$173+ Cheap flights from San Jose, CA (SJC) to Midway (MDW)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/8. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — MDW
Oct 7 — Oct 141
Round-trip
1 adult, Economy
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Find cheap flights from San Jose to Midway with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from San Jose to Midway
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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 September 7, 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 September 7, 2026.
This Southwest deal was found by Cheapflights users on 9/3. 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.
Sat 9/266:50 am -
1 stop7h 30m
Sat 9/266:25 pm -
Nonstop4h 30m
Deal found 9/3![Southwest logo]()
$306
This Southwest deal was found by Cheapflights users on 9/3. 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.
Fri 9/2511:00 pm -
Nonstop4h 00m
Sat 9/261:15 pm -
Nonstop4h 30m
Deal found 9/3![Southwest logo]()
$313
This Southwest deal was found by Cheapflights users on 9/3. 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 12/1611:55 am -
2 stops7h 30m
Sat 1/910:15 am -
1 stop7h 35m
Deal found 9/3![Southwest logo]()
$317
This Southwest deal was found by Cheapflights users on 9/3. 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.
Fri 10/25:15 pm -
1 stop5h 40m
Sat 10/1012:50 pm -
Nonstop4h 35m
Deal found 9/3![Southwest logo]()
$319
This Southwest deal was found by Cheapflights users on 9/2. 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 10/268:55 pm -
1 stop6h 45m
Mon 11/210:15 am -
2 stops8h 00m
Deal found 9/2![Southwest logo]()
$321
This Southwest deal was found by Cheapflights users on 9/3. 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.
Thu 10/298:25 am -
2 stops7h 20m
Mon 11/25:20 pm -
2 stops7h 10m
Deal found 9/3![Southwest logo]()
$327
This Southwest deal was found by Cheapflights users on 9/2. 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.
Thu 9/247:35 pm -
1 stop7h 30m
Mon 9/286:15 am -
1 stop6h 15m
Deal found 9/2![Southwest logo]()
$328
This Southwest deal was found by Cheapflights users on 9/2. 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.
Thu 10/13:30 pm -
1 stop7h 05m
Mon 10/57:00 am -
1 stop7h 45m
Deal found 9/2![Southwest logo]()
$333
This Southwest deal was found by Cheapflights users on 9/3. 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.
Mon 10/265:15 pm -
1 stop5h 45m
Fri 10/309:45 am -
2 stops7h 50m
Deal found 9/3![Southwest logo]()
$334
This Delta deal was found by Cheapflights users on 9/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/256:19 pm -
2 stops12h 48m
Wed 1/136:00 am -
1 stop7h 56m
Deal found 9/3![Delta logo]()
$338
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 September 7, 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 September 7, 2026.
This Delta deal was found by Cheapflights users on 9/4. 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 10/105:42 pm -
2 stops13h 02m
Thu 10/1512:49 pm -
1 stop10h 36m
Deal found 9/4![Delta logo]()
$386
This Southwest deal was found by Cheapflights users on 9/4. 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 11/78:30 am -
Nonstop4h 00m
Sat 12/123:00 pm -
1 stop6h 25m
Deal found 9/4![Southwest logo]()
$419
This Southwest deal was found by Cheapflights users on 9/6. 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.
Wed 9/308:00 am -
2 stops7h 10m
Fri 10/29:15 pm -
Nonstop4h 35m
Deal found 9/6![Southwest logo]()
$428
This Delta deal was found by Cheapflights users on 9/6. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/1212:57 pm -
1 stop7h 36m
Thu 10/156:04 am -
1 stop7h 40m
Deal found 9/6![Delta logo]()
$466
This Southwest deal was found by Cheapflights users on 9/6. 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.
Wed 9/306:45 am -
2 stops7h 20m
Sat 10/312:50 pm -
Nonstop4h 35m
Deal found 9/6![Southwest logo]()
$428
This Southwest deal was found by Cheapflights users on 9/4. 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 11/196:00 am -
Nonstop4h 10m
Sun 11/224:45 pm -
1 stop6h 25m
Deal found 9/4![Southwest logo]()
$431
This Southwest deal was found by Cheapflights users on 9/5. 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.
Wed 11/2511:00 pm -
Nonstop4h 00m
Tue 12/15:50 am -
1 stop7h 20m
Deal found 9/5![Southwest logo]()
$435
This Southwest deal was found by Cheapflights users on 9/5. 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.
Sun 10/411:00 pm -
Nonstop4h 00m
Sat 10/1010:40 am -
2 stops9h 25m
Deal found 9/5![Southwest logo]()
$460
This Southwest deal was found by Cheapflights users on 9/6. 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.
Fri 10/168:00 am -
2 stops7h 25m
Thu 10/225:25 am -
1 stop7h 35m
Deal found 9/6![Southwest logo]()
$488
This Southwest deal was found by Cheapflights users on 9/5. 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.
Thu 10/111:00 pm -
Nonstop4h 00m
Sun 10/49:20 pm -
Nonstop4h 35m
Deal found 9/5![Southwest logo]()
$489
Last-minute flights from San Jose to MidwayDiscover last-minute flight deals from San Jose to Midway. Data last updated September 7, 2026 and is based on user searches.
Discover last-minute flight deals from San Jose to Midway. Data last updated September 7, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 9/2. 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.
Thu 9/247:35 pm -
1 stop7h 30m
Mon 9/286:15 am -
1 stop6h 15m
Deal found 9/2![Southwest logo]()
$328
This Southwest deal was found by Cheapflights users on 9/3. 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.
Fri 9/2511:00 pm -
Nonstop4h 00m
Sat 9/261:15 pm -
Nonstop4h 30m
Deal found 9/3![Southwest logo]()
$313
This Delta deal was found by Cheapflights users on 9/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/256:19 pm -
2 stops12h 48m
Thu 1/146:00 am -
1 stop7h 56m
Deal found 9/3![Delta logo]()
$338
This Southwest deal was found by Cheapflights users on 9/3. 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.
Sat 9/266:50 am -
1 stop7h 30m
Sat 9/266:25 pm -
Nonstop4h 30m
Deal found 9/3![Southwest logo]()
$306
This Southwest deal was found by Cheapflights users on 9/2. 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.
Thu 10/13:30 pm -
1 stop7h 05m
Mon 10/57:00 am -
1 stop7h 45m
Deal found 9/2![Southwest logo]()
$333
This Southwest deal was found by Cheapflights users on 9/3. 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.
Fri 10/25:15 pm -
1 stop5h 40m
Sat 10/1012:50 pm -
Nonstop4h 35m
Deal found 9/3![Southwest logo]()
$319
This Southwest deal was found by Cheapflights users on 9/2. 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 10/268:55 pm -
1 stop6h 45m
Mon 11/210:15 am -
2 stops8h 00m
Deal found 9/2![Southwest logo]()
$321
This Southwest deal was found by Cheapflights users on 9/3. 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.
Mon 10/265:15 pm -
1 stop5h 45m
Fri 10/309:45 am -
2 stops7h 50m
Deal found 9/3![Southwest logo]()
$334
This Southwest deal was found by Cheapflights users on 9/3. 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.
Thu 10/298:25 am -
2 stops7h 20m
Mon 11/25:20 pm -
2 stops7h 10m
Deal found 9/3![Southwest logo]()
$327
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 September 7, 2026.
Search for one-way flight options from San Jose to Midway. Find affordable one-way fares based on user searches. Data last updated September 7, 2026.
This Delta deal was found by Cheapflights users on 9/2. 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.
Thu 10/811:41 am -
2 stops19h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Delta logo]()
$173
This Kiwi.com deal was found by Cheapflights users on 9/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/152:15 pm -
2 stops31h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Frontier logo]()
$174
This Kiwi.com deal was found by Cheapflights users on 9/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/59:07 pm -
2 stops24h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Frontier logo]()
$178
This Southwest deal was found by Cheapflights users on 9/3. 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.
Sat 10/106:30 am -
2 stops9h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Southwest logo]()
$183
This Southwest deal was found by Cheapflights users on 9/3. 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.
Fri 10/211:00 pm -
Nonstop4h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Southwest logo]()
$185
This Kiwi.com deal was found by Cheapflights users on 9/4. 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 10/51:38 pm -
2 stops26h 08m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Frontier logo]()
$189
This Delta deal was found by Cheapflights users on 9/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/307:00 am -
2 stops24h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Delta logo]()
$193
This Delta deal was found by Cheapflights users on 9/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/16:10 am -
2 stops10h 23m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Delta logo]()
$195
This Delta deal was found by Cheapflights users on 9/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/28:41 pm -
2 stops10h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Delta logo]()
$200
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 September 7, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $306 (Southwest) |
One-way from | $173 (Delta) |
Popular in | June |
Cheapest in | October |
Average price | $417 |
Good round-trip deal | $397 or less |
Good one-way deal | $199 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 7,457,451 searches. Data last updated September 7, 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 San Jose - MDW Chicago Midway
SJCMDW
San Jose
Wed 10/14
11:00 pm-5:00 am
Nonstop4h 00m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$207
San JoseChicago
SJC San Jose - MDW Chicago Midway
SJCMDW
San Jose
Sat 10/10
11:00 pm-5:00 am
Nonstop4h 00m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$207
San JoseChicago
SJC San Jose - MDW Chicago Midway
SJCMDW
San Jose
Mon 10/5
11:00 pm-5:00 am
Nonstop4h 00m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$207
San JoseChicago
SJC San Jose - MDW Chicago Midway
SJCMDW
San Jose
Fri 10/9
4:31 pm-9:32 am
2 stops15h 01m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$217
San JoseChicago
SJC San Jose - MDW Chicago Midway
SJCMDW
San Jose
Sun 10/11
11:00 pm-5:00 am
Nonstop4h 00m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$219
San JoseChicago
SJC San Jose - MDW Chicago Midway
SJCMDW
San Jose
Mon 10/5
10:50 pm-10:03 am
1 stop9h 13m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$227
San JoseChicago
SJC San Jose - MDW Chicago Midway
SJCMDW
San Jose
Sat 10/31
6:20 am-4:47 pm
1 stop8h 27m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$227
San JoseChicago
SJC San Jose - MDW Chicago Midway
SJCMDW
San Jose
Sun 11/8
7:05 am-2:50 pm
1 stop5h 45m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$229
San JoseChicago
SJC San Jose - MDW Chicago Midway
SJCMDW
San Jose
Mon 11/30
3:05 pm-12:10 am
1 stop7h 05m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$269
San JoseChicago
SJC San Jose - MDW Chicago Midway
SJCMDW
San Jose
Sat 9/19
11:00 pm-5:00 am
Nonstop4h 00m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$294
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 September.
| 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 $403). Flying from San Jose, California to Chicago Midway Airport in June is currently the most expensive (average of $919). 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 September 7, 2026.
A simple way to save on the total cost of your ticket is to fly from San Jose, California to Chicago Midway Airport in the afternoon. If you’re flexible enough to do this you can expect to save up to 36% on your trip compared to booking a flight at noon.
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 September 7, 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.
Overall
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
Find useful and relevant information for your journey from San Jose to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago Midway Airport?
Book flights to Chicago Midway Airport if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
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Explore flights to Midway departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on September 7, 2026.
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Browse other San Jose and Midway flight options. Last updated on September 7, 2026.
Other flights from San Jose
Browse through other flights departing from San Jose. Flights are based on user searches made on Cheapflights and were last updated on September 7, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top airline flying from San Jose to Midway
Discover the top airline that operate flights from San Jose to Midway. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated September 7, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$310 | Average$539 | FlexibilityNo cancel fee | On-time63% |