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Cheap flights from San Jose, California to Chicago from $144

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 6/2. 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.
Southwest Logo
9:10 pm - 5:00 am
SJC
-
MDW
5h 50m
1 stop
Southwest Logo
6:00 am - 11:25 am
MDW
-
SJC
7h 25m
1 stop
$277Southwest
Wed, Jun 3 - Wed, Jun 10
Southwest Logo
1:45 pm - 10:00 pm
SJC
-
MDW
6h 15m
1 stop
Southwest Logo
5:30 pm - 11:00 pm
MDW
-
SJC
7h 30m
2 stops
$282Southwest
Tue, Jun 2 - Wed, Jun 3
Southwest Logo
9:45 am - 7:30 pm
SJC
-
MDW
7h 45m
2 stops
Southwest Logo
5:30 pm - 11:00 pm
MDW
-
SJC
7h 30m
2 stops
$287Southwest
Tue, Jun 2 - Wed, Jun 3
Delta Logo
6:20 am - 6:31 pm
SJC
-
MDW
10h 11m
2 stops
Delta Logo
1:26 pm - 8:39 pm
MDW
-
SJC
9h 13m
2 stops
$288Delta
Wed, Jun 10 - Tue, Jun 16
Delta Logo
5:01 pm - 9:08 am
SJC
-
MDW
14h 07m
2 stops
Delta Logo
6:00 am - 11:30 am
MDW
-
SJC
7h 30m
1 stop
$292Delta
Tue, Jul 14 - Wed, Jul 29
Delta Logo
8:19 pm - 8:37 am
SJC
-
MDW
10h 18m
2 stops
Delta Logo
11:05 am - 7:32 pm
MDW
-
SJC
10h 27m
2 stops
$298Delta
Tue, Jul 14 - Tue, Jul 28
Southwest Logo
10:55 pm - 5:00 am
SJC
-
MDW
4h 05mnonstop
Southwest Logo
6:20 am - 10:45 am
MDW
-
SJC
6h 25m
1 stop
$312Southwest
Wed, Jun 3 - Wed, Jun 10
Southwest Logo
2:10 pm - 11:50 pm
SJC
-
MDW
7h 40m
1 stop
Southwest Logo
6:00 am - 11:25 am
MDW
-
SJC
7h 25m
1 stop
$322Southwest
Wed, Jun 10 - Tue, Jun 16
Southwest Logo
2:10 pm - 11:50 pm
SJC
-
MDW
7h 40m
1 stop
Southwest Logo
5:50 pm - 11:00 pm
MDW
-
SJC
7h 10m
2 stops
$327Southwest
Wed, Jun 10 - Tue, Jun 23
Southwest Logo
10:55 pm - 5:00 am
SJC
-
MDW
4h 05mnonstop
Southwest Logo
3:40 pm - 6:15 pm
MDW
-
SJC
4h 35mnonstop
$330Southwest
Tue, Jun 2 - Wed, Jun 3

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
Jun 10
SJC6:20 amSan Jose
10h 11m
2 stops
MDW6:31 pmChicago Midway
Jun 16
MDW1:26 pmChicago Midway
9h 13m
2 stops
SJC8:39 pmSan Jose
$288
Delta
Jul 14
SJC6:35 amSan Jose
7h 40m
1 stop
MDW4:15 pmChicago Midway
Jul 28
MDW11:05 amChicago Midway
10h 27m
2 stops
SJC7:32 pmSan Jose
$292
Delta
Jul 14
SJC8:19 pmSan Jose
10h 18m
2 stops
MDW8:37 amChicago Midway
Jul 28
MDW11:05 amChicago Midway
10h 27m
2 stops
SJC7:32 pmSan Jose
$298

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
Jun 3
SJC9:10 pmSan Jose
5h 50m
1 stop
MDW5:00 amChicago Midway
Jun 10
MDW6:00 amChicago Midway
7h 25m
1 stop
SJC11:25 amSan Jose
$277
Southwest
Jun 2
SJC1:45 pmSan Jose
6h 15m
1 stop
MDW10:00 pmChicago Midway
Jun 3
MDW5:30 pmChicago Midway
7h 30m
2 stops
SJC11:00 pmSan Jose
$282
Southwest
Jun 2
SJC9:45 amSan Jose
7h 45m
2 stops
MDW7:30 pmChicago Midway
Jun 3
MDW5:30 pmChicago Midway
7h 30m
2 stops
SJC11:00 pmSan Jose
$287

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 May 10, 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

Wed 6/3

9:10 pm-5:00 am

1 stop5h 50m

Chicago Midway

Wed 6/10

6:00 am-11:25 am

1 stop7h 25m

$277

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Tue 6/2

1:45 pm-10:00 pm

1 stop6h 15m

Chicago Midway

Wed 6/3

5:30 pm-11:00 pm

2 stops7h 30m

$282

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Tue 6/2

9:45 am-7:30 pm

2 stops7h 45m

Chicago Midway

Wed 6/3

5:30 pm-11:00 pm

2 stops7h 30m

$287

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Wed 6/10

6:20 am-6:31 pm

2 stops10h 11m

Chicago Midway

Tue 6/16

1:26 pm-8:39 pm

2 stops9h 13m

$288

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Tue 7/14

5:01 pm-9:08 am

2 stops14h 07m

Chicago Midway

Wed 7/29

6:00 am-11:30 am

1 stop7h 30m

$292

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Tue 7/14

8:19 pm-8:37 am

2 stops10h 18m

Chicago Midway

Tue 7/28

11:05 am-7:32 pm

2 stops10h 27m

$298

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Wed 6/3

10:55 pm-5:00 am

Nonstop4h 05m

Chicago Midway

Wed 6/10

6:20 am-10:45 am

1 stop6h 25m

$312

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Wed 6/10

2:10 pm-11:50 pm

1 stop7h 40m

Chicago Midway

Tue 6/16

6:00 am-11:25 am

1 stop7h 25m

$322

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Wed 6/10

2:10 pm-11:50 pm

1 stop7h 40m

Chicago Midway

Tue 6/23

5:50 pm-11:00 pm

2 stops7h 10m

$327
Quickest round-trip

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Tue 6/2

10:55 pm-5:00 am

Nonstop4h 05m

Chicago Midway

Wed 6/3

3:40 pm-6:15 pm

Nonstop4h 35m

$330

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 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 $379. 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 $443.

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

According to our data, Wednesday is the cheapest day to fly to Chicago Midway Airport from San Jose, California. The lowest ticket price found for a Wednesday departure recently was $453. 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 $574.

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 at noon is the least expensive time of day to depart. momondo users have found prices as low as $426 when looking at flights departing at noon. Try not to purchase tickets in the morning because they tend to be around $482. 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

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

You could potentially save up to 33% 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

$203

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 $203. The best round-trip flight deal from San Jose, California to Chicago Midway Airport found on momondo in the last 72 hours is $460.
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 $305Free CancellationRating
8.0
4,304 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 11 flights/week on average for this route. A good Southwest flight deal for San Jose, California to Chicago Midway Airport starts from $305 round-trip, up to an average price of $537. 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
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Munster
Schererville
Crown Point
Monticello
Chesterton
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.

An easier way to manage your Chicago Midway Airport trip

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