$129+ 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 6/30. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJC
Jun 2 — Jun 91
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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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 May 3, 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 May 3, 2026.
This Southwest deal was found by Cheapflights users on 5/1. 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.
Wed 6/108:55 pm
MDW
- SJC
Nonstop4h 30m
Southwest
Wed 6/241:30 pm
SJC
- MDW
1 stop7h 35m
Southwest
Deal found 5/1![Southwest logo]()
$292
This Southwest deal was found by Cheapflights users on 4/30. 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.
Wed 5/275:35 pm
MDW
- SJC
1 stop6h 35m
Southwest
Wed 6/310:40 am
SJC
- MDW
1 stop6h 55m
Southwest
Deal found 4/30![Southwest logo]()
$302
This Southwest deal was found by Cheapflights users on 5/2. 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 6/23:40 pm
MDW
- SJC
Nonstop4h 35m
Southwest
Tue 6/910:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Deal found 5/2![Southwest logo]()
$310
This Southwest deal was found by Cheapflights users on 5/1. 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 6/48:50 pm
MDW
- SJC
Nonstop4h 35m
Southwest
Tue 6/910:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Deal found 5/1![Southwest logo]()
$322
This Southwest deal was found by Cheapflights users on 4/28. 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 8/206:15 am
MDW
- SJC
1 stop6h 15m
Southwest
Wed 9/211:00 pm
SJC
- MDW
Nonstop4h 00m
Southwest
Deal found 4/28![Southwest logo]()
$328
This Southwest deal was found by Cheapflights users on 5/2. 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 6/18:25 pm
MDW
- SJC
Nonstop4h 35m
Southwest
Tue 6/910:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Deal found 5/2![Southwest logo]()
$330
This Southwest deal was found by Cheapflights users on 5/2. 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 6/25:30 pm
MDW
- SJC
2 stops7h 30m
Southwest
Sun 6/710:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Deal found 5/2![Southwest logo]()
$337
This Southwest deal was found by Cheapflights users on 5/3. 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 6/246:00 am
MDW
- SJC
1 stop7h 25m
Southwest
Wed 7/88:55 pm
SJC
- MDW
1 stop6h 30m
Southwest
Deal found 5/3![Southwest logo]()
$342
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 May 3, 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 May 3, 2026.
This Southwest deal was found by Cheapflights users on 5/2. 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 6/210:20 am
MDW
- SJC
Nonstop4h 35m
Southwest
Tue 6/910:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Deal found 5/2![Southwest logo]()
$310
This Delta deal was found by Cheapflights users on 5/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/101:21 pm
MDW
- SJC
2 stops10h 55m
Delta
Mon 6/228:19 pm
SJC
- MDW
2 stops10h 18m
Delta
Deal found 5/1![Delta logo]()
$352
This Delta deal was found by Cheapflights users on 4/29. 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 6/31:22 pm
MDW
- SJC
2 stops10h 52m
Delta
Mon 6/88:19 pm
SJC
- MDW
2 stops10h 18m
Delta
Deal found 4/29![Delta logo]()
$352
This Delta deal was found by Cheapflights users on 5/2. 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 5/239:23 am
MDW
- SJC
2 stops8h 46m
Delta
Tue 5/2610:00 pm
SJC
- MDW
1 stop10h 00m
Delta
Deal found 5/2![Delta logo]()
$355
This Southwest deal was found by Cheapflights users on 5/2. 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 7/310:05 am
MDW
- SJC
Nonstop4h 25m
Southwest
Wed 7/810:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Deal found 5/2![Southwest logo]()
$407
This Southwest deal was found by Cheapflights users on 4/28. 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 10/2010:30 am
MDW
- SJC
Nonstop4h 30m
Southwest
Mon 10/2611:45 am
SJC
- MDW
Nonstop4h 05m
Southwest
Deal found 4/28![Southwest logo]()
$407
This Southwest deal was found by Cheapflights users on 5/1. 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.
Fri 6/268:50 pm
MDW
- SJC
Nonstop4h 35m
Southwest
Mon 6/294:20 pm
SJC
- MDW
1 stop5h 55m
Southwest
Deal found 5/1![Southwest logo]()
$413
This Delta deal was found by Cheapflights users on 4/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/209:55 am
MDW
- SJC
2 stops8h 21m
Delta
Mon 10/2610:20 pm
SJC
- MDW
1 stop9h 32m
Delta
Deal found 4/30![Delta logo]()
$432
This Southwest deal was found by Cheapflights users on 4/29. 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 6/275:25 am
MDW
- SJC
1 stop6h 00m
Southwest
Mon 6/2910:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Deal found 4/29![Southwest logo]()
$417
This Southwest deal was found by Cheapflights users on 5/1. 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 6/115:20 am
MDW
- SJC
1 stop6h 20m
Southwest
Mon 6/158:20 pm
SJC
- MDW
1 stop7h 05m
Southwest
Deal found 5/1![Southwest logo]()
$427
This Southwest deal was found by Cheapflights users on 4/30. 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.
Sat 5/3010:05 am
MDW
- SJC
2 stops7h 40m
Southwest
Mon 6/85:00 pm
SJC
- MDW
1 stop6h 25m
Southwest
Deal found 4/30![Southwest logo]()
$432
Last-minute flights from Midway to San JoseDiscover last-minute flight deals from Midway to San Jose. Data last updated May 3, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to San Jose. Data last updated May 3, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 4/28. 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 5/218:25 pm
MDW
- SJC
Nonstop4h 35m
Southwest
Wed 5/277:00 pm
SJC
- MDW
1 stop7h 35m
Southwest
Deal found 4/28![Southwest logo]()
$340
This Delta deal was found by Cheapflights users on 4/29. 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.
Sat 5/231:59 pm
MDW
- SJC
1 stop8h 39m
Delta
Tue 5/2610:00 pm
SJC
- MDW
1 stop10h 00m
Delta
Deal found 4/29![Delta logo]()
$350
This Southwest deal was found by Cheapflights users on 4/29. 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.
Tue 5/263:55 pm
MDW
- SJC
1 stop7h 25m
Southwest
Wed 5/276:45 am
SJC
- MDW
1 stop6h 40m
Southwest
Deal found 4/29![Southwest logo]()
$362
This Southwest deal was found by Cheapflights users on 5/2. 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 5/267:30 am
MDW
- SJC
2 stops8h 15m
Southwest
Tue 6/231:30 pm
SJC
- MDW
1 stop7h 35m
Southwest
Deal found 5/2![Southwest logo]()
$367
This Southwest deal was found by Cheapflights users on 4/29. 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 5/2711:45 am
MDW
- SJC
1 stop8h 05m
Southwest
Tue 6/210:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Deal found 4/29![Southwest logo]()
$292
This Southwest deal was found by Cheapflights users on 4/30. 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.
Wed 5/275:35 pm
MDW
- SJC
1 stop6h 35m
Southwest
Wed 6/310:40 am
SJC
- MDW
1 stop6h 55m
Southwest
Deal found 4/30![Southwest logo]()
$302
This Delta deal was found by Cheapflights users on 5/2. 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 5/2710:59 am
MDW
- SJC
1 stop10h 03m
Delta
Fri 6/268:19 pm
SJC
- MDW
2 stops10h 18m
Delta
Deal found 5/2![Delta logo]()
$347
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 May 3, 2026.
Search for one-way flight options from Midway to San Jose. Find affordable one-way fares based on user searches. Data last updated May 3, 2026.
This Delta deal was found by Cheapflights users on 4/29. 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 6/301:49 pm
MDW
- SJC
1 stop8h 50m
Delta
Deal found 4/29![Delta logo]()
$129
This Delta deal was found by Cheapflights users on 4/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/276:23 am
MDW
- SJC
2 stops12h 39m
Delta
Deal found 4/28![Delta logo]()
$134
This Southwest deal was found by Cheapflights users on 5/1. 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.
Wed 5/273:40 pm
MDW
- SJC
Nonstop4h 35m
Southwest
Deal found 5/1![Southwest logo]()
$164
This Kiwi.com deal was found by Cheapflights users on 4/30. 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.
Sat 5/3011:59 am
MDW
- SJC
2 stops21h 37m
Frontier
Deal found 4/30![Frontier logo]()
$175
This Kiwi.com deal was found by Cheapflights users on 4/30. 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.
Sun 5/246:00 am
MDW
- SJC
2 stops31h 59m
Frontier
Deal found 4/30![Frontier logo]()
$179
This Kiwi.com deal was found by Cheapflights users on 5/2. 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 8/1512:11 pm
MDW
- SJC
2 stops33h 28m
Frontier
Deal found 5/2![Frontier logo]()
$181
This Kiwi.com deal was found by Cheapflights users on 5/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/112:04 pm
MDW
- SJC
2 stops27h 13m
Frontier
Deal found 5/1![Frontier logo]()
$190
This Kiwi.com deal was found by Cheapflights users on 4/29. 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 7/256:00 am
MDW
- SJC
2 stops15h 39m
Frontier
Deal found 4/29![Frontier logo]()
$191
This Southwest deal was found by Cheapflights users on 4/28. 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.
Wed 6/108:55 pm
MDW
- SJC
Nonstop4h 30m
Southwest
Deal found 4/28![Southwest logo]()
$192
This Delta deal was found by Cheapflights users on 4/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/267:13 pm
MDW
- SJC
2 stops17h 32m
Delta
Deal found 4/28![Delta logo]()
$193
This Delta deal was found by Cheapflights users on 5/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/109:54 am
MDW
- SJC
2 stops9h 23m
Delta
Deal found 5/1![Delta logo]()
$195
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 May 3, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $292 (Southwest) |
One-way from | $129 (Delta) |
Popular in | March |
Cheapest in | April |
Average price | $576 |
Good round-trip deal | $396 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 May 3, 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
Tue 6/2
10:20 am-12:55 pm
Nonstop4h 35m
San Jose
Tue 6/9
10:55 pm-5:00 am
Nonstop4h 05m
$310
ChicagoSan Jose
MDW - SJC
MDWSJC
Chicago Midway
Wed 6/10
1:21 pm-10:16 pm
2 stops10h 55m
San Jose
Mon 6/22
8:19 pm-8:37 am
2 stops10h 18m
$352
ChicagoSan Jose
MDW - SJC
MDWSJC
Chicago Midway
Wed 6/3
1:22 pm-10:14 pm
2 stops10h 52m
San Jose
Mon 6/8
8:19 pm-8:37 am
2 stops10h 18m
$352
ChicagoSan Jose
MDW - SJC
MDWSJC
Chicago Midway
Sat 5/23
9:23 am-4:09 pm
2 stops8h 46m
San Jose
Tue 5/26
10:00 pm-10:00 am
1 stop10h 00m
$355
Quickest round-trip
ChicagoSan Jose
MDW - SJC
MDWSJC
Chicago Midway
Fri 7/3
10:05 am-12:30 pm
Nonstop4h 25m
San Jose
Wed 7/8
10:55 pm-5:00 am
Nonstop4h 05m
$407
ChicagoSan Jose
MDW - SJC
MDWSJC
Chicago Midway
Tue 10/20
10:30 am-1:00 pm
Nonstop4h 30m
San Jose
Mon 10/26
11:45 am-5:50 pm
Nonstop4h 05m
$407
ChicagoSan Jose
MDW - SJC
MDWSJC
Chicago Midway
Fri 6/26
8:50 pm-11:25 pm
Nonstop4h 35m
San Jose
Mon 6/29
4:20 pm-12:15 am
1 stop5h 55m
$413
ChicagoSan Jose
MDW - SJC
MDWSJC
Chicago Midway
Sat 6/27
5:25 am-9:25 am
1 stop6h 00m
San Jose
Mon 6/29
10:55 pm-5:00 am
Nonstop4h 05m
$417
ChicagoSan Jose
MDW - SJC
MDWSJC
Chicago Midway
Thu 6/11
5:20 am-9:40 am
1 stop6h 20m
San Jose
Mon 6/15
8:20 pm-5:25 am
1 stop7h 05m
$427
ChicagoSan Jose
MDW - SJC
MDWSJC
Chicago Midway
Tue 10/20
9:55 am-4:16 pm
2 stops8h 21m
San Jose
Mon 10/26
10:20 pm-9:52 am
1 stop9h 32m
$432
Showing 1-10 of 19 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 May.
| 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
What is the cheapest time of day to fly from MDW to SJC?
Find hourly flight availability from Midway to San Jose. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 3, 2026.
One of the essential ways to save on airfare from Chicago Midway Airport to San Jose, California is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight at noon could potentially save you up to 20% on airfare.
How much does it cost to fly round-trip from Chicago Midway Airport to San Jose, California?
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 May 3, 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.
Boarding
8.1
Crew
8.6
Comfort
8.0
Overall
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Crew
8.6
Comfort
8.0
Overall
8.0
Entertainment
7.5
Food
7.0
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 Jose. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Midway to San Jose
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Complete your trip
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Midway and San Jose flights
Browse other Midway and San Jose flight options. Last updated on May 3, 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 May 3, 2026.
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Check out other popular destinations found by fellow travelers in 2026
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 May 3, 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 May 3, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$332 | Average$518 | FlexibilityNo cancel fee | On-time63% |