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Cheap flights from San Jose to Chicago from $62

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 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 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.
1:11 pm - 12:13 amSJC-MDW
9h 02m1 stop
7:15 am - 12:08 pmMDW-SJC
6h 53m1 stop
$128Frontier
Find Deal
Thu, Jan 9 - Mon, Jan 13
4:03 pm - 12:17 amSJC-MDW
6h 14m1 stop
7:05 am - 3:03 pmMDW-SJC
9h 58m1 stop
$134Frontier
Find Deal
Wed, Feb 26 - Wed, Mar 5
11:36 am - 9:52 pmSJC-ORD
8h 16m1 stop
1:39 pm - 7:07 pmORD-SJC
7h 28m1 stop
$141Spirit Airlines
Find Deal
Sat, Feb 8 - Tue, Feb 11
9:34 pm - 5:31 amSJC-ORD
5h 57m1 stop
10:47 pm - 10:41 amORD-SJC
13h 54m1 stop
$154Spirit Airlines
Find Deal
Wed, Jan 22 - Fri, Jan 24
6:15 am - 4:58 pmSJC-ORD
32h 43m2 stops
7:00 pm - 6:04 pmORD-SJC
25h 04m2 stops
$318Alaska Airlines
Find Deal
Tue, Feb 25 - Tue, Mar 4
8:55 am - 11:59 pmSJC-ORD
13h 04m2 stops
3:21 pm - 9:56 pmORD-SJC
8h 35m1 stop
$321Alaska Airlines
Find Deal
Sat, Apr 26 - Wed, Apr 30
11:10 am - 5:15 pmSJC-MDW
4h 05mnonstop
8:35 am - 11:25 amMDW-SJC
4h 50mnonstop
$371Southwest
Find Deal
Wed, Feb 26 - Wed, Mar 5
11:10 am - 5:15 pmSJC-MDW
4h 05mnonstop
4:15 pm - 9:10 pmMDW-SJC
6h 55m1 stop
$376Southwest
Find Deal
Wed, Feb 26 - Wed, Mar 5
6:30 am - 12:50 pmSJC-ORD
4h 20mnonstop
9:05 am - 11:56 amORD-SJC
4h 51mnonstop
$396United Airlines
Find Deal
Sat, Feb 8 - Tue, Feb 11
8:25 am - 7:31 pmSJC-ORD
9h 06m1 stop
9:05 am - 11:56 amORD-SJC
4h 51mnonstop
$406United Airlines
Find Deal
Sat, Feb 8 - Tue, Feb 11
4:03 pm - 12:17 amSJC-MDW
6h 14m1 stop
$62Frontier
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Wed, Feb 26
1:11 pm - 12:17 amSJC-MDW
9h 06m1 stop
$63Frontier
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Mon, Feb 10
8:02 pm - 5:31 amSJC-ORD
7h 29m1 stop
$71Spirit Airlines
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Tue, Feb 4
9:34 pm - 5:31 amSJC-ORD
5h 57m1 stop
$74Spirit Airlines
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Wed, Jan 22
3:03 pm - 5:40 amSJC-ORD
12h 37m2 stops
$162Alaska Airlines
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Tue, Apr 15
5:19 pm - 1:07 pmSJC-ORD
17h 48m2 stops
$165Alaska Airlines
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Sun, Feb 9
6:30 am - 12:50 pmSJC-ORD
4h 20mnonstop
$186United Airlines
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Tue, Jan 21
11:10 am - 5:15 pmSJC-MDW
4h 05mnonstop
$186Southwest
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Tue, Jan 21
1:35 pm - 9:30 pmSJC-MDW
5h 55m1 stop
$195Southwest
Find Deal
Tue, Feb 18
6:30 am - 12:50 pmSJC-ORD
4h 20mnonstop
$211United Airlines
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Mon, Jan 20
7:00 pm - 8:37 amSJC-ORD
11h 37m1 stop
9:54 pm - 7:46 amORD-SJC
11h 52m1 stop
$327Spirit Airlines
Find Deal
Fri, Dec 27 - Sun, Jan 5
7:00 pm - 8:37 amSJC-ORD
11h 37m1 stop
9:54 pm - 9:35 amORD-SJC
13h 41m1 stop
$356Spirit Airlines
Find Deal
Fri, Dec 27 - Sun, Jan 5
12:35 pm - 11:46 pmSJC-ORD
9h 11m1 stop
1:07 pm - 11:45 amORD-SJC
24h 38m1 stop
$361Frontier
Find Deal
Fri, Dec 27 - Thu, Jan 2
12:35 pm - 11:46 pmSJC-ORD
9h 11m1 stop
1:07 pm - 11:45 amORD-SJC
24h 38m1 stop
$391Frontier
Find Deal
Fri, Dec 27 - Thu, Jan 2
3:21 pm - 4:40 amSJC-ORD
11h 19m2 stops
7:00 am - 12:54 pmORD-SJC
7h 54m1 stop
$798Alaska Airlines
Find Deal
Fri, Dec 27 - Sun, Jan 5
9:45 am - 3:50 pmSJC-MDW
4h 05mnonstop
9:40 am - 3:10 pmMDW-SJC
7h 30m1 stop
$855Southwest
Find Deal
Fri, Dec 27 - Sun, Jan 5
10:40 pm - 4:57 amSJC-ORD
4h 17mnonstop
8:00 pm - 10:49 pmORD-SJC
4h 49mnonstop
$891United Airlines
Find Deal
Fri, Dec 27 - Sun, Jan 5
3:21 pm - 4:40 amSJC-ORD
11h 19m2 stops
2:01 pm - 9:06 pmORD-SJC
9h 05m1 stop
$898Alaska Airlines
Find Deal
Fri, Dec 27 - Wed, Jan 1
10:55 pm - 10:46 amSJC-ORD
9h 51m1 stop
8:00 pm - 10:49 pmORD-SJC
4h 49mnonstop
$901United Airlines
Find Deal
Fri, Dec 27 - Sun, Jan 5
9:45 am - 3:50 pmSJC-MDW
4h 05mnonstop
2:10 pm - 6:20 pmMDW-SJC
6h 10m1 stop
$975Southwest
Find Deal
Fri, Dec 27 - Thu, Jan 2
6:20 am - 12:35 pmSJC-ORD
4h 15mnonstop
9:08 am - 12:03 pmORD-SJC
4h 55mnonstop
$371United Airlines
Find Deal
Wed, Feb 26 - Wed, Mar 5
11:10 am - 5:15 pmSJC-MDW
4h 05mnonstop
8:35 am - 11:25 amMDW-SJC
4h 50mnonstop
$371Southwest
Find Deal
Wed, Feb 26 - Wed, Mar 5
6:30 am - 12:50 pmSJC-ORD
4h 20mnonstop
9:05 am - 11:56 amORD-SJC
4h 51mnonstop
$396United Airlines
Find Deal
Thu, Jan 9 - Wed, Jan 15
11:10 am - 5:15 pmSJC-MDW
4h 05mnonstop
8:35 am - 11:25 amMDW-SJC
4h 50mnonstop
$396Southwest
Find Deal
Thu, Jan 9 - Wed, Jan 15
6:30 am - 12:50 pmSJC-ORD
4h 20mnonstop
9:05 am - 11:56 amORD-SJC
4h 51mnonstop
$402United Airlines
Find Deal
Tue, Feb 4 - Fri, Feb 7
11:50 am - 5:55 pmSJC-MDW
4h 05mnonstop
8:35 am - 11:25 amMDW-SJC
4h 50mnonstop
$417Southwest
Find Deal
Sun, Jan 12 - Tue, Jan 14
11:10 am - 5:15 pmSJC-MDW
4h 05mnonstop
9:45 am - 12:35 pmMDW-SJC
4h 50mnonstop
$421Southwest
Find Deal
Mon, Jan 13 - Thu, Jan 16
6:30 am - 12:50 pmSJC-ORD
4h 20mnonstop
9:05 am - 11:56 amORD-SJC
4h 51mnonstop
$421United Airlines
Find Deal
Mon, Jan 13 - Thu, Jan 16
11:10 am - 5:15 pmSJC-MDW
4h 05mnonstop
8:35 am - 11:25 amMDW-SJC
4h 50mnonstop
$427Southwest
Find Deal
Wed, Jan 22 - Fri, Jan 24
11:35 am - 5:40 pmSJC-MDW
4h 05mnonstop
5:05 pm - 7:40 pmMDW-SJC
4h 35mnonstop
$433Southwest
Find Deal
Wed, Apr 16 - Tue, Apr 22

Spirit Airlines flights from San Jose to Chicago

Our best Spirit Airlines deals on San Jose to Chicago flight tickets
Spirit Airlines
Feb 8
SJC11:36 amSan Jose
8h 16m
1 stop
ORD9:52 pmChicago O'Hare Intl
Feb 11
ORD1:39 pmChicago O'Hare Intl
7h 28m
1 stop
SJC7:07 pmSan Jose
Spirit Airlines
Jan 22
SJC9:34 pmSan Jose
5h 57m
1 stop
ORD5:31 amChicago O'Hare Intl
Jan 24
ORD10:47 pmChicago O'Hare Intl
13h 54m
1 stop
SJC10:41 amSan Jose
Spirit Airlines
Jan 9
SJC3:35 pmSan Jose
11h 55m
1 stop
ORD5:30 amChicago O'Hare Intl
Jan 13
ORD1:39 pmChicago O'Hare Intl
22h 45m
1 stop
SJC10:24 amSan Jose

Delta flights from San Jose to Chicago

Our best Delta deals on San Jose to Chicago flight tickets
Delta
Jan 16
SJC2:25 pmSan Jose
7h 46m
1 stop
ORD12:11 amChicago O'Hare Intl
Jan 20
ORD7:15 amChicago O'Hare Intl
8h 28m
1 stop
SJC1:43 pmSan Jose
Delta
Feb 26
SJC11:45 amSan Jose
10h 11m
1 stop
ORD11:56 pmChicago O'Hare Intl
Mar 5
ORD7:05 amChicago O'Hare Intl
14h 11m
2 stops
SJC7:16 pmSan Jose
Delta
Apr 16
SJC6:20 amSan Jose
9h 34m
1 stop
ORD5:54 pmChicago O'Hare Intl
Apr 22
ORD2:20 pmChicago O'Hare Intl
9h 38m
1 stop
SJC9:58 pmSan Jose

See travel insights to Chicago from

How to get the cheapest flight ticket from San Jose to Chicago

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?

The month of September is, on average, the cheapest month to fly to Chicago from San Jose, with most prices found around $353. If you’re not able to fly to Chicago in September, then November is your next best option. Flight prices from San Jose to Chicago during November average around $374.

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

The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as $335. This is often the case because there is less demand to fly during this day of the week. When flying out on a Friday, the most expensive travel day of the week, you can expect to see flight prices from San Jose to Chicago for around $465.

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

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from San Jose to Chicago during this time can be as low as $328. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $429.

What is the cheapest San Jose to Chicago flight route?

Fly from San Jose to Chicago O'Hare Intl for the best San Jose - Chicago flight prices

How far in advance should I book a flight to Chicago?

The best time to book a flight to Chicago from San Jose is 42 days out, which is when prices tend to be around $462. Don’t hesitate to check prices now though because momondo users recently found tickets for as low as $217.

What cabin class options are available on San Jose to Chicago flights?

There are 4 cabin classes available to choose from on San Jose to Chicago 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 flights?

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

How have San Jose to Chicago flight prices changed over time?

As of December 2024, prices for San Jose to Chicago flights are approximately 19% cheaper when compared to flights at the same time last year.

When to book flights from San Jose to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from San Jose to Chicago according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap San Jose to Chicago (SJC to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from San Jose to Chicago

Best Price Found

$62

Fastest flight time

4h 05m

Direct flights

Every day

Airports in Chicago

3 airports
The best one-way flight to Chicago from San Jose in the past 72 hours is $62. The best round-trip flight deal from San Jose to Chicago found on momondo in the last 72 hours is $128.
The fastest flight from San Jose to Chicago takes 4h 05m
Direct flights go from San Jose to Chicago every day.
There are 3 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW), Chicago Greater Rockford (RFD)

  • How far is San Jose to Chicago by plane?

    The straight-line distance from San Jose to Chicago is 1836.7 mi. By plane, this route typically takes 4h 05m.

  • When did momondo last update prices for flights from San Jose Airport to Chicago?

    Prices for flights from San Jose Airport to Chicago are updated daily.

  • How many operators does momondo search for flights from San Jose Airport to Chicago?

  • How old do you have to be to fly from San Jose Airport to Chicago?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from San Jose Airport to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The travel and health documents required for your trip to Chicago can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular plane model from San Jose to Chicago?

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


Best airlines flying from San Jose to Chicago

Compare and see reviews for airlines that fly from San Jose to Chicago with momondo
Airline
Rating
Free Cancellation
Price
Alaska AirlinesPriceFrom $100Free CancellationRating
8.0
9,549 reviews
Search Alaska Airlines flights
FrontierPriceFrom $106Free CancellationRating
6.1
3,469 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $134Free CancellationRating
6.3
8,113 reviews
Search Spirit Airlines flights
United AirlinesPriceFrom $203Free CancellationRating
7.4
9,022 reviews
Search United Airlines flights
DeltaPriceFrom $236Free CancellationRating
8.0
8,594 reviews
Search Delta flights
American AirlinesPriceFrom $279Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
SouthwestPriceFrom $367Free CancellationRating
8.1
4,780 reviews
Search Southwest flights
  • Southwest Flights From San Jose to Chicago

    Southwest operates around 9 flights from San Jose to Chicago every week. The average price of these flights found in the last 72 hours has been $549, but momondo users have found Southwest deals from San Jose to Chicago from as low as $367 round-trip. Southwest has been scored 8.1/10 in 4,780 reviews.

  • United Airlines Flights From San Jose to Chicago

    The best United Airlines deal for San Jose to Chicago flight tickets found on momondo in the last 72 hours was $203, round-trip. It should be noted that an average United Airlines flight deal for this route in this time was higher, at $516 round-trip. United Airlines operates 5 flights out of San Jose into Chicago in an average week, so prices vary by time and availability. 9,028 United Airlines reviews by users on momondo have scored the airline at 7.4/10.


Why use momondo?

Why should I use momondo to find a flight deal from San Jose to Chicago?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from San Jose to Chicago. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from San Jose to Chicago with flexible booking policies on momondo?

Flights from San Jose to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from San Jose to Chicago?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from San Jose to Chicago.

I’m not ready to book a flight from San Jose to Chicago right now. Can momondo alert me if prices change?

If you are not ready to book a flight from San Jose to Chicago now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Chicago and let you know when they change.


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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago