$90+ Cheap flights from Midway (MDW) to San José (SJO)
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 4/9. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJO
Apr 24 — May 11
Round-trip
1 adult, Economy
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Find cheap flights from Midway to San José with Cheapflights
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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 March 25, 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 March 25, 2026.
This Priceline deal was found by Cheapflights users on 3/25. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/82:56 pm
MDW
- SJO
1 stop22h 16m
Frontier
Sat 4/1110:06 am
SJO
- MDW
1 stop11h 59m
Frontier
Deal found 3/25![Frontier logo]()
$341
This Justfly.com deal was found by Cheapflights users on 3/23. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/56:00 am
MDW
- SJO
1 stop7h 12m
Frontier
Thu 4/91:27 pm
SJO
- MDW
1 stop29h 40m
Frontier
Deal found 3/23![Frontier logo]()
$366
This FlightHub deal was found by Cheapflights users on 3/24. 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.
Sat 4/42:56 pm
MDW
- SJO
1 stop22h 16m
Frontier
Thu 4/91:27 pm
SJO
- MDW
1 stop29h 40m
Frontier
Deal found 3/24![Frontier logo]()
$374
This Justfly.com deal was found by Cheapflights users on 3/23. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/35:30 am
MDW
- SJO
1 stop28h 31m
Frontier
Thu 4/91:27 pm
SJO
- MDW
1 stop29h 40m
Frontier
Deal found 3/23![Frontier logo]()
$376
This Frontier deal was found by Cheapflights users on 3/22. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/56:00 am
MDW
- SJO
1 stop7h 12m
Frontier
Sat 4/1110:06 am
SJO
- MDW
1 stop11h 59m
Frontier
Deal found 3/22![Frontier logo]()
$388
This Frontier deal was found by Cheapflights users on 3/25. 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 4/26:00 am
MDW
- SJO
1 stop7h 12m
Frontier
Sat 4/1110:06 am
SJO
- MDW
1 stop11h 59m
Frontier
Deal found 3/25![Frontier logo]()
$393
This CheapOair deal was found by Cheapflights users on 3/21. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/82:56 pm
MDW
- SJO
1 stop22h 16m
Frontier
Fri 5/299:35 am
SJO
- MDW
2 stops35h 27m
Frontier
Deal found 3/21![Frontier logo]()
$395
This Kiwi.com deal was found by Cheapflights users on 3/25. 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 4/125:05 am
MDW
- SJO
1 stop30h 37m
Multiple Airlines
Sat 4/187:45 am
SJO
- MDW
2 stops13h 29m
Multiple Airlines
Deal found 3/25![Multiple Airlines logo]()
$406
This Kiwi.com deal was found by Cheapflights users on 3/25. 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 4/136:30 am
MDW
- SJO
1 stop9h 35m
Multiple Airlines
Sat 4/187:45 am
SJO
- MDW
2 stops13h 29m
Multiple Airlines
Deal found 3/25![Multiple Airlines logo]()
$420
This FlightHub deal was found by Cheapflights users on 3/22. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/272:41 pm
MDW
- SJO
1 stop20h 49m
Frontier
Sat 4/412:59 pm
SJO
- MDW
1 stop8h 30m
Frontier
Deal found 3/22![Frontier logo]()
$422
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 March 25, 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 March 25, 2026.
This Southwest deal was found by Cheapflights users on 3/20. 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 5/165:00 am
MDW
- SJO
1 stop8h 15m
Southwest
Mon 5/189:00 am
SJO
- MDW
1 stop9h 00m
Southwest
Deal found 3/20![Southwest logo]()
$484
This Southwest deal was found by Cheapflights users on 3/20. 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 5/512:15 pm
MDW
- SJO
1 stop7h 45m
Southwest
Tue 5/129:00 am
SJO
- MDW
2 stops9h 45m
Southwest
Deal found 3/20![Southwest logo]()
$488
This Southwest deal was found by Cheapflights users on 3/22. 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 4/2912:15 pm
MDW
- SJO
1 stop7h 45m
Southwest
Tue 5/59:00 am
SJO
- MDW
2 stops12h 15m
Southwest
Deal found 3/22![Southwest logo]()
$488
This Southwest deal was found by Cheapflights users on 3/22. 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 5/25:00 am
MDW
- SJO
1 stop8h 15m
Southwest
Sun 5/102:00 pm
SJO
- MDW
2 stops9h 20m
Southwest
Deal found 3/22![Southwest logo]()
$514
This Southwest deal was found by Cheapflights users on 3/23. 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 5/197:00 am
MDW
- SJO
2 stops13h 00m
Southwest
Sat 5/231:35 pm
SJO
- MDW
1 stop8h 10m
Southwest
Deal found 3/23![Southwest logo]()
$518
This Southwest deal was found by Cheapflights users on 3/25. 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 4/145:40 am
MDW
- SJO
2 stops14h 20m
Southwest
Fri 4/241:10 pm
SJO
- MDW
1 stop7h 45m
Southwest
Deal found 3/25![Southwest logo]()
$549
This Southwest deal was found by Cheapflights users on 3/25. 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 4/135:35 am
MDW
- SJO
1 stop7h 35m
Southwest
Thu 4/169:00 am
SJO
- MDW
1 stop9h 00m
Southwest
Deal found 3/25![Southwest logo]()
$584
This Southwest deal was found by Cheapflights users on 3/22. 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 4/207:50 am
MDW
- SJO
2 stops12h 10m
Southwest
Mon 4/279:00 am
SJO
- MDW
2 stops10h 15m
Southwest
Deal found 3/22![Southwest logo]()
$592
This Southwest deal was found by Cheapflights users on 3/25. 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 4/126:50 am
MDW
- SJO
1 stop7h 10m
Southwest
Thu 4/161:10 pm
SJO
- MDW
1 stop7h 45m
Southwest
Deal found 3/25![Southwest logo]()
$600
This Southwest deal was found by Cheapflights users on 3/24. 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 5/1912:15 pm
MDW
- SJO
1 stop7h 45m
Southwest
Tue 5/269:00 am
SJO
- MDW
1 stop9h 45m
Southwest
Deal found 3/24![Southwest logo]()
$615
This Southwest deal was found by Cheapflights users on 3/25. 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 5/1812:10 pm
MDW
- SJO
1 stop7h 50m
Southwest
Sun 5/249:00 am
SJO
- MDW
2 stops11h 25m
Southwest
Deal found 3/25![Southwest logo]()
$645
Last-minute flights from Midway to San JoséDiscover last-minute flight deals from Midway to San José. Data last updated March 25, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to San José. Data last updated March 25, 2026 and is based on user searches.
This FlightHub deal was found by Cheapflights users on 3/22. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/272:41 pm
MDW
- SJO
1 stop20h 49m
Frontier
Sat 4/412:59 pm
SJO
- MDW
1 stop8h 30m
Frontier
Deal found 3/22![Frontier logo]()
$422
This Frontier deal was found by Cheapflights users on 3/25. 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 4/26:00 am
MDW
- SJO
1 stop7h 12m
Frontier
Sat 4/1110:06 am
SJO
- MDW
1 stop11h 59m
Frontier
Deal found 3/25![Frontier logo]()
$393
This Justfly.com deal was found by Cheapflights users on 3/23. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/35:30 am
MDW
- SJO
1 stop28h 31m
Frontier
Thu 4/91:27 pm
SJO
- MDW
1 stop29h 40m
Frontier
Deal found 3/23![Frontier logo]()
$376
This FlightHub deal was found by Cheapflights users on 3/24. 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.
Sat 4/42:56 pm
MDW
- SJO
1 stop22h 16m
Frontier
Thu 4/91:27 pm
SJO
- MDW
1 stop29h 40m
Frontier
Deal found 3/24![Frontier logo]()
$374
This Justfly.com deal was found by Cheapflights users on 3/23. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/56:00 am
MDW
- SJO
1 stop7h 12m
Frontier
Thu 4/91:27 pm
SJO
- MDW
1 stop29h 40m
Frontier
Deal found 3/23![Frontier logo]()
$366
This Frontier deal was found by Cheapflights users on 3/22. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/56:00 am
MDW
- SJO
1 stop7h 12m
Frontier
Sat 4/1110:06 am
SJO
- MDW
1 stop11h 59m
Frontier
Deal found 3/22![Frontier logo]()
$388
This Priceline deal was found by Cheapflights users on 3/25. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/82:56 pm
MDW
- SJO
1 stop22h 16m
Frontier
Sat 4/1110:06 am
SJO
- MDW
1 stop11h 59m
Frontier
Deal found 3/25![Frontier logo]()
$341
This CheapOair deal was found by Cheapflights users on 3/21. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/82:56 pm
MDW
- SJO
1 stop22h 16m
Frontier
Fri 5/299:35 am
SJO
- MDW
2 stops35h 27m
Frontier
Deal found 3/21![Frontier logo]()
$395
This Kiwi.com deal was found by Cheapflights users on 3/25. 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 4/125:05 am
MDW
- SJO
1 stop30h 37m
Multiple Airlines
Sat 4/187:45 am
SJO
- MDW
2 stops13h 29m
Multiple Airlines
Deal found 3/25![Multiple Airlines logo]()
$406
This Kiwi.com deal was found by Cheapflights users on 3/25. 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 4/136:30 am
MDW
- SJO
1 stop9h 35m
Multiple Airlines
Sat 4/187:45 am
SJO
- MDW
2 stops13h 29m
Multiple Airlines
Deal found 3/25![Multiple Airlines logo]()
$420
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 March 25, 2026.
Search for one-way flight options from Midway to San José. Find affordable one-way fares based on user searches. Data last updated March 25, 2026.
This Frontier deal was found by Cheapflights users on 3/22. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/96:00 am
MDW
- SJO
1 stop7h 12m
Frontier
Deal found 3/22![Frontier logo]()
$90
This Priceline deal was found by Cheapflights users on 3/23. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/105:30 am
MDW
- SJO
1 stop28h 31m
Frontier
Deal found 3/23![Frontier logo]()
$104
This Justfly.com deal was found by Cheapflights users on 3/25. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/82:56 pm
MDW
- SJO
1 stop22h 16m
Frontier
Deal found 3/25![Frontier logo]()
$110
This Trip.com deal was found by Cheapflights users on 3/21. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/116:30 am
MDW
- SJO
1 stop9h 56m
Multiple Airlines
Deal found 3/21![Multiple Airlines logo]()
$151
This Kiwi.com deal was found by Cheapflights users on 3/25. 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 6/23:07 pm
MDW
- SJO
2 stops45h 26m
Multiple Airlines
Deal found 3/25![Multiple Airlines logo]()
$161
This Kiwi.com deal was found by Cheapflights users on 3/23. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/612:04 pm
MDW
- SJO
2 stops24h 29m
Multiple Airlines
Deal found 3/23![Multiple Airlines logo]()
$166
This Kiwi.com deal was found by Cheapflights users on 3/24. 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.
Sat 5/3011:59 am
MDW
- SJO
2 stops24h 34m
Multiple Airlines
Deal found 3/24![Multiple Airlines logo]()
$179
This Kiwi.com deal was found by Cheapflights users on 3/25. 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 5/2712:04 pm
MDW
- SJO
2 stops21h 15m
Frontier
Deal found 3/25![Frontier logo]()
$188
This Kiwi.com deal was found by Cheapflights users on 3/23. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/125:05 am
MDW
- SJO
2 stops31h 09m
Multiple Airlines
Deal found 3/23![Multiple Airlines logo]()
$189
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 March 25, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $366 (Justfly.com) |
One-way from | $90 (Frontier) |
Popular in | December |
Cheapest in | September |
Average price | $598 |
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 2,558,603 searches. Data last updated March 25, 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 - SJO
MDWSJO
Chicago Midway
Sat 5/16
5:00 am-12:15 pm
1 stop8h 15m
San José Juan Santamaria Intl
Mon 5/18
9:00 am-7:00 pm
1 stop9h 00m
$484
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Tue 5/5
12:15 pm-7:00 pm
1 stop7h 45m
San José Juan Santamaria Intl
Tue 5/12
9:00 am-7:45 pm
2 stops9h 45m
$488
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Wed 4/29
12:15 pm-7:00 pm
1 stop7h 45m
San José Juan Santamaria Intl
Tue 5/5
9:00 am-10:15 pm
2 stops12h 15m
$488
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Sat 5/2
5:00 am-12:15 pm
1 stop8h 15m
San José Juan Santamaria Intl
Sun 5/10
2:00 pm-12:20 am
2 stops9h 20m
$514
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Tue 5/19
7:00 am-7:00 pm
2 stops13h 00m
San José Juan Santamaria Intl
Sat 5/23
1:35 pm-10:45 pm
1 stop8h 10m
$518
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Tue 4/14
5:40 am-7:00 pm
2 stops14h 20m
San José Juan Santamaria Intl
Fri 4/24
1:10 pm-9:55 pm
1 stop7h 45m
$549
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Mon 4/13
5:35 am-12:10 pm
1 stop7h 35m
San José Juan Santamaria Intl
Thu 4/16
9:00 am-7:00 pm
1 stop9h 00m
$584
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Mon 4/20
7:50 am-7:00 pm
2 stops12h 10m
San José Juan Santamaria Intl
Mon 4/27
9:00 am-8:15 pm
2 stops10h 15m
$592
Quickest round-trip
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Sun 4/12
6:50 am-1:00 pm
1 stop7h 10m
San José Juan Santamaria Intl
Thu 4/16
1:10 pm-9:55 pm
1 stop7h 45m
$600
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Tue 5/19
12:15 pm-7:00 pm
1 stop7h 45m
San José Juan Santamaria Intl
Tue 5/26
9:00 am-7:45 pm
1 stop9h 45m
$615
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 March.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Chicago Midway Airport-San José flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-San José flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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.
Cheapflights Insights
Everything you need to know about your flight from Chicago Midway Airport to San José
How often are flights from Chicago to San José delayed?
About 100% of weekly flights between Chicago and San José have experienced delays in the past year, with the average delay time being 97 minutes.
What is the most punctual flight time for Chicago to San José flights?
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the morning tend to experience delays more often.
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 March 25, 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.
Entertainment
7.5
Food
7.0
Boarding
8.1
Crew
8.6
Overall
8.0
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Food
7.0
Boarding
8.1
Crew
8.6
Overall
8.0
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
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
Monteverde
Jacó
Heredia
Dominical
Manuel Antonio
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Midway and San José flights
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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 2,558,603 searches. Data last updated March 25, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$394 | Average$547 | FlexibilityNo cancel fee | On-time63% |