$119+ Cheap flights from San Jose, CA (SJC) 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 8/19. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — MDW
Jun 2 — Jun 91
Round-trip
1 adult, Economy
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Find cheap flights from San Jose to Midway 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 San Jose to MidwayExplore the most affordable flight options available from San Jose to Midway. 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 San Jose to Midway. 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 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 5/2710:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Wed 6/33:40 pm
MDW
- SJC
Nonstop4h 35m
Southwest
Deal found 4/29![Southwest logo]()
$282
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.
Tue 5/2610:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Tue 6/25:35 pm
MDW
- SJC
1 stop6h 35m
Southwest
Deal found 5/1![Southwest logo]()
$292
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 5/196:00 am
SJC
- MDW
2 stops10h 33m
Delta
Wed 5/271:59 pm
MDW
- SJC
1 stop8h 39m
Delta
Deal found 4/28![Delta logo]()
$313
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.
Tue 5/265:59 pm
SJC
- MDW
2 stops12h 43m
Delta
Wed 5/2712:53 pm
MDW
- SJC
1 stop8h 09m
Delta
Deal found 5/2![Delta logo]()
$315
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.
Fri 8/1411:00 pm
SJC
- MDW
Nonstop4h 00m
Southwest
Wed 8/268:30 pm
MDW
- SJC
Nonstop4h 30m
Southwest
Deal found 4/28![Southwest logo]()
$322
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 6/1012:46 pm
SJC
- MDW
1 stop7h 31m
Delta
Tue 6/169:54 am
MDW
- SJC
2 stops8h 13m
Delta
Deal found 5/2![Delta logo]()
$323
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 5/2710:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Sat 5/3010:00 am
MDW
- SJC
1 stop6h 25m
Southwest
Deal found 4/29![Southwest logo]()
$328
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 5/2710:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Thu 5/288:25 pm
MDW
- SJC
Nonstop4h 35m
Southwest
Deal found 5/1![Southwest logo]()
$330
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.
Sun 6/710:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Tue 6/96:55 pm
MDW
- SJC
1 stop6h 30m
Southwest
Deal found 4/28![Southwest logo]()
$332
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.
Fri 8/219:40 am
SJC
- MDW
2 stops8h 00m
Southwest
Tue 9/18:30 pm
MDW
- SJC
Nonstop4h 30m
Southwest
Deal found 4/29![Southwest logo]()
$333
Best flights from San Jose to MidwayDiscover carefully curated flight deals from San Jose to Midway 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 San Jose to Midway 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 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.
Sat 8/2911:00 pm
SJC
- MDW
Nonstop4h 00m
Southwest
Wed 9/28:30 pm
MDW
- SJC
Nonstop4h 30m
Southwest
Deal found 4/28![Southwest logo]()
$322
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 6/106:00 am
SJC
- MDW
2 stops10h 18m
Delta
Tue 6/169:54 am
MDW
- SJC
2 stops8h 13m
Delta
Deal found 5/2![Delta logo]()
$328
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.
Tue 6/169:10 pm
SJC
- MDW
1 stop6h 00m
Southwest
Thu 6/188:50 pm
MDW
- SJC
Nonstop4h 35m
Southwest
Deal found 5/3![Southwest logo]()
$332
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.
Mon 5/2510:00 pm
SJC
- MDW
1 stop10h 00m
Delta
Wed 5/2712:53 pm
MDW
- SJC
1 stop8h 09m
Delta
Deal found 5/2![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.
Mon 6/810:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Wed 6/106:20 am
MDW
- SJC
1 stop6h 25m
Southwest
Deal found 4/29![Southwest logo]()
$332
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.
Fri 5/298:50 pm
SJC
- MDW
2 stops9h 52m
Delta
Tue 6/21:59 pm
MDW
- SJC
1 stop8h 39m
Delta
Deal found 5/2![Delta logo]()
$367
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.
Sun 6/74:10 pm
SJC
- MDW
1 stop6h 40m
Southwest
Tue 6/95:25 am
MDW
- SJC
2 stops8h 00m
Southwest
Deal found 5/2![Southwest logo]()
$347
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.
Sun 5/2410:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Wed 5/2711:45 am
MDW
- SJC
1 stop8h 05m
Southwest
Deal found 4/29![Southwest logo]()
$352
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.
Tue 5/2610:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Tue 6/210:20 am
MDW
- SJC
Nonstop4h 35m
Southwest
Deal found 5/1![Southwest 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.
Wed 5/2010:50 am
SJC
- MDW
Nonstop4h 05m
Southwest
Wed 5/275:30 pm
MDW
- SJC
1 stop6h 25m
Southwest
Deal found 5/2![Southwest logo]()
$407
Last-minute flights from San Jose to MidwayDiscover last-minute flight deals from San Jose to Midway. Data last updated May 3, 2026 and is based on user searches.
Discover last-minute flight deals from San Jose to Midway. Data last updated May 3, 2026 and is based on user searches.
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 5/196:00 am
SJC
- MDW
2 stops10h 33m
Delta
Wed 5/271:59 pm
MDW
- SJC
1 stop8h 39m
Delta
Deal found 4/28![Delta logo]()
$313
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 5/1911:15 am
SJC
- MDW
1 stop6h 40m
Southwest
Mon 6/18:25 pm
MDW
- SJC
Nonstop4h 35m
Southwest
Deal found 4/29![Southwest logo]()
$332
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.
Sat 5/232:51 pm
SJC
- MDW
2 stops15h 51m
Delta
Tue 6/91:49 pm
MDW
- SJC
1 stop8h 50m
Delta
Deal found 4/28![Delta logo]()
$344
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.
Tue 5/2610:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Tue 6/25:35 pm
MDW
- SJC
1 stop6h 35m
Southwest
Deal found 5/1![Southwest logo]()
$292
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.
Tue 5/265:59 pm
SJC
- MDW
2 stops12h 43m
Delta
Wed 5/2712:53 pm
MDW
- SJC
1 stop8h 09m
Delta
Deal found 5/2![Delta logo]()
$315
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 5/2710:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Wed 6/33:40 pm
MDW
- SJC
Nonstop4h 35m
Southwest
Deal found 4/29![Southwest logo]()
$282
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 5/2710:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Sat 5/3010:00 am
MDW
- SJC
1 stop6h 25m
Southwest
Deal found 4/29![Southwest logo]()
$328
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 5/2710:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Thu 5/288:25 pm
MDW
- SJC
Nonstop4h 35m
Southwest
Deal found 5/1![Southwest logo]()
$330
One-way flights from San Jose to MidwaySearch for one-way flight options from San Jose to Midway. Find affordable one-way fares based on user searches. Data last updated May 3, 2026.
Search for one-way flight options from San Jose to Midway. Find affordable one-way fares based on user searches. Data last updated May 3, 2026.
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 5/2710:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Deal found 4/29![Southwest logo]()
$119
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 5/278:50 pm
SJC
- MDW
2 stops9h 52m
Delta
Deal found 4/29![Delta logo]()
$134
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.
Mon 6/112:57 pm
SJC
- MDW
2 stops20h 15m
Frontier
Deal found 5/1![Frontier logo]()
$155
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 5/2610:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Deal found 4/29![Southwest logo]()
$164
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.
Fri 5/2912:57 pm
SJC
- MDW
2 stops31h 05m
Frontier
Deal found 4/29![Frontier logo]()
$169
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.
Fri 6/512:57 pm
SJC
- MDW
2 stops31h 05m
Frontier
Deal found 5/1![Frontier logo]()
$171
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 5/2011:15 am
SJC
- MDW
1 stop6h 40m
Southwest
Deal found 4/29![Southwest logo]()
$174
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 6/39:45 am
SJC
- MDW
2 stops7h 45m
Southwest
Deal found 5/1![Southwest logo]()
$179
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.
Mon 6/112:57 pm
SJC
- MDW
2 stops23h 15m
Multiple Airlines
Deal found 4/29![Multiple Airlines logo]()
$183
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.
Fri 7/178:25 pm
SJC
- MDW
2 stops12h 42m
Frontier
Deal found 4/30![Frontier logo]()
$187
Find flight deals from San Jose to Midway
Discover tips and strategies to find the most affordable flight options for your journey from San Jose (SJC) 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 May 3, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $282 (Southwest) |
One-way from | $119 (Southwest) |
Popular in | March |
Cheapest in | October |
Average price | $459 |
Good round-trip deal | $434 or less |
Good one-way deal | $203 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from San Jose 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 May 3, 2026.
Use the filters below to find and compare flights from San Jose to Chicago Midway Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Sat 8/29
11:00 pm-5:00 am
Nonstop4h 00m
Chicago Midway
Wed 9/2
8:30 pm-11:00 pm
Nonstop4h 30m
$322
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Wed 6/10
6:00 am-6:18 pm
2 stops10h 18m
Chicago Midway
Tue 6/16
9:54 am-4:07 pm
2 stops8h 13m
$328
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Tue 6/16
9:10 pm-5:10 am
1 stop6h 00m
Chicago Midway
Thu 6/18
8:50 pm-11:25 pm
Nonstop4h 35m
$332
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Mon 6/8
10:55 pm-5:00 am
Nonstop4h 05m
Chicago Midway
Wed 6/10
6:20 am-10:45 am
1 stop6h 25m
$332
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Sun 6/7
4:10 pm-12:50 am
1 stop6h 40m
Chicago Midway
Tue 6/9
5:25 am-11:25 am
2 stops8h 00m
$347
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Mon 5/25
10:00 pm-10:00 am
1 stop10h 00m
Chicago Midway
Wed 5/27
12:53 pm-7:02 pm
1 stop8h 09m
$350
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Sun 5/24
10:55 pm-5:00 am
Nonstop4h 05m
Chicago Midway
Wed 5/27
11:45 am-5:50 pm
1 stop8h 05m
$352
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Tue 5/26
10:55 pm-5:00 am
Nonstop4h 05m
Chicago Midway
Tue 6/2
10:20 am-12:55 pm
Nonstop4h 35m
$355
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Fri 5/29
8:50 pm-8:42 am
2 stops9h 52m
Chicago Midway
Tue 6/2
1:59 pm-8:38 pm
1 stop8h 39m
$367
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Wed 5/20
10:50 am-4:55 pm
Nonstop4h 05m
Chicago Midway
Wed 5/27
5:30 pm-9:55 pm
1 stop6h 25m
$407
Showing 1-10 of 20 resultsSorted by cheapest first
Compare providers for flights from San Jose 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 Jose to Midway 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 San Jose, California-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 Jose, California-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from San Jose, California-Chicago Midway Airport flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on San Jose, California-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 Jose, California-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 Jose to Midway
Have a flexible travel schedule? Discover the best time to fly to Midway from San Jose with our price prediction graph.
SJC-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 Jose to Chicago Midway Airport
Prices
Airlines
What is the cheapest month to book a flight from San Jose, California to Chicago Midway Airport?
Currently, October is the cheapest month in which you can book a flight from San Jose, California to Chicago Midway Airport (average of $379). Flying from San Jose, California to Chicago Midway Airport in March is currently the most expensive (average of $1,029). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from SJC to MDW?
Find hourly flight availability from San Jose to Midway. 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.
A simple way to save on the total cost of your ticket is to fly from San Jose, California to Chicago Midway Airport at noon. If you’re flexible enough to do this you can expect to save up to 10% on your trip compared to booking a flight in the afternoon.
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 May 3, 2026.
Peruse reviews from past customers who have flown with Southwest from San Jose to Chicago Midway Airport to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.6
Food
7.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Crew
8.6
Food
7.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
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| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$305 | Average$538 | FlexibilityNo cancel fee | On-time63% |