Cheap Flight Tickets from San Jose (SJC) to Chicago (MDW), Starting at $277

Good to Know: Cheapest and Fastest SJC - MDW Flights

Useful information for finding best airline tickets from Norman Y. Mineta San Jose International to Chicago Midway International on your next trip.

Cheapest Round Trip Flight

$707

WN Southwest Airlines • 1 stop • 11h 50m

Sep 26 – Oct 03

The cheapest round trip flight from San Jose to Chicago (SJC-MDW-SJC) is currently $707

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Cheapest Direct Flight

$277

WN Southwest Airlines • nonstop • 6h 45m

Sep 23

The cheapest nonstop flight from San Jose to Chicago (SJC-MDW) is currently $277

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Fastest Flight

6h 40m

The fastest nonstop flight from San Jose to Chicago (SJC-MDW) takes 6h 40m

Top Airlines Flying from San Jose to Chicago

Southwest Airlines-WN

Southwest Airlines

Delta Airline, DL

Delta Airlines

Latest Flight Deals from San Jose (SJC) to Chicago (MDW)

Compare and book low fare round-trip air tickets from San Jose to Chicago. Ideal for travelers with confirmed return itineraries.

Sep 26 - Oct 03, Economy
WN
San Jose → Chicago
11h 50m
10:25 AM - 7:35 PM • 1 stop
WN
San Jose → Chicago
7h 15m
7:10 PM - 9:45 PM • nonstop
$707
Southwest Airlines
Sep 26 - Oct 03, Economy
WN
San Jose → Chicago
13h 30m
7:30 PM - 5:40 AM • 1 stop
WN
San Jose → Chicago
7h 15m
7:10 PM - 9:45 PM • nonstop
$707
Southwest Airlines
Sep 26 - Oct 03, Economy
WN
San Jose → Chicago
15h 35m
10:45 AM - 10:20 PM • 1 stop
WN
San Jose → Chicago
7h 15m
12:50 PM - 3:25 PM • nonstop
$707
Southwest Airlines
Sep 26 - Oct 03, Economy
WN
San Jose → Chicago
12h 15m
6:30 AM - 4:05 PM • 1 stop
WN
San Jose → Chicago
7h 15m
7:10 PM - 9:45 PM • nonstop
$707
Southwest Airlines
Sep 26 - Oct 03, Economy
WN
San Jose → Chicago
12h 10m
6:50 AM - 4:20 PM • 1 stop
WN
San Jose → Chicago
7h 15m
7:10 PM - 9:45 PM • nonstop
$707
Southwest Airlines
Sep 26 - Oct 03, Economy
WN
San Jose → Chicago
12h 20m
9:55 AM - 7:35 PM • 2 stops
WN
San Jose → Chicago
7h 15m
12:50 PM - 3:25 PM • nonstop
$712
Southwest Airlines

Fly from San Jose to Chicago with the Best Airfare Deals on FareLeaders

Looking for a cheap last-minute deal or the best round-trip flight from San Jose to Chicago? Find the biggest savings on one-way and round-trip tickets right here.

FAQs on San Jose to Chicago Flights

What are the airports in San Jose?
SJC
What’s the most popular airline flying from SJC to MDW?
The most popular airline flying from San Jose to Chicago are
Can I fly from SJC to MDW non-stop?
Yes, you can fly SJC to MDW non-stop on
Which airlines fly nonstop between San Jose and Chicago?
The non-stop flights between San Jose and Chicago are .
What’s the earliest departure time from SJC to MDW Airport?
The earliest flight leaves SJC at 6:10 am and lands in MDW - Chicago Midway International
What are the airports in Chicago?
ORD,MDW
Can I make changes to my San Jose to Chicago flight tickets or cancel them on FareLeaders.com?
No. We are an airfare comparison site. All the tickets are booked by the travel agent offering the flight deal and any changes or cancellations to be made are directly done directly by them or the airlines.
Can I cancel my flight tickets from SJC to MDW?
Read the fare rules of the San Jose to Chicago air tickets booked. Some airlines allow you to cancel the tickets within a stipulated time period with a cancellation fee.
Which airline alliances offer flights from San Jose and Chicago?
operate flights between San Jose and Chicago
How long does a flight from San Jose to Chicago take?
It takes approximately 4 hour to fly non-stop from SJC to MDW, which is 1837.59 miles by air.
Which airlines provide the cheapest flights from San Jose (SJC) to Chicago (MDW) ?
In the past couple of days, the cheapest tickets to MDW from SJC were found on WN : USD 707
Do I need a passport to fly between SJC and MDW?
No
What’s the latest departure time from SJC to MDW ?
The last flight leaves SJC at 11:00 pm

Essential Information for Booking Flights from San Jose (SJC) - AI Insights

What's the cheapest airline from sjc to mdw?
You can find the cheapest flights from San Jose International Airport (sjc) to Chicago Midway International Airport (mdw) with Southwest Airlines (WN). For a one-way trip, consider booking in advance to secure the best fares. Look for airfare deals on websites like fareleaders.com for the latest cheap flights.
What's the popular airline to fly from sjc to mdw?
Southwest Airlines offers flights from San Jose International Airport (SJC) to Chicago Midway International Airport (MDW) with a one-way trip, suitable for 2 passengers traveling in Economy class.
What's the cheapest day of the week to fly from sjc to mdw?
The cheapest day to fly from San Jose International Airport (SJC) to Chicago Midway International Airport (MDW) is Saturday. Flying on Saturdays tends to offer the lowest fares for this route. You can expect to find budget-friendly flights on this day, making it an ideal choice for travelers.
What's the cheapest month to fly from sjc to mdw?
The cheapest month to fly from San Jose International Airport (SJC) to Chicago Midway International Airport (MDW) is November, as it tends to offer lower fares compared to other months. This is because many airlines adjust their prices based on seasonal demand, and November is typically a slower month for travel. By booking in advance, you can secure a budget-friendly flight for your one-way trip.
Which airline/airlines fly from sjc to mdw?
Frontier Airlines, Alaska Airlines, Delta Airlines, Volaris Airline, and Southwest Airlines offer flights from San Jose International Airport (sjc) to Chicago Midway International Airport (mdw). You can find the best fares on their websites.
What is the cost of a one-way flight from San Jose to Chicago?
The cost of a one-way flight from San Jose to Chicago varies depending on the airline and time of booking, but you can find affordable options with Southwest Airlines (WN) starting from $200.
How far in advance can I book a flight from San Jose to Chicago?
It is recommended to book a flight from San Jose to Chicago at least 30 days in advance to get the best deals.
What is the best airline to fly from San Jose to Chicago?
Southwest Airlines (WN) is a popular choice for flights from San Jose to Chicago, offering affordable fares and convenient schedules.
Can I get a bus from San Jose to Chicago?
Unfortunately, there are no direct bus services from San Jose to Chicago, but you can explore other transportation options like trains or car rentals.
How do I book a flight on your website?
To book a flight on our website, simply enter your travel dates, destinations, and preferred airlines, and our system will provide you with the best options.
What are the cheapest flights from Milwaukee to Chicago?
You can find affordable flights from Milwaukee to Chicago with airlines like Frontier Airlines (F9), Alaska Airlines (AS), and Delta Airlines (DL).
Can I book a flight for July or December?
Yes, you can book a flight for July or December, but keep in mind that prices may vary depending on the airline and availability.
How do I know if I have the best airfare for my trip?
To ensure you have the best airfare for your trip, compare prices across multiple airlines and book in advance to get the best deals.
Can I get a flight with awesome amenities?
Yes, some airlines offer flights with awesome amenities like extra legroom, priority boarding, or in-flight entertainment. Be sure to check the airline's website for more information.
Is it worth it to book a flight with rich features?
It depends on your personal preferences and travel needs. If you value convenience and extra features, booking a flight with rich features might be worth it for you.

San Jose (SJC) to Chicago (MDW): Airport Information

Origin Airport Norman Y. Mineta San Jose International , San Jose, US
Destination Airport Chicago Midway International , Chicago, US
Distance 1838 miles

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