$188+ Cheap flights from Midway (MDW) to San José (SJO)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/1. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJO
Oct 23 — Oct 301
Round-trip
1 adult, Economy
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Find cheap flights from Midway to San José 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 Midway to San José
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Best
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Cheapest flights from Midway to San JoséExplore the most affordable flight options available from Midway to San José. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 23, 2026.
Explore the most affordable flight options available from Midway to San José. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 23, 2026.
This Delta deal was found by Cheapflights users on 9/20. 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.
Sun 11/156:00 am -
1 stop16h 15m
Thu 12/32:37 pm -
1 stop8h 17m
Deal found 9/20![Delta logo]()
$418
This Delta deal was found by Cheapflights users on 9/20. 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.
Sun 11/156:00 am -
1 stop16h 15m
Wed 12/22:37 pm -
2 stops22h 24m
Deal found 9/20![Delta logo]()
$423
This Delta deal was found by Cheapflights users on 9/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/276:04 am -
1 stop6h 56m
Tue 11/102:37 pm -
1 stop8h 17m
Deal found 9/22![Delta logo]()
$465
This Southwest deal was found by Cheapflights users on 9/19. 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 10/315:55 am -
1 stop7h 05m
Sat 11/72:05 pm -
1 stop7h 40m
Deal found 9/19![Southwest logo]()
$467
This Delta deal was found by Cheapflights users on 9/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/149:30 am -
2 stops12h 45m
Mon 11/237:00 am -
2 stops11h 04m
Deal found 9/21![Delta logo]()
$470
This Southwest deal was found by Cheapflights users on 9/22. 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.
Thu 10/2211:50 am -
1 stop8h 50m
Thu 10/299:00 am -
1 stop10h 20m
Deal found 9/22![Southwest logo]()
$479
This Southwest deal was found by Cheapflights users on 9/23. 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.
Sat 11/285:55 am -
1 stop8h 55m
Sat 12/52:05 pm -
1 stop7h 35m
Deal found 9/23![Southwest logo]()
$484
This Southwest deal was found by Cheapflights users on 9/22. 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.
Fri 10/307:50 am -
2 stops12h 50m
Tue 11/32:15 pm -
1 stop8h 50m
Deal found 9/22![Southwest logo]()
$488
This Southwest deal was found by Cheapflights users on 9/22. 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.
Sun 11/15:15 am -
1 stop7h 05m
Sat 11/72:40 pm -
1 stop7h 45m
Deal found 9/22![Southwest logo]()
$507
This Southwest deal was found by Cheapflights users on 9/22. 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.
Thu 10/2211:50 am -
1 stop8h 50m
Tue 10/271:00 pm -
1 stop9h 15m
Deal found 9/22![Southwest logo]()
$510
This Delta deal was found by Cheapflights users on 9/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1111:27 am -
1 stop10h 48m
Sat 11/147:00 am -
1 stop8h 12m
Deal found 9/22![Delta logo]()
$512
Best flights from Midway to San JoséDiscover carefully curated flight deals from Midway to San José that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 23, 2026.
Discover carefully curated flight deals from Midway to San José that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 23, 2026.
This Delta deal was found by Cheapflights users on 9/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/276:04 am -
1 stop6h 56m
Wed 11/42:25 pm -
1 stop8h 08m
Deal found 9/21![Delta logo]()
$465
This Southwest deal was found by Cheapflights users on 9/21. 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.
Tue 10/278:15 am -
2 stops12h 25m
Wed 11/41:20 pm -
1 stop8h 00m
Deal found 9/21![Southwest logo]()
$592
This Delta deal was found by Cheapflights users on 9/20. 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.
Tue 10/276:04 am -
1 stop6h 56m
Mon 11/22:25 pm -
1 stop8h 08m
Deal found 9/20![Delta logo]()
$465
This Southwest deal was found by Cheapflights users on 9/18. 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 10/2010:15 am -
1 stop10h 25m
Mon 11/21:20 pm -
2 stops11h 45m
Deal found 9/18![Southwest logo]()
$604
This Delta deal was found by Cheapflights users on 9/20. 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.
Fri 12/46:00 am -
1 stop16h 17m
Tue 12/82:37 pm -
1 stop8h 17m
Deal found 9/20![Delta logo]()
$569
This Delta deal was found by Cheapflights users on 9/18. 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 11/56:04 am -
1 stop6h 56m
Mon 11/92:37 pm -
1 stop8h 17m
Deal found 9/18![Delta logo]()
$569
This Southwest deal was found by Cheapflights users on 9/21. 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 1/135:25 am -
1 stop8h 20m
Mon 1/182:45 pm -
1 stop8h 00m
Deal found 9/21![Southwest logo]()
$660
This Delta deal was found by Cheapflights users on 9/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/291:00 pm -
2 stops9h 05m
Fri 2/57:05 am -
1 stop9h 20m
Deal found 9/22![Delta logo]()
$621
This Southwest deal was found by Cheapflights users on 9/22. 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 1/305:20 am -
1 stop8h 25m
Sat 2/61:05 pm -
1 stop8h 15m
Deal found 9/22![Southwest logo]()
$686
This Southwest deal was found by Cheapflights users on 9/21. 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 11/135:10 am -
1 stop8h 05m
Mon 11/231:20 pm -
1 stop9h 40m
Deal found 9/21![Southwest logo]()
$691
This Delta deal was found by Cheapflights users on 9/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/169:30 am -
2 stops12h 35m
Sun 2/77:05 am -
1 stop9h 20m
Deal found 9/19![Delta logo]()
$697
Last-minute flights from Midway to San JoséDiscover last-minute flight deals from Midway to San José. Data last updated September 23, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to San José. Data last updated September 23, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 9/23. 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.
Mon 10/1911:50 am -
1 stop8h 50m
Thu 10/299:00 am -
2 stops10h 10m
Deal found 9/23![Southwest logo]()
$526
This Southwest deal was found by Cheapflights users on 9/22. 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.
Thu 10/2211:50 am -
1 stop8h 50m
Thu 10/299:00 am -
1 stop10h 20m
Deal found 9/22![Southwest logo]()
$479
This Southwest deal was found by Cheapflights users on 9/22. 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.
Thu 10/2211:50 am -
1 stop8h 50m
Tue 10/271:00 pm -
1 stop9h 15m
Deal found 9/22![Southwest logo]()
$510
This Southwest deal was found by Cheapflights users on 9/22. 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.
Thu 10/2211:50 am -
1 stop8h 50m
Mon 10/269:00 am -
2 stops13h 15m
Deal found 9/22![Southwest logo]()
$528
This Delta deal was found by Cheapflights users on 9/20. 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.
Sat 10/246:04 am -
1 stop6h 56m
Mon 11/22:25 pm -
2 stops22h 22m
Deal found 9/20![Delta logo]()
$470
This Delta deal was found by Cheapflights users on 9/20. 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.
Sat 10/246:04 am -
1 stop6h 56m
Tue 11/32:25 pm -
1 stop8h 08m
Deal found 9/20![Delta logo]()
$512
This Delta deal was found by Cheapflights users on 9/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/276:04 am -
1 stop6h 56m
Tue 11/102:37 pm -
1 stop8h 17m
Deal found 9/22![Delta logo]()
$465
This Southwest deal was found by Cheapflights users on 9/22. 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.
Fri 10/307:50 am -
2 stops12h 50m
Tue 11/32:15 pm -
1 stop8h 50m
Deal found 9/22![Southwest logo]()
$488
This Southwest deal was found by Cheapflights users on 9/19. 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 10/315:55 am -
1 stop7h 05m
Sat 11/72:05 pm -
1 stop7h 40m
Deal found 9/19![Southwest logo]()
$467
One-way flights from Midway to San JoséSearch for one-way flight options from Midway to San José. Find affordable one-way fares based on user searches. Data last updated September 23, 2026.
Search for one-way flight options from Midway to San José. Find affordable one-way fares based on user searches. Data last updated September 23, 2026.
This Southwest deal was found by Cheapflights users on 9/21. 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 11/15:15 am -
1 stop7h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Southwest logo]()
$188
This Southwest deal was found by Cheapflights users on 9/21. 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 10/315:55 am -
1 stop7h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Southwest logo]()
$205
This Southwest deal was found by Cheapflights users on 9/22. 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.
Thu 10/2211:50 am -
1 stop8h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Southwest logo]()
$235
This Kiwi.com deal was found by Cheapflights users on 9/22. 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 10/226:40 pm -
2 stops38h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Frontier logo]()
$245
This Southwest deal was found by Cheapflights users on 9/22. 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.
Mon 10/1911:50 am -
1 stop8h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Southwest logo]()
$252
This FlightHub deal was found by Cheapflights users on 9/21. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/319:23 pm -
1 stop14h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Frontier logo]()
$269
This KAYAK deal was found by Cheapflights users on 9/21. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/285:45 am -
1 stop7h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Southwest logo]()
$270
This Kiwi.com deal was found by Cheapflights users on 9/22. 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 10/151:12 pm -
2 stops44h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Frontier logo]()
$275
This Kiwi.com deal was found by Cheapflights users on 9/21. 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.
Fri 10/161:12 pm -
2 stops20h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Frontier logo]()
$276
This Frontier deal was found by Cheapflights users on 9/20. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/19:23 pm -
1 stop12h 16m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Frontier logo]()
$287
Find flight deals from Midway to San José
Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to San José (SJO). 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 September 23, 2026.
Most accurate provider | Ovago 3 stars |
|---|---|
Most trusted provider | Ovago 3 stars |
Round-trip from | $418 (Delta) |
One-way from | $188 (Southwest) |
Popular in | December |
Cheapest in | October |
Average price | $546 |
Cheapflights Fare Finder
Customize your flight search to find flights from Midway to San José 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 September 23, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to San José that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoSan José
MDW Chicago Midway - SJO San José Juan Santamaria Intl
MDWSJO
Chicago Midway
Mon 2/1
5:25 am-1:45 pm
1 stop8h 20m
San José Juan Santamaria Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$188
ChicagoSan José
MDW Chicago Midway - SJO San José Juan Santamaria Intl
MDWSJO
Chicago Midway
Sun 1/24
5:25 am-1:45 pm
1 stop8h 20m
San José Juan Santamaria Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$188
ChicagoSan José
MDW Chicago Midway - SJO San José Juan Santamaria Intl
MDWSJO
Chicago Midway
Thu 12/31
9:23 pm-12:16 pm
1 stop14h 53m
San José Juan Santamaria Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$273
Quickest round-trip
ChicagoSan José
MDW Chicago Midway - SJO San José Juan Santamaria Intl
MDWSJO
Chicago Midway
Tue 10/20
5:45 am-12:05 pm
1 stop7h 20m
San José Juan Santamaria Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$275
ChicagoSan José
MDW Chicago Midway - SJO San José Juan Santamaria Intl
MDWSJO
Chicago Midway
Wed 10/21
9:40 am-7:40 pm
2 stops11h 00m
San José Juan Santamaria Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$303
ChicagoSan José
MDW Chicago Midway - SJO San José Juan Santamaria Intl
MDWSJO
Chicago Midway
Tue 10/13
6:21 am-9:04 am
3 stops27h 43m
San José Juan Santamaria Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$311
ChicagoSan José
MDW Chicago Midway - SJO San José Juan Santamaria Intl
MDWSJO
Chicago Midway
Fri 10/16
5:00 am-12:35 pm
1 stop8h 35m
San José Juan Santamaria Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$313
ChicagoSan José
MDW Chicago Midway - SJO San José Juan Santamaria Intl
MDWSJO
Chicago Midway
Sat 10/17
10:30 am-7:40 pm
1 stop10h 10m
San José Juan Santamaria Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$363
ChicagoSan José
MDW Chicago Midway - SJO San José Juan Santamaria Intl
MDWSJO
Chicago Midway
Thu 10/15
5:00 am-12:35 pm
1 stop8h 35m
San José Juan Santamaria Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$363
ChicagoSan José
MDW Chicago Midway - SJO San José Juan Santamaria Intl
MDWSJO
Chicago Midway
Sun 10/18
5:10 am-12:40 pm
1 stop8h 30m
San José Juan Santamaria Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$363
Showing 1-10 of 21 resultsSorted by cheapest first
Compare providers for flights from Midway to San José
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Midway to San José in September.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Chicago Midway Airport-San José flights, users find the pricing of Ovago to be most consistent on Cheapflights vs. Ovago Users can find the same prices on Chicago Midway Airport-San José flight deals on Cheapflights vs. Ovago >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-San José flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago Midway Airport-San José flights, Cheapflights users trust Ovago the most. Ovago has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago Midway Airport-San José flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Midway to San José
Have a flexible travel schedule? Discover the best time to fly to San José from Midway with our price prediction graph.
MDW-SJO
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.
Reviews of airlines servicing San José
Get insights into the airlines that provide service to San José. 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 San José. Reviews last updated September 23, 2026.
Read through reviews of airlines operating flights from Chicago Midway Airport to San José, such as Southwest. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.6
Food
7.0
Entertainment
7.5
Boarding
8.1
Overall
8.0
Comfort
8.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Crew
8.6
Food
7.0
Entertainment
7.5
Boarding
8.1
Overall
8.0
Comfort
8.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Related info for your journey
Find useful and relevant information for your journey from Midway to San José. 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 San José?
Book flights to San José if you plan to visit one of these locationsAlajuela
Jacó
Heredia
Dominical
Manuel Antonio
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San José flight routes
Alternative routes for Midway to San José
See prices for flight routes from nearby airports that may be better suited for you.
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Find flights from Midway to San José, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Midway and San José flights
Browse other Midway and San José flight options. Last updated on September 23, 2026.
Other flights from Midway
Browse through other flights departing from Midway. Flights are based on user searches made on Cheapflights and were last updated on September 23, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Other flights to San José
Explore flights to San José departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on September 23, 2026.
Top airline flying from Midway to San José
Discover the top airline that operate flights from Midway to San José. 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 September 23, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$503 | Average$813 | FlexibilityNo cancel fee | On-time63% |