$210+ Cheap flights from San José (SJO) 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 5/8. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — MDW
Apr 13 — Apr 201
Round-trip
1 adult, Economy
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Find cheap flights from San José 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
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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 José to Midway
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Best
Last-minute
One-way
Cheapest flights from San José to MidwayExplore the most affordable flight options available from San José to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 14, 2026.
Explore the most affordable flight options available from San José to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 14, 2026.
This Kiwi.com deal was found by Cheapflights users on 3/12. 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 4/911:38 am
SJO
- MDW
1 stop8h 43m
Multiple Airlines
Tue 4/147:30 am
MDW
- SJO
2 stops28h 08m
Multiple Airlines
Deal found 3/12![Multiple Airlines logo]()
$428
This Kiwi.com deal was found by Cheapflights users on 3/13. 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 4/911:38 am
SJO
- MDW
2 stops27h 21m
Multiple Airlines
Mon 4/136:30 am
MDW
- SJO
1 stop9h 35m
Multiple Airlines
Deal found 3/13![Multiple Airlines logo]()
$441
This Southwest deal was found by Cheapflights users on 3/10. 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 4/221:10 pm
SJO
- MDW
1 stop8h 55m
Southwest
Tue 4/286:00 am
MDW
- SJO
1 stop7h 10m
Southwest
Deal found 3/10![Southwest logo]()
$453
This eDestinos deal was found by Cheapflights users on 3/10. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/2211:23 am
SJO
- MDW
2 stops24h 37m
Multiple Airlines
Tue 4/287:30 am
MDW
- SJO
2 stops28h 08m
Multiple Airlines
Deal found 3/10![Multiple Airlines logo]()
$457
This eDestinos deal was found by Cheapflights users on 3/10. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/234:18 pm
SJO
- MDW
2 stops28h 32m
Multiple Airlines
Tue 4/287:30 am
MDW
- SJO
2 stops28h 08m
Multiple Airlines
Deal found 3/10![Multiple Airlines logo]()
$459
This Southwest deal was found by Cheapflights users on 3/9. 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.
Mon 5/111:10 pm
SJO
- MDW
1 stop7h 45m
Southwest
Fri 5/1512:10 pm
MDW
- SJO
1 stop7h 50m
Southwest
Deal found 3/9![Southwest logo]()
$464
This Southwest deal was found by Cheapflights users on 3/10. 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 4/161:10 pm
SJO
- MDW
1 stop7h 45m
Southwest
Mon 4/205:35 am
MDW
- SJO
1 stop7h 35m
Southwest
Deal found 3/10![Southwest logo]()
$465
This Expedia deal was found by Cheapflights users on 3/9. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/1411:45 am
SJO
- MDW
1 stop9h 24m
Frontier
Sat 4/112:56 pm
MDW
- SJO
1 stop22h 16m
Frontier
Deal found 3/9![Frontier logo]()
$473
This Delta deal was found by Cheapflights users on 3/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/21:21 pm
SJO
- MDW
1 stop8h 07m
Delta
Sat 5/96:23 am
MDW
- SJO
1 stop7h 52m
Delta
Deal found 3/10![Delta logo]()
$476
Best flights from San José to MidwayDiscover carefully curated flight deals from San José to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated March 14, 2026.
Discover carefully curated flight deals from San José to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated March 14, 2026.
This Delta deal was found by Cheapflights users on 3/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/21:21 pm
SJO
- MDW
1 stop8h 07m
Delta
Sat 5/96:23 am
MDW
- SJO
1 stop7h 52m
Delta
Deal found 3/11![Delta logo]()
$476
This Southwest deal was found by Cheapflights users on 3/13. 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 4/301:10 pm
SJO
- MDW
1 stop7h 45m
Southwest
Wed 5/612:15 pm
MDW
- SJO
1 stop7h 45m
Southwest
Deal found 3/13![Southwest logo]()
$515
This Southwest deal was found by Cheapflights users on 3/12. 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 5/69:00 am
SJO
- MDW
2 stops11h 50m
Southwest
Wed 5/138:00 am
MDW
- SJO
2 stops12h 00m
Southwest
Deal found 3/12![Southwest logo]()
$541
This Delta deal was found by Cheapflights users on 3/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/11:21 pm
SJO
- MDW
1 stop8h 07m
Delta
Sat 5/96:23 am
MDW
- SJO
1 stop7h 52m
Delta
Deal found 3/9![Delta logo]()
$573
This Southwest deal was found by Cheapflights users on 3/12. 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 5/289:00 am
SJO
- MDW
2 stops13h 30m
Southwest
Sun 5/3111:05 am
MDW
- SJO
2 stops8h 55m
Southwest
Deal found 3/12![Southwest logo]()
$545
This Southwest deal was found by Cheapflights users on 3/9. 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.
Fri 4/249:00 am
SJO
- MDW
2 stops12h 45m
Southwest
Sun 4/266:50 am
MDW
- SJO
1 stop7h 10m
Southwest
Deal found 3/9![Southwest logo]()
$562
This Southwest deal was found by Cheapflights users on 3/10. 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 4/231:10 pm
SJO
- MDW
1 stop7h 45m
Southwest
Tue 4/2810:15 am
MDW
- SJO
1 stop9h 45m
Southwest
Deal found 3/10![Southwest logo]()
$567
This Southwest deal was found by Cheapflights users on 3/12. 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 5/149:00 am
SJO
- MDW
1 stop9h 00m
Southwest
Sun 5/176:50 am
MDW
- SJO
1 stop7h 10m
Southwest
Deal found 3/12![Southwest logo]()
$576
This Southwest deal was found by Cheapflights users on 3/12. 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 5/299:00 am
SJO
- MDW
1 stop9h 00m
Southwest
Wed 6/39:50 am
MDW
- SJO
2 stops10h 10m
Southwest
Deal found 3/12![Southwest logo]()
$577
Last-minute flights from San José to MidwayDiscover last-minute flight deals from San José to Midway. Data last updated March 14, 2026 and is based on user searches.
Discover last-minute flight deals from San José to Midway. Data last updated March 14, 2026 and is based on user searches.
This Expedia deal was found by Cheapflights users on 3/9. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/1411:45 am
SJO
- MDW
1 stop9h 24m
Frontier
Sat 4/112:56 pm
MDW
- SJO
1 stop22h 16m
Frontier
Deal found 3/9![Frontier logo]()
$473
This Kiwi.com deal was found by Cheapflights users on 3/12. 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 4/911:38 am
SJO
- MDW
1 stop8h 43m
Multiple Airlines
Tue 4/147:30 am
MDW
- SJO
2 stops28h 08m
Multiple Airlines
Deal found 3/12![Multiple Airlines logo]()
$428
This Kiwi.com deal was found by Cheapflights users on 3/13. 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 4/911:38 am
SJO
- MDW
2 stops27h 21m
Multiple Airlines
Mon 4/136:30 am
MDW
- SJO
1 stop9h 35m
Multiple Airlines
Deal found 3/13![Multiple Airlines logo]()
$441
This Southwest deal was found by Cheapflights users on 3/10. 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 4/161:10 pm
SJO
- MDW
1 stop7h 45m
Southwest
Mon 4/205:35 am
MDW
- SJO
1 stop7h 35m
Southwest
Deal found 3/10![Southwest logo]()
$465
This Southwest deal was found by Cheapflights users on 3/10. 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 4/221:10 pm
SJO
- MDW
1 stop8h 55m
Southwest
Tue 4/286:00 am
MDW
- SJO
1 stop7h 10m
Southwest
Deal found 3/10![Southwest logo]()
$453
This eDestinos deal was found by Cheapflights users on 3/10. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/2211:23 am
SJO
- MDW
2 stops24h 37m
Multiple Airlines
Tue 4/287:30 am
MDW
- SJO
2 stops28h 08m
Multiple Airlines
Deal found 3/10![Multiple Airlines logo]()
$457
This eDestinos deal was found by Cheapflights users on 3/10. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/234:18 pm
SJO
- MDW
2 stops28h 32m
Multiple Airlines
Tue 4/287:30 am
MDW
- SJO
2 stops28h 08m
Multiple Airlines
Deal found 3/10![Multiple Airlines logo]()
$459
This eDestinos deal was found by Cheapflights users on 3/10. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/247:00 am
SJO
- MDW
1 stop9h 54m
Multiple Airlines
Tue 4/287:30 am
MDW
- SJO
2 stops28h 08m
Multiple Airlines
Deal found 3/10![Multiple Airlines logo]()
$485
One-way flights from San José to MidwaySearch for one-way flight options from San José to Midway. Find affordable one-way fares based on user searches. Data last updated March 14, 2026.
Search for one-way flight options from San José to Midway. Find affordable one-way fares based on user searches. Data last updated March 14, 2026.
This Kiwi.com deal was found by Cheapflights users on 3/10. 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.
Fri 5/812:38 pm
SJO
- MDW
2 stops21h 26m
Multiple Airlines
Deal found 3/10![Multiple Airlines logo]()
$210
This Kiwi.com deal was found by Cheapflights users on 3/9. 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.
Fri 4/2412:38 pm
SJO
- MDW
2 stops28h 59m
Multiple Airlines
Deal found 3/9![Multiple Airlines logo]()
$229
This Kiwi.com deal was found by Cheapflights users on 3/10. 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.
Wed 5/611:23 am
SJO
- MDW
2 stops24h 37m
Multiple Airlines
Deal found 3/10![Multiple Airlines logo]()
$245
This Kiwi.com deal was found by Cheapflights users on 3/10. 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.
Thu 5/712:38 pm
SJO
- MDW
2 stops21h 31m
Multiple Airlines
Deal found 3/10![Multiple Airlines logo]()
$250
This Southwest deal was found by Cheapflights users on 3/9. 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.
Wed 4/221:10 pm
SJO
- MDW
1 stop8h 55m
Southwest
Deal found 3/9![Southwest logo]()
$257
This Kiwi.com deal was found by Cheapflights users on 3/9. 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.
Thu 4/2312:38 pm
SJO
- MDW
2 stops29h 53m
Multiple Airlines
Deal found 3/9![Multiple Airlines logo]()
$260
This Kiwi.com deal was found by Cheapflights users on 3/12. 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 4/712:19 pm
SJO
- MDW
2 stops30h 48m
Multiple Airlines
Deal found 3/12![Multiple Airlines logo]()
$261
This Kiwi.com deal was found by Cheapflights users on 3/10. 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 3/3111:38 am
SJO
- MDW
2 stops33h 41m
Multiple Airlines
Deal found 3/10![Multiple Airlines logo]()
$267
This Kiwi.com deal was found by Cheapflights users on 3/10. 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.
Mon 5/47:45 pm
SJO
- MDW
3 stops25h 17m
Multiple Airlines
Deal found 3/10![Multiple Airlines logo]()
$273
This Kiwi.com deal was found by Cheapflights users on 3/9. 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.
Sat 4/257:45 am
SJO
- MDW
2 stops13h 29m
Multiple Airlines
Deal found 3/9![Multiple Airlines logo]()
$274
This Kiwi.com deal was found by Cheapflights users on 3/11. 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 4/611:38 am
SJO
- MDW
2 stops33h 41m
Multiple Airlines
Deal found 3/11![Multiple Airlines logo]()
$277
Find flight deals from San José to Midway
Discover tips and strategies to find the most affordable flight options for your journey from San José (SJO) 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 March 14, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $423 (Priceline) |
One-way from | $210 (Kiwi.com) |
Popular in | July |
Cheapest in | January |
Average price | $401 |
Cheapflights Fare Finder
Customize your flight search to find flights from San José 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 March 14, 2026.
Use the filters below to find and compare flights from San José to Chicago Midway Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
San JoséChicago
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Sat 5/2
1:21 pm-10:28 pm
1 stop8h 07m
Chicago Midway
Sat 5/9
6:23 am-1:15 pm
1 stop7h 52m
$476
Quickest round-trip
San JoséChicago
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Thu 4/30
1:10 pm-9:55 pm
1 stop7h 45m
Chicago Midway
Wed 5/6
12:15 pm-7:00 pm
1 stop7h 45m
$515
San JoséChicago
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Wed 5/6
9:00 am-9:50 pm
2 stops11h 50m
Chicago Midway
Wed 5/13
8:00 am-7:00 pm
2 stops12h 00m
$541
San JoséChicago
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Thu 5/28
9:00 am-11:30 pm
2 stops13h 30m
Chicago Midway
Sun 5/31
11:05 am-7:00 pm
2 stops8h 55m
$545
San JoséChicago
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Fri 4/24
9:00 am-10:45 pm
2 stops12h 45m
Chicago Midway
Sun 4/26
6:50 am-1:00 pm
1 stop7h 10m
$562
San JoséChicago
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Thu 4/23
1:10 pm-9:55 pm
1 stop7h 45m
Chicago Midway
Tue 4/28
10:15 am-7:00 pm
1 stop9h 45m
$567
San JoséChicago
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Fri 5/1
1:21 pm-10:28 pm
1 stop8h 07m
Chicago Midway
Sat 5/9
6:23 am-1:15 pm
1 stop7h 52m
$573
San JoséChicago
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Thu 5/14
9:00 am-7:00 pm
1 stop9h 00m
Chicago Midway
Sun 5/17
6:50 am-1:00 pm
1 stop7h 10m
$576
San JoséChicago
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Fri 5/29
9:00 am-7:00 pm
1 stop9h 00m
Chicago Midway
Wed 6/3
9:50 am-7:00 pm
2 stops10h 10m
$577
Cheapest one-way
Quickest one-way
San JoséChicago
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Wed 4/22
1:10 pm-11:05 pm
1 stop8h 55m
$257
Showing 1-10 of 20 resultsSorted by cheapest first
Compare providers for flights from San José to Midway
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 San José to Midway in March.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on San José-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on San José-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from San José-Chicago Midway Airport flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on San José-Chicago Midway Airport 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 San José-Chicago Midway Airport 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 San José to Midway
Have a flexible travel schedule? Discover the best time to fly to Midway from San José with our price prediction graph.
SJO-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 José to Chicago Midway Airport
How often are flights from San José to Chicago delayed?
About 0% of weekly flights between San José and Chicago have experienced delays in the past year, with the average delay time being 0 minutes.
What is the most punctual flight time for San José to Chicago flights?
Historically, flights departing in the early afternoon are less likely to be delayed, whereas flights leaving in the early afternoon tend to experience delays more often.
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 March 14, 2026.
Read through reviews of airlines operating flights from San José to Chicago Midway Airport, such as Southwest. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
8.0
Crew
8.6
Entertainment
7.5
Overall
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Comfort
8.0
Crew
8.6
Entertainment
7.5
Overall
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Related info for your journey
Find useful and relevant information for your journey from San José 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 locationsLansing
Merrillville
Hammond
Porter
Benton Harbor
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Alternative routes for San José to Midway
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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 March 14, 2026.
San José and Midway flights
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Other flights from San José
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Top airline flying from San José to Midway
Discover the top airline that operate flights from San José to Midway. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated March 14, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$463 | Average$523 | FlexibilityNo cancel fee | On-time63% |