$107+ 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 5/4. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — MDW
Apr 9 — Apr 161
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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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 March 10, 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 March 10, 2026.
This Southwest deal was found by Cheapflights users on 3/6. 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.
Mon 4/2010:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Mon 4/276:15 am
MDW
- SJC
1 stop6h 15m
Southwest
Deal found 3/6![Southwest logo]()
$273
This Southwest deal was found by Cheapflights users on 3/8. 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.
Mon 3/3010:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Mon 4/65:05 am
MDW
- SJC
1 stop7h 05m
Southwest
Deal found 3/8![Southwest logo]()
$277
This Southwest deal was found by Cheapflights users on 3/7. 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.
Mon 5/410:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Thu 5/710:00 am
MDW
- SJC
2 stops7h 50m
Southwest
Deal found 3/7![Southwest logo]()
$282
This Southwest deal was found by Cheapflights users on 3/5. 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.
Mon 4/610:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Tue 4/73:40 pm
MDW
- SJC
Nonstop4h 35m
Southwest
Deal found 3/5![Southwest logo]()
$283
This Delta deal was found by Cheapflights users on 3/9. 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.
Tue 5/2610:55 pm
SJC
- MDW
1 stop7h 48m
Delta
Wed 5/271:59 pm
MDW
- SJC
1 stop8h 39m
Delta
Deal found 3/9![Delta logo]()
$287
This Southwest deal was found by Cheapflights users on 3/8. 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.
Wed 4/221:45 pm
SJC
- MDW
2 stops7h 35m
Southwest
Mon 4/276:15 am
MDW
- SJC
1 stop6h 15m
Southwest
Deal found 3/8![Southwest logo]()
$288
This Delta deal was found by Cheapflights users on 3/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/88:45 pm
SJC
- MDW
2 stops9h 57m
Delta
Sat 5/161:59 pm
MDW
- SJC
1 stop8h 39m
Delta
Deal found 3/7![Delta logo]()
$290
This Delta deal was found by Cheapflights users on 3/9. 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.
Tue 5/267:59 pm
SJC
- MDW
2 stops10h 43m
Delta
Tue 6/21:59 pm
MDW
- SJC
1 stop8h 39m
Delta
Deal found 3/9![Delta logo]()
$292
This Delta deal was found by Cheapflights users on 3/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/16:32 pm
SJC
- MDW
2 stops12h 34m
Delta
Tue 5/51:24 pm
MDW
- SJC
2 stops10h 51m
Delta
Deal found 3/7![Delta logo]()
$294
This Delta deal was found by Cheapflights users on 3/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/88:45 pm
SJC
- MDW
2 stops9h 57m
Delta
Mon 5/119:23 am
MDW
- SJC
2 stops10h 57m
Delta
Deal found 3/7![Delta logo]()
$296
This Southwest deal was found by Cheapflights users on 3/6. 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.
Tue 5/51:45 pm
SJC
- MDW
2 stops7h 35m
Southwest
Tue 5/125:30 pm
MDW
- SJC
2 stops7h 30m
Southwest
Deal found 3/6![Southwest logo]()
$297
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 March 10, 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 March 10, 2026.
This Southwest deal was found by Cheapflights users on 3/7. 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.
Mon 4/279:05 pm
SJC
- MDW
1 stop5h 55m
Southwest
Wed 4/297:30 am
MDW
- SJC
2 stops8h 15m
Southwest
Deal found 3/7![Southwest logo]()
$292
This Delta deal was found by Cheapflights users on 3/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/138:45 pm
SJC
- MDW
2 stops9h 57m
Delta
Tue 5/199:23 am
MDW
- SJC
2 stops9h 52m
Delta
Deal found 3/7![Delta logo]()
$296
This Southwest deal was found by Cheapflights users on 3/9. 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.
Wed 4/89:10 pm
SJC
- MDW
1 stop5h 50m
Southwest
Fri 4/107:40 pm
MDW
- SJC
1 stop6h 15m
Southwest
Deal found 3/9![Southwest logo]()
$332
This Delta deal was found by Cheapflights users on 3/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/1010:56 pm
SJC
- MDW
1 stop7h 46m
Delta
Tue 7/72:00 pm
MDW
- SJC
1 stop8h 53m
Delta
Deal found 3/7![Delta logo]()
$347
This Southwest deal was found by Cheapflights users on 3/7. 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.
Wed 5/139:10 pm
SJC
- MDW
1 stop5h 50m
Southwest
Mon 5/187:40 pm
MDW
- SJC
1 stop6h 15m
Southwest
Deal found 3/7![Southwest logo]()
$347
This Delta deal was found by Cheapflights users on 3/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/248:20 pm
SJC
- MDW
2 stops10h 27m
Delta
Sat 4/251:24 pm
MDW
- SJC
2 stops10h 51m
Delta
Deal found 3/7![Delta logo]()
$357
This Southwest deal was found by Cheapflights users on 3/5. 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 4/238:40 pm
SJC
- MDW
1 stop7h 10m
Southwest
Sun 4/269:20 pm
MDW
- SJC
Nonstop4h 35m
Southwest
Deal found 3/5![Southwest logo]()
$358
This Delta deal was found by Cheapflights users on 3/9. 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.
Fri 4/178:20 pm
SJC
- MDW
2 stops10h 46m
Delta
Mon 4/202:12 pm
MDW
- SJC
1 stop8h 25m
Delta
Deal found 3/9![Delta logo]()
$418
This Southwest deal was found by Cheapflights users on 3/5. 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 4/510:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Wed 4/83:40 pm
MDW
- SJC
Nonstop4h 35m
Southwest
Deal found 3/5![Southwest logo]()
$396
This Delta deal was found by Cheapflights users on 3/5. 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.
Wed 5/2710:55 pm
SJC
- MDW
1 stop7h 48m
Delta
Fri 5/295:08 pm
MDW
- SJC
1 stop7h 47m
Delta
Deal found 3/5![Delta logo]()
$427
This Southwest deal was found by Cheapflights users on 3/8. 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.
Fri 4/1711:30 am
SJC
- MDW
Nonstop4h 05m
Southwest
Sun 4/195:10 am
MDW
- SJC
1 stop7h 05m
Southwest
Deal found 3/8![Southwest logo]()
$397
Last-minute flights from San Jose to MidwayDiscover last-minute flight deals from San Jose to Midway. Data last updated March 10, 2026 and is based on user searches.
Discover last-minute flight deals from San Jose to Midway. Data last updated March 10, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 3/8. 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.
Mon 3/3010:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Mon 4/65:05 am
MDW
- SJC
1 stop7h 05m
Southwest
Deal found 3/8![Southwest logo]()
$277
This Delta deal was found by Cheapflights users on 3/8. 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.
Tue 3/318:35 pm
SJC
- MDW
2 stops10h 15m
Delta
Tue 4/142:12 pm
MDW
- SJC
1 stop8h 25m
Delta
Deal found 3/8![Delta logo]()
$292
This Southwest deal was found by Cheapflights users on 3/5. 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.
Mon 4/610:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Tue 4/73:40 pm
MDW
- SJC
Nonstop4h 35m
Southwest
Deal found 3/5![Southwest logo]()
$283
This Southwest deal was found by Cheapflights users on 3/8. 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.
Tue 4/710:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Tue 4/145:30 pm
MDW
- SJC
2 stops7h 30m
Southwest
Deal found 3/8![Southwest logo]()
$282
This Delta deal was found by Cheapflights users on 3/10. 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.
Mon 4/1311:00 pm
SJC
- MDW
1 stop8h 56m
Delta
Sat 4/186:00 am
MDW
- SJC
1 stop8h 21m
Delta
Deal found 3/10![Delta logo]()
$307
This Southwest deal was found by Cheapflights users on 3/6. 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.
Sat 4/186:25 am
SJC
- MDW
2 stops8h 25m
Southwest
Sat 4/2510:05 am
MDW
- SJC
2 stops7h 40m
Southwest
Deal found 3/6![Southwest logo]()
$297
This Southwest deal was found by Cheapflights users on 3/6. 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.
Mon 4/2010:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Mon 4/276:15 am
MDW
- SJC
1 stop6h 15m
Southwest
Deal found 3/6![Southwest logo]()
$273
This Delta deal was found by Cheapflights users on 3/9. 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.
Mon 4/208:20 pm
SJC
- MDW
2 stops10h 27m
Delta
Thu 4/231:24 pm
MDW
- SJC
2 stops10h 37m
Delta
Deal found 3/9![Delta logo]()
$298
This Southwest deal was found by Cheapflights users on 3/8. 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.
Wed 4/221:45 pm
SJC
- MDW
2 stops7h 35m
Southwest
Mon 4/276:15 am
MDW
- SJC
1 stop6h 15m
Southwest
Deal found 3/8![Southwest logo]()
$288
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 March 10, 2026.
Search for one-way flight options from San Jose to Midway. Find affordable one-way fares based on user searches. Data last updated March 10, 2026.
This Kiwi.com deal was found by Cheapflights users on 3/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/48:22 pm
SJC
- MDW
2 stops23h 57m
Frontier
Deal found 3/10![Frontier logo]()
$107
This Southwest deal was found by Cheapflights users on 3/10. 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.
Tue 4/1410:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Deal found 3/10![Southwest logo]()
$119
This Kiwi.com deal was found by Cheapflights users on 3/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/118:20 pm
SJC
- MDW
2 stops23h 59m
Frontier
Deal found 3/7![Frontier logo]()
$131
This Kiwi.com deal was found by Cheapflights users on 3/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/208:22 pm
SJC
- MDW
2 stops23h 52m
Frontier
Deal found 3/10![Frontier logo]()
$138
This Southwest deal was found by Cheapflights users on 3/9. 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.
Mon 6/84:20 pm
SJC
- MDW
1 stop5h 55m
Southwest
Deal found 3/9![Southwest logo]()
$139
This Kiwi.com deal was found by Cheapflights users on 3/5. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/87:02 pm
SJC
- MDW
2 stops41h 47m
Frontier
Deal found 3/5![Frontier logo]()
$140
This Southwest deal was found by Cheapflights users on 3/9. 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.
Mon 5/119:05 pm
SJC
- MDW
1 stop5h 55m
Southwest
Deal found 3/9![Southwest logo]()
$144
This Southwest deal was found by Cheapflights users on 3/5. 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.
Mon 4/610:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Deal found 3/5![Southwest logo]()
$145
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 March 10, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $273 (Southwest) |
One-way from | $107 (Kiwi.com) |
Popular in | November |
Cheapest in | April |
Average price | $710 |
Good round-trip deal | $427 or less |
Good one-way deal | $213 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 March 10, 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 - MDW
SJCMDW
San Jose
Mon 4/27
9:05 pm-5:00 am
1 stop5h 55m
Chicago Midway
Wed 4/29
7:30 am-1:45 pm
2 stops8h 15m
$292
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Wed 5/13
8:45 pm-8:42 am
2 stops9h 57m
Chicago Midway
Tue 5/19
9:23 am-5:15 pm
2 stops9h 52m
$296
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Wed 4/8
9:10 pm-5:00 am
1 stop5h 50m
Chicago Midway
Fri 4/10
7:40 pm-11:55 pm
1 stop6h 15m
$332
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Wed 6/10
10:56 pm-8:42 am
1 stop7h 46m
Chicago Midway
Tue 7/7
2:00 pm-8:53 pm
1 stop8h 53m
$347
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Wed 5/13
9:10 pm-5:00 am
1 stop5h 50m
Chicago Midway
Mon 5/18
7:40 pm-11:55 pm
1 stop6h 15m
$347
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Fri 4/24
8:20 pm-8:47 am
2 stops10h 27m
Chicago Midway
Sat 4/25
1:24 pm-10:15 pm
2 stops10h 51m
$357
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Thu 4/23
8:40 pm-5:50 am
1 stop7h 10m
Chicago Midway
Sun 4/26
9:20 pm-11:55 pm
Nonstop4h 35m
$358
Quickest round-trip
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Sun 4/5
10:55 pm-5:00 am
Nonstop4h 05m
Chicago Midway
Wed 4/8
3:40 pm-6:15 pm
Nonstop4h 35m
$396
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Fri 4/17
11:30 am-5:35 pm
Nonstop4h 05m
Chicago Midway
Sun 4/19
5:10 am-10:15 am
1 stop7h 05m
$397
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Fri 4/17
8:20 pm-9:06 am
2 stops10h 46m
Chicago Midway
Mon 4/20
2:12 pm-8:37 pm
1 stop8h 25m
$418
Showing 1-10 of 23 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 March.
| 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 $151). Flying from San Jose, California to Chicago Midway Airport in June is currently the most expensive (average of $245). 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 March 10, 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 6% on your trip compared to booking a flight in the evening.
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 March 10, 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.
Food
7.0
Overall
8.0
Entertainment
7.5
Crew
8.6
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Food
7.0
Overall
8.0
Entertainment
7.5
Crew
8.6
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
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 locationsLansing
Merrillville
Hammond
Porter
Benton Harbor
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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 2,558,603 searches. Data last updated March 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$330 | Average$535 | FlexibilityNo cancel fee | On-time63% |