$162+ 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 9/29. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — MDW
Aug 5 — Aug 121
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 July 6, 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 July 6, 2026.
This Southwest deal was found by Cheapflights users on 7/1. 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.
Mon 9/78:30 pm
SJC
- MDW
1 stop7h 10m
Southwest
Wed 9/910:20 am
MDW
- SJC
Nonstop4h 25m
Southwest
Deal found 7/1![Southwest logo]()
$332
This Southwest deal was found by Cheapflights users on 7/1. 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.
Fri 8/76:55 pm
SJC
- MDW
1 stop7h 35m
Southwest
Sat 8/152:05 pm
MDW
- SJC
1 stop6h 10m
Southwest
Deal found 7/1![Southwest logo]()
$337
This Delta deal was found by Cheapflights users on 7/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1112:40 pm
SJC
- MDW
1 stop7h 56m
Delta
Tue 8/1810:54 am
MDW
- SJC
2 stops13h 19m
Delta
Deal found 7/1![Delta logo]()
$341
This Delta deal was found by Cheapflights users on 7/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/1410:20 pm
SJC
- MDW
1 stop9h 50m
Delta
Tue 8/181:51 pm
MDW
- SJC
1 stop8h 33m
Delta
Deal found 7/1![Delta logo]()
$342
This Southwest deal was found by Cheapflights users on 7/2. 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 8/196:45 am
SJC
- MDW
2 stops7h 15m
Southwest
Sun 8/237:10 am
MDW
- SJC
1 stop8h 05m
Southwest
Deal found 7/2![Southwest logo]()
$343
This Southwest deal was found by Cheapflights users on 7/3. 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 11/78:30 am
SJC
- MDW
Nonstop4h 00m
Southwest
Mon 11/910:10 am
MDW
- SJC
Nonstop4h 45m
Southwest
Deal found 7/3![Southwest logo]()
$344
This Delta deal was found by Cheapflights users on 7/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1112:40 pm
SJC
- MDW
1 stop7h 56m
Delta
Mon 8/177:25 pm
MDW
- SJC
2 stops15h 46m
Delta
Deal found 7/1![Delta logo]()
$357
This Southwest deal was found by Cheapflights users on 7/3. 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 8/1711:00 pm
SJC
- MDW
Nonstop4h 00m
Southwest
Mon 8/2410:15 am
MDW
- SJC
Nonstop4h 30m
Southwest
Deal found 7/3![Southwest logo]()
$359
This Southwest deal was found by Cheapflights users on 7/2. 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.
Tue 7/287:35 pm
SJC
- MDW
1 stop7h 05m
Southwest
Sat 8/15:10 pm
MDW
- SJC
1 stop7h 45m
Southwest
Deal found 7/2![Southwest logo]()
$362
This Southwest deal was found by Cheapflights users on 7/3. 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 8/811:00 pm
SJC
- MDW
Nonstop4h 00m
Southwest
Sat 8/152:05 pm
MDW
- SJC
1 stop6h 10m
Southwest
Deal found 7/3![Southwest logo]()
$365
This Southwest deal was found by Cheapflights users on 7/2. 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.
Tue 8/47:00 pm
SJC
- MDW
1 stop7h 30m
Southwest
Sun 8/95:35 pm
MDW
- SJC
2 stops7h 20m
Southwest
Deal found 7/2![Southwest logo]()
$367
This Delta deal was found by Cheapflights users on 7/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1212:40 pm
SJC
- MDW
1 stop7h 56m
Delta
Thu 8/205:10 pm
MDW
- SJC
1 stop7h 48m
Delta
Deal found 7/1![Delta logo]()
$369
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 July 6, 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 July 6, 2026.
This Delta deal was found by Cheapflights users on 7/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/710:20 pm
SJC
- MDW
1 stop10h 17m
Delta
Wed 9/99:59 am
MDW
- SJC
1 stop9h 47m
Delta
Deal found 7/1![Delta logo]()
$342
This Southwest deal was found by Cheapflights users on 7/2. 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.
Tue 7/287:35 pm
SJC
- MDW
1 stop7h 05m
Southwest
Sat 8/15:10 pm
MDW
- SJC
1 stop7h 45m
Southwest
Deal found 7/2![Southwest logo]()
$362
This Southwest deal was found by Cheapflights users on 7/3. 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 8/811:00 pm
SJC
- MDW
Nonstop4h 00m
Southwest
Sat 8/152:05 pm
MDW
- SJC
1 stop6h 10m
Southwest
Deal found 7/3![Southwest logo]()
$365
This Delta deal was found by Cheapflights users on 7/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/106:40 am
SJC
- MDW
1 stop7h 35m
Delta
Fri 8/2112:46 pm
MDW
- SJC
1 stop8h 06m
Delta
Deal found 7/1![Delta logo]()
$403
This Southwest deal was found by Cheapflights users on 7/1. 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.
Mon 9/76:30 am
SJC
- MDW
1 stop5h 40m
Southwest
Wed 9/92:05 pm
MDW
- SJC
2 stops8h 15m
Southwest
Deal found 7/1![Southwest logo]()
$389
This Delta deal was found by Cheapflights users on 7/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/256:40 am
SJC
- MDW
1 stop7h 35m
Delta
Mon 8/319:59 am
MDW
- SJC
2 stops14h 14m
Delta
Deal found 7/1![Delta logo]()
$411
This Southwest deal was found by Cheapflights users on 7/3. 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
SJC
- MDW
Nonstop4h 00m
Southwest
Tue 10/64:35 pm
MDW
- SJC
1 stop6h 50m
Southwest
Deal found 7/3![Southwest logo]()
$393
This Southwest deal was found by Cheapflights users on 7/4. 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 9/1711:00 pm
SJC
- MDW
Nonstop4h 00m
Southwest
Sun 9/208:40 pm
MDW
- SJC
Nonstop4h 30m
Southwest
Deal found 7/4![Southwest logo]()
$407
This Southwest deal was found by Cheapflights users on 7/6. 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.
Thu 8/2011:00 pm
SJC
- MDW
Nonstop4h 00m
Southwest
Thu 8/2710:15 am
MDW
- SJC
Nonstop4h 30m
Southwest
Deal found 7/6![Southwest logo]()
$407
This Southwest deal was found by Cheapflights users on 7/4. 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.
Fri 8/711:00 pm
SJC
- MDW
Nonstop4h 00m
Southwest
Wed 8/128:30 pm
MDW
- SJC
Nonstop4h 30m
Southwest
Deal found 7/4![Southwest logo]()
$407
This Southwest deal was found by Cheapflights users on 7/2. 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 8/166:10 am
SJC
- MDW
Nonstop4h 10m
Southwest
Sun 8/237:10 am
MDW
- SJC
1 stop8h 05m
Southwest
Deal found 7/2![Southwest logo]()
$413
Last-minute flights from San Jose to MidwayDiscover last-minute flight deals from San Jose to Midway. Data last updated July 6, 2026 and is based on user searches.
Discover last-minute flight deals from San Jose to Midway. Data last updated July 6, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 7/2. 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.
Tue 7/287:35 pm
SJC
- MDW
1 stop7h 05m
Southwest
Sat 8/15:10 pm
MDW
- SJC
1 stop7h 45m
Southwest
Deal found 7/2![Southwest logo]()
$362
This Southwest deal was found by Cheapflights users on 7/2. 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.
Tue 8/47:00 pm
SJC
- MDW
1 stop7h 30m
Southwest
Sun 8/95:35 pm
MDW
- SJC
2 stops7h 20m
Southwest
Deal found 7/2![Southwest logo]()
$367
This Southwest deal was found by Cheapflights users on 7/1. 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.
Fri 8/76:55 pm
SJC
- MDW
1 stop7h 35m
Southwest
Sat 8/152:05 pm
MDW
- SJC
1 stop6h 10m
Southwest
Deal found 7/1![Southwest logo]()
$337
This Southwest deal was found by Cheapflights users on 7/3. 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 8/811:00 pm
SJC
- MDW
Nonstop4h 00m
Southwest
Sat 8/152:05 pm
MDW
- SJC
1 stop6h 10m
Southwest
Deal found 7/3![Southwest logo]()
$365
This Delta deal was found by Cheapflights users on 7/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1112:40 pm
SJC
- MDW
1 stop7h 56m
Delta
Tue 8/1810:54 am
MDW
- SJC
2 stops13h 19m
Delta
Deal found 7/1![Delta logo]()
$341
This Delta deal was found by Cheapflights users on 7/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1112:40 pm
SJC
- MDW
1 stop7h 56m
Delta
Mon 8/177:25 pm
MDW
- SJC
2 stops15h 46m
Delta
Deal found 7/1![Delta logo]()
$357
This Delta deal was found by Cheapflights users on 7/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1212:40 pm
SJC
- MDW
1 stop7h 56m
Delta
Thu 8/205:10 pm
MDW
- SJC
1 stop7h 48m
Delta
Deal found 7/1![Delta logo]()
$369
This Delta deal was found by Cheapflights users on 7/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/1410:20 pm
SJC
- MDW
1 stop9h 50m
Delta
Sat 8/226:11 am
MDW
- SJC
1 stop7h 17m
Delta
Deal found 7/1![Delta logo]()
$342
This Southwest deal was found by Cheapflights users on 7/3. 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 8/1711:00 pm
SJC
- MDW
Nonstop4h 00m
Southwest
Mon 8/2410:15 am
MDW
- SJC
Nonstop4h 30m
Southwest
Deal found 7/3![Southwest logo]()
$359
This Southwest deal was found by Cheapflights users on 7/2. 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 8/196:45 am
SJC
- MDW
2 stops7h 15m
Southwest
Sun 8/237:10 am
MDW
- SJC
1 stop8h 05m
Southwest
Deal found 7/2![Southwest logo]()
$343
This Southwest deal was found by Cheapflights users on 7/3. 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 8/199:55 am
SJC
- MDW
Nonstop4h 05m
Southwest
Tue 8/252:05 pm
MDW
- SJC
2 stops8h 15m
Southwest
Deal found 7/3![Southwest logo]()
$370
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 July 6, 2026.
Search for one-way flight options from San Jose to Midway. Find affordable one-way fares based on user searches. Data last updated July 6, 2026.
This Kiwi.com deal was found by Cheapflights users on 7/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/299:03 pm
SJC
- MDW
2 stops22h 55m
Frontier
Deal found 7/2![Frontier logo]()
$162
This Kiwi.com deal was found by Cheapflights users on 7/3. 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.
Sat 8/18:23 pm
SJC
- MDW
2 stops22h 09m
Frontier
Deal found 7/3![Frontier logo]()
$163
This Southwest deal was found by Cheapflights users on 7/1. 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 8/2511:00 pm
SJC
- MDW
Nonstop4h 00m
Southwest
Deal found 7/1![Southwest logo]()
$165
This Southwest deal was found by Cheapflights users on 7/1. 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 7/291:10 pm
SJC
- MDW
1 stop7h 50m
Southwest
Deal found 7/1![Southwest logo]()
$175
This Delta deal was found by Cheapflights users on 7/2. 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 8/196:40 am
SJC
- MDW
1 stop7h 35m
Delta
Deal found 7/2![Delta logo]()
$180
This Kiwi.com deal was found by Cheapflights users on 7/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/289:03 pm
SJC
- MDW
2 stops22h 55m
Frontier
Deal found 7/2![Frontier logo]()
$188
This Southwest deal was found by Cheapflights users on 7/3. 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 8/202:40 pm
SJC
- MDW
1 stop7h 05m
Southwest
Deal found 7/3![Southwest logo]()
$190
This Kiwi.com deal was found by Cheapflights users on 7/3. 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.
Wed 9/309:03 pm
SJC
- MDW
2 stops22h 55m
Frontier
Deal found 7/3![Frontier logo]()
$194
This Southwest deal was found by Cheapflights users on 7/3. 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 8/137:55 am
SJC
- MDW
2 stops7h 15m
Southwest
Deal found 7/3![Southwest logo]()
$195
This Southwest deal was found by Cheapflights users on 7/3. 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 8/310:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Deal found 7/3![Southwest logo]()
$204
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 July 6, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $332 (Southwest) |
One-way from | $162 (Kiwi.com) |
Popular in | June |
Cheapest in | October |
Average price | $551 |
Good round-trip deal | $469 or less |
Good one-way deal | $255 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 July 6, 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 9/7
10:20 pm-10:37 am
1 stop10h 17m
Chicago Midway
Wed 9/9
9:59 am-5:46 pm
1 stop9h 47m
$342
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Tue 7/28
7:35 pm-4:40 am
1 stop7h 05m
Chicago Midway
Sat 8/1
5:10 pm-10:55 pm
1 stop7h 45m
$362
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Sat 8/8
11:00 pm-5:00 am
Nonstop4h 00m
Chicago Midway
Sat 8/15
2:05 pm-6:15 pm
1 stop6h 10m
$365
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Mon 9/7
6:30 am-2:10 pm
1 stop5h 40m
Chicago Midway
Wed 9/9
2:05 pm-8:20 pm
2 stops8h 15m
$389
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Fri 10/2
11:00 pm-5:00 am
Nonstop4h 00m
Chicago Midway
Tue 10/6
4:35 pm-9:25 pm
1 stop6h 50m
$393
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Mon 8/10
6:40 am-4:15 pm
1 stop7h 35m
Chicago Midway
Fri 8/21
12:46 pm-6:52 pm
1 stop8h 06m
$403
Quickest round-trip
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Thu 9/17
11:00 pm-5:00 am
Nonstop4h 00m
Chicago Midway
Sun 9/20
8:40 pm-11:10 pm
Nonstop4h 30m
$407
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Thu 8/20
11:00 pm-5:00 am
Nonstop4h 00m
Chicago Midway
Thu 8/27
10:15 am-12:45 pm
Nonstop4h 30m
$407
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Fri 8/7
11:00 pm-5:00 am
Nonstop4h 00m
Chicago Midway
Wed 8/12
8:30 pm-11:00 pm
Nonstop4h 30m
$407
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Tue 8/25
6:40 am-4:15 pm
1 stop7h 35m
Chicago Midway
Mon 8/31
9:59 am-10:13 pm
2 stops14h 14m
$411
Showing 1-10 of 22 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 July.
| 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 $464). 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 July 6, 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 12% on your trip compared to booking a flight in the morning.
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 July 6, 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
Crew
8.6
Boarding
8.1
Overall
7.9
Entertainment
7.5
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Crew
8.6
Boarding
8.1
Overall
7.9
Entertainment
7.5
Food
7.0
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
Hammond
Lansing
Merrillville
Valparaiso
Porter
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Other flights to Midway
Explore flights to Midway departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on July 6, 2026.
San Jose and Midway flights
Browse other San Jose and Midway flight options. Last updated on July 6, 2026.
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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 July 6, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$330 | Average$554 | FlexibilityNo cancel fee | On-time63% |