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Cheap flights from San Jose, California to Chicago from $163

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from San Jose, California to Chicago departing on 8/22. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from San Jose, California to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
8:30 pm - 5:40 am
SJC
-
MDW
7h 10m
1 stop
Southwest Logo
8:30 pm - 11:00 pm
MDW
-
SJC
4h 30mnonstop
$332Southwest
Fri, Aug 14 - Tue, Aug 18
Southwest Logo
11:00 pm - 5:00 am
SJC
-
MDW
4h 00mnonstop
Southwest Logo
2:05 pm - 6:15 pm
MDW
-
SJC
6h 10m
1 stop
$335Southwest
Sat, Aug 15 - Sat, Aug 22
Southwest Logo
11:00 pm - 5:00 am
SJC
-
MDW
4h 00mnonstop
Southwest Logo
5:00 pm - 9:05 pm
MDW
-
SJC
6h 05m
1 stop
$336Southwest
Sat, Aug 8 - Mon, Aug 10
Southwest Logo
11:00 pm - 5:00 am
SJC
-
MDW
4h 00mnonstop
Southwest Logo
2:05 pm - 8:20 pm
MDW
-
SJC
8h 15m
2 stops
$337Southwest
Sat, Aug 8 - Wed, Aug 12
Southwest Logo
11:00 pm - 5:00 am
SJC
-
MDW
4h 00mnonstop
Southwest Logo
12:50 pm - 7:30 pm
MDW
-
SJC
8h 40m
1 stop
$339Southwest
Wed, Oct 28 - Sat, Oct 31
Delta Logo
4:30 pm - 8:39 am
SJC
-
MDW
14h 09m
2 stops
Delta Logo
6:05 am - 11:22 am
MDW
-
SJC
7h 17m
1 stop
$341Delta
Tue, Aug 11 - Wed, Aug 19
Delta Logo
10:40 pm - 9:50 am
SJC
-
MDW
9h 10m
1 stop
Delta Logo
9:59 am - 5:46 pm
MDW
-
SJC
9h 47m
1 stop
$342Delta
Sun, Sep 27 - Sat, Oct 3
Southwest Logo
11:00 pm - 5:00 am
SJC
-
MDW
4h 00mnonstop
Southwest Logo
2:15 pm - 9:20 pm
MDW
-
SJC
9h 05m
2 stops
$344Southwest
Sat, Aug 15 - Sat, Aug 22
Southwest Logo
11:00 pm - 5:00 am
SJC
-
MDW
4h 00mnonstop
Southwest Logo
8:30 pm - 11:00 pm
MDW
-
SJC
4h 30mnonstop
$346Southwest
Thu, Sep 17 - Tue, Sep 22
Southwest Logo
6:55 pm - 5:25 am
SJC
-
MDW
8h 30m
1 stop
Southwest Logo
2:05 pm - 8:20 pm
MDW
-
SJC
8h 15m
2 stops
$347Southwest
Wed, Sep 9 - Tue, Sep 15

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Southwest flights from San Jose, California to Chicago Midway Airport

Our best Southwest deals on San Jose, California to Chicago Midway Airport flight tickets
Southwest
Aug 14
SJC11:00 pmSan Jose
4h 00m
MDW5:00 amChicago Midway
Aug 18
MDW8:30 pmChicago Midway
4h 30m
SJC11:00 pmSan Jose
$332
Southwest
Aug 15
SJC11:00 pmSan Jose
4h 00m
MDW5:00 amChicago Midway
Aug 22
MDW2:05 pmChicago Midway
6h 10m
1 stop
SJC6:15 pmSan Jose
$335
Southwest
Aug 8
SJC11:00 pmSan Jose
4h 00m
MDW5:00 amChicago Midway
Aug 10
MDW5:00 pmChicago Midway
6h 05m
1 stop
SJC9:05 pmSan Jose
$336

Delta flights from San Jose, California to Chicago Midway Airport

Our best Delta deals on San Jose, California to Chicago Midway Airport flight tickets
Delta
Aug 11
SJC4:30 pmSan Jose
14h 09m
2 stops
MDW8:39 amChicago Midway
Aug 19
MDW6:05 amChicago Midway
7h 17m
1 stop
SJC11:22 amSan Jose
$341
Delta
Sep 27
SJC10:40 pmSan Jose
9h 10m
1 stop
MDW9:50 amChicago Midway
Oct 3
MDW9:59 amChicago Midway
9h 47m
1 stop
SJC5:46 pmSan Jose
$342
Delta
Aug 10
SJC9:34 amSan Jose
21h 05m
2 stops
MDW8:39 amChicago Midway
Aug 19
MDW1:51 pmChicago Midway
8h 33m
1 stop
SJC8:24 pmSan Jose
$357

momondo Fare Finder

 
Customize your flight search to find flights from San Jose, California to Chicago Midway Airport 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, momondo users made 832,500 searches. Data last updated June 29, 2026.
Use the filters below to find and compare flights from San Jose, California to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Fri 8/14

8:30 pm-5:40 am

1 stop7h 10m

Chicago Midway

Tue 8/18

8:30 pm-11:00 pm

Nonstop4h 30m

$332

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Sat 8/15

11:00 pm-5:00 am

Nonstop4h 00m

Chicago Midway

Sat 8/22

2:05 pm-6:15 pm

1 stop6h 10m

$335

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Sat 8/8

11:00 pm-5:00 am

Nonstop4h 00m

Chicago Midway

Mon 8/10

5:00 pm-9:05 pm

1 stop6h 05m

$336

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Sat 8/8

11:00 pm-5:00 am

Nonstop4h 00m

Chicago Midway

Wed 8/12

2:05 pm-8:20 pm

2 stops8h 15m

$337

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Wed 10/28

11:00 pm-5:00 am

Nonstop4h 00m

Chicago Midway

Sat 10/31

12:50 pm-7:30 pm

1 stop8h 40m

$339

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Tue 8/11

4:30 pm-8:39 am

2 stops14h 09m

Chicago Midway

Wed 8/19

6:05 am-11:22 am

1 stop7h 17m

$341

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Sun 9/27

10:40 pm-9:50 am

1 stop9h 10m

Chicago Midway

Sat 10/3

9:59 am-5:46 pm

1 stop9h 47m

$342

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Sat 8/15

11:00 pm-5:00 am

Nonstop4h 00m

Chicago Midway

Sat 8/22

2:15 pm-9:20 pm

2 stops9h 05m

$344
Quickest round-trip

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Thu 9/17

11:00 pm-5:00 am

Nonstop4h 00m

Chicago Midway

Tue 9/22

8:30 pm-11:00 pm

Nonstop4h 30m

$346

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Wed 9/9

6:55 pm-5:25 am

1 stop8h 30m

Chicago Midway

Tue 9/15

2:05 pm-8:20 pm

2 stops8h 15m

$347

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
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See travel insights to Chicago from

How to get the cheapest flight ticket from San Jose, California to Chicago Midway Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the typical price of a round-trip flight between San Jose, California and Chicago Midway Airport?

What is the cheapest month to fly to Chicago Midway Airport?

The month of October is, on average, the cheapest month to fly to Chicago Midway Airport from San Jose, California, with most prices found around $464. If you are unable to visit Chicago Midway Airport during the month of October, then departing from San Jose, California during the month April is also very affordable. Most momondo users find prices during this month for around $467.

What is the cheapest day to depart on your flight to Chicago Midway Airport?

According to our data, Saturday is the cheapest day to fly to Chicago Midway Airport from San Jose, California. The lowest ticket price found for a Saturday departure recently was $440. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Sunday is the most expensive day to depart from San Jose, California because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $707.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from San Jose, California in the evening is the least expensive time of day to depart. momondo users have found prices as low as $480 when looking at flights departing in the evening. Try not to purchase tickets in the morning because they tend to be around $522. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest San Jose to Chicago Midway flight route?

Fly from San Jose to Chicago Midway for the best San Jose - Chicago Midway flight prices

What cabin class options are available on San Jose, California to Chicago Midway Airport flights?

There is only 1 cabin class available to choose from on San Jose, California to Chicago Midway Airport flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

When to book flights from San Jose, California to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from San Jose, California to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap San Jose, California to Chicago Midway Airport (SJC to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from San Jose, California to Chicago Midway Airport

Best Price Found

$236

Fastest flight time

4h 00m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from San Jose, California in the past 72 hours is $236. The best round-trip flight deal from San Jose, California to Chicago Midway Airport found on momondo in the last 72 hours is $472.
The fastest flight from San Jose, California to Chicago Midway Airport takes 4h 00m
Direct flights go from San Jose, California to Chicago Midway Airport every day.
Search flight deals

Frequently asked questions about flying from San Jose, California to Chicago Midway Airport

  • How far is San Jose to Chicago Midway by plane?

    Chicago Midway is 1830.8 mi away from San Jose. 4h 00m is a normal flight duration for this route.

  • When did momondo last update prices for flights from San Jose Airport to Chicago Midway Airport?

    Prices for flights from San Jose Airport to Chicago Midway Airport are refreshed on a daily basis.

  • How many operators does momondo search for flights from San Jose Airport to Chicago Midway Airport?

  • How old do you have to be to fly from San Jose Airport to Chicago Midway Airport?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from San Jose Airport to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The required travel and health documents for your Chicago Midway Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago Midway Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular plane model from San Jose, California to Chicago Midway Airport?

  • What is the most popular airline from San Jose, California to Chicago Midway Airport?

Best airlines flying from San Jose, California to Chicago Midway Airport

Compare and see reviews for airlines that fly from San Jose, California to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $330Free CancellationRating
7.9
4,246 reviews
Search Southwest flights

  • Southwest Flights From San Jose, California to Chicago Midway Airport

    Southwest is one of the most popular airlines flying from San Jose, California to Chicago Midway Airport, operating 14 flights/week on average for this route. A good Southwest flight deal for San Jose, California to Chicago Midway Airport starts from $330 round-trip, up to an average price of $553. Our users have rated Southwest at 7.9/10.

Traveling to a place near Chicago?

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Why use momondo?

Why should I use momondo to find a flight deal from San Jose to Chicago?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from San Jose to Chicago for you.

Can I find flights from San Jose to Chicago with flexible booking policies on momondo?

Yes. All flights to Chicago from San Jose on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from San Jose to Chicago?

Once all potential San Jose to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from San Jose to Chicago right now. Can momondo alert me if prices change?

Price alerts on flights to Chicago from San Jose are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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