Cheap Flights from Greenville (PGV) to Chicago (MDW)

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Find available prices by choosing your travel dates.
Flights from Greenville (PGV) to Chicago (MDW)
Origin airport
Pitt-Greenville
Destination airport
Midway Intl.
Distance
701 mi

Greenville to Chicago Flights

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

The best time to book a flight from Greenville to Chicago

Sunday is one of the best days to book for cheap flights from Greenville 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 Greenville 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 Greenville 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 Greenville 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 Greenville 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

Is it cheaper to buy a plane ticket from Pitt-Greenville Airport (PGV) to Midway Airport last minute?
Booking your journey from PGV to MDW last minute could save you some dough if you happen to find a real steal. However, tickets usually don’t come down in price as the date of departure nears. If you wait, flights could also be booked solid or the best seats taken (because who wants the middle seat?). If you want to be on the safe side, book well in advance of when you want to leave. In fact, you can find some of the biggest deals up to 12 months in advance. If your preferred carrier hasn’t released tickets yet, check back regularly as deals are constantly updated on Expedia.
What airports do you fly into for Chicago from Greenville?
With Midway Intl. Airport (MDW), O’Hare Intl. Airport (ORD) and Lewis University Airport (LOT) to pick from, getting from Greenville to Chicago is a snap. The city’s main gateway, Midway Intl. Airport (MDW), is roughly 9 mi southwest of the downtown area. Along with the price of tickets, consider things like transportation options from the airport and the distance to your hotel when deciding where to fly into. Get your Chicago trip off to a fun start by discovering Wrigley Field and Millennium Park.
Can I change the date of my flight from Pitt-Greenville Airport (PGV) to Chicago Airport?
Quickly and easily make changes to your Pitt-Greenville Airport to Midway Intl. Airport (MDW) journey by logging in to the Expedia Trips portal. But before doing so, read through the conditions in your itinerary to see what the airline will let you do and if charges apply. Some airlines have a change fee per person, plus any difference in prices. But if you booked in the last 24 hours, you may be able to cancel for free and arrange new flights. You can also take a look at our Customer Service portal for more advice and to connect with our Virtual Agent.

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