$366 Cheap Flights from Sun Valley (SUN) to Chicago (MDW)

View $366 flight on Sat, Jun 13, 2026Opens in a new window

Popular airlines from Sun Valley, ID (SUN-Friedman Memorial) to Chicago Midway Airport (MDW)

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Cheap Flights from Sun Valley to Chicago (SUN-MDW)

Prices were available within the past 7 days and start at $366 for one-way flights and for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frequently asked questions

How much does a flight from Friedman Memorial Airport (SUN) to Midway Intl. Airport (MDW) cost?
Lock in a cheap one-way flight from $366 or cheap return flight from Friedman Memorial Airport (SUN) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight offers on this route.
What is the cheapest month to fly from Friedman Memorial Airport (SUN) to Midway Intl. Airport (MDW)?
is the cheapest month to fly from SUN to MDW. Timing your trip outside of the busy season is often the key to landing a great deal.
What is the cheapest airline that flies from Friedman Memorial Airport (SUN) to Midway Intl. Airport (MDW)?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that'll take you from SUN to MDW. Then, sort your results by "Price (lowest to highest)" to score the best deal available.
How many flights per day from Friedman Memorial Airport (SUN) to Midway Intl. Airport (MDW)?
Direct flights from Friedman Memorial Airport (SUN) to Midway Intl. Airport (MDW) aren't available daily, so you'll need to take a flight with a layover. Explore your options with Expedia's filters. Enter your dates and pick either "1 Stop" or "2+ Stops."
What day of the week has the most flights from SUN to MDW?
You'll typically find Tuesday the quietest day for flights, while Fridays are often the busiest.* However this can change from season to season and during peak travel times or public holidays.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Friedman Memorial Airport (SUN) to Midway Intl. Airport (MDW)?
To arrive at Midway Intl. Airport (MDW) without delays, opt for a flight that leaves Friedman Memorial Airport (SUN) before 3 PM. The chance of cancellations is 22% higher, on average, for departures after this time.**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 Friedman Memorial Airport (SUN)?
O'Hare Intl. Airport (ORD) is the only airport in Chicago with direct flights from Friedman Memorial Airport (SUN). Consider the available options and discover affordable fares on Expedia.
Is it cheaper to buy a plane ticket from Friedman Memorial Airport (SUN) to Midway Intl. Airport (MDW) last-minute?
Waiting until just before your trip to book a ticket from SUN to MDW generally means paying more. While it's possible to find some last-minute offers, they aren't always guaranteed. Be flexible with your travel plans for a better chance of scoring a bargain.
Is it cheaper to book a SUN to MDW flight and hotel package?
Compared with arranging flights and hotels separately, booking a SUN to MDW flight and hotel package with Expedia could result in significant savings. Better yet, having everything in one place will take the hassle out of planning your trip. Simply pick your flights and choose from our wide range of stays, then customize your trip with other add-ons like car rentals and activities.
Can I cancel or change the date of my flight from Friedman Memorial Airport (SUN) to Midway Intl. Airport (MDW)?
Typically, you can modify or cancel your SUN to MDW flight. However, additional fees may apply, especially if you booked more than 24 hours ago. Check your itinerary for the airline's fees and rules on flight changes, or if you'd like more information, visit our Customer Service portal.

Travel information

Origin airport
Friedman Memorial
Destination airport
Midway Intl.
Distance
1349 mi

Book with confidence

Sun Valley to Chicago Flights

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

 

The best time to book a flight from Sun Valley to Chicago

Sunday is one of the best days to book for cheap flights from Sun Valley 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 Sun Valley 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 Sun Valley to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $366 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 Sun Valley 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 Sun Valley 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.

 

Sun Valley to Chicago Flights

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*Available to One Key members.