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

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.
Delta Logo
6:08 pm - 8:55 amSJC  San Jose-MDW Chicago Midway
12h 47m2 stops Los Angeles Minneapolis St Paul
Delta Logo
5:12 pm - 10:41 amMDW  Chicago Midway-SJC San Jose
19h 29m2 stops Atlanta Hartsfield-Jackson Los Angeles
$333Delta
Wed, Dec 2 - Mon, Dec 7
Southwest Logo
11:00 pm - 5:00 amSJC  San Jose-MDW Chicago Midway
4h 00mnonstop
Southwest Logo
9:50 am - 12:25 pmMDW  Chicago Midway-SJC San Jose
4h 35mnonstop
$337Southwest
Wed, Oct 28 - Thu, Oct 29
Southwest Logo
11:00 pm - 5:00 amSJC  San Jose-MDW Chicago Midway
4h 00mnonstop
Southwest Logo
10:35 am - 1:10 pmMDW  Chicago Midway-SJC San Jose
4h 35mnonstop
$337Southwest
Thu, Oct 29 - Sat, Oct 31
Southwest Logo
11:15 am - 5:15 pmSJC  San Jose-MDW Chicago Midway
4h 00mnonstop
Southwest Logo
10:35 am - 1:10 pmMDW  Chicago Midway-SJC San Jose
4h 35mnonstop
$337Southwest
Tue, Oct 27 - Sat, Oct 31
Southwest Logo
6:00 am - 12:10 pmSJC  San Jose-MDW Chicago Midway
4h 10mnonstop
Southwest Logo
10:10 am - 12:55 pmMDW  Chicago Midway-SJC San Jose
4h 45mnonstop
$337Southwest
Mon, Dec 7 - Mon, Dec 14
Southwest Logo
11:00 pm - 5:00 amSJC  San Jose-MDW Chicago Midway
4h 00mnonstop
Southwest Logo
10:10 am - 12:55 pmMDW  Chicago Midway-SJC San Jose
4h 45mnonstop
$337Southwest
Tue, Oct 27 - Tue, Nov 3
Southwest Logo
6:00 am - 12:10 pmSJC  San Jose-MDW Chicago Midway
4h 10mnonstop
Southwest Logo
10:10 am - 12:55 pmMDW  Chicago Midway-SJC San Jose
4h 45mnonstop
$337Southwest
Mon, Dec 7 - Mon, Dec 14
Southwest Logo
11:00 pm - 5:00 amSJC  San Jose-MDW Chicago Midway
4h 00mnonstop
Southwest Logo
10:35 am - 1:10 pmMDW  Chicago Midway-SJC San Jose
4h 35mnonstop
$337Southwest
Wed, Oct 28 - Sat, Oct 31
Southwest Logo
11:00 pm - 5:00 amSJC  San Jose-MDW Chicago Midway
4h 00mnonstop
Southwest Logo
10:10 am - 12:55 pmMDW  Chicago Midway-SJC San Jose
4h 45mnonstop
$337Southwest
Wed, Oct 28 - Wed, Nov 4
Delta Logo
12:45 pm - 10:10 pmSJC  San Jose-MDW Chicago Midway
7h 25m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:00 am - 11:56 amMDW  Chicago Midway-SJC San Jose
7h 56m1 stop Atlanta Hartsfield-Jackson
$357Delta
Sat, Feb 13 - Tue, Feb 16

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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
Oct 28
SJC11:00 pmSan Jose
4h 00m
MDW5:00 amChicago Midway
Nov 7
MDW6:10 pmChicago Midway
4h 50m
SJC9:00 pmSan Jose
$337
Southwest
Oct 27
SJC11:15 amSan Jose
4h 00m
MDW5:15 pmChicago Midway
Oct 31
MDW9:35 amChicago Midway
5h 55m
1 stop
SJC1:30 pmSan Jose
$343
Southwest
Oct 28
SJC1:35 pmSan Jose
7h 10m
1 stop
MDW10:45 pmChicago Midway
Nov 7
MDW6:10 pmChicago Midway
4h 50m
SJC9:00 pmSan Jose
$347

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 2
SJC6:08 pmSan Jose
12h 47m
2 stops
MDW8:55 amChicago Midway
Dec 7
MDW5:12 pmChicago Midway
19h 29m
2 stops
SJC10:41 amSan Jose
$333
Delta
Oct 28
SJC6:20 amSan Jose
8h 27m
1 stop
MDW4:47 pmChicago Midway
Oct 31
MDW10:12 amChicago Midway
8h 08m
2 stops
SJC4:20 pmSan Jose
$362
Delta
Oct 26
SJC10:45 pmSan Jose
12h 02m
2 stops
MDW12:47 pmChicago Midway
Oct 29
MDW10:12 amChicago Midway
8h 08m
2 stops
SJC4:20 pmSan Jose
$368

momondo Fare Finder

 
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 San Jose - MDW Chicago Midway

SJCMDW

San Jose

Wed 12/2

6:08 pm-8:55 am

2 stops12h 47m

Chicago Midway

Mon 12/7

5:12 pm-10:41 am

2 stops19h 29m

$333
Quickest round-trip

San JoseChicago

SJC San Jose - MDW Chicago Midway

SJCMDW

San Jose

Wed 10/28

11:00 pm-5:00 am

Nonstop4h 00m

Chicago Midway

Thu 10/29

9:50 am-12:25 pm

Nonstop4h 35m

$337

San JoseChicago

SJC San Jose - MDW Chicago Midway

SJCMDW

San Jose

Thu 10/29

11:00 pm-5:00 am

Nonstop4h 00m

Chicago Midway

Sat 10/31

10:35 am-1:10 pm

Nonstop4h 35m

$337

San JoseChicago

SJC San Jose - MDW Chicago Midway

SJCMDW

San Jose

Tue 10/27

11:15 am-5:15 pm

Nonstop4h 00m

Chicago Midway

Sat 10/31

10:35 am-1:10 pm

Nonstop4h 35m

$337

San JoseChicago

SJC San Jose - MDW Chicago Midway

SJCMDW

San Jose

Mon 12/7

6:00 am-12:10 pm

Nonstop4h 10m

Chicago Midway

Mon 12/14

10:10 am-12:55 pm

Nonstop4h 45m

$337

San JoseChicago

SJC San Jose - MDW Chicago Midway

SJCMDW

San Jose

Tue 10/27

11:00 pm-5:00 am

Nonstop4h 00m

Chicago Midway

Tue 11/3

10:10 am-12:55 pm

Nonstop4h 45m

$337

San JoseChicago

SJC San Jose - MDW Chicago Midway

SJCMDW

San Jose

Mon 12/7

6:00 am-12:10 pm

Nonstop4h 10m

Chicago Midway

Mon 12/14

10:10 am-12:55 pm

Nonstop4h 45m

$337

San JoseChicago

SJC San Jose - MDW Chicago Midway

SJCMDW

San Jose

Wed 10/28

11:00 pm-5:00 am

Nonstop4h 00m

Chicago Midway

Sat 10/31

10:35 am-1:10 pm

Nonstop4h 35m

$337

San JoseChicago

SJC San Jose - MDW Chicago Midway

SJCMDW

San Jose

Wed 10/28

11:00 pm-5:00 am

Nonstop4h 00m

Chicago Midway

Wed 11/4

10:10 am-12:55 pm

Nonstop4h 45m

$337

San JoseChicago

SJC San Jose - MDW Chicago Midway

SJCMDW

San Jose

Sat 2/13

12:45 pm-10:10 pm

1 stop7h 25m

Chicago Midway

Tue 2/16

6:00 am-11:56 am

1 stop7h 56m

$357

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?

Prices are currently low for flights on this route.

Typical prices usually range from $353 to $547.
The lowest price recently found on this route was $333.

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

The month of September is, on average, the cheapest month to fly to Chicago Midway Airport from San Jose, California, with most prices found around $403. If you are unable to visit Chicago Midway Airport during the month of September, then departing from San Jose, California during the month August is also very affordable. Most momondo users find prices during this month for around $407.

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 $457. 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 $679.

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 $491 when looking at flights departing in the evening. Try not to purchase tickets in the morning because they tend to be around $538. 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.

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

No. A direct flight is the cheapest option for a flight between San Jose, California to Chicago Midway Airport.

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

$144

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 $144. The best round-trip flight deal from San Jose, California to Chicago Midway Airport found on momondo in the last 72 hours is $333.
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 $310Free CancellationRating
7.9
4,215 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 17 flights/week on average for this route. A good Southwest flight deal for San Jose, California to Chicago Midway Airport starts from $310 round-trip, up to an average price of $528. 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
Portage
Benton Harbor
Saint Joseph
Lansing
Valparaiso
Schererville
Munster
Chesterton
Monticello
Crown Point
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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