$157+ 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 10/6. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MDW
Aug 6 — Aug 131
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
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Puerto Rico to Midway
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Cheapest flights from Puerto Rico to MidwayExplore the most affordable flight options available from Puerto Rico to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 7, 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 July 7, 2026.
This Southwest deal was found by Cheapflights users on 7/6. 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 8/276:30 am
SJU
- MDW
2 stops8h 15m
Southwest
Sun 8/308:20 am
MDW
- SJU
1 stop13h 25m
Southwest
Deal found 7/6![Southwest logo]()
$246
This Southwest deal was found by Cheapflights users on 7/6. 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 8/265:15 am
SJU
- MDW
2 stops7h 50m
Southwest
Tue 9/112:45 pm
MDW
- SJU
2 stops8h 15m
Southwest
Deal found 7/6![Southwest logo]()
$256
This Southwest deal was found by Cheapflights users on 7/4. 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 8/265:15 am
SJU
- MDW
2 stops7h 50m
Southwest
Sat 8/297:50 am
MDW
- SJU
2 stops7h 50m
Southwest
Deal found 7/4![Southwest logo]()
$266
This Southwest deal was found by Cheapflights users on 7/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/239:25 pm
SJU
- MDW
1 stop13h 35m
Southwest
Thu 8/2711:15 am
MDW
- SJU
1 stop9h 55m
Southwest
Deal found 7/6![Southwest logo]()
$291
This Southwest deal was found by Cheapflights users on 7/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/116:30 am
SJU
- MDW
2 stops8h 15m
Southwest
Tue 9/1512:45 pm
MDW
- SJU
2 stops8h 15m
Southwest
Deal found 7/6![Southwest logo]()
$296
This Southwest deal was found by Cheapflights users on 7/5. 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 8/198:20 am
SJU
- MDW
2 stops9h 35m
Southwest
Thu 8/273:15 pm
MDW
- SJU
1 stop6h 50m
Southwest
Deal found 7/5![Southwest logo]()
$306
This Delta deal was found by Cheapflights users on 7/6. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2612:56 pm
SJU
- MDW
1 stop10h 40m
Delta
Sat 8/296:11 am
MDW
- SJU
1 stop9h 27m
Delta
Deal found 7/6![Delta logo]()
$311
This Southwest deal was found by Cheapflights users on 7/6. 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 7/2310:20 pm
SJU
- MDW
2 stops12h 40m
Southwest
Tue 7/284:40 pm
MDW
- SJU
1 stop6h 40m
Southwest
Deal found 7/6![Southwest logo]()
$316
This Southwest deal was found by Cheapflights users on 7/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/75:00 am
SJU
- MDW
2 stops8h 25m
Southwest
Fri 8/147:50 pm
MDW
- SJU
1 stop12h 35m
Southwest
Deal found 7/6![Southwest logo]()
$326
This Southwest deal was found by Cheapflights users on 7/5. 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.
Tue 8/115:15 am
SJU
- MDW
1 stop7h 50m
Southwest
Mon 8/1711:15 am
MDW
- SJU
1 stop9h 55m
Southwest
Deal found 7/5![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 July 7, 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 July 7, 2026.
This Southwest deal was found by Cheapflights users on 7/2. 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 8/2710:00 am
SJU
- MDW
1 stop6h 35m
Southwest
Wed 9/26:15 am
MDW
- SJU
1 stop9h 10m
Southwest
Deal found 7/2![Southwest logo]()
$246
This Delta deal was found by Cheapflights users on 7/5. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/212:59 pm
SJU
- MDW
1 stop8h 37m
Delta
Mon 8/246:05 am
MDW
- SJU
1 stop9h 33m
Delta
Deal found 7/5![Delta logo]()
$356
This Southwest deal was found by Cheapflights users on 7/3. 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.
Tue 8/255:15 am
SJU
- MDW
1 stop7h 50m
Southwest
Wed 9/212:45 pm
MDW
- SJU
2 stops8h 15m
Southwest
Deal found 7/3![Southwest logo]()
$246
This Southwest deal was found by Cheapflights users on 7/6. 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.
Sat 8/226:25 am
SJU
- MDW
2 stops11h 40m
Southwest
Tue 9/112:20 pm
MDW
- SJU
1 stop7h 45m
Southwest
Deal found 7/6![Southwest logo]()
$256
This Southwest deal was found by Cheapflights users on 7/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/75:00 am
SJU
- MDW
2 stops8h 25m
Southwest
Mon 8/103:15 pm
MDW
- SJU
1 stop6h 50m
Southwest
Deal found 7/6![Southwest logo]()
$336
This Southwest deal was found by Cheapflights users on 7/4. 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 9/35:30 am
SJU
- MDW
2 stops10h 25m
Southwest
Thu 9/101:00 pm
MDW
- SJU
2 stops8h 50m
Southwest
Deal found 7/4![Southwest logo]()
$356
This Southwest deal was found by Cheapflights users on 7/2. 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.
Sat 9/1910:25 am
SJU
- MDW
1 stop10h 15m
Southwest
Mon 9/219:10 am
MDW
- SJU
1 stop9h 55m
Southwest
Deal found 7/2![Southwest logo]()
$376
This Southwest deal was found by Cheapflights users on 7/2. 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 9/185:30 am
SJU
- MDW
2 stops10h 25m
Southwest
Mon 9/217:25 am
MDW
- SJU
1 stop8h 30m
Southwest
Deal found 7/2![Southwest logo]()
$376
Last-minute flights from Puerto Rico to MidwayDiscover last-minute flight deals from Puerto Rico to Midway. Data last updated July 7, 2026 and is based on user searches.
Discover last-minute flight deals from Puerto Rico to Midway. Data last updated July 7, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 7/2. 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 7/1610:20 pm
SJU
- MDW
2 stops12h 40m
Southwest
Mon 7/208:55 pm
MDW
- SJU
1 stop11h 05m
Southwest
Deal found 7/2![Southwest logo]()
$346
This Southwest deal was found by Cheapflights users on 7/6. 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 7/2310:20 pm
SJU
- MDW
2 stops12h 40m
Southwest
Tue 7/284:40 pm
MDW
- SJU
1 stop6h 40m
Southwest
Deal found 7/6![Southwest logo]()
$316
This Southwest deal was found by Cheapflights users on 7/6. 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 8/65:30 am
SJU
- MDW
2 stops10h 25m
Southwest
Fri 8/142:55 pm
MDW
- SJU
1 stop6h 15m
Southwest
Deal found 7/6![Southwest logo]()
$336
This Southwest deal was found by Cheapflights users on 7/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/75:00 am
SJU
- MDW
2 stops8h 25m
Southwest
Fri 8/147:50 pm
MDW
- SJU
1 stop12h 35m
Southwest
Deal found 7/6![Southwest logo]()
$326
This Southwest deal was found by Cheapflights users on 7/5. 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.
Tue 8/115:15 am
SJU
- MDW
1 stop7h 50m
Southwest
Wed 9/212:45 pm
MDW
- SJU
1 stop8h 15m
Southwest
Deal found 7/5![Southwest logo]()
$341
This Southwest deal was found by Cheapflights users on 7/5. 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 8/198:20 am
SJU
- MDW
2 stops9h 35m
Southwest
Thu 8/273:15 pm
MDW
- SJU
1 stop6h 50m
Southwest
Deal found 7/5![Southwest logo]()
$306
This Southwest deal was found by Cheapflights users on 7/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/239:25 pm
SJU
- MDW
1 stop13h 35m
Southwest
Thu 8/2711:15 am
MDW
- SJU
1 stop9h 55m
Southwest
Deal found 7/6![Southwest logo]()
$291
This Southwest deal was found by Cheapflights users on 7/6. 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 8/265:15 am
SJU
- MDW
2 stops7h 50m
Southwest
Tue 9/112:45 pm
MDW
- SJU
2 stops8h 15m
Southwest
Deal found 7/6![Southwest logo]()
$256
This Southwest deal was found by Cheapflights users on 7/4. 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 8/265:15 am
SJU
- MDW
2 stops7h 50m
Southwest
Sat 8/297:50 am
MDW
- SJU
2 stops7h 50m
Southwest
Deal found 7/4![Southwest logo]()
$266
This Delta deal was found by Cheapflights users on 7/6. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2612:56 pm
SJU
- MDW
1 stop10h 40m
Delta
Sat 8/296:11 am
MDW
- SJU
1 stop9h 27m
Delta
Deal found 7/6![Delta logo]()
$311
This Southwest deal was found by Cheapflights users on 7/6. 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 8/2711:35 am
SJU
- MDW
1 stop7h 25m
Southwest
Sun 8/308:05 pm
MDW
- SJU
1 stop12h 05m
Southwest
Deal found 7/6![Southwest logo]()
$246
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 July 7, 2026.
Search for one-way flight options from Puerto Rico to Midway. Find affordable one-way fares based on user searches. Data last updated July 7, 2026.
This Kiwi.com deal was found by Cheapflights users on 7/4. 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.
Tue 10/69:05 pm
SJU
- MDW
2 stops14h 53m
Frontier
Deal found 7/4![Frontier logo]()
$157
This Kiwi.com deal was found by Cheapflights users on 7/2. 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.
Thu 10/15:12 pm
SJU
- MDW
2 stops42h 46m
Frontier
Deal found 7/2![Frontier logo]()
$158
This Kiwi.com deal was found by Cheapflights users on 7/2. 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.
Fri 10/24:39 pm
SJU
- MDW
2 stops19h 19m
Frontier
Deal found 7/2![Frontier logo]()
$162
This Kiwi.com deal was found by Cheapflights users on 7/2. 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.
Tue 9/294:39 pm
SJU
- MDW
2 stops19h 19m
Frontier
Deal found 7/2![Frontier logo]()
$166
This Southwest deal was found by Cheapflights users on 7/6. 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.
Tue 9/18:20 am
SJU
- MDW
2 stops9h 35m
Southwest
Deal found 7/6![Southwest logo]()
$168
This Kiwi.com deal was found by Cheapflights users on 7/2. 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 9/94:39 pm
SJU
- MDW
2 stops19h 19m
Frontier
Deal found 7/2![Frontier logo]()
$169
This Kiwi.com deal was found by Cheapflights users on 7/2. 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.
Tue 9/15:37 pm
SJU
- MDW
2 stops30h 10m
Frontier
Deal found 7/2![Frontier logo]()
$173
This Kiwi.com deal was found by Cheapflights users on 7/3. 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.
Thu 10/15:12 pm
SJU
- MDW
2 stops21h 22m
Multiple Airlines
Deal found 7/3![Multiple Airlines logo]()
$174
This Kiwi.com deal was found by Cheapflights users on 7/4. 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.
Mon 8/315:37 pm
SJU
- MDW
2 stops30h 10m
Frontier
Deal found 7/4![Frontier logo]()
$177
This Delta deal was found by Cheapflights users on 7/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/317:00 am
SJU
- MDW
1 stop9h 44m
Delta
Deal found 7/3![Delta logo]()
$178
This Kiwi.com deal was found by Cheapflights users on 7/2. 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 9/304:39 pm
SJU
- MDW
2 stops30h 19m
Frontier
Deal found 7/2![Frontier logo]()
$180
This Kiwi.com deal was found by Cheapflights users on 7/6. 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 8/1112:04 pm
BQN
- MDW
2 stops10h 59m
Frontier
Deal found 7/6![Frontier logo]()
$185
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 July 7, 2026.
Round-trip from | $246 (Southwest) |
|---|---|
One-way from | $157 (Kiwi.com) |
Popular in | June |
Cheapest in | February |
Average price | $333 |
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 July 7, 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 - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 8/27
10:00 am-3:35 pm
1 stop6h 35m
Chicago Midway
Wed 9/2
6:15 am-4:25 pm
1 stop9h 10m
$246
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Tue 8/25
5:15 am-12:05 pm
1 stop7h 50m
Chicago Midway
Wed 9/2
12:45 pm-10:00 pm
2 stops8h 15m
$246
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Sat 8/22
6:25 am-5:05 pm
2 stops11h 40m
Chicago Midway
Tue 9/1
12:20 pm-9:05 pm
1 stop7h 45m
$256
Quickest round-trip
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Fri 8/7
5:00 am-12:25 pm
2 stops8h 25m
Chicago Midway
Mon 8/10
3:15 pm-11:05 pm
1 stop6h 50m
$336
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Fri 8/21
2:59 pm-10:36 pm
1 stop8h 37m
Chicago Midway
Mon 8/24
6:05 am-4:38 pm
1 stop9h 33m
$356
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 9/3
5:30 am-2:55 pm
2 stops10h 25m
Chicago Midway
Thu 9/10
1:00 pm-10:50 pm
2 stops8h 50m
$356
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Sat 9/19
10:25 am-7:40 pm
1 stop10h 15m
Chicago Midway
Mon 9/21
9:10 am-8:05 pm
1 stop9h 55m
$376
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Fri 9/18
5:30 am-2:55 pm
2 stops10h 25m
Chicago Midway
Mon 9/21
7:25 am-4:55 pm
1 stop8h 30m
$376
Cheapest one-way
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 7/30
10:20 pm-9:15 am
1 stop11h 55m
$178
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Mon 8/3
10:20 pm-9:25 am
1 stop12h 05m
$183
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
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 July 7, 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 July 7, 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
Entertainment
7.5
Overall
7.9
Boarding
8.1
Crew
8.6
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Entertainment
7.5
Overall
7.9
Boarding
8.1
Crew
8.6
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
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Top airline flying from Puerto Rico to Midway
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| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$266 | Average$476 | FlexibilityNo cancel fee | On-time63% |