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$132+ Cheap flights from Greensboro (GSO) to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/24. Fares are subject to change and may not be available on all flights or dates of travel.
GSO — CHI
Aug 26 — Sep 21
Wed 8/26
Wed 9/2
1 adult, Economy
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Cheapflights Tip: The best prices from Greensboro/H. Point to Chicago are usually found in November or February, booked 44 days in advance, depart on a Friday or Thursday and return on a Wednesday

Cheap flight deals from Greensboro to Chicago

Cheapest flights from Greensboro to Chicago
Explore the most affordable flight options available from Greensboro to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 27, 2026.

This American Airlines deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/297:49 am
GSO
-
ORD
Nonstop2h 21m
American Airlines
Sat 9/53:18 pm
ORD
-
GSO
Nonstop2h 01m
American Airlines
Deal found 7/25$269
This American Airlines deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/116:46 pm
GSO
-
ORD
Nonstop2h 38m
American Airlines
Sun 9/139:59 am
ORD
-
GSO
Nonstop2h 07m
American Airlines
Deal found 7/26$274
This United Airlines deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/46:40 am
GSO
-
ORD
Nonstop2h 17m
United Airlines
Sun 9/66:15 pm
ORD
-
GSO
Nonstop2h 05m
United Airlines
Deal found 7/23$279
This United Airlines deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/116:35 am
GSO
-
ORD
Nonstop2h 17m
United Airlines
Sun 9/138:42 am
ORD
-
GSO
1 stop4h 30m
United Airlines
Deal found 7/23$284
This Delta deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/56:08 am
GSO
-
MDW
1 stop4h 09m
Delta
Wed 9/96:05 am
MDW
-
GSO
1 stop4h 33m
Delta
Deal found 7/22$289
This Delta deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/55:03 pm
GSO
-
ORD
1 stop4h 52m
Delta
Thu 9/103:40 pm
ORD
-
GSO
1 stop4h 17m
Delta
Deal found 7/22$289
This Delta deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/256:08 am
GSO
-
MDW
1 stop4h 09m
Delta
Thu 9/36:05 am
MDW
-
GSO
1 stop4h 29m
Delta
Deal found 7/23$294
This Delta deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/111:14 pm
GSO
-
ORD
1 stop3h 59m
Delta
Sun 9/136:40 am
ORD
-
GSO
1 stop6h 24m
Delta
Deal found 7/22$294
This American Airlines deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/187:31 am
GSO
-
ORD
Nonstop2h 34m
American Airlines
Sat 11/217:15 pm
ORD
-
GSO
Nonstop2h 11m
American Airlines
Deal found 7/22$298
This Delta deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/27:04 pm
GSO
-
MDW
1 stop4h 40m
Delta
Sun 10/46:05 am
MDW
-
GSO
1 stop6h 59m
Delta
Deal found 7/22$299
This Delta deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/146:51 pm
GSO
-
ORD
1 stop6h 06m
Delta
Sun 8/165:30 am
ORD
-
GSO
1 stop3h 55m
Delta
Deal found 7/22$299
This American Airlines deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/42:04 pm
GSO
-
ORD
Nonstop2h 15m
American Airlines
Sat 8/153:18 pm
ORD
-
GSO
Nonstop2h 01m
American Airlines
Deal found 7/22$303

Find flight deals from Greensboro to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Greensboro (GSO) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated July 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$269
(American Airlines)

One-way from

$132
(Kiwi.com)

Popular in

July

Cheapest in

November

Average price

$339

Good round-trip deal

$362 or less

Good one-way deal

$323 or less
Provider with most accurate pricing for Greensboro/H. Point-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Greensboro/H. Point-Chicago (CHI) flights.
Search Deals
From Greensboro/H. Point to Chicago (CHI)
Search Deals
One-way flight from Greensboro/H. Point to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($17 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 0% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
Search Deals
Price to beat on a round-trip flight from Greensboro/H. Point to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Greensboro/H. Point to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Greensboro to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 27, 2026.
Use the filters below to find and compare flights from Greensboro to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

GreensboroChicago

GSO - ORD

GSOORD

Greensboro/H. Point

Sat 9/5

5:51 pm-7:05 pm

Nonstop2h 14m

Chicago O'Hare Intl

Mon 9/7

6:15 pm-9:20 pm

Nonstop2h 05m

$274

GreensboroChicago

GSO - ORD

GSOORD

Greensboro/H. Point

Fri 9/25

1:44 pm-7:38 pm

1 stop6h 54m

Chicago O'Hare Intl

Sun 9/27

7:39 pm-10:49 pm

Nonstop2h 10m

$289

GreensboroChicago

GSO - ORD

GSOORD

Greensboro/H. Point

Sun 9/6

8:18 am-12:40 pm

1 stop5h 22m

Chicago O'Hare Intl

Wed 9/9

8:05 am-2:04 pm

1 stop4h 59m

$289

GreensboroChicago

GSO - ORD

GSOORD

Greensboro/H. Point

Sat 9/5

11:10 am-2:48 pm

1 stop4h 38m

Chicago O'Hare Intl

Wed 9/9

8:05 am-3:12 pm

1 stop6h 07m

$289

GreensboroChicago

GSO - MDW

GSOMDW

Greensboro/H. Point

Fri 9/11

5:00 pm-10:44 pm

1 stop6h 44m

Chicago Midway

Mon 9/14

5:10 pm-11:55 pm

1 stop5h 45m

$294

GreensboroChicago

GSO - ORD

GSOORD

Greensboro/H. Point

Tue 9/1

12:27 pm-4:51 pm

1 stop5h 24m

Chicago O'Hare Intl

Fri 9/11

7:05 am-12:03 pm

1 stop3h 58m

$294

GreensboroChicago

GSO - MDW

GSOMDW

Greensboro/H. Point

Thu 8/20

6:51 pm-10:36 pm

1 stop4h 45m

Chicago Midway

Sun 8/23

6:05 am-1:53 pm

1 stop6h 48m

$299

GreensboroChicago

GSO - MDW

GSOMDW

Greensboro/H. Point

Mon 9/14

7:04 pm-10:44 pm

1 stop4h 40m

Chicago Midway

Mon 9/21

6:05 am-2:04 pm

1 stop6h 59m

$299

GreensboroChicago

GSO - MDW

GSOMDW

Greensboro/H. Point

Fri 10/2

7:04 pm-10:44 pm

1 stop4h 40m

Chicago Midway

Sun 10/4

6:05 am-11:38 am

1 stop4h 33m

$299

GreensboroChicago

GSO - MDW

GSOMDW

Greensboro/H. Point

Mon 8/24

6:39 am-9:59 am

1 stop4h 20m

Chicago Midway

Sun 8/30

6:05 am-1:53 pm

1 stop6h 48m

$299

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/26

Showing 1-10 of 40 resultsSorted by cheapest first
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Compare providers for flights from Greensboro to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Greensboro to Chicago in July.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Greensboro-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Greensboro-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Greensboro-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Greensboro-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Greensboro-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Greensboro to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Greensboro with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

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

What is the cheapest month to book a flight from Greensboro to Chicago?

Currently, November is the cheapest month in which you can book a flight from Greensboro to Chicago (average of $255). Flying from Greensboro to Chicago in July is currently the most expensive (average of $365). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from GSO to CHI?

Find hourly flight availability from Greensboro to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 27, 2026.

Unlike in the morning, when flights are generally more expensive, you can save up to 26% on flights from Greensboro to Chicago by exploring options for tickets in the evening.

Weekly flight availability from Greensboro to Chicago

Explore weekly flight availability from Greensboro to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated July 27, 2026.

The most flights from GSO to CHI are scheduled on a Friday (17 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (13 on average).

How much does it cost to fly round-trip from Greensboro to Chicago?

Airfare is below average for this route at the moment.
Greensboro to Chicago flights typically cost between $287 and $426 in August.
The cheapest round-trip price found within the last 5 days was $269 on American Airlines (Aug 29-Sep 5).

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

The best time to book flights from Greensboro to Chicago is 69 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

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

Use this chart to determine the cheapest time to fly round-trip from Greensboro to Chicago. Price data was last updated on July 18, 2026.

Travelers seeking maximum savings on their Greensboro to Chicago flight should consider departing on Monday evenings when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated July 27, 2026.
Read reviews from past customers who have flown United Airlines and American Airlines from Greensboro to Chicago. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
10,040 reviews

Comfort

7.3

Food

6.6

Overall

7.4

Crew

8.1

Entertainment

7.1

Boarding

7.7

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
United Airlines
7.4
Good
10,040 reviews
United Airlines
7.4
Good
10,040 reviews

Comfort

7.3

Food

6.6

Overall

7.4

Crew

8.1

Entertainment

7.1

Boarding

7.7

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
American Airlines
7.1
Good
11,844 reviews
United Airlines
7.4
Good
10,040 reviews

Comfort

7.3

Food

6.6

Overall

7.4

Crew

8.1

Entertainment

7.1

Boarding

7.7

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!

Related info for your journey

Find useful and relevant information for your journey from Greensboro to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Greensboro to Chicago?

    If you book a flight to Chicago from Greensboro, you will be flying from Greensboro/H. Point, which is the city’s only airport. Greensboro/H. Point (GSO) is located 8.4 mi from the center of Greensboro. There are 14 flights from Greensboro/H. Point to Chicago per day from 3 different airlines.

  • How long is the flight from Greensboro to Chicago?

    For as low as $274, United Airlines can have you in Chicago from Greensboro in 2h 14m. The distance between Greensboro and Chicago is about 589 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines flying from Greensboro to Chicago round-trip?

    Currently priced at $188, Delta will fly you from Greensboro to Chicago and back. In addition to Delta, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from United Airlines and American Airlines - these airlines can fly you to your destination from $199 and $209, respectively. These flights start at 38% lower than the current average price 3 months from now.

  • What are the most reliable airlines from Greensboro to Chicago?

    Consider ANA (91%), Air Canada (88%) or Air New Zealand (88%) when booking your flight. These represent the most reliable airlines when flying from Greensboro to Chicago.

  • What are the cheapest flights from Greensboro to Chicago?

    On average you can expect to pay $1,971 for a flight from Greensboro to Chicago. The cheapest flight overall is $213 while the most popular route, (Greensboro/H. Point - Chicago O'Hare Intl) is currently priced at $269.

  • Can I find deals for flights from Greensboro to Chicago that include hotel bookings?

    Yes. In addition to deals on Greensboro to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Greensboro to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Greensboro to Chicago.

  • Can I find deals for business class flights from Greensboro to Chicago?

    Yes. Cheapflights offers flight deals from Greensboro to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Greensboro to Chicago?

    Currently, November is the cheapest month in which you can book a flight from Greensboro to Chicago (average of $255). Flying from Greensboro to Chicago in July is currently the most expensive (average of $365). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Benton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter

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Top 3 airlines flying from Greensboro to Chicago

Discover the top 3 airlines that operate flights from Greensboro to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$188Average$300FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$199Average$302FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$209Average$304FlexibilityNo cancel feeOn-time71%

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