$141+ 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 10/6. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MDW
Aug 10 — Aug 171
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 July 11, 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 July 11, 2026.
This Southwest deal was found by Cheapflights users on 7/8. 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 8/268:20 am
SJU
- MDW
1 stop7h 25m
Southwest
Tue 9/112:45 pm
MDW
- SJU
2 stops8h 15m
Southwest
Deal found 7/8![Southwest logo]()
$246
This Delta deal was found by Cheapflights users on 7/8. 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 8/272:59 pm
SJU
- MDW
1 stop8h 37m
Delta
Sat 8/296:11 am
MDW
- SJU
1 stop9h 27m
Delta
Deal found 7/8![Delta logo]()
$251
This Southwest deal was found by Cheapflights users on 7/8. 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 8/202:35 pm
SJU
- MDW
1 stop9h 05m
Southwest
Sun 8/238:05 pm
MDW
- SJU
1 stop12h 05m
Southwest
Deal found 7/8![Southwest logo]()
$291
This Southwest deal was found by Cheapflights users on 7/8. 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 9/175:00 am
SJU
- MDW
2 stops8h 25m
Southwest
Sun 9/207:10 am
MDW
- SJU
2 stops8h 55m
Southwest
Deal found 7/8![Southwest logo]()
$296
This Delta deal was found by Cheapflights users on 7/8. 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 8/192:59 pm
SJU
- MDW
1 stop8h 37m
Delta
Mon 8/246:05 am
MDW
- SJU
1 stop9h 33m
Delta
Deal found 7/8![Delta logo]()
$301
This Delta deal was found by Cheapflights users on 7/8. 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 8/192:59 pm
SJU
- MDW
1 stop8h 37m
Delta
Thu 8/2712:46 pm
MDW
- SJU
1 stop8h 43m
Delta
Deal found 7/8![Delta 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 Faresmojo deal was found by Cheapflights users on 7/10. 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 Faresmojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/62:59 pm
SJU
- MDW
1 stop8h 37m
JetBlue
Tue 8/1112:46 pm
MDW
- SJU
1 stop8h 43m
JetBlue
Deal found 7/10![JetBlue 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.
Wed 8/198:20 am
SJU
- MDW
2 stops9h 35m
Southwest
Sun 8/232:15 pm
MDW
- SJU
1 stop8h 10m
Southwest
Deal found 7/6![Southwest logo]()
$326
This Southwest deal was found by Cheapflights users on 7/10. 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 8/148:55 pm
SJU
- MDW
1 stop13h 00m
Southwest
Fri 8/213:15 pm
MDW
- SJU
1 stop6h 50m
Southwest
Deal found 7/10![Southwest logo]()
$331
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 July 11, 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 July 11, 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.
Wed 9/210:30 am
SJU
- MDW
1 stop8h 10m
Southwest
Tue 9/812:45 pm
MDW
- SJU
2 stops8h 15m
Southwest
Deal found 7/6![Southwest logo]()
$246
This Southwest deal was found by Cheapflights users on 7/7. 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 8/206:30 am
SJU
- MDW
1 stop10h 05m
Southwest
Tue 8/258:30 am
MDW
- SJU
1 stop6h 55m
Southwest
Deal found 7/7![Southwest logo]()
$291
This Southwest deal was found by Cheapflights users on 7/11. 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 9/166:00 am
SJU
- MDW
2 stops8h 05m
Southwest
Sun 9/208:05 pm
MDW
- SJU
1 stop12h 05m
Southwest
Deal found 7/11![Southwest logo]()
$296
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 7/10. 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 8/195:15 am
SJU
- MDW
2 stops7h 50m
Southwest
Wed 8/267:30 am
MDW
- SJU
1 stop10h 30m
Southwest
Deal found 7/10![Southwest logo]()
$341
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 8/141:00 pm
MDW
- SJU
2 stops8h 50m
Southwest
Deal found 7/6![Southwest logo]()
$346
This Southwest deal was found by Cheapflights users on 7/7. 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 7/2310:20 pm
SJU
- MDW
2 stops12h 40m
Southwest
Mon 7/278:55 am
MDW
- SJU
1 stop11h 20m
Southwest
Deal found 7/7![Southwest logo]()
$356
This Southwest deal was found by Cheapflights users on 7/10. 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 7/145:30 am
SJU
- MDW
1 stop8h 15m
Southwest
Tue 7/214:40 pm
MDW
- SJU
1 stop6h 40m
Southwest
Deal found 7/10![Southwest logo]()
$398
This Southwest deal was found by Cheapflights users on 7/10. 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 8/58:20 am
SJU
- MDW
2 stops9h 35m
Southwest
Wed 8/1212:45 pm
MDW
- SJU
2 stops8h 15m
Southwest
Deal found 7/10![Southwest logo]()
$411
This Southwest deal was found by Cheapflights users on 7/8. 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 7/183:35 pm
SJU
- MDW
1 stop7h 25m
Southwest
Tue 7/2110:10 am
MDW
- SJU
2 stops8h 35m
Southwest
Deal found 7/8![Southwest logo]()
$425
This Southwest deal was found by Cheapflights users on 7/8. 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
SJU
- MDW
1 stop6h 55m
Southwest
Sun 10/111:55 pm
MDW
- SJU
1 stop8h 20m
Southwest
Deal found 7/8![Southwest logo]()
$426
Last-minute flights from San Juan to MidwayDiscover last-minute flight deals from San Juan to Midway. Data last updated July 11, 2026 and is based on user searches.
Discover last-minute flight deals from San Juan to Midway. Data last updated July 11, 2026 and is based on user searches.
This Faresmojo deal was found by Cheapflights users on 7/10. 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 Faresmojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/62:59 pm
SJU
- MDW
1 stop8h 37m
JetBlue
Tue 8/1112:46 pm
MDW
- SJU
1 stop8h 43m
JetBlue
Deal found 7/10![JetBlue logo]()
$316
This Southwest deal was found by Cheapflights users on 7/10. 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 8/148:55 pm
SJU
- MDW
1 stop13h 00m
Southwest
Fri 8/213:15 pm
MDW
- SJU
1 stop6h 50m
Southwest
Deal found 7/10![Southwest logo]()
$331
This Delta deal was found by Cheapflights users on 7/8. 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 8/192:59 pm
SJU
- MDW
1 stop8h 37m
Delta
Mon 8/246:05 am
MDW
- SJU
1 stop9h 33m
Delta
Deal found 7/8![Delta logo]()
$301
This Delta deal was found by Cheapflights users on 7/8. 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 8/192:59 pm
SJU
- MDW
1 stop8h 37m
Delta
Thu 8/2712:46 pm
MDW
- SJU
1 stop8h 43m
Delta
Deal found 7/8![Delta 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.
Wed 8/198:20 am
SJU
- MDW
2 stops9h 35m
Southwest
Sun 8/232:15 pm
MDW
- SJU
1 stop8h 10m
Southwest
Deal found 7/6![Southwest logo]()
$326
This Southwest deal was found by Cheapflights users on 7/8. 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 8/202:35 pm
SJU
- MDW
1 stop9h 05m
Southwest
Sun 8/238:05 pm
MDW
- SJU
1 stop12h 05m
Southwest
Deal found 7/8![Southwest logo]()
$291
This Southwest deal was found by Cheapflights users on 7/9. 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 8/202:35 pm
SJU
- MDW
1 stop9h 05m
Southwest
Mon 8/243:15 pm
MDW
- SJU
1 stop6h 50m
Southwest
Deal found 7/9![Southwest logo]()
$296
This Southwest deal was found by Cheapflights users on 7/8. 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 8/268:20 am
SJU
- MDW
1 stop7h 25m
Southwest
Tue 9/112:45 pm
MDW
- SJU
2 stops8h 15m
Southwest
Deal found 7/8![Southwest logo]()
$246
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 Delta deal was found by Cheapflights users on 7/8. 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 8/272:59 pm
SJU
- MDW
1 stop8h 37m
Delta
Sat 8/296:11 am
MDW
- SJU
1 stop9h 27m
Delta
Deal found 7/8![Delta logo]()
$251
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 July 11, 2026.
Search for one-way flight options from San Juan to Midway. Find affordable one-way fares based on user searches. Data last updated July 11, 2026.
This Kiwi.com deal was found by Cheapflights users on 7/8. 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 10/64:39 pm
SJU
- MDW
2 stops30h 19m
Frontier
Deal found 7/8![Frontier logo]()
$141
This Southwest deal was found by Cheapflights users on 7/8. 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 stop11h 55m
Southwest
Deal found 7/8![Southwest logo]()
$143
This Kiwi.com deal was found by Cheapflights users on 7/11. 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 10/125:12 pm
SJU
- MDW
2 stops29h 46m
Frontier
Deal found 7/11![Frontier logo]()
$144
This Kiwi.com deal was found by Cheapflights users on 7/8. 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 10/44:39 pm
SJU
- MDW
2 stops30h 19m
Frontier
Deal found 7/8![Frontier logo]()
$152
This Southwest deal was found by Cheapflights users on 7/10. 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 8/138:55 pm
SJU
- MDW
2 stops15h 30m
Southwest
Deal found 7/10![Southwest logo]()
$158
This Kiwi.com deal was found by Cheapflights users on 7/9. 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 8/125:22 pm
SJU
- MDW
2 stops29h 41m
Frontier
Deal found 7/9![Frontier logo]()
$161
This Kiwi.com deal was found by Cheapflights users on 7/8. 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 8/57:10 am
SJU
- MDW
2 stops38h 22m
Frontier
Deal found 7/8![Frontier logo]()
$162
This Kiwi.com deal was found by Cheapflights users on 7/11. 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 8/176:26 am
SJU
- MDW
2 stops29h 29m
Frontier
Deal found 7/11![Frontier logo]()
$164
This Kiwi.com deal was found by Cheapflights users on 7/10. 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 8/116:26 am
SJU
- MDW
2 stops28h 25m
Frontier
Deal found 7/10![Frontier logo]()
$166
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 July 11, 2026.
Round-trip from | $246 (Southwest) |
|---|---|
One-way from | $141 (Kiwi.com) |
Popular in | February |
Cheapest in | August |
Average price | $511 |
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 July 11, 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
10:30 am-5:40 pm
1 stop8h 10m
Chicago Midway
Tue 9/8
12:45 pm-10:00 pm
2 stops8h 15m
$246
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 8/20
6:30 am-3:35 pm
1 stop10h 05m
Chicago Midway
Tue 8/25
8:30 am-4:25 pm
1 stop6h 55m
$291
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Wed 9/16
6:00 am-1:05 pm
2 stops8h 05m
Chicago Midway
Sun 9/20
8:05 pm-9:10 am
1 stop12h 05m
$296
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
Fri 8/14
7:50 pm-9:25 am
1 stop12h 35m
$326
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Wed 8/19
5:15 am-12:05 pm
2 stops7h 50m
Chicago Midway
Wed 8/26
7:30 am-7:00 pm
1 stop10h 30m
$341
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 8/6
5:30 am-2:55 pm
2 stops10h 25m
Chicago Midway
Fri 8/14
1:00 pm-10:50 pm
2 stops8h 50m
$346
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 7/23
10:20 pm-10:00 am
2 stops12h 40m
Chicago Midway
Mon 7/27
8:55 am-9:15 pm
1 stop11h 20m
$356
Quickest round-trip
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Tue 7/14
5:30 am-12:45 pm
1 stop8h 15m
Chicago Midway
Tue 7/21
4:40 pm-12:20 am
1 stop6h 40m
$398
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Wed 8/5
8:20 am-4:55 pm
2 stops9h 35m
Chicago Midway
Wed 8/12
12:45 pm-10:00 pm
2 stops8h 15m
$411
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Sat 7/18
3:35 pm-10:00 pm
1 stop7h 25m
Chicago Midway
Tue 7/21
10:10 am-7:45 pm
2 stops8h 35m
$425
Showing 1-10 of 21 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 July 11, 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 July 11, 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.
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Overall
7.9
Crew
8.6
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Overall
7.9
Crew
8.6
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
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| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$266 | Average$476 | FlexibilityNo cancel fee | On-time63% |