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Cheap flights from San Jose to Chicago from $91

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 to Chicago departing on 10/20. 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 to Chicago

Cheap round-trip flights

Southwest Logo
8:00 am - 5:00 pmSJC-MDW
7h 00m1 stop
Southwest Logo
7:50 am - 10:35 amMDW-SJC
4h 45mnonstop
$213Southwest
Find Deal
Wed, Nov 5 - Sun, Nov 9
Southwest Logo
7:20 am - 4:15 pmSJC-MDW
6h 55m1 stop
Southwest Logo
4:10 pm - 6:40 pmMDW-SJC
4h 30mnonstop
$215Southwest
Find Deal
Sat, Oct 25 - Sat, Nov 1
Logo
7:12 pm - 8:52 pmSJC-MDW
23h 40m1 stop
Logo
7:03 pm - 8:00 pmMDW-SJC
26h 57m1 stop
$218
Find Deal
Thu, Sep 25 - Mon, Sep 29
Frontier Logo
12:35 pm - 12:24 amSJC-MDW
9h 49m1 stop
Frontier Logo
5:20 pm - 11:32 amMDW-SJC
20h 12m2 stops
$223Frontier
Find Deal
Mon, Oct 20 - Sat, Oct 25
Southwest Logo
6:35 am - 12:45 pmSJC-MDW
4h 10mnonstop
Southwest Logo
2:15 pm - 6:50 pmMDW-SJC
6h 35m1 stop
$226Southwest
Find Deal
Sun, Oct 19 - Sat, Oct 25
Southwest Logo
7:30 am - 1:35 pmSJC-MDW
4h 05mnonstop
Southwest Logo
5:05 am - 9:20 amMDW-SJC
6h 15m1 stop
$228Southwest
Find Deal
Tue, Oct 28 - Thu, Oct 30
Southwest Logo
9:00 pm - 5:00 amSJC-MDW
6h 00m1 stop
Southwest Logo
4:10 pm - 6:40 pmMDW-SJC
4h 30mnonstop
$233Southwest
Find Deal
Mon, Oct 20 - Sat, Oct 25
Logo
6:35 am - 9:58 pmSJC-MDW
13h 23m2 stops
Logo
7:03 pm - 10:45 amMDW-SJC
17h 42m1 stop
$244
Find Deal
Thu, Sep 25 - Mon, Sep 29
Delta Logo
11:35 am - 8:53 amSJC-MDW
19h 18m2 stops
Delta Logo
3:00 pm - 8:26 pmMDW-SJC
7h 26m1 stop
$254Delta
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Tue, Sep 30 - Sat, Oct 11
Delta Logo
6:20 am - 5:43 pmSJC-MDW
9h 23m1 stop
Delta Logo
3:00 pm - 8:26 pmMDW-SJC
7h 26m1 stop
$257Delta
Find Deal
Wed, Oct 22 - Sat, Oct 25

Delta flights from San Jose to Chicago Midway Airport

Our best Delta deals on San Jose to Chicago Midway Airport flight tickets
Delta
Sep 30
SJC11:35 amSan Jose
19h 18m
2 stops
MDW8:53 amChicago Midway
Oct 11
MDW3:00 pmChicago Midway
7h 26m
1 stop
SJC8:26 pmSan Jose
$254
Find similar
Delta
Oct 22
SJC6:20 amSan Jose
9h 23m
1 stop
MDW5:43 pmChicago Midway
Oct 25
MDW3:00 pmChicago Midway
7h 26m
1 stop
SJC8:26 pmSan Jose
$257
Find similar
Delta
Sep 30
SJC6:11 pmSan Jose
12h 42m
2 stops
MDW8:53 amChicago Midway
Oct 11
MDW1:06 pmChicago Midway
9h 59m
2 stops
SJC9:05 pmSan Jose
$259
Find similar

Southwest flights from San Jose to Chicago Midway Airport

Our best Southwest deals on San Jose to Chicago Midway Airport flight tickets
Southwest
Nov 5
SJC8:00 amSan Jose
7h 00m
1 stop
MDW5:00 pmChicago Midway
Nov 9
MDW7:50 amChicago Midway
4h 45m
SJC10:35 amSan Jose
$213
Find similar
Southwest
Oct 25
SJC7:20 amSan Jose
6h 55m
1 stop
MDW4:15 pmChicago Midway
Nov 1
MDW4:10 pmChicago Midway
4h 30m
SJC6:40 pmSan Jose
$215
Find similar
Southwest
Oct 19
SJC6:35 amSan Jose
4h 10m
MDW12:45 pmChicago Midway
Oct 25
MDW2:15 pmChicago Midway
6h 35m
1 stop
SJC6:50 pmSan Jose
$226
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momondo Fare Finder

 
Customize your flight search to find flights from San Jose 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 September 11, 2025.
Use the filters below to find and compare flights from San Jose to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Wed 11/5

8:00 am-5:00 pm

1 stop7h 00m

Chicago Midway

Sun 11/9

7:50 am-10:35 am

Nonstop4h 45m

$213

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Sat 10/25

7:20 am-4:15 pm

1 stop6h 55m

Chicago Midway

Sat 11/1

4:10 pm-6:40 pm

Nonstop4h 30m

$215

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Thu 9/25

7:12 pm-8:52 pm

1 stop23h 40m

Chicago Midway

Mon 9/29

7:03 pm-8:00 pm

1 stop26h 57m

$218

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Mon 10/20

12:35 pm-12:24 am

1 stop9h 49m

Chicago Midway

Sat 10/25

5:20 pm-11:32 am

2 stops20h 12m

$223

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Sun 10/19

6:35 am-12:45 pm

Nonstop4h 10m

Chicago Midway

Sat 10/25

2:15 pm-6:50 pm

1 stop6h 35m

$226

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Tue 10/28

7:30 am-1:35 pm

Nonstop4h 05m

Chicago Midway

Thu 10/30

5:05 am-9:20 am

1 stop6h 15m

$228

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Mon 10/20

9:00 pm-5:00 am

1 stop6h 00m

Chicago Midway

Sat 10/25

4:10 pm-6:40 pm

Nonstop4h 30m

$233

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Thu 9/25

6:35 am-9:58 pm

2 stops13h 23m

Chicago Midway

Mon 9/29

7:03 pm-10:45 am

1 stop17h 42m

$244

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Tue 9/30

11:35 am-8:53 am

2 stops19h 18m

Chicago Midway

Sat 10/11

3:00 pm-8:26 pm

1 stop7h 26m

$254

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Wed 10/22

6:20 am-5:43 pm

1 stop9h 23m

Chicago Midway

Sat 10/25

3:00 pm-8:26 pm

1 stop7h 26m

$257

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 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 November is, on average, the cheapest month to fly to Chicago Midway Airport from San Jose, with most prices found around $378. If you are unable to visit Chicago Midway Airport during the month of November, then departing from San Jose during the month September is also very affordable. Most momondo users find prices during this month for around $398.

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. The lowest ticket price found for a Tuesday departure recently was $426. 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 because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $537.

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

Flying to Chicago Midway Airport from San Jose in the evening is the least expensive time of day to depart. momondo users have found prices as low as $351 when looking at flights departing in the evening. Try not to purchase tickets in the morning because they tend to be around $463. 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 to Chicago Midway Airport flights?

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

When to book flights from San Jose to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from San Jose 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 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 to Chicago Midway Airport

Best Price Found

$169

Fastest flight time

4h 05m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from San Jose in the past 72 hours is $169. The best round-trip flight deal from San Jose to Chicago Midway Airport found on momondo in the last 72 hours is $301.
The fastest flight from San Jose to Chicago Midway Airport takes 4h 05m
Direct flights go from San Jose 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 to Chicago Midway Airport?

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

Best airlines flying from San Jose to Chicago Midway Airport

Compare and see reviews for airlines that fly from San Jose to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $128Free CancellationRating
5.8
3,177 reviews
Search Frontier flights
SouthwestPriceFrom $331Free CancellationRating
8.0
4,248 reviews
Search Southwest flights

  • Southwest Flights From San Jose to Chicago Midway Airport

    Southwest is one of the most popular airlines flying from San Jose to Chicago Midway Airport, operating 25 flights/week on average for this route. A good Southwest flight deal for San Jose to Chicago Midway Airport starts from $331 round-trip, up to an average price of $492. 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
Lansing
Portage
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.

An easier way to manage your Chicago Midway Airport trip

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