$103 Cheap Flights from San Jose (SJC) to Chicago (MDW)

View $103 flight on Thu, Aug 14, 2025Opens in a new window

Popular airlines from Norman Y. Mineta San Jose Intl. Airport (SJC) to Chicago Midway Airport (MDW)

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Cheap Flights from San Jose to Chicago (SJC-MDW)

Prices were available within the past 7 days and start at $103 for one-way flights and $225 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Mon, Oct 20 - Thu, Oct 23
SJC
San Jose
MDW
Chicago
$225 Roundtrip, found 6 days ago
$225
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Mon, Oct 20 from San Jose to Chicago, returning Thu, Oct 23, priced at $225 found 6 days ago
Southwest Airlines
Tue, Aug 12 - Tue, Aug 19
SJC
San Jose
MDW
Chicago
$245 Roundtrip, found 15 hours ago
$245
Roundtrip
found 15 hours ago
Select Southwest Airlines flight, departing Tue, Aug 12 from San Jose to Chicago, returning Tue, Aug 19, priced at $245 found 15 hours ago
Frontier Airlines
Mon, Oct 20 - Thu, Oct 23
SJC
San Jose
MDW
Chicago
$250 Roundtrip, found 6 days ago
$250
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Mon, Oct 20 from San Jose to Chicago, returning Thu, Oct 23, priced at $250 found 6 days ago
Southwest Airlines
Wed, Aug 20 - Sat, Aug 23
SJC
San Jose
MDW
Chicago
$251 Roundtrip, found 1 hour ago
$251
Roundtrip
found 1 hour ago
Select Southwest Airlines flight, departing Wed, Aug 20 from San Jose to Chicago, returning Sat, Aug 23, priced at $251 found 1 hour ago
Southwest Airlines
Wed, Aug 20 - Sat, Aug 23
SJC
San Jose
MDW
Chicago
$256 Roundtrip, found 1 hour ago
$256
Roundtrip
found 1 hour ago
Select Southwest Airlines flight, departing Wed, Aug 20 from San Jose to Chicago, returning Sat, Aug 23, priced at $256 found 1 hour ago
Delta
Tue, Oct 21 - Tue, Nov 4
SJC
San Jose
MDW
Chicago
$257 Roundtrip, just found
$257
Roundtrip
just found
Select Delta flight, departing Tue, Oct 21 from San Jose to Chicago, returning Tue, Nov 4, priced at $257 just found
Southwest Airlines
Wed, Aug 20 - Sat, Aug 23
SJC
San Jose
MDW
Chicago
$260 Roundtrip, found 1 hour ago
$260
Roundtrip
found 1 hour ago
Select Southwest Airlines flight, departing Wed, Aug 20 from San Jose to Chicago, returning Sat, Aug 23, priced at $260 found 1 hour ago
Frontier Airlines
Sun, Aug 3 - Sat, Aug 16
SJC
San Jose
MDW
Chicago
$261 Roundtrip, found 6 days ago
$261
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Sun, Aug 3 from San Jose to Chicago, returning Sat, Aug 16, priced at $261 found 6 days ago
Southwest Airlines
Wed, Aug 20 - Sat, Aug 23
SJC
San Jose
MDW
Chicago
$265 Roundtrip, found 1 hour ago
$265
Roundtrip
found 1 hour ago
Select Southwest Airlines flight, departing Wed, Aug 20 from San Jose to Chicago, returning Sat, Aug 23, priced at $265 found 1 hour ago
Southwest Airlines
Tue, Sep 16 - Sat, Sep 20
SJC
San Jose
MDW
Chicago
$266 Roundtrip, found 3 days ago
$266
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Tue, Sep 16 from San Jose to Chicago, returning Sat, Sep 20, priced at $266 found 3 days ago

Find the cheapest month to fly from San Jose (SJC) to Chicago (MDW)

October is typically the cheapest month to fly

From $138 - $533 per traveler.

Graph displaying average flight prices per month

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $295
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $295
Flights from San Jose (SJC) to Chicago (MDW)
Origin airport
Norman Y. Mineta San Jose Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$225
Distance
1833 mi
Average flight time
7 hours 46 mins

San Jose to Chicago Flights

The cheapest times to fly from San Jose to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from San Jose to Chicago are during the month of October. You can find some of the cheapest flights from San Jose to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from San Jose to Chicago

Sunday is one of the best days to book for cheap flights from San Jose to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from San Jose to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from San Jose to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $103 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap San Jose to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your San Jose to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from Norman Y. Mineta San Jose Intl. Airport (SJC) to Midway Intl. Airport (MDW) cost?
You can land cheap return fares from Norman Y. Mineta San Jose Intl. Airport (SJC) to Midway Intl. Airport (MDW) starting from $297. Book a seat and get ready to go. This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a Southwest Airlines flight leaving SJC on July 29 2025 and touching down at MDW. The price was last updated on July 2 2025 and has not changed since.
What is the cheapest month to fly from SJC to MDW?
The cheapest flights from SJC to MDW are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
Which airlines fly direct from Norman Y. Mineta San Jose Intl. Airport (SJC) to Midway Intl. Airport (MDW)?
Jump on a direct flight with Southwest Airlines and journey straight from Norman Y. Mineta San Jose Intl. Airport (SJC) to Midway Intl. Airport (MDW).
What is the cheapest airline that flies from SJC to MDW?
Currently, the cheapest carrier offering one-way flights from SJC to MDW is Southwest Airlines. You can book a seat on this route from $157. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from SJC on September 18 2025. Prices were last updated on July 2 2025 and have not changed since.
How many flights per day from Norman Y. Mineta San Jose Intl. Airport (SJC) to Midway Intl. Airport (MDW)?
On average, there is just 1 direct flight taking off from Norman Y. Mineta San Jose Intl. Airport (SJC) to Midway Intl. Airport (MDW) each day. If this doesn't fit your plans, consider flights with layovers. Just customize your search results on Expedia to include one or two stops to find the next best option.
What are the most popular departure times for flights from Norman Y. Mineta San Jose Intl. Airport (SJC) to Midway Intl. Airport (MDW)?
The 11 AM departures from SJC to MDW are the most sought after. These flights can come with a higher price due to their popularity. If you want to save on your trip, pick a less crowded time to fly.
What day of the week has the most flights from SJC to MDW?
Friday has the most flights from Norman Y. Mineta San Jose Intl. Airport (SJC) to Midway Intl. Airport (MDW). Consider taking off on this day and you'll have a greater chance of finding a departure that fits your itinerary.
What is the earliest flight from Norman Y. Mineta San Jose Intl. Airport (SJC) to Midway Intl. Airport (MDW)?
The first flight of the day taking off from Norman Y. Mineta San Jose Intl. Airport (SJC) is at around 8:00AM UTC-8. Hop on this flight and you'll reach Midway Intl. Airport (MDW) at approximately 2:05PM UTC-6. The overall travel time is 4h 5m.
How long does it take to fly from Norman Y. Mineta San Jose Intl. Airport (SJC) to Midway Intl. Airport (MDW)?
It takes approximately 4 hours and 5 minutes to cover the 1,850 mi from SJC to MDW.
What airline has the least delays from SJC to MDW?
Southwest Airlines has the best track record for on-time direct flights from Norman Y. Mineta San Jose Intl. Airport (SJC) to Midway Intl. Airport (MDW), with an on-time rating of 83%. Use the Expedia App to view your flight status before you head off and get real-time updates about any changes.
What is the best time to fly from Norman Y. Mineta San Jose Intl. Airport (SJC) to Midway Intl. Airport (MDW)?
Opt for a flight from Norman Y. Mineta San Jose Intl. Airport (SJC) to Midway Intl. Airport (MDW) that leaves before 3 PM to reduce the likelihood of delays. Departures after this time have a 22% higher chance of being canceled, on average.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Chicago from Norman Y. Mineta San Jose Intl. Airport (SJC)?
You can arrive at O'Hare Intl. Airport (ORD) or Midway Intl. Airport (MDW) when traveling to Chicago on a direct flight from Norman Y. Mineta San Jose Intl. Airport (SJC).
Is it cheaper to buy a plane ticket from Norman Y. Mineta San Jose Intl. Airport (SJC) to Midway Intl. Airport (MDW) last-minute?
Last-minute bookings from SJC to MDW are usually more expensive. For the lowest rates, start searching for flights early. That said, if your travel plans are flexible, you may score a cheap fare right before your trip.
Is it cheaper to book a SJC to MDW flight and hotel package?
Compared with arranging flights and hotels separately, booking a SJC to MDW flight and hotel package with Expedia could lead to significant savings. What's more, having everything in one convenient place will take the stress out of planning your trip. Just pick your flights and select from our wide range of hotels, then tailor your trip with extras like activities and car rentals.
Can I cancel or change the date of my flight from Norman Y. Mineta San Jose Intl. Airport (SJC) to Midway Intl. Airport (MDW)?
Typically, it's possible to cancel or reschedule your SJC to MDW flight. However, for bookings made more than 24 hours ago, additional fees may apply. Check your airline's policies in your itinerary to see what changes are possible and whether any costs are involved. You'll also find more information on our Customer Service portal.

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