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Cheap flights from San Jose to Chicago from $45

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 12/11. 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.
8:12 pm - 12:05 pmSJC-ORD
13h 53m1 stop
9:54 pm - 9:35 amORD-SJC
13h 41m1 stop
$120Spirit Airlines
Find Deal
Wed, Dec 11 - Wed, Dec 18
1:23 pm - 5:30 amSJC-ORD
14h 07m1 stop
9:10 pm - 7:46 amORD-SJC
12h 36m1 stop
$131Spirit Airlines
Find Deal
Thu, Dec 5 - Tue, Dec 10
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
5:23 pm - 7:25 pmSJC-ORD
24h 02m1 stop
7:25 am - 12:08 pmORD-SJC
6h 43m1 stop
$158Frontier
Find Deal
Thu, Jan 9 - Sun, Jan 12
12:47 pm - 11:47 pmSJC-ORD
9h 00m1 stop
1:07 pm - 7:30 pmORD-SJC
8h 23m1 stop
$326Alaska Airlines
Find Deal
Tue, Dec 10 - Wed, Dec 11
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
8:28 am - 11:47 pmSJC-ORD
13h 19m2 stops
7:00 am - 2:15 pmORD-SJC
9h 15m1 stop
$339Alaska Airlines
Find Deal
Tue, Dec 10 - Wed, Dec 11
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
8:12 pm - 12:05 pmSJC-ORD
13h 53m1 stop
$45Spirit Airlines
Find Deal
Wed, Dec 11
8:12 pm - 12:05 pmSJC-ORD
13h 53m1 stop
$47Spirit Airlines
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Wed, Dec 11
4:03 pm - 12:17 amSJC-MDW
6h 14m1 stop
$63Frontier
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Wed, Feb 12
4:03 pm - 12:44 amSJC-ORD
6h 41m1 stop
$63Frontier
Find Deal
Mon, Feb 24
8:46 pm - 5:53 amSJC-ORD
7h 07m1 stop
$181Alaska Airlines
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Mon, Feb 17
6:15 am - 11:59 pmSJC-ORD
15h 44m2 stops
$182Alaska Airlines
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Sat, Mar 1
6:30 am - 12:50 pmSJC-ORD
4h 20mnonstop
$187United Airlines
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Tue, Jan 7
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
6:30 am - 12:50 pmSJC-ORD
4h 20mnonstop
$206United Airlines
Find Deal
Mon, Feb 10
9:17 am - 7:50 pmSJC-MDW
8h 33m1 stop
7:15 am - 12:08 pmMDW-SJC
6h 53m1 stop
$238Frontier
Find Deal
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
9:00 am - 9:30 pmSJC-ORD
10h 30m1 stop
5:25 am - 10:43 amORD-SJC
7h 18m1 stop
$290Spirit Airlines
Find Deal
Tue, Nov 26 - Thu, Dec 5
6:30 am - 11:43 pmSJC-ORD
15h 13m2 stops
9:53 pm - 7:46 amORD-SJC
11h 53m1 stop
$292Spirit Airlines
Find Deal
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
Find Deal
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
6:30 am - 12:50 pmSJC-ORD
4h 20mnonstop
9:10 am - 11:59 amORD-SJC
4h 49mnonstop
$813United Airlines
Find Deal
Tue, Nov 26 - Fri, Nov 29
12:55 pm - 9:11 pmSJC-ORD
6h 16m1 stop
9:10 am - 11:59 amORD-SJC
4h 49mnonstop
$823United Airlines
Find Deal
Tue, Nov 26 - Fri, Nov 29
10:10 pm - 8:15 amSJC-ORD
8h 05m1 stop
5:00 pm - 10:51 pmORD-SJC
7h 51m1 stop
$985Delta
Find Deal
Fri, Nov 22 - Fri, Nov 29
12:30 pm - 9:46 pmSJC-MDW
7h 16m1 stop
9:31 am - 7:28 pmMDW-SJC
11h 57m2 stops
$990Delta
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
6:30 am - 12:50 pmSJC-ORD
4h 20mnonstop
9:05 am - 11:54 amORD-SJC
4h 49mnonstop
$383United Airlines
Find Deal
Sat, Dec 14 - Wed, Dec 18
6:30 am - 12:50 pmSJC-ORD
4h 20mnonstop
9:05 am - 11:56 amORD-SJC
4h 51mnonstop
$398United Airlines
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
$403United Airlines
Find Deal
Thu, Jan 9 - Sun, Jan 12
6:30 am - 12:50 pmSJC-ORD
4h 20mnonstop
9:05 am - 11:56 amORD-SJC
4h 51mnonstop
$413United Airlines
Find Deal
Sun, Jan 26 - Wed, Jan 29
11:10 am - 5:15 pmSJC-MDW
4h 05mnonstop
8:05 am - 10:55 amMDW-SJC
4h 50mnonstop
$414Southwest
Find Deal
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 - 12:50 pmSJC-ORD
4h 20mnonstop
9:05 am - 11:56 amORD-SJC
4h 51mnonstop
$473United Airlines
Find Deal
Thu, Jan 16 - Tue, Jan 21
6:40 am - 1:00 pmSJC-ORD
4h 20mnonstop
9:00 am - 11:36 amORD-SJC
4h 36mnonstop
$476United Airlines
Find Deal
Thu, Apr 10 - Sun, Apr 13
6:20 am - 12:35 pmSJC-ORD
4h 15mnonstop
9:08 am - 12:03 pmORD-SJC
4h 55mnonstop
$493United Airlines
Find Deal
Thu, Feb 20 - Sun, Feb 23

Spirit Airlines flights from San Jose to Chicago

Our best Spirit Airlines deals on San Jose to Chicago flight tickets
Spirit Airlines
Dec 11
SJC8:12 pmSan Jose
13h 53m
1 stop
ORD12:05 pmChicago O'Hare Intl
Dec 18
ORD9:54 pmChicago O'Hare Intl
13h 41m
1 stop
SJC9:35 amSan Jose
Spirit Airlines
Dec 5
SJC1:23 pmSan Jose
14h 07m
1 stop
ORD5:30 amChicago O'Hare Intl
Dec 10
ORD9:10 pmChicago O'Hare Intl
12h 36m
1 stop
SJC7:46 amSan Jose
Spirit Airlines
Dec 11
SJC8:12 pmSan Jose
13h 53m
1 stop
ORD12:05 pmChicago O'Hare Intl
Dec 18
ORD9:54 pmChicago O'Hare Intl
17h 38m
2 stops
SJC1:32 pmSan Jose

Frontier flights from San Jose to Chicago

Our best Frontier deals on San Jose to Chicago flight tickets
Frontier
Jan 9
SJC5:23 pmSan Jose
24h 02m
1 stop
ORD7:25 pmChicago O'Hare Intl
Jan 12
ORD7:25 amChicago O'Hare Intl
6h 43m
1 stop
SJC12:08 pmSan Jose
Frontier
Dec 6
SJC2:28 pmSan Jose
8h 07m
1 stop
ORD12:35 amChicago O'Hare Intl
Dec 8
ORD7:25 amChicago O'Hare Intl
6h 43m
1 stop
SJC12:08 pmSan Jose
Frontier
Dec 5
SJC5:08 pmSan Jose
24h 22m
1 stop
ORD7:30 pmChicago O'Hare Intl
Dec 15
ORD6:36 pmChicago O'Hare Intl
23h 42m
1 stop
SJC4:18 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 January is your next best option. Flight prices from San Jose to Chicago during January 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 $329. 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 $471.

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 afternoon. Flights from San Jose to Chicago during this time can be as low as $302. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $427.

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 59 days out, which is when prices tend to be around $409. Don’t hesitate to check prices now though because momondo users recently found tickets for as low as $141.

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 74% 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 November 2024, prices for San Jose to Chicago flights are approximately 17% 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

$45

Fastest flight time

4h 05m

Direct flights

Every day

Airports in Chicago

2 airports
The best one-way flight to Chicago from San Jose in the past 72 hours is $45. The best round-trip flight deal from San Jose to Chicago found on momondo in the last 72 hours is $120.
The fastest flight from San Jose to Chicago takes 4h 05m
Direct flights go from San Jose to Chicago every day.
There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)

  • 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
9,464 reviews
Search Alaska Airlines flights
Spirit AirlinesPriceFrom $111Free CancellationRating
6.3
8,169 reviews
Search Spirit Airlines flights
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 $236Free CancellationRating
8.0
8,755 reviews
Search Delta flights
American AirlinesPriceFrom $279Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
SouthwestPriceFrom $358Free CancellationRating
8.1
5,005 reviews
Search Southwest flights
  • Southwest Flights From San Jose to Chicago

    Southwest operates around 8 flights from San Jose to Chicago every week. The average price of these flights found in the last 72 hours has been $512, but momondo users have found Southwest deals from San Jose to Chicago from as low as $358 round-trip. Southwest has been scored 8.1/10 in 5,005 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 $515 round-trip. United Airlines operates 7 flights out of San Jose into Chicago in an average week, so prices vary by time and availability. 9,172 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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Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago