:45 am -
2 stops34h 06m
Deal found 8/6![Frontier logo]()
$139
This Kiwi.com deal was found by Cheapflights users on 8/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/43:08 am -
2 stops21h 36m
Deal found 8/4![Frontier logo]()
$142
This Kiwi.com deal was found by Cheapflights users on 8/7. 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.
Sun 9/137:00 am -
2 stops35h 51m
Deal found 8/7![Frontier logo]()
$145
This Kiwi.com deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/183:10 am -
2 stops20h 37m
Deal found 8/6![Frontier logo]()
$332
This Kiwi.com deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/257:27 pm -
1 stop18h 57m
Deal found 8/6![Frontier logo]()
$394
This Frontier deal was found by Cheapflights users on 8/3. 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.
Mon 11/233:30 am -
1 stop10h 54m
Deal found 8/3![Frontier logo]()
$473
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 August 8, 2026.
Round-trip from | $256 (Southwest) |
|---|---|
One-way from | $127 (Trip.com) |
Popular in | June |
Cheapest in | February |
Average price | $287 |
Good round-trip deal | $565 or less |
Good one-way deal | $279 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 2,558,603 searches. Data last updated August 8, 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
Quickest round-trip
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Wed 9/16
1:20 pm-7:10 pm
1 stop6h 50m
Chicago Midway
Sat 9/19
7:40 am-4:40 pm
2 stops8h 00m
$310
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Tue 9/15
1:20 pm-7:10 pm
1 stop6h 50m
Chicago Midway
Sat 9/19
11:45 am-10:00 pm
2 stops9h 15m
$320
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Fri 9/18
6:00 am-2:30 pm
2 stops9h 30m
Chicago Midway
Sun 9/20
8:05 pm-9:10 am
1 stop12h 05m
$320
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 10/22
5:30 am-1:25 pm
2 stops8h 55m
Chicago Midway
Mon 10/26
1:20 pm-11:05 pm
2 stops8h 45m
$326
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Tue 8/25
5:15 am-12:05 pm
2 stops7h 50m
Chicago Midway
Wed 9/9
12:45 pm-10:05 pm
1 stop8h 20m
$341
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Fri 9/18
6:00 am-2:30 pm
2 stops9h 30m
Chicago Midway
Mon 9/21
1:20 pm-11:55 pm
2 stops9h 35m
$351
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Sun 10/4
6:35 am-2:15 pm
2 stops8h 40m
Chicago Midway
Fri 10/9
4:15 pm-1:20 am
2 stops8h 05m
$351
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Sat 9/19
6:25 am-4:45 pm
2 stops11h 20m
Chicago Midway
Mon 9/21
3:10 pm-11:55 pm
2 stops7h 45m
$376
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 9/3
6:00 am-2:30 pm
2 stops9h 30m
Chicago Midway
Mon 9/7
3:15 pm-11:10 pm
1 stop6h 55m
$411
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Mon 8/17
6:30 am-2:10 pm
2 stops8h 40m
Chicago Midway
Mon 8/24
3:10 pm-11:50 pm
2 stops7h 40m
$445
Showing 1-10 of 24 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 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 August 8, 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 August 8, 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
8.0
Boarding
8.1
Food
7.0
Entertainment
7.5
Comfort
8.0
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
8.0
Boarding
8.1
Food
7.0
Entertainment
7.5
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
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 August 8, 2026.
Puerto Rico and Midway flights
Browse other Puerto Rico and Midway flight options. Last updated on August 8, 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 August 8, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$266 | Average$552 | FlexibilityNo cancel fee | On-time63% |