$128+ 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 9/1. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MDW
Sep 22 — Sep 291
Round-trip
1 adult, Economy
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Find cheap flights from San Juan 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 San Juan to Midway
Cheapest
Best
Last-minute
One-way
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 August 23, 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 August 23, 2026.
This Southwest deal was found by Cheapflights users on 8/21. 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 9/242:35 pm -
1 stop9h 10m
Tue 9/297:30 am -
1 stop10h 35m
Deal found 8/21![Southwest logo]()
$226
This Southwest deal was found by Cheapflights users on 8/18. 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 9/176:00 am -
2 stops9h 30m
Sat 9/261:55 pm -
1 stop7h 05m
Deal found 8/18![Southwest logo]()
$246
This Faresmojo deal was found by Cheapflights users on 8/18. 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 Faresmojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/296:25 am -
1 stop11h 50m
Thu 10/18:40 pm -
1 stop11h 40m
Deal found 8/18![JetBlue logo]()
$247
This Southwest deal was found by Cheapflights users on 8/23. 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
Wed 9/212:45 pm -
2 stops8h 15m
Deal found 8/23![Southwest logo]()
$266
This Southwest deal was found by Cheapflights users on 8/23. 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 9/176:00 am -
2 stops9h 30m
Tue 9/2212:45 pm -
2 stops8h 20m
Deal found 8/23![Southwest logo]()
$281
This Southwest deal was found by Cheapflights users on 8/21. 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 9/125:05 am -
1 stop6h 55m
Tue 9/158:30 am -
1 stop6h 55m
Deal found 8/21![Southwest logo]()
$286
This Faresmojo deal was found by Cheapflights users on 8/18. 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 Faresmojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/218:15 am -
1 stop12h 35m
Wed 10/284:40 pm -
1 stop6h 05m
Deal found 8/18![JetBlue logo]()
$292
This Southwest deal was found by Cheapflights users on 8/21. 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 9/115:00 am -
1 stop7h 45m
Fri 9/112:55 pm -
1 stop8h 00m
Deal found 8/21![Southwest logo]()
$296
This Southwest deal was found by Cheapflights users on 8/21. 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 9/22:25 pm -
1 stop7h 20m
Tue 9/159:00 am -
2 stops8h 10m
Deal found 8/21![Southwest logo]()
$301
This Southwest deal was found by Cheapflights users on 8/22. 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 10/107:50 am -
1 stop7h 25m
Tue 10/271:15 pm -
1 stop6h 15m
Deal found 8/22![Southwest logo]()
$306
This Travelocity deal was found by Cheapflights users on 8/19. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/95:11 pm -
1 stop7h 32m
Mon 10/126:15 am -
1 stop8h 51m
Deal found 8/19![Frontier logo]()
$308
This Southwest deal was found by Cheapflights users on 8/19. 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 9/176:30 am -
1 stop10h 05m
Thu 9/249:20 am -
2 stops9h 45m
Deal found 8/19![Southwest logo]()
$311
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 August 23, 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 August 23, 2026.
This Southwest deal was found by Cheapflights users on 8/19. 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 10/16:30 am -
1 stop10h 45m
Mon 10/52:15 pm -
1 stop9h 05m
Deal found 8/19![Southwest logo]()
$246
This Southwest deal was found by Cheapflights users on 8/22. 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 9/305:15 am -
2 stops7h 50m
Sat 10/2411:55 am -
1 stop7h 10m
Deal found 8/22![Southwest logo]()
$246
This Southwest deal was found by Cheapflights users on 8/22. 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 10/148:15 am -
2 stops12h 05m
Sat 10/172:40 pm -
1 stop6h 30m
Deal found 8/22![Southwest logo]()
$246
This Southwest deal was found by Cheapflights users on 8/22. 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 9/28:20 am -
1 stop7h 25m
Sun 9/610:55 am -
2 stops9h 20m
Deal found 8/22![Southwest logo]()
$301
This Southwest deal was found by Cheapflights users on 8/21. 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
Thu 10/82:50 pm -
2 stops8h 15m
Deal found 8/21![Southwest logo]()
$326
This Southwest deal was found by Cheapflights users on 8/18. 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 9/32:35 pm -
1 stop7h 55m
Sun 9/61:35 pm -
1 stop6h 40m
Deal found 8/18![Southwest logo]()
$336
This Southwest deal was found by Cheapflights users on 8/20. 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 10/810:50 pm -
1 stop10h 55m
Mon 10/126:40 pm -
1 stop13h 30m
Deal found 8/20![Southwest logo]()
$346
This Southwest deal was found by Cheapflights users on 8/23. 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 10/78:15 am -
1 stop7h 30m
Wed 10/143:25 pm -
1 stop7h 20m
Deal found 8/23![Southwest logo]()
$346
Last-minute flights from San Juan to MidwayDiscover last-minute flight deals from San Juan to Midway. Data last updated August 23, 2026 and is based on user searches.
Discover last-minute flight deals from San Juan to Midway. Data last updated August 23, 2026 and is based on user searches.
This Faresmojo deal was found by Cheapflights users on 8/18. 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 Faresmojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/296:25 am -
1 stop11h 50m
Thu 10/18:40 pm -
1 stop11h 40m
Deal found 8/18![JetBlue logo]()
$247
This Southwest deal was found by Cheapflights users on 8/23. 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
Wed 9/212:45 pm -
2 stops8h 15m
Deal found 8/23![Southwest logo]()
$266
This Southwest deal was found by Cheapflights users on 8/21. 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 9/22:25 pm -
1 stop7h 20m
Tue 9/159:00 am -
2 stops8h 10m
Deal found 8/21![Southwest logo]()
$301
This Frontier deal was found by Cheapflights users on 8/18. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/105:11 pm -
1 stop7h 33m
Thu 9/176:25 am -
1 stop8h 41m
Deal found 8/18![Frontier logo]()
$308
This Southwest deal was found by Cheapflights users on 8/21. 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 9/115:00 am -
1 stop7h 45m
Fri 9/112:55 pm -
1 stop8h 00m
Deal found 8/21![Southwest logo]()
$296
This Southwest deal was found by Cheapflights users on 8/21. 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 9/125:05 am -
2 stops9h 05m
Tue 9/1512:35 pm -
2 stops8h 30m
Deal found 8/21![Southwest logo]()
$286
This Southwest deal was found by Cheapflights users on 8/18. 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 9/176:00 am -
2 stops9h 30m
Sat 9/261:55 pm -
1 stop7h 05m
Deal found 8/18![Southwest logo]()
$246
This Southwest deal was found by Cheapflights users on 8/23. 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 9/176:00 am -
2 stops9h 30m
Tue 9/2212:45 pm -
2 stops8h 20m
Deal found 8/23![Southwest logo]()
$281
This Southwest deal was found by Cheapflights users on 8/19. 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 9/176:30 am -
1 stop10h 05m
Thu 9/249:20 am -
2 stops9h 45m
Deal found 8/19![Southwest logo]()
$311
This Southwest deal was found by Cheapflights users on 8/20. 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.
Fri 9/186:30 am -
2 stops8h 15m
Tue 9/2212:45 pm -
2 stops8h 20m
Deal found 8/20![Southwest logo]()
$306
This CheapOair deal was found by Cheapflights users on 8/18. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/186:30 am -
1 stop12h 21m
Mon 9/286:25 am -
1 stop7h 54m
Deal found 8/18![Frontier logo]()
$315
This Southwest deal was found by Cheapflights users on 8/21. 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 9/242:35 pm -
1 stop9h 10m
Tue 9/297:30 am -
1 stop10h 35m
Deal found 8/21![Southwest logo]()
$226
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 August 23, 2026.
Search for one-way flight options from San Juan to Midway. Find affordable one-way fares based on user searches. Data last updated August 23, 2026.
This Southwest deal was found by Cheapflights users on 8/19. 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 9/12:25 pm -
1 stop7h 20m
Deal found 8/19![Southwest logo]()
$128
This Southwest deal was found by Cheapflights users on 8/19. 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 9/25:15 am -
2 stops7h 50m
Deal found 8/19![Southwest logo]()
$133
This Kiwi.com deal was found by Cheapflights users on 8/22. 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 10/218:45 am -
2 stops34h 00m
Deal found 8/22![Frontier logo]()
$134
This Kiwi.com deal was found by Cheapflights users on 8/21. 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 10/208:45 am -
2 stops15h 58m
Deal found 8/21![Frontier logo]()
$135
This Kiwi.com deal was found by Cheapflights users on 8/21. 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 11/178:45 am -
2 stops35h 02m
Deal found 8/21![Frontier logo]()
$141
This Kiwi.com deal was found by Cheapflights users on 8/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/168:45 am -
2 stops34h 01m
Deal found 8/19![Frontier logo]()
$143
This Kiwi.com deal was found by Cheapflights users on 8/22. 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 10/227:00 am -
2 stops11h 45m
Deal found 8/22![Frontier logo]()
$144
This Kiwi.com deal was found by Cheapflights users on 8/22. 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 9/277:00 am -
2 stops35h 51m
Deal found 8/22![Frontier logo]()
$145
This Kiwi.com deal was found by Cheapflights users on 8/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/167:00 am -
2 stops17h 43m
Deal found 8/20![Frontier logo]()
$152
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 August 23, 2026.
Round-trip from | $226 (Southwest) |
|---|---|
One-way from | $128 (Southwest) |
Popular in | February |
Cheapest in | September |
Average price | $301 |
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 7,457,451 searches. Data last updated August 23, 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 San Juan Luis Munoz Marin Intl - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 10/1
6:30 am-4:15 pm
1 stop10h 45m
Chicago Midway
Mon 10/5
2:15 pm-12:20 am
1 stop9h 05m
$246
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Wed 9/30
5:15 am-12:05 pm
2 stops7h 50m
Chicago Midway
Sat 10/24
11:55 am-8:05 pm
1 stop7h 10m
$246
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Wed 10/14
8:15 am-7:20 pm
2 stops12h 05m
Chicago Midway
Sat 10/17
2:40 pm-10:10 pm
1 stop6h 30m
$246
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Wed 9/2
8:20 am-2:45 pm
1 stop7h 25m
Chicago Midway
Sun 9/6
10:55 am-9:15 pm
2 stops9h 20m
$301
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
Thu 10/8
2:50 pm-12:05 am
2 stops8h 15m
$326
Quickest round-trip
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 9/3
2:35 pm-9:30 pm
1 stop7h 55m
Chicago Midway
Sun 9/6
1:35 pm-9:15 pm
1 stop6h 40m
$336
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 10/8
10:50 pm-8:45 am
1 stop10h 55m
Chicago Midway
Mon 10/12
6:40 pm-9:10 am
1 stop13h 30m
$346
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Wed 10/7
8:15 am-2:45 pm
1 stop7h 30m
Chicago Midway
Wed 10/14
3:25 pm-11:45 pm
1 stop7h 20m
$346
Cheapest one-way
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Fri 8/28
6:30 am-1:45 pm
2 stops8h 15m
$133
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Sun 9/13
9:25 pm-8:45 am
1 stop12h 20m
$133
Showing 1-10 of 18 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
How much does it cost to fly round-trip from San Juan to Chicago Midway Airport?
Airfare is below average for this route at the moment.
San Juan to Chicago Midway Airport flights typically cost between $271 and $371 in September.The cheapest round-trip price found within the last 5 days was $226 on Southwest (Sep 24-Sep 29).
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 23, 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.
Overall
8.0
Food
7.0
Boarding
8.1
Crew
8.6
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
8.0
Food
7.0
Boarding
8.1
Crew
8.6
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
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
Valparaiso
Hammond
Saint Joseph
Porter
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Complete your trip
Complete your trip to Midway by adding a car rental and/or hotel reservation to your travel itinerary.
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Find flights from San Juan 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 23, 2026.
San Juan and Midway flights
Browse other San Juan and Midway flight options. Last updated on August 23, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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 7,457,451 searches. Data last updated August 23, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$266 | Average$540 | FlexibilityNo cancel fee | On-time63% |