$91 Cheap Flights from San Jose (SJC) to Chicago (MDW)

View $91 flight on Fri, Oct 17, 2025Opens in a new window

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

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

Prices were available within the past 7 days and start at $91 for one-way flights and $170 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Sun, Oct 26 - Thu, Nov 13
SJC
San Jose
MDW
Chicago
$170 Roundtrip, found 13 hours ago
$170
Roundtrip
found 13 hours ago
Select Frontier Airlines flight, departing Sun, Oct 26 from San Jose to Chicago, returning Thu, Nov 13, priced at $170 found 13 hours ago
Frontier Airlines
Thu, Oct 2 - Thu, Oct 16
SJC
San Jose
MDW
Chicago
$172 Roundtrip, found 4 days ago
$172
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Thu, Oct 2 from San Jose to Chicago, returning Thu, Oct 16, priced at $172 found 4 days ago
Frontier Airlines
Fri, Oct 10 - Thu, Oct 16
SJC
San Jose
MDW
Chicago
$185 Roundtrip, found 2 hours ago
$185
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Fri, Oct 10 from San Jose to Chicago, returning Thu, Oct 16, priced at $185 found 2 hours ago
Frontier Airlines
Thu, Sep 25 - Thu, Oct 16
SJC
San Jose
MDW
Chicago
$190 Roundtrip, found 4 days ago
$190
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Thu, Sep 25 from San Jose to Chicago, returning Thu, Oct 16, priced at $190 found 4 days ago
Frontier Airlines
Sun, Oct 5 - Thu, Oct 16
SJC
San Jose
MDW
Chicago
$206 Roundtrip, found 2 hours ago
$206
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Sun, Oct 5 from San Jose to Chicago, returning Thu, Oct 16, priced at $206 found 2 hours ago
Frontier Airlines
Thu, Sep 25 - Thu, Oct 9
SJC
San Jose
MDW
Chicago
$227 Roundtrip, found 4 days ago
$227
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Thu, Sep 25 from San Jose to Chicago, returning Thu, Oct 9, priced at $227 found 4 days ago
Frontier Airlines
Sun, Sep 21 - Thu, Oct 9
SJC
San Jose
MDW
Chicago
$236 Roundtrip, found 6 days ago
$236
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Sun, Sep 21 from San Jose to Chicago, returning Thu, Oct 9, priced at $236 found 6 days ago
Frontier Airlines
Sun, Oct 5 - Thu, Oct 9
SJC
San Jose
MDW
Chicago
$242 Roundtrip, found 11 hours ago
$242
Roundtrip
found 11 hours ago
Select Frontier Airlines flight, departing Sun, Oct 5 from San Jose to Chicago, returning Thu, Oct 9, priced at $242 found 11 hours ago
Delta
Sat, Oct 4 - Sat, Oct 11
SJC
San Jose
MDW
Chicago
$269 Roundtrip, found 2 hours ago
$269
Roundtrip
found 2 hours ago
Select Delta flight, departing Sat, Oct 4 from San Jose to Chicago, returning Sat, Oct 11, priced at $269 found 2 hours ago
Southwest Airlines
Tue, Oct 21 - Tue, Oct 28
SJC
San Jose
MDW
Chicago
$290 Roundtrip, found 2 hours ago
$290
Roundtrip
found 2 hours ago
Select Southwest Airlines flight, departing Tue, Oct 21 from San Jose to Chicago, returning Tue, Oct 28, priced at $290 found 2 hours ago

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

October is typically the cheapest month to fly

From $138 - $619 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 $258
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $258
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
$170
Distance
1833 mi
Average flight time
8 hours 30 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 $91 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?
Grab a cheap one-way flight from $91 or cheap return flight from $170 from Norman Y. Mineta San Jose Intl. Airport (SJC) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight deals on this route.
What is the cheapest month to fly from Norman Y. Mineta San Jose Intl. Airport (SJC) to Midway Intl. Airport (MDW)?
Planning your trip for October may help you find better deals, as it's the cheapest month for flights between SJC and MDW. You'll typically find the lowest prices during off-peak months.
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 Norman Y. Mineta San Jose Intl. Airport (SJC) to Midway Intl. Airport (MDW)?
Use the filter tool on Expedia to compare airlines and find the most affordable carrier that'll take you from SJC to MDW. Then, sort your results by "Price (lowest to highest)" to pick up the best deal available.
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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*Available to One Key members.