GSO - CHI

$90 Find Cheap Flights from Greensboro to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Greensboro to Chicago departing on 1/12. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Greensboro to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Greensboro to Chicago, as well as popular online travel agencies
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$199
Overall average: $319
American Airlines
Wed 4/29Wed 5/6
GSO - ORD • Non-stop
Cheapest one-way
$90
Typical prices: $162-$318
Multiple Airlines
Mon 1/12
GSO - ORD • 1 stop
Our travelers' advice
AI-powered summary based on content written by travel experts. AI can make mistakes.
Choose Main Cabin Extra on American for drinks.
United's Economy Plus offers extra legroom benefits.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
United Airlines
Cheapest • from $199 (round-trip)
Delta
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top routes
GSO-ORD
Cheapest
GSO-ORD
Most popular
Insights
Insights
Insights
Insights
When to book
4 weeks
in advance
Our data shows that travelers who book at least 4 weeks in advance save around 17% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
November
Cheapest • 13% price drop
August
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
Flight Deals
Booking Insights
Expert advice
Flight Deals

Cheap Flights from Greensboro to Chicago (GSO-CHI)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Greensboro to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Greensboro to Chicago

Wed, Apr 29 - Wed, May 6
American Airlines Logo
11:31 am - 12:40 pm
GSO
-
ORD
2h 09mnonstop
American Airlines Logo
8:00 am - 10:55 am
ORD
-
GSO
1h 55mnonstop
$199American Airlines
Thu, Jan 22 - Tue, Jan 27
United Airlines Logo
5:25 pm - 6:49 pm
GSO
-
ORD
2h 24mnonstop
United Airlines Logo
1:40 pm - 4:44 pm
ORD
-
GSO
2h 04mnonstop
$204United Airlines
Thu, Jan 15 - Sun, Jan 18
American Airlines Logo
5:25 pm - 6:55 pm
GSO
-
ORD
2h 30mnonstop
American Airlines Logo
7:50 pm - 10:47 pm
ORD
-
GSO
1h 57mnonstop
$208American Airlines
Fri, Jan 16 - Sun, Jan 18
American Airlines Logo
5:25 pm - 6:55 pm
GSO
-
ORD
2h 30mnonstop
American Airlines Logo
7:50 pm - 10:47 pm
ORD
-
GSO
1h 57mnonstop
$209American Airlines
Thu, Jan 22 - Tue, Jan 27
United Airlines Logo
8:00 am - 9:24 am
GSO
-
ORD
2h 24mnonstop
United Airlines Logo
1:00 pm - 7:01 pm
ORD
-
GSO
5h 01m1 stop
$214United Airlines
Tue, May 19 - Sat, May 23
Delta Logo
5:15 pm - 9:45 pm
GSO
-
MDW
5h 30m1 stop
Delta Logo
5:59 pm - 10:56 pm
MDW
-
GSO
3h 57m1 stop
$219Delta
Tue, Jan 20 - Tue, Jan 27
Delta Logo
11:04 am - 4:30 pm
GSO
-
ORD
6h 26m1 stop
Delta Logo
6:00 pm - 11:16 pm
ORD
-
GSO
4h 16m1 stop
$219Delta
Tue, May 19 - Sun, May 24
Delta Logo
5:15 pm - 9:45 pm
GSO
-
MDW
5h 30m1 stop
Delta Logo
9:30 am - 4:33 pm
MDW
-
GSO
6h 03m1 stop
$224Delta
Thu, Jan 22 - Sat, Jan 24
Delta Logo
5:20 am - 8:42 am
GSO
-
ORD
4h 22m1 stop
Delta Logo
5:35 pm - 11:16 pm
ORD
-
GSO
4h 41m1 stop
$224Delta
Thu, Feb 12 - Sun, Feb 15
Delta Logo
2:18 pm - 5:45 pm
GSO
-
MDW
4h 27m1 stop
Delta Logo
11:01 am - 4:30 pm
MDW
-
GSO
4h 29m1 stop
$229Delta
Booking Insights

KAYAK's insights & trends for Greensboro to Chicago flights

Get data-powered insights and trends into flights from Greensboro to Chicago to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Greensboro to Chicago flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest return flight from Greensboro to Chicago costs $209 on the route between Greensboro (GSO) and Chicago O'Hare Intl Airport (ORD). It is also the most popular route.

What’s the cheapest day of the week to fly from Greensboro to Chicago?

The average price of all round-trip flights from Greensboro to Chicago clicked on KAYAK for each day over the last 12 months.

If your flying dates are flexible, you should consider flying to Chicago on a Friday, as we generally find the cheapest rates on that day for this route. On the other hand, Sunday is the most expensive day to fly from Greensboro to Chicago. For your return ticket, we recommend flying on a Saturday and avoiding Sundays for the best deals.

What is the cheapest month to fly from Greensboro to Chicago?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Greensboro to Chicago, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Greensboro to Chicago is November, where tickets cost $266 (return) on average. On the other hand, the most expensive months are March and January, where the average cost of round-trip tickets is $368 and $329 respectively.

Can I save money by flying with a layover from Greensboro to Chicago?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $293 on average.

How far in advance should I book a flight from Greensboro to Chicago?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Greensboro to Chicago, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Greensboro to Chicago, you should book around 4 weeks before departure, which saves you about 17% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 9 weeks before departure.

Expert advice

Expert advice for your flight from Greensboro to Chicago

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airlines
American Airlines

Consider Main Cabin Extra for early boarding and complimentary drinks on short flights.


Download the American Airlines app for in-flight entertainment on your device.

United Airlines

Opt for Economy Plus for up to six inches more legroom.


Purchase Priority Boarding to ensure overhead bin space.

Our travel experts
Harriet Baskas

Harriet Baskas

Expert on American Airlines

Harriet Baskas

Harriet Baskas

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Read more
Stefanie Waldek

Stefanie Waldek

Expert on United Airlines

Stefanie Waldek

Stefanie Waldek

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Read more

Good to know

Low seasonNovember
Cheapest flight$90
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly with an average 4% increase in price.
Flight from Greensboro to Chicago O'Hare Airport

When to book flights from Greensboro to Chicago

Are your dates flexible? Find out the best times to travel from Greensboro to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Greensboro to Chicago

  • What is the cheapest flight from Greensboro to Chicago?

    In the last 3 days, the lowest price for a flight from Greensboro to Chicago was $90 for a one-way ticket and $199 for a round-trip.

  • Do I need a passport to fly between Greensboro and Chicago?

    A passport is not required to fly from Greensboro to Chicago.

  • Which airports will I be using when flying from Greensboro to Chicago?

    Greensboro is served by only 1 airport and there are 2 airports in Chicago. You will leave Greensboro from Greensboro/H. Point and you will be arriving in Chicago at one of these airports: Chicago Midway or Chicago O'Hare Intl.

  • Which airlines offer Wi-Fi service onboard planes from Greensboro to Chicago?

    American Airlines, Delta, Air Canada, JetBlue, and Alaska Airlines offer inflight Wi-Fi service on the Greensboro to Chicago flight route.

  • Which aircraft models fly most regularly from Greensboro to Chicago?

    The Embraer 175 (Enhanced Winglets) is the aircraft model that flies most regularly on the Greensboro to Chicago flight route.

  • Which airline alliances offer flights from Greensboro to Chicago?

    SkyTeam, Star Alliance, and oneworld are the airline alliances operating flights between Greensboro and Chicago, with SkyTeam being the most commonly used for this route.

  • On which days can I fly direct from Greensboro to Chicago?

    There are nonstop flights from Greensboro to Chicago on a daily basis.

  • Which is the best airline for flights from Greensboro to Chicago, Delta or United Airlines?

    The two airlines most popular with KAYAK users for flights from Greensboro to Chicago are Delta and United Airlines. With an average price for the route of $287 and an overall rating of 7.9, Delta is the most popular choice. United Airlines is also a great choice for the route, with an average price of $339 and an overall rating of 7.4.

  • How does KAYAK find such low prices on flights from Greensboro to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Greensboro to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Greensboro to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Greensboro is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Greensboro to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Greensboro with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Greensboro to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Greensboro up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Greensboro to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $272 or less one-way and $298 or less round-trip.

Prefer to fly direct from Greensboro to Chicago?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Greensboro/H. Point to Chicago.
Find which airlines fly direct from Greensboro/H. Point Airport to Chicago, which days they fly and book direct flights.

Direct departures

Greensboro/H. Point to Chicago

Monday

American Airlines, United Airlines

American Airlines, United Airlines

Tuesday

American Airlines, United Airlines

American Airlines, United Airlines

Wednesday

American Airlines, United Airlines

American Airlines, United Airlines

Thursday

American Airlines, United Airlines

American Airlines, United Airlines

Friday

American Airlines, United Airlines

American Airlines, United Airlines

Saturday

American Airlines, United Airlines

American Airlines, United Airlines

Sunday

American Airlines, United Airlines

American Airlines, United Airlines

See more direct flights

Direct returns

Chicago to Greensboro/H. Point

Monday

American Airlines, United Airlines

American Airlines, United Airlines

Tuesday

American Airlines, United Airlines

American Airlines, United Airlines

Wednesday

American Airlines, United Airlines

American Airlines, United Airlines

Thursday

American Airlines, United Airlines

American Airlines, United Airlines

Friday

American Airlines, United Airlines

American Airlines, United Airlines

Saturday

American Airlines, United Airlines

American Airlines, United Airlines

Sunday

American Airlines, United Airlines

American Airlines, United Airlines

See more direct flights

Reviews of the top 3 airlines serving from Greensboro to Chicago

 
See real verified KAYAK customer reviews for airlines flying from Greensboro to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Greensboro to Chicago? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.9
DeltaOverall score based on 8014 reviews
8.1Boarding
7.9Comfort
8.5Crew
7.3Food
7.9Entertainment
Airline reviews

The plant way delayed departing by 3 hours. It was an old airplane with broken seats and armrests. The bathroom made a hollering sound. A really crappy flight experience and travel day all around.

2.0 MediocrePeter, Dec 2025
JFK - MEM
Read more Delta reviews

The plant way delayed departing by 3 hours. It was an old airplane with broken seats and armrests. The bathroom made a hollering sound. A really crappy flight experience and travel day all around.

Flight delays both to Detroits and return flight . The flight to Detroit was associated with mechanical difficulty

I am extremely disappointed that delta internal pilot manuals now refer to the Gulf of Mexico as the “gulf of America”. You can bow down to the Orange turd on your own. I will never fly delta again

Wasn't a Delta issue I don't think, but seems there was a Delta flight at each of the 2 Dallas airports at the same exact time, both to Atlanta. I was evidently booked on the one at Love Airport, but the Carey transport shuttle took me to DFW instead and I ended up missing the flight by just a few minutes. Was able to book a Southwest flight from Love Airport, but was a big loss of time and an inconvenience.

Great. I had to modify a flight. That was easy and free. Thank You

I noticed that the planes seem to be outdated. There was no entertainment per se. Also, the waiting area did not have any working electrical outlets

Original flight was cancelled and when i was rebooked by the airline, they couldn't seat me in the same type of seat as I had originally booked (went from window/aisle to middle/middle and one was a bulkhead seat, and other wasn't in the same class)

Lady Pilot was perfect in every way wheels up to wheels down communication, professionalism, excellent on time departure and on time arrival, excellent communication! Fantastic job with Superb attitude!!

The food is terrible. The staff is wonderful. Comfort is good.

Left on time, a bit delayed due to headwinds most of the trip.

They did the one thing that really matters - got to Chicago early.

The flight was on time. I generally don’t drink or eat on short flights and the seats were good and the flight attendants were friendly. That’s all I expect

It was nice to have gotten up upgraded to first class with a meal on a three hour flight

Very bad! They kept delaying my flight and wouldn’t do anything about it

Door to door, the crew and staff were amazing. It was a stressful travel day with delays, but they were focused on customers and doing what they could to get us to our destinations.

Flight was delayed only slightly before takeoff due to traffic control. However, the flight arrived early to ORD. Good flight. United has been very reliable for me.

Another delayed flight. When the delays exceed the duration of the flight, it’s a problem.

After boarding the plane in Chicago, the passengers were told that there was a technical problem with the plane. Passengers remained on the plane as they tried to fix the problem. After what was probably an hour passengers were told that there was a need to change planes as the problem was not solved. Passengers disembarked and boarded another plane. After taxing to the runway and waiting for takeoff, passengers were told that owing to the thunderstorm the flight was unable to take off but would try and reroute. After some time passengers were told there wasn't enough fuel for the new route and the plane had to return to the gate for additional fuel. after another log delay the flight got underway. On the plane there was food, drinks, ice or entertainment. We were a glass of water, which appeared rationed. Flight arrived about 5 hours late. The pilot was fantastic and communicated with the passengers throughout the ordeal.

Better WiFi. I cannot understand that in 2025, United is so behind on a technology that is now a necessity and still painfully unreliable, slow and keeps disconnecting.

Trip was great. A wild landing in Ottawa with the wind and rain, but the pilot did a great job. Always love flying United.👍

Awful. They won’t help me with anything. I booked on American but they abdicated to Iberia. The ticket was overpriced. Everything negative

I enjoyed the extra leg room compared to other airlines. The first stewards made my daughter’s birthday special by giving her an extra snack. Then the last one coming home from Chicago to Appleton made our night really enjoyable Thanks for making our trip enjoyable

It was good..clean, comfy seat. Friendly warm welcoming crew. Was able to check my cabin luggage at the gate which I was able to pickup in a decent time from baggage claim. The app gave all updates from delays to baggage claim info. Overall smooth flight.

It was a typical flight. We had a delay which seems to be the normality now. And we had no in flight service due to conditions.

After we landed we sat on the tarmac for 1.5 hours waiting to get to our gate. Ridiculous.

Terrible. Flight delayed for more than 8 hours with only a $12 meal voucher provided for the inconvenience. The airplane did not have breaks on arrival yet they still made us go through the motions and board on time knowing we could not take off then sit for 40+ minutes before having to get of the time. A complete waste of my time. I cannot believe they can stay business with these shenanigans. I’ll avoid this company like the plague moving forward as the lack of accountability is disgraceful.

This was the best 2 flights I have had with American out of SGF. Great crew both flights.

Excellent - explanations were clear staff was nice and flight was comfortable

Lost bag and 2 days no word leaving for cruise no clothes or stuff

Any flight to ORD after about 2pm this summer has been challenging. Flight was delayed getting in (coming from ORD) and that led to it not leaving before a ground stop due to lightening before they could fuel the plane, and so forth. They made up some time but we were still late in arriving at ORD, and that led to missed connections.

Everything you need to know for your flight from Greensboro to Chicago

Information on your arrival and departure airports