Cheap Flights from Chicago (MDW) to Napa (APC)

Popular airlines from Chicago Midway Airport (MDW) to Napa, CA (APC-Napa Valley)

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Napa, CA (APC-Napa Valley) cost?
Snag a cheap one-way flight or cheap return flight from Midway Intl. Airport (MDW) to Napa, CA (APC-Napa Valley) 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 Midway Intl. Airport (MDW) to Napa, CA (APC-Napa Valley)?
is the most affordable month to fly from MDW to APC. Timing your trip outside of the busy season is often the key to better flight prices.
What is the cheapest airline that flies from Midway Intl. Airport (MDW) to Napa, CA (APC-Napa Valley)?
Use the filter tool on Expedia to compare airlines and find the most affordable carrier that'll take you from MDW to APC. Then, sort your results by "Price (lowest to highest)" to snap up a good deal.
How many flights per day from Midway Intl. Airport (MDW) to Napa, CA (APC-Napa Valley)?
There are no daily direct flights from Midway Intl. Airport (MDW) to Napa, CA (APC-Napa Valley). But you can book flights with layovers. Filter your search results on Expedia to include one or more stops, and you'll be cruising above the clouds in no time.
What day of the week has the most flights from MDW to APC?
Friday is usually the busiest day for flights, while Tuesday tends to be the quietest.* Just remember that flight schedules can change depending on various factors, including the carrier and season.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Midway Intl. Airport (MDW) to Napa, CA (APC-Napa Valley)?
To avoid potential delays on the Midway Intl. Airport (MDW) to Napa, CA (APC-Napa Valley) route, aim to travel before 3 PM. Departures after this time have a 22% higher chance of being canceled.**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 Napa from Midway Intl. Airport (MDW)?
Take a direct flight from Midway Intl. Airport (MDW) to Napa and you'll land at any one of these airports:

  • San Francisco Intl. Airport (SFO)
  • Sacramento Intl. Airport (SMF)
  • Oakland Intl. Airport (OAK)

Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to Napa, CA (APC-Napa Valley) last-minute?
Last-minute fares from MDW to APC are generally more expensive. For the best prices, start searching for flights early. That said, if you're flexible with your travel dates, you may find a cheap fare just before your departure.
Is it cheaper to book a MDW to APC flight and hotel package?
You'll generally save money by booking a MDW to APC flight and hotel package compared to booking separately. In fact, travelers could save hundreds of dollars by bundling with Expedia. And it's simple to manage everything in one place. After selecting your ideal accommodations and flights, consider adding extras including activities, car rentals and tours.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Napa, CA (APC-Napa Valley)?
If you booked your MDW to APC flight within the last 24 hours, you may be able to modify or cancel it without fees. Depending on the airline and the type of ticket you purchased, additional charges may apply for changes beyond that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you want more information.

Travel information

Travel information

Origin airport
Midway Intl.
Destination airport
Napa Valley
Distance
1831 mi

Book with confidence

Book with confidence

Chicago to Napa Flights

The cheapest times to fly from Chicago to Napa

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 Chicago to Napa are during the month of . You can find some of the cheapest flights from Chicago to Napa with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Napa

Sunday is one of the best days to book for cheap flights from Chicago to Napa: 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 Chicago to Napa

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 Chicago to Napa in 2025. You can also book with separate airlines for your outbound and return journeys, from 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 Chicago to Napa 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 Chicago to Napa 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.

 

Chicago to Napa Flights

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*Available to One Key members.