$154 Cheap Flights from Greensboro (GSO) to Chicago (ORD)

View $154 flight on Sun, Aug 31, 2025Opens in a new window

Popular airlines from Piedmont Triad Intl. Airport (GSO) to Chicago O'Hare Intl. Airport (ORD)

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Cheap Flights from Greensboro to Chicago (GSO-ORD)

Prices were available within the past 7 days and start at $154 for one-way flights and $199 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Sat, Oct 4 - Sat, Oct 11
GSO
Greensboro
ORD
Chicago
$199 Roundtrip, just found
$199
Roundtrip
just found
Select American Airlines flight, departing Sat, Oct 4 from Greensboro to Chicago, returning Sat, Oct 11, priced at $199 just found
United
Sat, Oct 4 - Sat, Oct 11
GSO
Greensboro
ORD
Chicago
$199 Roundtrip, just found
$199
Roundtrip
just found
Select United flight, departing Sat, Oct 4 from Greensboro to Chicago, returning Sat, Oct 11, priced at $199 just found
American Airlines
Mon, Sep 8 - Sat, Sep 13
GSO
Greensboro
ORD
Chicago
$204 Roundtrip, found 1 hour ago
$204
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Mon, Sep 8 from Greensboro to Chicago, returning Sat, Sep 13, priced at $204 found 1 hour ago
United
Thu, Aug 28 - Tue, Sep 2
GSO
Greensboro
ORD
Chicago
$207 Roundtrip, found 1 day ago
$207
Roundtrip
found 1 day ago
Select United flight, departing Thu, Aug 28 from Greensboro to Chicago, returning Tue, Sep 2, priced at $207 found 1 day ago
United
Sat, Oct 4 - Sat, Oct 11
GSO
Greensboro
ORD
Chicago
$209 Roundtrip, just found
$209
Roundtrip
just found
Select United flight, departing Sat, Oct 4 from Greensboro to Chicago, returning Sat, Oct 11, priced at $209 just found
United
Wed, Aug 20 - Sat, Aug 23
GSO
Greensboro
ORD
Chicago
$212 Roundtrip, found 21 hours ago
$212
Roundtrip
found 21 hours ago
Select United flight, departing Wed, Aug 20 from Greensboro to Chicago, returning Sat, Aug 23, priced at $212 found 21 hours ago
United
Mon, Sep 8 - Sat, Sep 13
GSO
Greensboro
ORD
Chicago
$214 Roundtrip, found 1 hour ago
$214
Roundtrip
found 1 hour ago
Select United flight, departing Mon, Sep 8 from Greensboro to Chicago, returning Sat, Sep 13, priced at $214 found 1 hour ago
United
Thu, Aug 28 - Tue, Sep 2
GSO
Greensboro
ORD
Chicago
$218 Roundtrip, found 1 day ago
$218
Roundtrip
found 1 day ago
Select United flight, departing Thu, Aug 28 from Greensboro to Chicago, returning Tue, Sep 2, priced at $218 found 1 day ago
United
Thu, Oct 30 - Sun, Nov 2
GSO
Greensboro
ORD
Chicago
$219 Roundtrip, found 1 hour ago
$219
Roundtrip
found 1 hour ago
Select United flight, departing Thu, Oct 30 from Greensboro to Chicago, returning Sun, Nov 2, priced at $219 found 1 hour ago
United
Thu, Aug 28 - Tue, Sep 2
GSO
Greensboro
ORD
Chicago
$221 Roundtrip, found 1 day ago
$221
Roundtrip
found 1 day ago
Select United flight, departing Thu, Aug 28 from Greensboro to Chicago, returning Tue, Sep 2, priced at $221 found 1 day ago

Find the cheapest month to fly from Greensboro (GSO) to Chicago (ORD)

December is typically the cheapest month to fly

From $115 - $366 per traveler.

Graph displaying average flight prices per month

Flights from Greensboro (GSO) to Chicago (ORD)
Origin airport
Piedmont Triad Intl.
Destination airport
O'Hare Intl.
Airlines serving
American Airlines, Delta, United
Roundtrip price
$199
Distance
588 mi
Average flight time
1 hour 15 mins

Greensboro to Chicago Flights

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

 

The best time to book a flight from Greensboro to Chicago

Sunday is one of the best days to book for cheap flights from Greensboro 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 Greensboro 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 Greensboro to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $154 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 Greensboro 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 Greensboro 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

How much does a flight from Piedmont Triad Intl. Airport (GSO) to O'Hare Intl. Airport (ORD) cost?
Snag cheap return flights starting from $163 from Piedmont Triad Intl. Airport (GSO) to O'Hare Intl. Airport (ORD). This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a United flight leaving GSO on August 8 2025 and touching down at ORD. The price was last updated on July 14 2025 and has not changed since.
What is the cheapest month to fly from GSO to ORD?
The cheapest flights from GSO to ORD are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
Which airlines fly direct from Piedmont Triad Intl. Airport (GSO) to O'Hare Intl. Airport (ORD)?
When departing from Piedmont Triad Intl. Airport (GSO), you can get on a direct flight to O'Hare Intl. Airport (ORD) with United Airlines.
What is the cheapest airline that flies from GSO to ORD?
With tickets starting at $133 for a one-way flight from GSO to ORD, United is currently the cheapest airline for this route. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from GSO on August 19 2025. Prices were last updated on July 14 2025 and have not changed since.
How many flights per day from Piedmont Triad Intl. Airport (GSO) to O'Hare Intl. Airport (ORD)?
When flying out of Piedmont Triad Intl. Airport (GSO), you'll have a choice from an average of 3 daily nonstop flights to O'Hare Intl. Airport (ORD).
What are the most popular departure times for flights from Piedmont Triad Intl. Airport (GSO) to O'Hare Intl. Airport (ORD)?
The 6 AM departures from GSO to ORD are the most sought after. Prices can be higher for these popular slots. If you're looking to save, book during off-peak hours.
What day of the week has the most flights from GSO to ORD?
Friday has the most flights from Piedmont Triad Intl. Airport (GSO) to O'Hare Intl. Airport (ORD). Consider taking off on this day and you'll have the best chance of finding a schedule that works for you.
What is the earliest flight from Piedmont Triad Intl. Airport (GSO) to O'Hare Intl. Airport (ORD)?
Piedmont Triad Intl. Airport (GSO)'s earliest flight to O'Hare Intl. Airport (ORD) leaves at approximately 6:35AM UTC-5. With a total journey time of 2h 23m, you'll arrive at around 7:58AM UTC-6.
How long does it take to fly from Piedmont Triad Intl. Airport (GSO) to O'Hare Intl. Airport (ORD)?
The average flight time from GSO to ORD is 2 hours and 20 minutes, covering a total distance of 590 mi.
What airline has the least delays from GSO to ORD?
Consider traveling with United Airlines if you'd like to fly straight from Piedmont Triad Intl. Airport (GSO) to O'Hare Intl. Airport (ORD) without any delays. This carrier has the strongest track record for punctuality, with an on-time performance of 80%. Want to be notified if anything changes? You can keep an eye on your flight status using the Expedia App.
What is the best time to fly from Piedmont Triad Intl. Airport (GSO) to O'Hare Intl. Airport (ORD)?
Select a flight from Piedmont Triad Intl. Airport (GSO) to O'Hare Intl. Airport (ORD) that leaves before 3 PM to reduce the likelihood of delays. Departures later than this have a 22% higher chance of being canceled, on average.**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 Piedmont Triad Intl. Airport (GSO)?
Browse your flight options from Piedmont Triad Intl. Airport (GSO) to O'Hare Intl. Airport (ORD). This is the only Chicago airport you can arrive at if you're taking a direct flight.
Is it cheaper to buy a plane ticket from Piedmont Triad Intl. Airport (GSO) to O'Hare Intl. Airport (ORD) last-minute?
Waiting until just before your departure to book a ticket from GSO to ORD generally means paying more. While you might find some last-minute discounts, they aren't always guaranteed. Keep your travel schedule open to boost your chances of getting a bargain.
Is it cheaper to book a GSO to ORD flight and hotel package?
Compared with arranging hotels and flights separately, booking a GSO to ORD flight and hotel package with Expedia could result in significant savings. What's more, managing everything in one place will take the stress out of planning your trip. Just pick your flights and select from our extensive range of hotels, then tailor your trip with extras like tours, activities and car rentals.
Can I cancel or change the date of my flight from Piedmont Triad Intl. Airport (GSO) to O'Hare Intl. Airport (ORD)?
It's generally possible to reschedule or cancel your GSO to ORD flight. However, if the booking was made more than 24 hours ago, additional charges may apply. Check your airline's policies in your itinerary to see what changes are possible and whether any costs are involved. You'll also find further details on our Customer Service portal.

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