Cheap Flights from Pilot Point (PIP) to Chicago (MDW)

Popular airlines from Pilot Point, AK (PIP) to Chicago Midway Airport (MDW)

Frequently asked questions

How much does a flight from Pilot Point, AK (PIP) to Midway Intl. Airport (MDW) cost?
Get a cheap one-way flight or cheap return flight from Pilot Point, AK (PIP) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight offers on this route.
What is the cheapest month to fly from Pilot Point, AK (PIP) to Midway Intl. Airport (MDW)?
Flying in is a good way to save, as it's the cheapest month for flights between PIP and MDW. You'll often find the lowest fares during off-peak months.
What is the cheapest airline that flies from Pilot Point, AK (PIP) to Midway Intl. Airport (MDW)?
To find the cheapest airline flying from PIP to MDW, use Expedia's filter tool. Tailor your search based on your travel needs, such as preferred carriers and seat class. You can then sort your results by "Price (lowest to highest)" to see the cheapest flights first.
How many flights per day from Pilot Point, AK (PIP) to Midway Intl. Airport (MDW)?
Nonstop flights from Pilot Point, AK (PIP) 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 travel details and select either "1 Stop" or "2+ Stops."
What day of the week has the most flights from PIP to MDW?
Typically you'll find the widest variety of flight choices on a Friday. Tuesdays tend to be the quietest.* However, this can vary based on the season, airline and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Pilot Point, AK (PIP) to Midway Intl. Airport (MDW)?
Book a flight from Pilot Point, AK (PIP) to Midway Intl. Airport (MDW) that leaves before 3 PM to reduce the likelihood of delays and cancellations. Departures after this time are on average 22% more likely to be 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.
Is it cheaper to buy a plane ticket from Pilot Point, AK (PIP) to Midway Intl. Airport (MDW) last-minute?
Holding off until just before your departure to book a flight from PIP to MDW often results in higher prices. While you might find some last-minute deals, they're not always guaranteed. Allow some flexibility in your schedule for the best chance of getting a bargain.
Is it cheaper to book a PIP to MDW flight and hotel package?
You'll typically save money by securing a PIP to MDW 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 it all in one convenient place. Once you've selected your preferred flights and accommodations, you can add extras like activities, car rentals and tours.
Can I cancel or change the date of my flight from Pilot Point, AK (PIP) to Midway Intl. Airport (MDW)?
If you reserved your PIP to MDW flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you purchased, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, visit our Customer Service portal if you'd like more information.

Travel information

Travel information

Origin airport
Pilot Point
Destination airport
Midway Intl.
Distance
3146 mi

Book with confidence

Book with confidence

Pilot Point to Chicago Flights

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

 

The best time to book a flight from Pilot Point to Chicago

Sunday is one of the best days to book for cheap flights from Pilot Point 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 Pilot Point 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 Pilot Point to Chicago 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 Pilot Point 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 Pilot Point 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.

 

Pilot Point to Chicago Flights

Explore a world of travel with Expedia

Explore a world of travel with Expedia

*Available to One Key members.