$158+ 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 8/18. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJC
jul 10 — jul 171
Round-trip
1 adult, Economy
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Find cheap flights from Midway to San Jose with Cheapflights
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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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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 junho 10, 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 junho 10, 2026.
This Southwest deal was found by Cheapflights users on 6/10. 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.
qua 7/14:40 pm
MDW
- SJC
1 stop7h 40m
Southwest
qua 7/81:10 pm
SJC
- MDW
1 stop7h 50m
Southwest
Deal found 6/10![Southwest logo]()
$273
This Delta deal was found by Cheapflights users on 6/8. 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.
qua 8/261:51 pm
MDW
- SJC
1 stop8h 33m
Delta
ter 9/112:40 pm
SJC
- MDW
1 stop7h 56m
Delta
Deal found 6/8![Delta logo]()
$275
This Delta deal was found by Cheapflights users on 6/9. 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.
qua 7/229:54 am
MDW
- SJC
2 stops9h 18m
Delta
ter 8/412:40 pm
SJC
- MDW
1 stop7h 56m
Delta
Deal found 6/9![Delta logo]()
$279
This Delta deal was found by Cheapflights users on 6/5. 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.
sáb 10/39:49 am
MDW
- SJC
1 stop9h 47m
Delta
ter 10/610:20 pm
SJC
- MDW
1 stop9h 32m
Delta
Deal found 6/5![Delta logo]()
$281
This Southwest deal was found by Cheapflights users on 6/5. 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.
ter 7/75:30 am
MDW
- SJC
1 stop7h 10m
Southwest
ter 7/287:35 pm
SJC
- MDW
1 stop7h 05m
Southwest
Deal found 6/5![Southwest logo]()
$283
This Southwest deal was found by Cheapflights users on 6/10. 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.
ter 10/610:30 am
MDW
- SJC
Nonstop4h 30m
Southwest
qua 11/411:10 am
SJC
- MDW
Nonstop4h 05m
Southwest
Deal found 6/10![Southwest logo]()
$296
This Delta deal was found by Cheapflights users on 6/10. 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.
ter 10/2010:35 am
MDW
- SJC
1 stop10h 17m
Delta
seg 10/2610:20 pm
SJC
- MDW
1 stop9h 32m
Delta
Deal found 6/10![Delta logo]()
$304
This Southwest deal was found by Cheapflights users on 6/10. 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.
ter 8/188:30 pm
MDW
- SJC
Nonstop4h 30m
Southwest
qua 9/26:40 am
SJC
- MDW
1 stop6h 25m
Southwest
Deal found 6/10![Southwest logo]()
$306
This Delta deal was found by Cheapflights users on 6/10. 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.
qua 9/94:30 pm
MDW
- SJC
1 stop8h 11m
Delta
sáb 9/127:00 am
SJC
- MDW
2 stops9h 31m
Delta
Deal found 6/10![Delta logo]()
$309
This Delta deal was found by Cheapflights users on 6/10. 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.
qua 7/159:54 am
MDW
- SJC
2 stops9h 18m
Delta
ter 7/218:25 pm
SJC
- MDW
2 stops10h 12m
Delta
Deal found 6/10![Delta logo]()
$316
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 junho 10, 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 junho 10, 2026.
This Delta deal was found by Cheapflights users on 6/10. 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.
ter 10/2010:35 am
MDW
- SJC
1 stop10h 17m
Delta
seg 10/2610:20 pm
SJC
- MDW
1 stop9h 32m
Delta
Deal found 6/10![Delta logo]()
$304
This Southwest deal was found by Cheapflights users on 6/10. 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.
ter 7/285:25 am
MDW
- SJC
2 stops8h 00m
Southwest
qua 7/297:50 pm
SJC
- MDW
1 stop7h 35m
Southwest
Deal found 6/10![Southwest logo]()
$355
This Delta deal was found by Cheapflights users on 6/9. 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.
qua 9/99:30 am
MDW
- SJC
2 stops12h 05m
Delta
sáb 9/127:00 am
SJC
- MDW
2 stops9h 31m
Delta
Deal found 6/9![Delta logo]()
$314
This Southwest deal was found by Cheapflights users on 6/9. 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.
qui 9/1010:15 am
MDW
- SJC
Nonstop4h 30m
Southwest
seg 9/1411:00 pm
SJC
- MDW
Nonstop4h 00m
Southwest
Deal found 6/9![Southwest logo]()
$363
This Delta deal was found by Cheapflights users on 6/9. 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.
qui 9/102:00 pm
MDW
- SJC
1 stop8h 53m
Delta
seg 9/148:25 pm
SJC
- MDW
2 stops10h 42m
Delta
Deal found 6/9![Delta logo]()
$338
This Southwest deal was found by Cheapflights users on 6/8. 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.
qui 8/206:15 am
MDW
- SJC
1 stop6h 15m
Southwest
seg 8/247:55 am
SJC
- MDW
2 stops7h 15m
Southwest
Deal found 6/8![Southwest logo]()
$383
This Southwest deal was found by Cheapflights users on 6/8. 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.
qua 7/810:05 am
MDW
- SJC
Nonstop4h 25m
Southwest
qua 7/2210:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Deal found 6/8![Southwest logo]()
$394
This Southwest deal was found by Cheapflights users on 6/8. 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.
qua 8/124:45 pm
MDW
- SJC
1 stop6h 40m
Southwest
dom 8/1612:10 pm
SJC
- MDW
2 stops7h 30m
Southwest
Deal found 6/8![Southwest logo]()
$397
This Southwest deal was found by Cheapflights users on 6/7. 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.
sáb 7/258:25 pm
MDW
- SJC
Nonstop4h 35m
Southwest
sáb 8/110:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Deal found 6/7![Southwest logo]()
$407
This Southwest deal was found by Cheapflights users on 6/6. 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.
sex 9/116:15 am
MDW
- SJC
1 stop6h 15m
Southwest
dom 9/1311:00 pm
SJC
- MDW
Nonstop4h 00m
Southwest
Deal found 6/6![Southwest logo]()
$413
This Southwest deal was found by Cheapflights users on 6/6. 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.
ter 10/2012:25 pm
MDW
- SJC
1 stop6h 30m
Southwest
seg 10/2611:00 pm
SJC
- MDW
Nonstop4h 00m
Southwest
Deal found 6/6![Southwest logo]()
$417
Last-minute flights from Midway to San JoseDiscover last-minute flight deals from Midway to San Jose. Data last updated junho 10, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to San Jose. Data last updated junho 10, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 6/10. 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.
qua 7/14:40 pm
MDW
- SJC
1 stop7h 40m
Southwest
qua 7/81:10 pm
SJC
- MDW
1 stop7h 50m
Southwest
Deal found 6/10![Southwest logo]()
$273
This Southwest deal was found by Cheapflights users on 6/9. 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.
qui 7/28:50 pm
MDW
- SJC
Nonstop4h 35m
Southwest
qua 7/810:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Deal found 6/9![Southwest logo]()
$350
This Southwest deal was found by Cheapflights users on 6/5. 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.
ter 7/75:30 am
MDW
- SJC
1 stop7h 10m
Southwest
ter 7/287:35 pm
SJC
- MDW
1 stop7h 05m
Southwest
Deal found 6/5![Southwest logo]()
$283
This Southwest deal was found by Cheapflights users on 6/8. 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.
qua 7/85:50 pm
MDW
- SJC
2 stops7h 15m
Southwest
qua 7/221:30 pm
SJC
- MDW
1 stop6h 20m
Southwest
Deal found 6/8![Southwest logo]()
$355
This Southwest deal was found by Cheapflights users on 6/9. 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.
qui 7/98:50 pm
MDW
- SJC
Nonstop4h 40m
Southwest
qua 7/2210:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Deal found 6/9![Southwest logo]()
$330
This Delta deal was found by Cheapflights users on 6/9. 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.
qua 7/229:54 am
MDW
- SJC
2 stops9h 18m
Delta
ter 8/412:40 pm
SJC
- MDW
1 stop7h 56m
Delta
Deal found 6/9![Delta logo]()
$279
This Delta deal was found by Cheapflights users on 6/9. 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.
qua 7/229:54 am
MDW
- SJC
2 stops9h 18m
Delta
qui 7/238:25 pm
SJC
- MDW
2 stops10h 12m
Delta
Deal found 6/9![Delta logo]()
$326
This Southwest deal was found by Cheapflights users on 6/9. 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.
qua 7/225:25 am
MDW
- SJC
1 stop7h 35m
Southwest
qui 7/234:20 pm
SJC
- MDW
1 stop6h 00m
Southwest
Deal found 6/9![Southwest logo]()
$345
This Delta deal was found by Cheapflights users on 6/8. 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.
qua 7/296:00 am
MDW
- SJC
2 stops13h 12m
Delta
ter 8/412:40 pm
SJC
- MDW
1 stop7h 56m
Delta
Deal found 6/8![Delta logo]()
$352
This Delta deal was found by Cheapflights users on 6/8. 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.
sex 7/316:00 am
MDW
- SJC
2 stops11h 46m
Delta
qua 8/512:40 pm
SJC
- MDW
1 stop7h 56m
Delta
Deal found 6/8![Delta logo]()
$356
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 junho 10, 2026.
Search for one-way flight options from Midway to San Jose. Find affordable one-way fares based on user searches. Data last updated junho 10, 2026.
This Southwest deal was found by Cheapflights users on 6/8. 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.
ter 8/188:35 am
MDW
- SJC
1 stop7h 45m
Southwest
Deal found 6/8![Southwest logo]()
$158
This Delta deal was found by Cheapflights users on 6/9. 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.
sex 6/191:49 pm
MDW
- SJC
1 stop8h 50m
Delta
Deal found 6/9![Delta logo]()
$179
This Southwest deal was found by Cheapflights users on 6/10. 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.
qui 8/138:50 pm
MDW
- SJC
Nonstop4h 30m
Southwest
Deal found 6/10![Southwest logo]()
$182
This Delta deal was found by Cheapflights users on 6/9. 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.
sáb 6/276:00 am
MDW
- SJC
2 stops13h 17m
Delta
Deal found 6/9![Delta logo]()
$184
This Southwest deal was found by Cheapflights users on 6/8. 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.
sex 8/78:50 pm
MDW
- SJC
Nonstop4h 30m
Southwest
Deal found 6/8![Southwest logo]()
$185
This Southwest deal was found by Cheapflights users on 6/8. 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.
qui 8/65:40 am
MDW
- SJC
1 stop7h 40m
Southwest
Deal found 6/8![Southwest logo]()
$191
This Delta deal was found by Cheapflights users on 6/8. 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.
sex 12/410:35 am
MDW
- SJC
1 stop10h 17m
Delta
Deal found 6/8![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 junho 10, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $273 (Southwest) |
One-way from | $158 (Southwest) |
Popular in | March |
Cheapest in | April |
Average price | $522 |
Good round-trip deal | $407 or less |
Good one-way deal | $128 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 junho 10, 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
ter 10/20
10:35 am-6:52 pm
1 stop10h 17m
San Jose
seg 10/26
10:20 pm-9:52 am
1 stop9h 32m
$304
ChicagoSan Jose
MDW - SJC
MDWSJC
Chicago Midway
qua 9/9
9:30 am-7:35 pm
2 stops12h 05m
San Jose
sáb 9/12
7:00 am-6:31 pm
2 stops9h 31m
$314
ChicagoSan Jose
MDW - SJC
MDWSJC
Chicago Midway
qui 9/10
2:00 pm-8:53 pm
1 stop8h 53m
San Jose
seg 9/14
8:25 pm-9:07 am
2 stops10h 42m
$338
ChicagoSan Jose
MDW - SJC
MDWSJC
Chicago Midway
ter 7/28
5:25 am-11:25 am
2 stops8h 00m
San Jose
qua 7/29
7:50 pm-5:25 am
1 stop7h 35m
$355
Quickest round-trip
ChicagoSan Jose
MDW - SJC
MDWSJC
Chicago Midway
qui 9/10
10:15 am-12:45 pm
Nonstop4h 30m
San Jose
seg 9/14
11:00 pm-5:00 am
Nonstop4h 00m
$363
ChicagoSan Jose
MDW - SJC
MDWSJC
Chicago Midway
qui 8/20
6:15 am-10:30 am
1 stop6h 15m
San Jose
seg 8/24
7:55 am-5:10 pm
2 stops7h 15m
$383
ChicagoSan Jose
MDW - SJC
MDWSJC
Chicago Midway
qua 7/8
10:05 am-12:30 pm
Nonstop4h 25m
San Jose
qua 7/22
10:55 pm-5:00 am
Nonstop4h 05m
$394
ChicagoSan Jose
MDW - SJC
MDWSJC
Chicago Midway
qua 8/12
4:45 pm-9:25 pm
1 stop6h 40m
San Jose
dom 8/16
12:10 pm-9:40 pm
2 stops7h 30m
$397
ChicagoSan Jose
MDW - SJC
MDWSJC
Chicago Midway
sáb 7/25
8:25 pm-11:00 pm
Nonstop4h 35m
San Jose
sáb 8/1
10:55 pm-5:00 am
Nonstop4h 05m
$407
ChicagoSan Jose
MDW - SJC
MDWSJC
Chicago Midway
sex 9/11
6:15 am-10:30 am
1 stop6h 15m
San Jose
dom 9/13
11:00 pm-5:00 am
Nonstop4h 00m
$413
Showing 1-10 of 23 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 June.
| 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 junho 10, 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 in the afternoon could potentially save you up to 25% 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 junho 10, 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
Comfort
8.0
Food
7.0
Crew
8.6
Overall
7.9
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentWalter,May 2026
LAS - BUR
Boarding
8.1
Comfort
8.0
Food
7.0
Crew
8.6
Overall
7.9
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentWalter,May 2026
LAS - BUR
Related info for your journey
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Top airline flying from Midway to San Jose
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| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$299 | Average$523 | FlexibilityNo cancel fee | On-time63% |