Cheap flights from San Jose to Chicago from $56

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Flight information for San Jose to Chicago
(SJC to CHI)

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

Best Price Found

$56

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 $56. The best round-trip flight deal from San Jose to Chicago found on momondo in the last 72 hours is $127.
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 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 from San Jose to Chicago?

January. The cheapest time of year to fly to Chicago from San Jose is January. Most expensive is June

What is the cheapest day to depart San Jose for Chicago?

Tuesday. The cheapest day of the week is typically Tuesday. The most expensive is typically Friday

When is the cheapest time to fly from San Jose to Chicago?

In the evening. San Jose to Chicago flights are approximately 22% more expensive in the morning than in the evening

What is the cheapest airline that flies to Chicago from San Jose?

Frontier. Alaska Airlines, American Airlines, and Delta are the most popular carriers operating from San Jose to Chicago

What is the cheapest San Jose to Chicago flight route?

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

How far in advance should you book San Jose to Chicago flights?

22 days before. The cheapest time to buy a flight from San Jose to Chicago is approximately 22 days to departure

How many flights depart from San Jose to Chicago on average per day?

As of October 2023, 6 flights take off from San Jose and land in Chicago each day. The most common flight departure time for this route is 5:00AM, with 57% of daily flights taking off at noon.

How many flights depart from San Jose to Chicago on average per week?

42 flights are operational weekly from San Jose to Chicago as of October 2023. The most popular departure day for this route is Monday, with 19% of flights per week taking off on this day.

Can stopping save me money on San Jose to Chicago flights?

You could potentially save up to 3% on your flight if you consider stops on a San Jose to Chicago flight.

When traveling from San Jose to Chicago, the most popular airport to fly into is Chicago O'Hare Intl Airport. The majority of travelers flying into Chicago O'Hare Intl Airport from San Jose are departing from San Jose Airport. You may be looking for an airport near San Jose Airport to depart from when traveling to Chicago and luckily, there are options! You can try San Francisco Airport which is located in San Francisco, Oakland Airport which is located in Oakland, or Monterey Regional Airport which is located in Monterey. When traveling from San Jose, it is helpful to have an alternative airport to fly into when you land in Chicago. Good options for arrival airports in Chicago, you can try Chicago Midway Airport (in Chicago) or Chicago Greater Rockford Airport (in Chicago). The least expensive flight option from San Jose to Chicago will typically be SFO — MDW during the month of October with an average price of $68 RT.

San Francisco Airport (SFO) to Chicago O'Hare Intl Airport (ORD)$111
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Oakland Airport (OAK) to Chicago O'Hare Intl Airport (ORD)$125
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San Francisco Airport (SFO) to Chicago Midway Airport (MDW)$68
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San Jose Airport (SJC) to Chicago O'Hare Intl Airport (ORD)$154
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San Jose Airport (SJC) to Chicago Midway Airport (MDW)$123
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Oakland Airport (OAK) to Chicago Midway Airport (MDW)$149
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Easily compare round-trip flights from San Jose to Chicago

Below you can see the best fares for your round-trip flight route over the next six months. All fares were found on momondo this week. Browse the quickest and cheapest flights from San Jose to Chicago by changing tabs
Multiple Airlines
Oct 31
SJC7:00 amSan Jose
11h 55m
2 stops
MDW8:55 pmChicago Midway
Nov 7
MDW10:08 pmChicago Midway
22h 41m
1 stop
SJC6:49 pmSan Jose
Spirit Airlines
Nov 1
SJC7:45 pmSan Jose
8h 50m
1 stop
ORD6:35 amChicago O'Hare Intl
Nov 7
ORD6:21 pmChicago O'Hare Intl
7h 51m
1 stop
SJC12:12 amSan Jose
Multiple Airlines
Oct 30
SJC7:39 pmSan Jose
12h 50m
2 stops
MDW10:29 amChicago Midway
Nov 6
MDW12:32 pmChicago Midway
24h 17m
1 stop
SJC10:49 amSan Jose
Spirit Airlines
Oct 24
SJC7:39 pmSan Jose
13h 20m
1 stop
ORD10:59 amChicago O'Hare Intl
Oct 28
ORD3:38 pmChicago O'Hare Intl
9h 59m
1 stop
SJC11:37 pmSan Jose
Delta
Oct 25
SJC2:30 pmSan Jose
7h 28m
1 stop
ORD11:58 pmChicago O'Hare Intl
Oct 29
ORD6:15 amChicago O'Hare Intl
9h 14m
1 stop
SJC1:29 pmSan Jose
Multiple Airlines
Nov 1
SJC7:45 pmSan Jose
15h 26m
1 stop
MDW1:11 pmChicago Midway
Nov 8
MDW11:31 amChicago Midway
14h 41m
2 stops
SJC12:12 amSan Jose

Find the cheapest one-way flights from San Jose to Chicago

If you're looking for one-way flights from San Jose to Chicago, view some of our deals below provided by Spirit Airlines and United Airlines
Multiple Airlines
Nov 28
SJC7:05 amSan Jose
26h 23m
1 stop
MDW11:28 amChicago Midway
Spirit Airlines
Oct 30
SJC7:39 pmSan Jose
8h 56m
1 stop
ORD6:35 amChicago O'Hare Intl
Spirit Airlines
Oct 17
SJC7:39 pmSan Jose
13h 20m
1 stop
ORD10:59 amChicago O'Hare Intl

Search last-minute flights to Chicago from San Jose

Find and compare round-trip flight prices for your last-minute flight from San Jose to Chicago
Spirit Airlines
Oct 11
SJC7:00 amSan Jose
12h 42m
2 stops
ORD9:42 pmChicago O'Hare Intl
Oct 18
ORD7:00 amChicago O'Hare Intl
13h 49m
1 stop
SJC6:49 pmSan Jose
Multiple Airlines
Oct 10
SJC7:00 amSan Jose
22h 42m
2 stops
ORD7:42 amChicago O'Hare Intl
Oct 18
ORD3:38 pmChicago O'Hare Intl
10h 34m
1 stop
SJC12:12 amSan Jose
Spirit Airlines
Oct 12
SJC7:00 amSan Jose
9h 20m
2 stops
ORD6:20 pmChicago O'Hare Intl
Oct 17
ORD6:21 pmChicago O'Hare Intl
7h 51m
1 stop
SJC12:12 amSan Jose
Spirit Airlines
Oct 11
SJC7:00 amSan Jose
15h 06m
3 stops
ORD12:06 amChicago O'Hare Intl
Oct 18
ORD7:00 amChicago O'Hare Intl
13h 49m
1 stop
SJC6:49 pmSan Jose
Spirit Airlines
Oct 12
SJC7:00 amSan Jose
9h 20m
2 stops
ORD6:20 pmChicago O'Hare Intl
Oct 18
ORD7:00 amChicago O'Hare Intl
13h 49m
1 stop
SJC6:49 pmSan Jose
Multiple Airlines
Oct 10
SJC7:39 pmSan Jose
8h 56m
1 stop
ORD6:35 amChicago O'Hare Intl
Oct 13
ORD10:45 pmChicago O'Hare Intl
16h 57m
2 stops
SJC1:42 pmSan Jose

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 $107Free CancellationRating
7.9
3,001 reviews
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FrontierPriceFrom $122Free CancellationRating
5.8
1,041 reviews
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Spirit AirlinesPriceFrom $162Free CancellationRating
6.0
2,809 reviews
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United AirlinesPriceFrom $218Free CancellationRating
7.2
2,719 reviews
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American AirlinesPriceFrom $248Free CancellationRating
7.1
2,893 reviews
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DeltaPriceFrom $284Free CancellationRating
7.8
1,565 reviews
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Spirit Airlines flights from San Jose to Chicago

Our best Spirit Airlines deals on San Jose to Chicago flight tickets
Spirit Airlines
Nov 1
SJC7:45 pmSan Jose
8h 50m
1 stop
ORD6:35 amChicago O'Hare Intl
Nov 7
ORD6:21 pmChicago O'Hare Intl
7h 51m
1 stop
SJC12:12 amSan Jose
Spirit Airlines
Oct 24
SJC7:39 pmSan Jose
13h 20m
1 stop
ORD10:59 amChicago O'Hare Intl
Oct 28
ORD3:38 pmChicago O'Hare Intl
9h 59m
1 stop
SJC11:37 pmSan Jose
Spirit Airlines
Oct 31
SJC7:00 amSan Jose
10h 44m
1 stop
ORD7:44 pmChicago O'Hare Intl
Nov 7
ORD6:21 pmChicago O'Hare Intl
7h 51m
1 stop
SJC12:12 amSan Jose

Delta flights from San Jose to Chicago

Our best Delta deals on San Jose to Chicago flight tickets
Delta
Oct 25
SJC2:30 pmSan Jose
7h 28m
1 stop
ORD11:58 pmChicago O'Hare Intl
Oct 29
ORD6:15 amChicago O'Hare Intl
9h 14m
1 stop
SJC1:29 pmSan Jose
Delta
Oct 27
SJC1:30 pmSan Jose
6h 39m
1 stop
ORD10:09 pmChicago O'Hare Intl
Oct 29
ORD6:15 amChicago O'Hare Intl
9h 14m
1 stop
SJC1:29 pmSan Jose
Delta
Jan 4
SJC12:15 pmSan Jose
9h 59m
1 stop
ORD12:14 amChicago O'Hare Intl
Jan 5
ORD6:00 amChicago O'Hare Intl
7h 50m
1 stop
SJC11:50 amSan Jose

  • 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 5h 38m.

  • 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 are the benefits of the different airports in San Jose and Chicago?

SJC is the main airport in San Jose, serving most flights in and out of the city. The airport is well-connected to downtown and has many transport options, including a train to downtown. You can get domestic and international flights from SJC, including direct flights to Chicago offered by Alaska Airlines and Southwest. Its compact size makes it easy to clear security, with wait times of less than 20min. Moreover, you’ll have plenty of amenities to enjoy, including free Wi-Fi. The two airports serving flights from San Jose to Chicago are ORD and MDW, and each has its benefits. If you want easier access to downtown, MDW is the better option as it is closer, and transportation fares are much cheaper. Moreover, you’ll have an easier time getting through security at MDW. However, ORD is a much larger airport, offering many domestic and international flights, and offers travelers more flexibility. ORD also has more amenities than MDW, including premium lounges like Polaris.


What is the best way to get in and out of airports in San Jose and Chicago?

SJC is well-connected to downtown San Jose, and there are many transport options to and from downtown. The first option is car rentals, and many rental agencies, including Hertz, Avis, Budget, Thrifty, Enterprise, and Alamo, have rental counters at SJC. Taxis are another option, available outside Terminals A and B. All are metered, and prior reservations aren’t required. Shared-ride shuttles are also available, and they provide door-to-door services to and from the airport. You can get these shuttles at the Terminal A parking garage. The final option is the train; the Airport Flyer has frequent trips from Santa Clara Caltrain Station. Similarly, you’ll have many options from Chicago airports to downtown. The first is bus transportation; CTA buses offer regular trips downtown, while the PACE buses serve the Chicago suburbs. Another cheap option is the CTA Blue Line, or the "L" train, operating 24h between Chicago airports and downtown. Taxis are also available curbside, and car rentals are available at Chicago airports, with companies like Avis, Thrifty, Hertz, National, Alamo, Avis, Budget, and SIXT at both ORD and MDW.

Which cities can you get to from Chicago Airports?

Several cities are within driving distance of both Chicago airports, and a rental car will be the best way of getting to these cities. You can rent cars at Midway and O’Hare and drive to many cities from Chicago in less than 3h, including Michigan City, Milwaukee, Grand Rapids, South Bend, Indianapolis, and Ann Arbor. You also can take regional buses available at ORD, which offer regional service to Iowa, Illinois, Wisconsin, and Indiana.


Alternative routes for San Jose to Chicago

Compare alternative flights to and from nearby airports and cities to discover the best prices and most convenient flight times
Los Angeles to Chicago Flights
Fastest flight time4h 05m
Cheapest price$105
Burbank to Chicago Flights
Fastest flight time5h 55m
Cheapest price$125
Santa Ana to Chicago Flights
Fastest flight time3h 45m
Cheapest price$111
Oakland, California to Chicago Flights
Fastest flight time5h 50m
Cheapest price$125
San Francisco to Chicago Flights
Fastest flight time4h 09m
Cheapest price$68
Ontario to Chicago Flights
Fastest flight time3h 55m
Cheapest price$115
San Diego to Chicago Flights
Fastest flight time6h 03m
Cheapest price$100
Los Angeles to St. Louis Flights
Fastest flight time3h 31m
Cheapest price$111
Long Beach to Chicago Flights
Fastest flight time6h 35m
Cheapest price$297
Ontario to St. Louis Flights
Fastest flight time4h 58m
Cheapest price$118
Sacramento to Chicago Flights
Fastest flight time6h 39m
Cheapest price$103
San Francisco to St. Louis Flights
Fastest flight time5h 18m
Cheapest price$152

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Why use momondo?

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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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