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Cheap flights from San Jose to Chicago Midway Airport from $63

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 Midway Airport departing on 2/12. 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 to Chicago

Cheap round-trip flights

These are some of the best round-trip flight deals from San Jose to Chicago that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from San Jose to Chicago.

Cheap last minute flights

Planning a quick getaway from San Jose to Chicago? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Chicago, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from San Jose to Chicago

Find recent round-trip train or bus tickets from San Jose to Chicago.

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
5:23 pm - 11:48 amSJC-MDW
16h 25m1 stop
7:15 am - 12:08 pmMDW-SJC
6h 53m1 stop
$158Frontier
Find Deal
Thu, Jan 9 - Sun, Jan 12
2:28 pm - 12:13 amSJC-MDW
7h 45m1 stop
7:15 am - 12:08 pmMDW-SJC
6h 53m1 stop
$168Frontier
Find Deal
Fri, Dec 13 - Sun, Dec 15
5:19 pm - 11:48 amSJC-MDW
16h 29m1 stop
10:27 pm - 11:50 amMDW-SJC
15h 23m1 stop
$178Frontier
Find Deal
Sat, Dec 14 - Wed, Dec 18
6:06 pm - 5:33 amSJC-MDW
33h 27m2 stops
10:44 am - 9:35 amMDW-SJC
24h 51m2 stops
Sun, Dec 29 - Sun, Jan 5
6:06 pm - 5:33 amSJC-MDW
33h 27m2 stops
1:24 pm - 7:46 amMDW-SJC
20h 22m2 stops
Sun, Dec 29 - Fri, Jan 3
6:29 am - 4:21 pmSJC-MDW
7h 52m1 stop
6:00 am - 12:10 pmMDW-SJC
8h 10m1 stop
$326Delta
Find Deal
Tue, Jan 14 - Tue, Jan 21
5:55 am - 6:32 pmSJC-MDW
10h 37m2 stops
2:15 pm - 9:07 pmMDW-SJC
8h 52m1 stop
$331Delta
Find Deal
Sat, Dec 14 - Wed, Dec 18
11:10 am - 5:15 pmSJC-MDW
4h 05mnonstop
9:45 am - 12:35 pmMDW-SJC
4h 50mnonstop
$374Southwest
Find Deal
Mon, Jan 13 - Thu, Jan 16
11:10 am - 5:15 pmSJC-MDW
4h 05mnonstop
4:15 pm - 9:10 pmMDW-SJC
6h 55m1 stop
$379Southwest
Find Deal
Tue, Jan 14 - Tue, Jan 21
2:58 pm - 8:59 pmSJC-MDW
28h 01m3 stops
8:39 pm - 9:02 amMDW-SJC
14h 23m1 stop
$814Volaris
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Sat, Mar 29 - Mon, Mar 31
4:03 pm - 12:17 amSJC-MDW
6h 14m1 stop
$63Frontier
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Wed, Feb 12
2:28 pm - 12:13 amSJC-MDW
7h 45m1 stop
$64Frontier
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Mon, Dec 9
6:35 am - 4:12 pmSJC-MDW
7h 37m1 stop
$163Delta
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Wed, Dec 11
6:15 am - 10:06 pmSJC-MDW
13h 51m2 stops
$168Delta
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Wed, Dec 25
11:10 am - 5:15 pmSJC-MDW
4h 05mnonstop
$187Southwest
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Wed, Jan 8
8:00 am - 5:20 pmSJC-MDW
7h 20m1 stop
$196Southwest
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Tue, Jan 7
10:32 am - 12:27 amSJC-MDW
35h 55m3 stops
Fri, Dec 20
8:43 am - 9:49 amSJC-MDW
23h 06m2 stops
Sat, Dec 21
2:58 pm - 8:59 pmSJC-MDW
28h 01m3 stops
$398Volaris
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Fri, Mar 14
2:58 pm - 8:59 pmSJC-MDW
28h 01m3 stops
$408Volaris
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Sun, Mar 16
9:17 am - 7:50 pmSJC-MDW
8h 33m1 stop
7:15 am - 12:08 pmMDW-SJC
6h 53m1 stop
$238Frontier
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Tue, Nov 26 - Thu, Dec 5
9:17 am - 7:50 pmSJC-MDW
8h 33m1 stop
7:00 am - 12:41 pmMDW-SJC
7h 41m1 stop
$256Frontier
Find Deal
Tue, Nov 26 - Fri, Nov 29
9:59 pm - 11:44 amSJC-MDW
11h 45m1 stop
7:00 am - 12:41 pmMDW-SJC
7h 41m1 stop
$302Frontier
Find Deal
Mon, Nov 25 - Fri, Nov 29
9:17 am - 7:50 pmSJC-MDW
8h 33m1 stop
7:00 am - 12:41 pmMDW-SJC
7h 41m1 stop
$322Frontier
Find Deal
Tue, Nov 26 - Fri, Nov 29
6:30 am - 11:55 amSJC-MDW
27h 25m2 stops
7:55 pm - 9:02 amMDW-SJC
15h 07m1 stop
Tue, Nov 26 - Thu, Dec 5
6:30 am - 11:55 amSJC-MDW
27h 25m2 stops
7:55 pm - 8:15 pmMDW-SJC
26h 20m2 stops
Tue, Nov 26 - Thu, Dec 5
9:45 am - 3:50 pmSJC-MDW
4h 05mnonstop
1:30 pm - 6:15 pmMDW-SJC
6h 45m1 stop
$703Southwest
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Tue, Nov 26 - Thu, Dec 5
9:45 am - 3:50 pmSJC-MDW
4h 05mnonstop
9:50 am - 12:35 pmMDW-SJC
4h 45mnonstop
$722Southwest
Find Deal
Tue, Nov 26 - Thu, Dec 5
12:30 pm - 9:46 pmSJC-MDW
7h 16m1 stop
9:31 am - 7:28 pmMDW-SJC
11h 57m2 stops
$990Delta
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Sat, Nov 23 - Fri, Nov 29
9:16 am - 9:46 pmSJC-MDW
10h 30m2 stops
9:31 am - 7:28 pmMDW-SJC
11h 57m2 stops
$995Delta
Find Deal
Sat, Nov 23 - Fri, Nov 29
11:10 am - 5:15 pmSJC-MDW
4h 05mnonstop
9:45 am - 12:35 pmMDW-SJC
4h 50mnonstop
$374Southwest
Find Deal
Mon, Jan 13 - Thu, Jan 16
11:10 am - 5:15 pmSJC-MDW
4h 05mnonstop
8:05 am - 10:55 amMDW-SJC
4h 50mnonstop
$414Southwest
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Wed, Feb 12 - Sun, Feb 16
6:30 am - 12:40 pmSJC-MDW
4h 10mnonstop
6:25 pm - 9:00 pmMDW-SJC
4h 35mnonstop
$434Southwest
Find Deal
Thu, May 8 - Mon, May 12
6:30 am - 12:40 pmSJC-MDW
4h 10mnonstop
6:25 pm - 9:00 pmMDW-SJC
4h 35mnonstop
$504Southwest
Find Deal
Thu, May 15 - Mon, May 19
6:50 am - 12:55 pmSJC-MDW
4h 05mnonstop
9:35 am - 12:20 pmMDW-SJC
4h 45mnonstop
$539Southwest
Find Deal
Sat, Mar 29 - Mon, Mar 31
7:05 am - 1:15 pmSJC-MDW
4h 10mnonstop
9:30 am - 12:15 pmMDW-SJC
4h 45mnonstop
$556Southwest
Find Deal
Thu, Dec 12 - Sun, Dec 15
7:05 am - 1:15 pmSJC-MDW
4h 10mnonstop
9:30 am - 12:15 pmMDW-SJC
4h 45mnonstop
$563Southwest
Find Deal
Tue, Dec 10 - Sun, Dec 15
7:05 am - 1:15 pmSJC-MDW
4h 10mnonstop
9:30 am - 12:15 pmMDW-SJC
4h 45mnonstop
$574Southwest
Find Deal
Fri, Dec 6 - Sun, Dec 8
7:05 am - 1:15 pmSJC-MDW
4h 10mnonstop
9:30 am - 12:15 pmMDW-SJC
4h 45mnonstop
$694Southwest
Find Deal
Tue, Dec 3 - Sun, Dec 8
8:20 am - 2:25 pmSJC-MDW
4h 05mnonstop
9:35 am - 12:20 pmMDW-SJC
4h 45mnonstop
$712Southwest
Find Deal
Thu, Mar 20 - Mon, Mar 24

Delta flights from San Jose to Chicago Midway Airport

Our best Delta deals on San Jose to Chicago Midway Airport flight tickets
Delta
Jan 14
SJC6:29 amSan Jose
7h 52m
1 stop
MDW4:21 pmChicago Midway
Jan 21
MDW6:00 amChicago Midway
8h 10m
1 stop
SJC12:10 pmSan Jose
Delta
Dec 14
SJC5:55 amSan Jose
10h 37m
2 stops
MDW6:32 pmChicago Midway
Dec 18
MDW2:15 pmChicago Midway
8h 52m
1 stop
SJC9:07 pmSan Jose
Delta
Jan 14
SJC7:00 amSan Jose
9h 14m
2 stops
MDW6:14 pmChicago Midway
Jan 21
MDW2:08 pmChicago Midway
10h 48m
2 stops
SJC10:56 pmSan Jose

Frontier flights from San Jose to Chicago Midway Airport

Our best Frontier deals on San Jose to Chicago Midway Airport flight tickets
Frontier
Jan 9
SJC5:23 pmSan Jose
16h 25m
1 stop
MDW11:48 amChicago Midway
Jan 12
MDW7:15 amChicago Midway
6h 53m
1 stop
SJC12:08 pmSan Jose
Frontier
Dec 13
SJC2:28 pmSan Jose
7h 45m
1 stop
MDW12:13 amChicago Midway
Dec 15
MDW7:15 amChicago Midway
6h 53m
1 stop
SJC12:08 pmSan Jose
Frontier
Dec 14
SJC5:19 pmSan Jose
16h 29m
1 stop
MDW11:48 amChicago Midway
Dec 18
MDW10:27 pmChicago Midway
15h 23m
1 stop
SJC11:50 amSan Jose

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 day to depart on your flight to Chicago Midway Airport?

According to our data, Sunday is the cheapest day to fly to Chicago Midway Airport from San Jose. The lowest ticket price found for a Sunday departure recently was $0. 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, Thursday 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 $612.

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 at noon because they tend to be around $555. 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 are 1 cabin classes 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?

You could potentially save up to 66% on your flight if you consider stops on a San Jose to Chicago Midway Airport flight.

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

$63

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 $63. The best round-trip flight deal from San Jose to Chicago Midway Airport found on momondo in the last 72 hours is $158.
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.

  • 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
6.1
3,536 reviews
Search Frontier flights
United AirlinesPriceFrom $203Free CancellationRating
7.4
9,172 reviews
Search United Airlines flights
DeltaPriceFrom $313Free CancellationRating
8.0
8,755 reviews
Search Delta flights
SouthwestPriceFrom $358Free CancellationRating
8.1
5,005 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 8 flights/week on average for this route. A good Southwest flight deal for San Jose to Chicago Midway Airport starts from $358 round-trip, up to an average price of $483. Our users have rated Southwest at 8.1/10.


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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