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Cheap flights from San Jose, California to Chicago from $104

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 2/26. 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
10:45 pm - 9:53 am
SJC
-
MDW
9h 08m1 stop
Delta Logo
9:33 am - 10:07 pm
MDW
-
SJC
14h 34m2 stops
$353Delta
Tue, Jan 27 - Sat, Feb 7
Delta Logo
7:45 am - 8:52 am
SJC
-
MDW
23h 07m2 stops
Delta Logo
9:53 am - 5:40 pm
MDW
-
SJC
9h 47m2 stops
$354Delta
Fri, Jan 30 - Wed, Feb 4
Delta Logo
6:20 am - 5:34 pm
SJC
-
MDW
9h 14m2 stops
Delta Logo
9:50 am - 5:40 pm
MDW
-
SJC
9h 50m2 stops
$358Delta
Wed, Jan 14 - Wed, Jan 21
Delta Logo
7:45 am - 8:52 am
SJC
-
MDW
23h 07m2 stops
Delta Logo
6:25 am - 12:56 pm
MDW
-
SJC
8h 31m1 stop
$360Delta
Thu, Jan 29 - Sat, Feb 7
Delta Logo
7:45 am - 8:52 am
SJC
-
MDW
23h 07m2 stops
Delta Logo
9:53 am - 5:40 pm
MDW
-
SJC
9h 47m2 stops
$364Delta
Sun, Jan 25 - Thu, Feb 5
Delta Logo
11:40 am - 8:52 am
SJC
-
MDW
19h 12m2 stops
Delta Logo
1:26 pm - 11:58 pm
MDW
-
SJC
12h 32m2 stops
$365Delta
Sun, Jan 25 - Mon, Feb 2
Delta Logo
7:45 am - 10:07 pm
SJC
-
MDW
12h 22m2 stops
Delta Logo
1:49 pm - 9:28 pm
MDW
-
SJC
9h 39m1 stop
$380Delta
Thu, Jan 8 - Fri, Jan 9
Southwest Logo
10:50 am - 4:55 pm
SJC
-
MDW
4h 05mnonstop
Southwest Logo
5:20 pm - 7:55 pm
MDW
-
SJC
4h 35mnonstop
$387Southwest
Wed, May 6 - Sat, May 9
Southwest Logo
8:40 am - 4:35 pm
SJC
-
MDW
5h 55m1 stop
Southwest Logo
8:10 am - 2:15 pm
MDW
-
SJC
8h 05m1 stop
$388Southwest
Wed, Jan 14 - Wed, Jan 21
Southwest Logo
12:10 pm - 7:55 pm
SJC
-
MDW
5h 45m1 stop
Southwest Logo
8:35 am - 11:30 am
MDW
-
SJC
4h 55mnonstop
$390Southwest
Tue, Jan 20 - Sat, Jan 24

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
Jan 27
SJC6:25 pmSan Jose
12h 27m
2 stops
MDW8:52 amChicago Midway
Feb 3
MDW1:51 pmChicago Midway
9h 37m
1 stop
SJC9:28 pmSan Jose
$353
Find similar
Delta
Jan 30
SJC7:45 amSan Jose
23h 07m
2 stops
MDW8:52 amChicago Midway
Feb 4
MDW9:53 amChicago Midway
9h 47m
2 stops
SJC5:40 pmSan Jose
$354
Find similar
Delta
Jan 14
SJC6:20 amSan Jose
9h 14m
2 stops
MDW5:34 pmChicago Midway
Jan 21
MDW9:50 amChicago Midway
9h 50m
2 stops
SJC5:40 pmSan Jose
$358
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
May 6
SJC10:50 amSan Jose
4h 05m
MDW4:55 pmChicago Midway
May 9
MDW5:20 pmChicago Midway
4h 35m
SJC7:55 pmSan Jose
$387
Find similar
Southwest
Jan 14
SJC8:40 amSan Jose
5h 55m
1 stop
MDW4:35 pmChicago Midway
Jan 21
MDW8:10 amChicago Midway
8h 05m
1 stop
SJC2:15 pmSan Jose
$388
Find similar
Southwest
Jan 20
SJC12:10 pmSan Jose
5h 45m
1 stop
MDW7:55 pmChicago Midway
Jan 24
MDW8:35 amChicago Midway
4h 55m
SJC11:30 amSan Jose
$390
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 December 18, 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

Tue 1/27

10:45 pm-9:53 am

1 stop9h 08m

Chicago Midway

Sat 2/7

9:33 am-10:07 pm

2 stops14h 34m

$353

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Fri 1/30

7:45 am-8:52 am

2 stops23h 07m

Chicago Midway

Wed 2/4

9:53 am-5:40 pm

2 stops9h 47m

$354

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Wed 1/14

6:20 am-5:34 pm

2 stops9h 14m

Chicago Midway

Wed 1/21

9:50 am-5:40 pm

2 stops9h 50m

$358

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Thu 1/29

7:45 am-8:52 am

2 stops23h 07m

Chicago Midway

Sat 2/7

6:25 am-12:56 pm

1 stop8h 31m

$360

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Sun 1/25

7:45 am-8:52 am

2 stops23h 07m

Chicago Midway

Thu 2/5

9:53 am-5:40 pm

2 stops9h 47m

$364

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Sun 1/25

11:40 am-8:52 am

2 stops19h 12m

Chicago Midway

Mon 2/2

1:26 pm-11:58 pm

2 stops12h 32m

$365

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Thu 1/8

7:45 am-10:07 pm

2 stops12h 22m

Chicago Midway

Fri 1/9

1:49 pm-9:28 pm

1 stop9h 39m

$380

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Wed 5/6

10:50 am-4:55 pm

Nonstop4h 05m

Chicago Midway

Sat 5/9

5:20 pm-7:55 pm

Nonstop4h 35m

$387

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Wed 1/14

8:40 am-4:35 pm

1 stop5h 55m

Chicago Midway

Wed 1/21

8:10 am-2:15 pm

1 stop8h 05m

$388

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Tue 1/20

12:10 pm-7:55 pm

1 stop5h 45m

Chicago Midway

Sat 1/24

8:35 am-11:30 am

Nonstop4h 55m

$390

Flights are sorted by cheapest round-trip flights 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 $425. 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 at noon because they tend to be around $457. 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 8% 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

$150

Fastest flight time

4h 05m

Direct flights

Mon, Tue, Wed, Thu, Sat and Sun
The best one-way flight to Chicago Midway Airport from San Jose, California in the past 72 hours is $150. The best round-trip flight deal from San Jose, California to Chicago Midway Airport found on momondo in the last 72 hours is $453.
The fastest flight from San Jose, California to Chicago Midway Airport takes 4h 05m
Direct flights go from San Jose, California to Chicago Midway Airport on Monday, Tuesday, Wednesday, Thursday, Saturday and Sunday. There are no airlines offering direct flights.
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
United AirlinesPriceFrom $287Free CancellationRating
7.4
9,093 reviews
Search United Airlines flights
SouthwestPriceFrom $331Free CancellationRating
7.9
4,250 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 $511. Our users have rated Southwest at 7.9/10.

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
Valparaiso
Schererville
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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