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Cheap flights from San Jose, California to Chicago from $128

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 1/12. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from San Jose, California to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
11:40 am - 8:54 amSJC-MDW
19h 14m2 stops
Delta Logo
1:14 pm - 10:12 pmMDW-SJC
10h 58m2 stops
$314Delta
Find Deal
Mon, Dec 8 - Fri, Dec 12
Delta Logo
6:35 am - 4:34 pmSJC-MDW
7h 59m1 stop
Delta Logo
1:14 pm - 10:12 pmMDW-SJC
10h 58m2 stops
$350Delta
Find Deal
Tue, Dec 9 - Fri, Dec 12
Delta Logo
7:45 pm - 9:19 amSJC-MDW
11h 34m2 stops
Delta Logo
12:50 pm - 8:41 pmMDW-SJC
9h 51m1 stop
$360Delta
Find Deal
Mon, Dec 8 - Fri, Dec 12
Delta Logo
6:20 am - 6:00 pmSJC-MDW
9h 40m2 stops
Delta Logo
9:34 am - 6:56 pmMDW-SJC
11h 22m2 stops
$365Delta
Find Deal
Thu, Dec 11 - Tue, Dec 16
Delta Logo
1:26 pm - 8:54 amSJC-MDW
17h 28m2 stops
Delta Logo
1:49 pm - 8:53 pmMDW-SJC
9h 04m1 stop
$374Delta
Find Deal
Tue, Mar 3 - Wed, Mar 4
Southwest Logo
6:30 am - 12:40 pmSJC-MDW
4h 10mnonstop
Southwest Logo
8:45 am - 11:30 amMDW-SJC
4h 45mnonstop
$377Southwest
Find Deal
Thu, Dec 4 - Wed, Dec 10
Southwest Logo
8:40 am - 4:35 pmSJC-MDW
5h 55m1 stop
Southwest Logo
8:00 am - 10:50 amMDW-SJC
4h 50mnonstop
$383Southwest
Find Deal
Wed, Feb 25 - Sun, Mar 1
Delta Logo
10:30 pm - 10:01 amSJC-MDW
9h 31m1 stop
Delta Logo
6:00 am - 12:56 pmMDW-SJC
8h 56m1 stop
$387Delta
Find Deal
Tue, Jan 20 - Tue, Jan 27
Southwest Logo
6:50 am - 5:00 pmSJC-MDW
8h 10m2 stops
Southwest Logo
8:45 am - 11:30 amMDW-SJC
4h 45mnonstop
$392Southwest
Find Deal
Thu, Dec 4 - Wed, Dec 10
Southwest Logo
8:40 am - 4:35 pmSJC-MDW
5h 55m1 stop
Southwest Logo
8:05 am - 10:55 amMDW-SJC
4h 50mnonstop
$393Southwest
Find Deal
Fri, Jan 9 - Fri, Jan 16

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
Dec 8
SJC11:40 amSan Jose
19h 14m
2 stops
MDW8:54 amChicago Midway
Dec 12
MDW1:14 pmChicago Midway
10h 58m
2 stops
SJC10:12 pmSan Jose
$314
Find similar
Delta
Dec 9
SJC6:35 amSan Jose
7h 59m
1 stop
MDW4:34 pmChicago Midway
Dec 12
MDW1:14 pmChicago Midway
10h 58m
2 stops
SJC10:12 pmSan Jose
$350
Find similar
Delta
Dec 8
SJC7:45 pmSan Jose
11h 34m
2 stops
MDW9:19 amChicago Midway
Dec 12
MDW12:50 pmChicago Midway
9h 51m
1 stop
SJC8:41 pmSan Jose
$360
Find similar

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
Dec 4
SJC6:30 amSan Jose
4h 10m
MDW12:40 pmChicago Midway
Dec 10
MDW8:45 amChicago Midway
4h 45m
SJC11:30 amSan Jose
$377
Find similar
Southwest
Feb 25
SJC8:40 amSan Jose
5h 55m
1 stop
MDW4:35 pmChicago Midway
Mar 1
MDW8:00 amChicago Midway
4h 50m
SJC10:50 amSan Jose
$383
Find similar
Southwest
Dec 4
SJC6:50 amSan Jose
8h 10m
2 stops
MDW5:00 pmChicago Midway
Dec 10
MDW8:45 amChicago Midway
4h 45m
SJC11:30 amSan Jose
$392
Find similar

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 November 4, 2025.
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

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Mon 12/8

11:40 am-8:54 am

2 stops19h 14m

Chicago Midway

Fri 12/12

1:14 pm-10:12 pm

2 stops10h 58m

$314

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Tue 12/9

6:35 am-4:34 pm

1 stop7h 59m

Chicago Midway

Fri 12/12

1:14 pm-10:12 pm

2 stops10h 58m

$350

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Mon 12/8

7:45 pm-9:19 am

2 stops11h 34m

Chicago Midway

Fri 12/12

12:50 pm-8:41 pm

1 stop9h 51m

$360

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Thu 12/11

6:20 am-6:00 pm

2 stops9h 40m

Chicago Midway

Tue 12/16

9:34 am-6:56 pm

2 stops11h 22m

$365

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Tue 3/3

1:26 pm-8:54 am

2 stops17h 28m

Chicago Midway

Wed 3/4

1:49 pm-8:53 pm

1 stop9h 04m

$374

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Thu 12/4

6:30 am-12:40 pm

Nonstop4h 10m

Chicago Midway

Wed 12/10

8:45 am-11:30 am

Nonstop4h 45m

$377

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Wed 2/25

8:40 am-4:35 pm

1 stop5h 55m

Chicago Midway

Sun 3/1

8:00 am-10:50 am

Nonstop4h 50m

$383

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Tue 1/20

10:30 pm-10:01 am

1 stop9h 31m

Chicago Midway

Tue 1/27

6:00 am-12:56 pm

1 stop8h 56m

$387

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Thu 12/4

6:50 am-5:00 pm

2 stops8h 10m

Chicago Midway

Wed 12/10

8:45 am-11:30 am

Nonstop4h 45m

$392

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Fri 1/9

8:40 am-4:35 pm

1 stop5h 55m

Chicago Midway

Fri 1/16

8:05 am-10:55 am

Nonstop4h 50m

$393

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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 cheapest month to fly to Chicago Midway Airport?

The month of February is, on average, the cheapest month to fly to Chicago Midway Airport from San Jose, California, with most prices found around $413. If you are unable to visit Chicago Midway Airport during the month of February, then departing from San Jose, California during the month March is also very affordable. Most momondo users find prices during this month for around $420.

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

According to our data, Tuesday is the cheapest day to fly to Chicago Midway Airport from San Jose, California. The lowest ticket price found for a Tuesday departure recently was $428. 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 $542.

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 afternoon is the least expensive time of day to depart. momondo users have found prices as low as $433 when looking at flights departing in the afternoon. Try not to purchase tickets in the morning because they tend to be around $461. 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 to Chicago Midway flights?

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

Can stopping save me money on San Jose, California to Chicago Midway Airport flights?

You could potentially save up to 28% on your flight if you consider stops on a San Jose, California to Chicago Midway Airport flight.

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

$193

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 $193. The best round-trip flight deal from San Jose, California to Chicago Midway Airport found on momondo in the last 72 hours is $446.
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

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

    Chicago Midway is 1830.8 mi away from San Jose. 4h 05m 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
FrontierPriceFrom $186Free CancellationRating
5.8
3,116 reviews
Search Frontier flights
United AirlinesPriceFrom $287Free CancellationRating
7.4
8,998 reviews
Search United Airlines flights
SouthwestPriceFrom $331Free CancellationRating
8.0
4,237 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 6 flights/week on average for this route. A good Southwest flight deal for San Jose, California to Chicago Midway Airport starts from $331 round-trip, up to an average price of $514. Our users have rated Southwest at 8.0/10.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
Porter
Griffith
Saint John

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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