$123+ 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 11/16. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — MDW
Nov 23 — Nov 301
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
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 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 October 24, 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 October 24, 2026.
This Southwest deal was found by Cheapflights users on 10/21. 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 12/32:00 pm -
1 stop6h 00m
Mon 12/76:05 am -
1 stop6h 20m
Deal found 10/21![Southwest logo]()
$318
This Southwest deal was found by Cheapflights users on 10/19. 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 12/211:55 am -
2 stops7h 35m
Sat 12/53:00 pm -
1 stop6h 25m
Deal found 10/19![Southwest logo]()
$319
This Southwest deal was found by Cheapflights users on 10/23. 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 11/166:00 am -
Nonstop4h 10m
Wed 11/1810:10 am -
Nonstop4h 45m
Deal found 10/23![Southwest logo]()
$323
This Southwest deal was found by Cheapflights users on 10/20. 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 12/711:55 am -
2 stops7h 35m
Thu 12/105:05 pm -
1 stop6h 55m
Deal found 10/20![Southwest logo]()
$324
This Southwest deal was found by Cheapflights users on 10/20. 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 12/46:00 am -
Nonstop4h 10m
Mon 12/76:05 am -
1 stop6h 20m
Deal found 10/20![Southwest logo]()
$326
This Delta deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/25:54 pm -
2 stops13h 43m
Sat 12/511:28 am -
2 stops12h 43m
Deal found 10/19![Delta logo]()
$327
This Southwest deal was found by Cheapflights users on 10/20. 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 11/911:00 pm -
Nonstop4h 00m
Tue 11/1010:10 am -
Nonstop4h 45m
Deal found 10/20![Southwest logo]()
$328
This Southwest deal was found by Cheapflights users on 10/21. 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 12/18:10 am -
2 stops7h 10m
Wed 12/21:20 pm -
2 stops8h 25m
Deal found 10/21![Southwest logo]()
$329
This Southwest deal was found by Cheapflights users on 10/20. 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 12/1011:10 am -
Nonstop4h 05m
Fri 1/2910:05 am -
2 stops8h 40m
Deal found 10/20![Southwest logo]()
$331
This Southwest deal was found by Cheapflights users on 10/19. 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 11/1211:00 pm -
Nonstop4h 00m
Tue 11/171:20 pm -
2 stops8h 25m
Deal found 10/19![Southwest 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 October 24, 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 October 24, 2026.
This Southwest deal was found by Cheapflights users on 10/19. 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 11/178:35 pm -
1 stop7h 20m
Sat 11/215:55 pm -
2 stops8h 00m
Deal found 10/19![Southwest logo]()
$336
This Delta deal was found by Cheapflights users on 10/23. 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.
Sun 11/225:58 pm -
2 stops12h 52m
Thu 11/2611:05 am -
2 stops25h 35m
Deal found 10/23![Delta logo]()
$412
This Southwest deal was found by Cheapflights users on 10/23. 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 11/1211:00 pm -
Nonstop4h 00m
Sat 11/1410:25 am -
1 stop7h 05m
Deal found 10/23![Southwest logo]()
$338
This Southwest deal was found by Cheapflights users on 10/20. 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 11/162:00 pm -
1 stop6h 00m
Thu 11/1910:05 am -
2 stops7h 45m
Deal found 10/20![Southwest logo]()
$425
This Delta deal was found by Cheapflights users on 10/20. 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 11/186:00 am -
2 stops8h 39m
Wed 11/251:31 pm -
2 stops10h 41m
Deal found 10/20![Delta logo]()
$503
This Southwest deal was found by Cheapflights users on 10/22. 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 11/128:30 pm -
1 stop7h 10m
Sat 11/215:55 pm -
2 stops8h 00m
Deal found 10/22![Southwest logo]()
$425
This Southwest deal was found by Cheapflights users on 10/19. 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 11/2111:00 pm -
Nonstop4h 00m
Tue 12/13:45 pm -
1 stop6h 55m
Deal found 10/19![Southwest logo]()
$497
This Southwest deal was found by Cheapflights users on 10/20. 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 11/910:00 am -
2 stops8h 05m
Tue 11/101:20 pm -
2 stops8h 25m
Deal found 10/20![Southwest logo]()
$501
This Southwest deal was found by Cheapflights users on 10/23. 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 11/203:00 pm -
1 stop7h 15m
Mon 11/239:15 pm -
Nonstop4h 40m
Deal found 10/23![Southwest logo]()
$520
This Southwest deal was found by Cheapflights users on 10/22. 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 11/197:20 am -
1 stop8h 00m
Sat 11/215:55 pm -
2 stops8h 00m
Deal found 10/22![Southwest logo]()
$522
Last-minute flights from San Jose to MidwayDiscover last-minute flight deals from San Jose to Midway. Data last updated October 24, 2026 and is based on user searches.
Discover last-minute flight deals from San Jose to Midway. Data last updated October 24, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 10/20. 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 11/911:00 pm -
Nonstop4h 00m
Tue 11/1010:10 am -
Nonstop4h 45m
Deal found 10/20![Southwest logo]()
$328
This Southwest deal was found by Cheapflights users on 10/23. 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 11/911:00 pm -
Nonstop4h 00m
Wed 11/111:20 pm -
2 stops8h 25m
Deal found 10/23![Southwest logo]()
$348
This Southwest deal was found by Cheapflights users on 10/19. 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 11/1211:00 pm -
Nonstop4h 00m
Tue 11/171:20 pm -
2 stops8h 25m
Deal found 10/19![Southwest logo]()
$338
This Delta deal was found by Cheapflights users on 10/19. 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 11/126:30 am -
1 stop7h 48m
Mon 11/1611:27 am -
1 stop9h 44m
Deal found 10/19![Delta logo]()
$341
This Southwest deal was found by Cheapflights users on 10/23. 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 11/166:00 am -
Nonstop4h 10m
Wed 11/1810:10 am -
Nonstop4h 45m
Deal found 10/23![Southwest logo]()
$323
This Southwest deal was found by Cheapflights users on 10/19. 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 11/176:00 am -
Nonstop4h 10m
Sat 11/215:55 pm -
2 stops8h 00m
Deal found 10/19![Southwest logo]()
$326
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 October 24, 2026.
Search for one-way flight options from San Jose to Midway. Find affordable one-way fares based on user searches. Data last updated October 24, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/23. 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 11/162:41 pm -
2 stops31h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Frontier logo]()
$123
This Kiwi.com deal was found by Cheapflights users on 10/21. 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 11/92:41 pm -
2 stops18h 41m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Frontier logo]()
$130
This Kiwi.com deal was found by Cheapflights users on 10/20. 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 12/33:52 pm -
2 stops15h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![Frontier logo]()
$133
This Southwest deal was found by Cheapflights users on 10/19. 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 11/2311:00 pm -
Nonstop4h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Southwest logo]()
$150
This Kiwi.com deal was found by Cheapflights users on 10/22. 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 12/245:59 pm -
2 stops16h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Frontier logo]()
$156
This Southwest deal was found by Cheapflights users on 10/23. 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 11/166:00 am -
Nonstop4h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Southwest logo]()
$162
This Delta deal was found by Cheapflights users on 10/19. 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 11/188:40 pm -
2 stops10h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Delta logo]()
$164
This Southwest deal was found by Cheapflights users on 10/19. 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 11/266:55 am -
2 stops7h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Southwest logo]()
$165
This Southwest deal was found by Cheapflights users on 10/21. 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 11/2211:00 pm -
Nonstop4h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Southwest logo]()
$167
This Delta deal was found by Cheapflights users on 10/19. 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 11/910:40 pm -
1 stop9h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Delta logo]()
$171
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 October 24, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $318 (Southwest) |
One-way from | $123 (Kiwi.com) |
Popular in | June |
Cheapest in | August |
Average price | $491 |
Good round-trip deal | $408 or less |
Good one-way deal | $228 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 October 24, 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
San JoseChicago
SJC San Jose - MDW Chicago Midway
SJCMDW
San Jose
Wed 12/16
6:00 am-12:10 pm
Nonstop4h 10m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$150
San JoseChicago
SJC San Jose - MDW Chicago Midway
SJCMDW
San Jose
Thu 12/24
8:35 pm-5:40 am
1 stop7h 05m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$159
San JoseChicago
SJC San Jose - MDW Chicago Midway
SJCMDW
San Jose
Mon 12/21
4:40 pm-12:40 am
1 stop6h 00m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$159
San JoseChicago
SJC San Jose - MDW Chicago Midway
SJCMDW
San Jose
Fri 12/25
6:00 am-12:10 pm
Nonstop4h 10m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$167
Quickest round-trip
San JoseChicago
SJC San Jose - MDW Chicago Midway
SJCMDW
San Jose
Sun 11/15
11:00 pm-5:00 am
Nonstop4h 00m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$167
San JoseChicago
SJC San Jose - MDW Chicago Midway
SJCMDW
San Jose
Wed 11/11
8:35 pm-5:40 am
1 stop7h 05m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$171
San JoseChicago
SJC San Jose - MDW Chicago Midway
SJCMDW
San Jose
Mon 11/23
4:19 pm-8:50 am
2 stops14h 31m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$222
San JoseChicago
SJC San Jose - MDW Chicago Midway
SJCMDW
San Jose
Sat 11/14
1:00 pm-10:54 pm
1 stop7h 54m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$247
San JoseChicago
SJC San Jose - MDW Chicago Midway
SJCMDW
San Jose
Wed 11/11
9:38 am-10:54 pm
2 stops11h 16m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$252
San JoseChicago
SJC San Jose - MDW Chicago Midway
SJCMDW
San Jose
Tue 11/17
8:35 pm-5:55 am
1 stop7h 20m
Chicago Midway
Sat 11/21
5:55 pm-11:55 pm
2 stops8h 00m
$336
Showing 1-10 of 19 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 October.
| 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, August is the cheapest month in which you can book a flight from San Jose, California to Chicago Midway Airport (average of $407). 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 October 24, 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 October 24, 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.
Comfort
8.0
Food
7.0
Crew
8.6
Entertainment
7.4
Overall
7.9
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Food
7.0
Crew
8.6
Entertainment
7.4
Overall
7.9
Boarding
8.1
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
Merrillville
Lansing
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 October 24, 2026.
San Jose and Midway flights
Browse other San Jose and Midway flight options. Last updated on October 24, 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 October 24, 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 October 24, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$315 | Average$535 | FlexibilityNo cancel fee | On-time63% |