Cheap flights from Piedmont Triad International to Chicago

Compare Piedmont Triad International to Chicago flight deals

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Flight deals from Piedmont Triad International to Chicago

Looking for a cheap last-minute deal or the best round-trip flight from Piedmont Triad International Airport to Chicago? If you want to travel next month, round-trip fares start from $264. Find the lowest prices on one-way and round-trip tickets right here.

Find the cheapest month to fly from Piedmont Triad International to Chicago

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Piedmont Triad International to Chicago flights are currently cheapest in September.

Direct flights from Piedmont Triad International to Chicago

Alternative Piedmont Triad International to Chicago routes

Looking for the cheapest, fastest or easiest route from Piedmont Triad International to Chicago? You could fly into the following airports instead.

Greensboro / High Point to Chicago: Flight information

The things to know before you go.
Cheapest flight found$259
Cheapest month to flyOctober
Average flight time2 hrs, 19 mins
Most popular airlineAmerican Airlines
Average flights per week202

Finding cheap flights from Piedmont Triad International to Chicago: Frequently asked questions

There are 4 airports in Chicago: Chicago Midway, Chicago O'Hare International, Chicago Dupage County, and Chicago Rockford.
The best price we found for a round-trip flight from Piedmont Triad International to Chicago is $259. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
2 hours and 19 minutes is the average flight time from Piedmont Triad International to Chicago.
American Airlines, Envoy Air and United fly direct from Piedmont Triad International to Chicago.
There are 202 flights per week flying from Piedmont Triad International to Chicago, as of May 2026.
The cheapest month to fly from Piedmont Triad International to Chicago is usually October.
If you're flying from Piedmont Triad International Airport, the cheapest airport near Chicago is Chicago O'Hare International – which is 25.4 km away from the center of Chicago. We've found flights to this airport from $259.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Piedmont Triad International Airport to Chicago on Saturday, October 10, 2026.
Yes – the average flight time is 2 hours and 19 minutes.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar, and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.
In May, the average temperature is usually around 13°C. July is typically the warmest month in Chicago, when it usually averages around 26°C. You can expect the least rain in January. The coldest month is January, with temperatures averaging -8°C. The rainiest month is August.
Currently, United offers the cheapest flight tickets to Chicago.

Flying from Piedmont Triad International Airport (GSO) to Chicago: what you need to know

  • Expect to be traveling for 2 hours. That's the average journey time for a direct flight from Piedmont Triad International Airport to Chicago.

  • Piedmont Triad International Airport is located in Greensboro / High Point. Following the UTC-5 timezone, Chicago is one hour behind Greensboro / High Point.

  • The most popular route is from Piedmont Triad International Airport (GSO) to O'Hare International Airport (ORD). Choose from 27 weekly services between these two airports. If you'd like to get on your way as soon as possible, the earliest flight from GSO to ORD is the 06:14 American Airlines service. If you're planning to fly out later on, the last departure is at 18:47 with American Airlines.

  • Give yourself enough time to get on your GSO to Chicago flight. As a general rule, arrive at least two hours before international departures and an hour ahead for domestic flights.

  • If you're traveling during a major holiday or another peak period, give yourself extra time. A good rule is two hours ahead of domestic flights and up to four hours before international departures. Check-in and security lines will be longer.

  • Begin your trip at GSO and travel straight to O'Hare International Airport (ORD). That's where you can expect to touch down when searching for Piedmont Triad International Airport to Chicago tickets.

  • Book your seat with United Airlines. This popular carrier offers direct flights from Piedmont Triad International Airport to Chicago.

  • Central Greensboro / High Point to GSO is around 0.16 kilometers. Depending on traffic conditions, it'll take you about 0 hours to reach there if you're driving, ride-sharing or catching a cab.

  • In search of a hotel close to GSO? If you're catching an early flight from Piedmont Triad International Airport to Chicago, these stays will put you moments from your departure lounge:

  • Of all flights departing from Piedmont Triad International Airport, 76.59% land on schedule at their destination.

  • GSO is located at International Airport.

How to find the cheapest flights from Piedmont Triad International Airport (GSO) to Chicago

  • The lowest price we've found for a one-way Piedmont Triad International Airport to Chicago flight is $135. The cheapest price for a return flight is $259. Keep in mind fares may change due to demand at the time of booking.

  • Book three months before your departure date. Pricing trends suggest that this is the ideal window for finding cheap flights from GSO to Chicago.

  • Organize your trip for July. That's the best month for landing an incredible deal on Piedmont Triad International Airport to Chicago tickets. If you're flexible with your dates, use the 'Whole month' tool to find the lowest price across each month.

  • You don't need to keep checking in to see if fares have dropped when you create a Price Alert. We'll notify you when there's an updated deal for cheap flights from GSO to Chicago.

  • Find a cheap flight from Piedmont Triad International Airport to Chicago with the help of our filters. Select your preferred times, number of stops and airlines, then sort the results by 'Cheapest' to see the best deals.

Airports in Chicago

O'Hare International Airport (ORD)

  • The distance from O'Hare International Airport (ORD) to central Chicago is roughly 40 kilometers. It'll take you about 35 minutes to get to the center driving.

  • If you're taking public transport, expect a journey time of around 55 minutes.

  • If you're coming in on a late flight from Piedmont Triad International Airport to Chicago, few things beat the convenience of staying near the terminal. Grab your luggage from the carousel and then be showered and snoozing soon after at one of these accommodation options near ORD:

  • Go wherever you want, whenever you want with an O'Hare International Airport rental car. Pick up a set of wheels from Routes Car Rentals, Dollar or Budget and see more of Chicago and beyond.

  • Reserving your ride from O'Hare International Airport about four weeks before your flight from GSO to Chicago can help you get the lowest rate.

  • ORD is located at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • Central Chicago is around 19 kilometers from Chicago Midway International Airport (MDW). Once your flight from Piedmont Triad International Airport to Chicago has touched down and you've made your way to arrivals, the drive should be around 20 minutes.

  • If you travel by public transport, the ride to the center takes 45 minutes or so.

  • You'll find some great places ready to welcome you near MDW. Unwind and get cozy after your GSO to Chicago flight at any of these well-located options:

  • Forget about inconvenient public transport schedules or long cab queues. Grab a Chicago Midway International Airport rental car and blaze your own trail. Compare offers from Dollar, Hertz and Budget.

  • Avoid potential price surges. Reserving your ride four weeks ahead of your arrival at MDW will help you save.

  • Chicago Midway International Airport is located at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • Chicago Rockford International Airport (RFD) is around 137 kilometers from the center of Chicago. It takes about 1 hour 25 minutes to get to the city center by cab or ride-share once you've stepped off your flight from Piedmont Triad International Airport to Chicago.

  • The journey will take about 4 hours 15 minutes on public transport.

  • If you don't want to travel into the center, head for a hotel near RFD. Get comfortable at one of these stays after your GSO to Chicago flight:

  • Begin your journey without stressing over how to get to where you're going with a Chicago Rockford International Airport rental car. Book your wheels with reliable names here like Budget, Alamo and National.

  • Booking at least a few weeks in advance of your flight from Piedmont Triad International Airport to Chicago is always smart. In addition to better deals, you'll likely have a better variety of makes and models to choose from at RFD.

  • Chicago Rockford International Airport's address is 2 Airport Cir.

Best time to go to Chicago

  • Travel to Chicago during the high season if you prefer a lively atmosphere, but remember that hotel prices are generally higher. Alternatively, book your flights from Piedmont Triad International Airport to Chicago in the low season when prices are cheaper and crowds are smaller.

  • Lock in a Piedmont Triad International Airport to Chicago flight ticket with a departure in July if you want to experience the city during its warmest month. You can expect temperatures to range from 15ºC (59ºF) to 29ºC (84ºF).

  • Look for cheap tickets from GSO to Chicago in January if you like traveling in cooler conditions. Temperatures are at their lowest then, ranging between -12ºC (10ºF) and 3ºC (37ºF) on average.

More about Chicago

Explore more of United States

  • Chicago has plenty going for it, but there are so many other parts of United States just waiting to be explored. About 451 kilometers south-east of Chicago, a visit to Columbus will fill your itinerary to the brim. Don't miss top attractions like Franklin Park Conservatory and Botanical Gardens, Ohio Statehouse and German Village.

  • If you're interested in discovering another corner of United States, consider Indianapolis, about 257 kilometers south-east of Chicago. The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo are the start of reasons to visit.

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.