$119+ Cheap flights from Midway (MDW) to San Jose, CA (SJC)
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 8/20. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJC
Sep 1 — Sep 81
Round-trip
1 adult, Economy
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Find cheap flights from Midway to San Jose 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 Jose
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Best
Last-minute
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Cheapest flights from Midway to San JoseExplore the most affordable flight options available from Midway to San Jose. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 2, 2026.
Explore the most affordable flight options available from Midway to San Jose. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 2, 2026.
This Southwest deal was found by Cheapflights users on 7/28. 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 9/122:05 pm
MDW
- SJC
1 stop6h 15m
Southwest
Sat 9/197:10 am
SJC
- MDW
Nonstop4h 05m
Southwest
Deal found 7/28![Southwest logo]()
$243
This Southwest deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/208:50 pm
MDW
- SJC
Nonstop4h 30m
Southwest
Wed 8/267:00 pm
SJC
- MDW
1 stop7h 30m
Southwest
Deal found 7/28![Southwest logo]()
$247
This Delta deal was found by Cheapflights users on 7/29. 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 10/2012:45 pm
MDW
- SJC
1 stop10h 40m
Delta
Mon 10/266:05 am
SJC
- MDW
1 stop8h 42m
Delta
Deal found 7/29![Delta logo]()
$257
This Delta deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2012:46 pm
MDW
- SJC
1 stop8h 06m
Delta
Wed 8/2612:37 pm
SJC
- MDW
1 stop7h 59m
Delta
Deal found 7/29![Delta logo]()
$258
This Southwest deal was found by Cheapflights users on 7/28. 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 8/2510:30 am
MDW
- SJC
2 stops7h 55m
Southwest
Tue 9/16:45 am
SJC
- MDW
2 stops7h 15m
Southwest
Deal found 7/28![Southwest logo]()
$267
This Delta deal was found by Cheapflights users on 7/29. 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 12/91:00 pm
MDW
- SJC
1 stop11h 08m
Delta
Thu 12/3110:20 pm
SJC
- MDW
1 stop9h 32m
Delta
Deal found 7/29![Delta logo]()
$288
This Southwest deal was found by Cheapflights users on 7/30. 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 9/36:15 am
MDW
- SJC
1 stop7h 40m
Southwest
Mon 9/76:30 am
SJC
- MDW
1 stop5h 40m
Southwest
Deal found 7/30![Southwest logo]()
$297
This Southwest deal was found by Cheapflights users on 7/29. 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 10/211:05 pm
MDW
- SJC
2 stops7h 55m
Southwest
Mon 10/265:15 pm
SJC
- MDW
1 stop5h 40m
Southwest
Deal found 7/29![Southwest logo]()
$298
This Southwest deal was found by Cheapflights users on 7/29. 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 9/35:00 pm
MDW
- SJC
1 stop6h 05m
Southwest
Thu 9/107:55 am
SJC
- MDW
2 stops7h 15m
Southwest
Deal found 7/29![Southwest logo]()
$302
Best flights from Midway to San JoseDiscover carefully curated flight deals from Midway to San Jose that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 2, 2026.
Discover carefully curated flight deals from Midway to San Jose that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 2, 2026.
This Southwest deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/208:50 pm
MDW
- SJC
Nonstop4h 30m
Southwest
Wed 8/267:00 pm
SJC
- MDW
1 stop7h 30m
Southwest
Deal found 7/28![Southwest logo]()
$247
This Delta deal was found by Cheapflights users on 7/29. 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 10/2012:45 pm
MDW
- SJC
1 stop10h 40m
Delta
Mon 10/266:05 am
SJC
- MDW
1 stop8h 42m
Delta
Deal found 7/29![Delta logo]()
$257
This Delta deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2012:46 pm
MDW
- SJC
1 stop8h 06m
Delta
Wed 8/2612:37 pm
SJC
- MDW
1 stop7h 59m
Delta
Deal found 7/29![Delta logo]()
$257
This Southwest deal was found by Cheapflights users on 7/29. 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 9/121:45 pm
MDW
- SJC
2 stops7h 55m
Southwest
Mon 9/213:15 pm
SJC
- MDW
1 stop6h 35m
Southwest
Deal found 7/29![Southwest logo]()
$302
This Southwest deal was found by Cheapflights users on 7/28. 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 9/118:50 pm
MDW
- SJC
Nonstop4h 35m
Southwest
Fri 9/1811:00 pm
SJC
- MDW
Nonstop4h 00m
Southwest
Deal found 7/28![Southwest logo]()
$320
This Delta deal was found by Cheapflights users on 7/31. 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 9/41:51 pm
MDW
- SJC
1 stop8h 33m
Delta
Sat 9/512:46 pm
SJC
- MDW
1 stop7h 50m
Delta
Deal found 7/31![Delta logo]()
$335
This Southwest deal was found by Cheapflights users on 7/29. 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 10/89:15 pm
MDW
- SJC
Nonstop4h 35m
Southwest
Sun 10/116:05 am
SJC
- MDW
Nonstop4h 00m
Southwest
Deal found 7/29![Southwest logo]()
$327
This Southwest deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/216:15 am
MDW
- SJC
1 stop6h 15m
Southwest
Tue 8/258:00 am
SJC
- MDW
2 stops7h 10m
Southwest
Deal found 7/28![Southwest logo]()
$336
This Southwest deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/276:15 am
MDW
- SJC
1 stop6h 15m
Southwest
Thu 9/37:55 am
SJC
- MDW
2 stops7h 15m
Southwest
Deal found 7/29![Southwest logo]()
$336
This Southwest deal was found by Cheapflights users on 7/31. 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 9/51:15 pm
MDW
- SJC
Nonstop4h 30m
Southwest
Mon 9/711:00 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Deal found 7/31![Southwest logo]()
$343
Last-minute flights from Midway to San JoseDiscover last-minute flight deals from Midway to San Jose. Data last updated August 2, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to San Jose. Data last updated August 2, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 7/28. 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 8/182:10 pm
MDW
- SJC
2 stops7h 55m
Southwest
Sat 8/2210:45 am
SJC
- MDW
1 stop7h 30m
Southwest
Deal found 7/28![Southwest logo]()
$262
This Southwest deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/208:50 pm
MDW
- SJC
Nonstop4h 30m
Southwest
Wed 8/267:00 pm
SJC
- MDW
1 stop7h 30m
Southwest
Deal found 7/28![Southwest logo]()
$247
This Delta deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2012:46 pm
MDW
- SJC
1 stop8h 06m
Delta
Wed 8/2612:37 pm
SJC
- MDW
1 stop7h 59m
Delta
Deal found 7/29![Delta logo]()
$257
This Southwest deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2110:15 am
MDW
- SJC
Nonstop4h 30m
Southwest
Tue 8/2511:00 pm
SJC
- MDW
Nonstop4h 00m
Southwest
Deal found 7/28![Southwest logo]()
$315
This Southwest deal was found by Cheapflights users on 7/28. 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 8/2510:30 am
MDW
- SJC
2 stops7h 55m
Southwest
Tue 9/16:45 am
SJC
- MDW
2 stops7h 15m
Southwest
Deal found 7/28![Southwest logo]()
$267
This Delta deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/261:51 pm
MDW
- SJC
1 stop8h 33m
Delta
Tue 9/112:40 pm
SJC
- MDW
1 stop7h 56m
Delta
Deal found 7/29![Delta logo]()
$288
This Southwest deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/276:15 am
MDW
- SJC
1 stop6h 15m
Southwest
Fri 9/1111:00 pm
SJC
- MDW
Nonstop4h 00m
Southwest
Deal found 8/1![Southwest logo]()
$309
This Southwest deal was found by Cheapflights users on 7/29. 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 8/291:45 pm
MDW
- SJC
2 stops7h 50m
Southwest
Sat 9/56:05 pm
SJC
- MDW
1 stop8h 25m
Southwest
Deal found 7/29![Southwest logo]()
$302
One-way flights from Midway to San JoseSearch for one-way flight options from Midway to San Jose. Find affordable one-way fares based on user searches. Data last updated August 2, 2026.
Search for one-way flight options from Midway to San Jose. Find affordable one-way fares based on user searches. Data last updated August 2, 2026.
This Southwest deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/208:50 pm
MDW
- SJC
Nonstop4h 30m
Southwest
Deal found 7/30![Southwest logo]()
$119
This Southwest deal was found by Cheapflights users on 7/29. 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 10/16:05 am
MDW
- SJC
1 stop7h 40m
Southwest
Deal found 7/29![Southwest logo]()
$129
This Southwest deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2710:25 am
MDW
- SJC
2 stops7h 50m
Southwest
Deal found 7/28![Southwest logo]()
$134
This Southwest deal was found by Cheapflights users on 7/28. 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 pm
MDW
- SJC
2 stops7h 20m
Southwest
Deal found 7/28![Southwest logo]()
$139
This Kiwi.com deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/266:05 am
MDW
- SJC
2 stops32h 02m
Frontier
Deal found 7/30![Frontier logo]()
$149
This Kiwi.com deal was found by Cheapflights users on 7/31. 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 10/2812:03 pm
MDW
- SJC
2 stops27h 26m
Frontier
Deal found 7/31![Frontier logo]()
$155
This Kiwi.com deal was found by Cheapflights users on 7/31. 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 9/211:50 am
MDW
- SJC
2 stops26h 17m
Frontier
Deal found 7/31![Frontier logo]()
$157
This Southwest deal was found by Cheapflights users on 7/30. 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 8/248:50 pm
MDW
- SJC
Nonstop4h 30m
Southwest
Deal found 7/30![Southwest logo]()
$159
This Delta deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/191:51 pm
MDW
- SJC
1 stop8h 33m
Delta
Deal found 7/29![Delta logo]()
$160
This Kiwi.com deal was found by Cheapflights users on 7/29. 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 8/296:05 am
MDW
- SJC
2 stops32h 02m
Frontier
Deal found 7/29![Frontier logo]()
$163
Find flight deals from Midway to San Jose
Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to San Jose (SJC). 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 2, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $243 (Southwest) |
One-way from | $119 (Southwest) |
Popular in | May |
Cheapest in | April |
Average price | $417 |
Good round-trip deal | $301 or less |
Good one-way deal | $203 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Midway to San Jose 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 August 2, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to San Jose that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoSan Jose
MDW - SJC
MDWSJC
Chicago Midway
Thu 8/20
8:50 pm-11:20 pm
Nonstop4h 30m
San Jose
Wed 8/26
7:00 pm-4:30 am
1 stop7h 30m
$247
ChicagoSan Jose
MDW - SJC
MDWSJC
Chicago Midway
Tue 10/20
12:45 pm-9:25 pm
1 stop10h 40m
San Jose
Mon 10/26
6:05 am-4:47 pm
1 stop8h 42m
$257
ChicagoSan Jose
MDW - SJC
MDWSJC
Chicago Midway
Thu 8/20
12:46 pm-6:52 pm
1 stop8h 06m
San Jose
Wed 8/26
12:37 pm-10:36 pm
1 stop7h 59m
$257
ChicagoSan Jose
MDW - SJC
MDWSJC
Chicago Midway
Sat 9/12
1:45 pm-7:40 pm
2 stops7h 55m
San Jose
Mon 9/21
3:15 pm-11:50 pm
1 stop6h 35m
$302
Quickest round-trip
ChicagoSan Jose
MDW - SJC
MDWSJC
Chicago Midway
Fri 9/11
8:50 pm-11:25 pm
Nonstop4h 35m
San Jose
Fri 9/18
11:00 pm-5:00 am
Nonstop4h 00m
$320
ChicagoSan Jose
MDW - SJC
MDWSJC
Chicago Midway
Thu 10/8
9:15 pm-11:50 pm
Nonstop4h 35m
San Jose
Sun 10/11
6:05 am-12:05 pm
Nonstop4h 00m
$327
ChicagoSan Jose
MDW - SJC
MDWSJC
Chicago Midway
Fri 9/4
1:51 pm-8:24 pm
1 stop8h 33m
San Jose
Sat 9/5
12:46 pm-10:36 pm
1 stop7h 50m
$335
ChicagoSan Jose
MDW - SJC
MDWSJC
Chicago Midway
Fri 8/21
6:15 am-10:30 am
1 stop6h 15m
San Jose
Tue 8/25
8:00 am-5:10 pm
2 stops7h 10m
$336
ChicagoSan Jose
MDW - SJC
MDWSJC
Chicago Midway
Thu 8/27
6:15 am-10:30 am
1 stop6h 15m
San Jose
Thu 9/3
7:55 am-5:10 pm
2 stops7h 15m
$336
ChicagoSan Jose
MDW - SJC
MDWSJC
Chicago Midway
Sat 9/5
1:15 pm-3:45 pm
Nonstop4h 30m
San Jose
Mon 9/7
11:00 pm-5:05 am
Nonstop4h 05m
$343
Showing 1-10 of 22 resultsSorted by cheapest first
Compare providers for flights from Midway to San Jose
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 Jose in August.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Chicago Midway Airport-San Jose, California 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 Jose, California flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-San Jose, California flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago Midway Airport-San Jose, California 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 Jose, California 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 Jose
Have a flexible travel schedule? Discover the best time to fly to San Jose from Midway with our price prediction graph.
MDW-SJC
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 Jose
The best insider tips for Chicago Midway Airport to San Jose flights
AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Chicago Midway Airport to San Jose trip
Our travel experts
Reviews of airlines servicing San Jose
Get insights into the airlines that provide service to San Jose. 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 Jose. Reviews last updated August 2, 2026.
Get a feel of what it's like to fly with Southwest from Chicago Midway Airport to San Jose by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.5
Overall
8.0
Food
7.0
Crew
8.6
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Entertainment
7.5
Overall
8.0
Food
7.0
Crew
8.6
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Related info for your journey
Find useful and relevant information for your journey from Midway to San Jose. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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Alternative routes for Midway to San Jose
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Complete your trip
Complete your trip to San Jose by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Midway to San Jose by cabin class
Find flights from Midway to San Jose, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Midway and San Jose flights
Browse other Midway and San Jose flight options. Last updated on August 2, 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 August 2, 2026.
Popular flight searches
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Other flights to San Jose
Explore flights to San Jose departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on August 2, 2026.
Top airline flying from Midway to San Jose
Discover the top airline that operate flights from Midway to San Jose. 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 August 2, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$298 | Average$521 | FlexibilityNo cancel fee | On-time63% |