$118+ Cheap flights from San Juan 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 8/13. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MDW
Jun 20 — Jun 271
Round-trip
1 adult, Economy
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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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Cheapest flights from San Juan to MidwayExplore the most affordable flight options available from San Juan to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 21, 2026.
Explore the most affordable flight options available from San Juan to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 21, 2026.
This Southwest deal was found by Cheapflights users on 5/18. 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 8/206:30 am
SJU
- MDW
2 stops8h 15m
Southwest
Tue 8/2512:20 pm
MDW
- SJU
1 stop7h 45m
Southwest
Deal found 5/18![Southwest logo]()
$236
This Southwest deal was found by Cheapflights users on 5/16. 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 8/155:05 am
SJU
- MDW
1 stop6h 55m
Southwest
Sun 8/305:00 am
MDW
- SJU
1 stop7h 00m
Southwest
Deal found 5/16![Southwest logo]()
$246
This Southwest deal was found by Cheapflights users on 5/18. 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 8/185:15 am
SJU
- MDW
2 stops7h 50m
Southwest
Tue 8/2512:45 pm
MDW
- SJU
2 stops8h 15m
Southwest
Deal found 5/18![Southwest logo]()
$256
This Delta deal was found by Cheapflights users on 5/18. 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 9/21:06 pm
SJU
- MDW
1 stop9h 40m
Delta
Sun 9/66:00 am
MDW
- SJU
1 stop9h 35m
Delta
Deal found 5/18![Delta logo]()
$266
This Southwest deal was found by Cheapflights users on 5/18. 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
SJU
- MDW
2 stops8h 20m
Southwest
Mon 8/317:15 am
MDW
- SJU
1 stop8h 40m
Southwest
Deal found 5/18![Southwest logo]()
$276
This Southwest deal was found by Cheapflights users on 5/17. 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 8/66:00 am
SJU
- MDW
2 stops9h 30m
Southwest
Tue 8/117:30 am
MDW
- SJU
1 stop10h 30m
Southwest
Deal found 5/17![Southwest logo]()
$286
This Southwest deal was found by Cheapflights users on 5/16. 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
2 stops7h 50m
Southwest
Tue 8/1812:45 pm
MDW
- SJU
2 stops8h 15m
Southwest
Deal found 5/16![Southwest logo]()
$301
This Southwest deal was found by Cheapflights users on 5/17. 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 8/66:00 am
SJU
- MDW
2 stops9h 30m
Southwest
Sun 8/92:15 pm
MDW
- SJU
1 stop8h 10m
Southwest
Deal found 5/17![Southwest logo]()
$306
This Southwest deal was found by Cheapflights users on 5/18. 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 8/55:15 am
SJU
- MDW
2 stops7h 50m
Southwest
Mon 8/179:10 am
MDW
- SJU
1 stop6h 45m
Southwest
Deal found 5/18![Southwest logo]()
$321
This Delta deal was found by Cheapflights users on 5/18. 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 8/206:48 am
SJU
- MDW
1 stop10h 27m
Delta
Tue 8/256:05 am
MDW
- SJU
1 stop6h 37m
Delta
Deal found 5/18![Delta logo]()
$331
This Southwest deal was found by Cheapflights users on 5/18. 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 stop12h 20m
Southwest
Sat 8/296:05 am
MDW
- SJU
1 stop11h 10m
Southwest
Deal found 5/18![Southwest logo]()
$336
This Southwest deal was found by Cheapflights users on 5/20. 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
1 stop12h 40m
Southwest
Mon 7/202:25 pm
MDW
- SJU
1 stop8h 10m
Southwest
Deal found 5/20![Southwest logo]()
$341
Best flights from San Juan to MidwayDiscover carefully curated flight deals from San Juan to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 21, 2026.
Discover carefully curated flight deals from San Juan to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 21, 2026.
This Delta deal was found by Cheapflights users on 5/20. 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 9/22:40 pm
SJU
- MDW
1 stop8h 06m
Delta
Mon 9/76:00 am
MDW
- SJU
1 stop9h 35m
Delta
Deal found 5/20![Delta logo]()
$331
This Southwest deal was found by Cheapflights users on 5/18. 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 8/305:00 am
SJU
- MDW
1 stop9h 45m
Southwest
Sun 9/66:55 am
MDW
- SJU
1 stop9h 25m
Southwest
Deal found 5/18![Southwest logo]()
$371
This Southwest deal was found by Cheapflights users on 5/16. 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
1 stop12h 40m
Southwest
Sat 7/255:05 pm
MDW
- SJU
1 stop7h 10m
Southwest
Deal found 5/16![Southwest logo]()
$416
This Southwest deal was found by Cheapflights users on 5/16. 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 7/1010:20 pm
SJU
- MDW
1 stop11h 30m
Southwest
Sat 7/185:05 pm
MDW
- SJU
1 stop7h 10m
Southwest
Deal found 5/16![Southwest logo]()
$426
This Southwest deal was found by Cheapflights users on 5/20. 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 6/2210:20 pm
SJU
- MDW
1 stop12h 30m
Southwest
Mon 7/202:25 pm
MDW
- SJU
1 stop8h 10m
Southwest
Deal found 5/20![Southwest logo]()
$446
This Southwest deal was found by Cheapflights users on 5/20. 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 10/105:30 am
SJU
- MDW
1 stop11h 30m
Southwest
Wed 10/141:35 pm
MDW
- SJU
2 stops9h 10m
Southwest
Deal found 5/20![Southwest logo]()
$466
This Southwest deal was found by Cheapflights users on 5/20. 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 8/26:25 am
SJU
- MDW
2 stops9h 55m
Southwest
Fri 8/73:15 pm
MDW
- SJU
1 stop6h 50m
Southwest
Deal found 5/20![Southwest logo]()
$466
This Southwest deal was found by Cheapflights users on 5/16. 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 6/238:35 pm
SJU
- MDW
1 stop13h 25m
Southwest
Sat 6/273:30 pm
MDW
- SJU
2 stops8h 45m
Southwest
Deal found 5/16![Southwest logo]()
$496
This Southwest deal was found by Cheapflights users on 5/19. 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 6/810:20 pm
SJU
- MDW
1 stop11h 40m
Southwest
Mon 6/221:00 pm
MDW
- SJU
2 stops10h 15m
Southwest
Deal found 5/19![Southwest logo]()
$496
This Southwest deal was found by Cheapflights users on 5/17. 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 6/186:00 am
SJU
- MDW
1 stop11h 20m
Southwest
Mon 6/228:55 pm
MDW
- SJU
1 stop11h 05m
Southwest
Deal found 5/17![Southwest logo]()
$516
This Southwest deal was found by Cheapflights users on 5/20. 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 6/2210:20 pm
SJU
- MDW
1 stop12h 30m
Southwest
Fri 7/175:10 pm
MDW
- SJU
1 stop7h 10m
Southwest
Deal found 5/20![Southwest logo]()
$521
Last-minute flights from San Juan to MidwayDiscover last-minute flight deals from San Juan to Midway. Data last updated May 21, 2026 and is based on user searches.
Discover last-minute flight deals from San Juan to Midway. Data last updated May 21, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 5/19. 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 5/231:10 pm
SJU
- MDW
Nonstop5h 10m
Southwest
Fri 6/122:45 pm
MDW
- SJU
2 stops8h 20m
Southwest
Deal found 5/19![Southwest logo]()
$456
This Southwest deal was found by Cheapflights users on 5/18. 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 6/98:35 pm
SJU
- MDW
1 stop13h 25m
Southwest
Sat 6/135:05 pm
MDW
- SJU
1 stop7h 10m
Southwest
Deal found 5/18![Southwest logo]()
$461
This Southwest deal was found by Cheapflights users on 5/19. 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 6/98:35 pm
SJU
- MDW
1 stop13h 25m
Southwest
Tue 7/74:40 pm
MDW
- SJU
1 stop6h 35m
Southwest
Deal found 5/19![Southwest logo]()
$481
This Southwest deal was found by Cheapflights users on 5/19. 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 6/108:35 pm
SJU
- MDW
1 stop13h 40m
Southwest
Thu 7/165:10 pm
MDW
- SJU
1 stop7h 10m
Southwest
Deal found 5/19![Southwest logo]()
$436
This Kiwi.com deal was found by Cheapflights users on 5/16. 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 6/105:15 pm
SJU
- MDW
1 stop18h 57m
Frontier
Sat 6/206:00 am
MDW
- SJU
2 stops41h 15m
Frontier
Deal found 5/16![Frontier logo]()
$469
This Southwest deal was found by Cheapflights users on 5/20. 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 6/1110:20 pm
SJU
- MDW
2 stops12h 40m
Southwest
Sat 7/412:30 pm
MDW
- SJU
1 stop8h 20m
Southwest
Deal found 5/20![Southwest logo]()
$416
This Southwest deal was found by Cheapflights users on 5/19. 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 6/1110:20 pm
SJU
- MDW
1 stop11h 55m
Southwest
Thu 6/258:55 pm
MDW
- SJU
1 stop11h 05m
Southwest
Deal found 5/19![Southwest logo]()
$446
This Southwest deal was found by Cheapflights users on 5/20. 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 6/1110:20 pm
SJU
- MDW
2 stops12h 40m
Southwest
Tue 6/308:10 pm
MDW
- SJU
1 stop11h 50m
Southwest
Deal found 5/20![Southwest logo]()
$466
This Southwest deal was found by Cheapflights users on 5/20. 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 6/168:35 pm
SJU
- MDW
1 stop13h 25m
Southwest
Sat 7/48:55 am
MDW
- SJU
2 stops9h 40m
Southwest
Deal found 5/20![Southwest logo]()
$431
This Southwest deal was found by Cheapflights users on 5/20. 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 6/2210:20 am
SJU
- MDW
2 stops8h 35m
Southwest
Mon 7/202:25 pm
MDW
- SJU
1 stop8h 10m
Southwest
Deal found 5/20![Southwest logo]()
$480
One-way flights from San Juan to MidwaySearch for one-way flight options from San Juan to Midway. Find affordable one-way fares based on user searches. Data last updated May 21, 2026.
Search for one-way flight options from San Juan to Midway. Find affordable one-way fares based on user searches. Data last updated May 21, 2026.
This Southwest deal was found by Cheapflights users on 5/17. 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 8/135:00 am
SJU
- MDW
2 stops8h 20m
Southwest
Deal found 5/17![Southwest logo]()
$118
This Southwest deal was found by Cheapflights users on 5/20. 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 8/155:05 am
SJU
- MDW
1 stop6h 55m
Southwest
Deal found 5/20![Southwest logo]()
$128
This Southwest deal was found by Cheapflights users on 5/17. 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 8/185:15 am
SJU
- MDW
2 stops7h 50m
Southwest
Deal found 5/17![Southwest logo]()
$138
This Kiwi.com deal was found by Cheapflights users on 5/18. 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 6/97:00 am
SJU
- MDW
2 stops16h 11m
Frontier
Deal found 5/18![Frontier logo]()
$142
This Delta deal was found by Cheapflights users on 5/17. 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 8/1212:56 pm
SJU
- MDW
1 stop10h 40m
Delta
Deal found 5/17![Delta logo]()
$148
This Kiwi.com deal was found by Cheapflights users on 5/17. 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 6/107:00 am
SJU
- MDW
2 stops16h 11m
Frontier
Deal found 5/17![Frontier logo]()
$159
This Southwest deal was found by Cheapflights users on 5/20. 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 8/169:25 pm
SJU
- MDW
1 stop12h 20m
Southwest
Deal found 5/20![Southwest logo]()
$168
This Kiwi.com deal was found by Cheapflights users on 5/17. 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 6/87:00 am
SJU
- MDW
2 stops29h 12m
Frontier
Deal found 5/17![Frontier logo]()
$171
Find flight deals from San Juan to Midway
Discover tips and strategies to find the most affordable flight options for your journey from San Juan (PR1) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated May 21, 2026.
Round-trip from | $236 (Southwest) |
|---|---|
One-way from | $118 (Southwest) |
Popular in | February |
Cheapest in | December |
Average price | $396 |
Cheapflights Fare Finder
Customize your flight search to find flights from San Juan 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 May 21, 2026.
Use the filters below to find and compare flights from San Juan 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
Wed 9/2
2:40 pm-9:46 pm
1 stop8h 06m
Chicago Midway
Mon 9/7
6:00 am-4:35 pm
1 stop9h 35m
$331
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Sun 8/30
5:00 am-1:45 pm
1 stop9h 45m
Chicago Midway
Sun 9/6
6:55 am-5:20 pm
1 stop9h 25m
$371
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 7/16
10:20 pm-10:00 am
1 stop12h 40m
Chicago Midway
Sat 7/25
5:05 pm-1:15 am
1 stop7h 10m
$416
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Fri 7/10
10:20 pm-8:50 am
1 stop11h 30m
Chicago Midway
Sat 7/18
5:05 pm-1:15 am
1 stop7h 10m
$426
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Mon 6/22
10:20 pm-9:50 am
1 stop12h 30m
Chicago Midway
Mon 7/20
2:25 pm-11:35 pm
1 stop8h 10m
$446
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Sat 10/10
5:30 am-4:00 pm
1 stop11h 30m
Chicago Midway
Wed 10/14
1:35 pm-11:45 pm
2 stops9h 10m
$466
Quickest round-trip
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Sun 8/2
6:25 am-3:20 pm
2 stops9h 55m
Chicago Midway
Fri 8/7
3:15 pm-11:05 pm
1 stop6h 50m
$466
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Tue 6/23
8:35 pm-9:00 am
1 stop13h 25m
Chicago Midway
Sat 6/27
3:30 pm-1:15 am
2 stops8h 45m
$496
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Mon 6/8
10:20 pm-9:00 am
1 stop11h 40m
Chicago Midway
Mon 6/22
1:00 pm-12:15 am
2 stops10h 15m
$496
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 6/18
6:00 am-4:20 pm
1 stop11h 20m
Chicago Midway
Mon 6/22
8:55 pm-9:00 am
1 stop11h 05m
$516
Showing 1-10 of 20 resultsSorted by cheapest first
Best time to book a flight from San Juan to Midway
Have a flexible travel schedule? Discover the best time to fly to Midway from San Juan with our price prediction graph.
PR1-MDW
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 San Juan to Chicago Midway Airport
PR1-MDW
SJU-MDW
What is the cheapest time of day to fly from SJU to MDW?
Find hourly flight availability from San Juan 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 May 21, 2026.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from San Juan to Chicago Midway Airport as you normally would.
How much does it cost to fly round-trip from San Juan to Chicago Midway Airport?
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 May 21, 2026.
Read reviews from past customers who have flown Southwest from San Juan 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
Comfort
8.0
Overall
7.9
Boarding
8.1
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Entertainment
7.5
Comfort
8.0
Overall
7.9
Boarding
8.1
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Related info for your journey
Find useful and relevant information for your journey from San Juan 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
Hammond
Porter
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Other flights to Midway
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San Juan and Midway flights
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Top airline flying from San Juan to Midway
Discover the top airline that operate flights from San Juan 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 May 21, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$326 | Average$559 | FlexibilityNo cancel fee | On-time63% |