HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$100+ 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 12/5. Fares are subject to change and may not be available on all flights or dates of travel.
GSO — CHI
Nov 27 — Dec 41
Thu 11/27
Thu 12/4
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Greensboro to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheapflights Tip: The best prices from Greensboro/H. Point to Chicago are usually found in July or February, booked 48 days in advance, depart on a Friday or Wednesday and return on a Saturday

Find 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 October 28, 2025.

This United Airlines deal was found by Cheapflights users on 10/27. 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.
Sat 12/135:32 pmGSO - ORD
Nonstop2h 23mUnited Airlines
Tue 1/68:52 amORD - GSO
1 stop4h 19mUnited Airlines
Deal found 10/27$209
This American Airlines deal was found by Cheapflights users on 10/27. 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.
Thu 11/138:05 pmGSO - ORD
Nonstop2h 14mAmerican Airlines
Mon 11/178:10 amORD - GSO
Nonstop1h 57mAmerican Airlines
Deal found 10/27$219
This United Airlines deal was found by Cheapflights users on 10/26. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/266:30 amGSO - ORD
Nonstop2h 24mUnited Airlines
Wed 12/311:30 pmORD - GSO
Nonstop2h 04mUnited Airlines
Deal found 10/26$222
This Delta deal was found by Cheapflights users on 10/27. 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 12/134:53 pmGSO - ORD
1 stop6h 50mDelta
Sun 12/145:30 amORD - GSO
1 stop7h 07mDelta
Deal found 10/27$224
This Delta deal was found by Cheapflights users on 10/27. 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.
Thu 12/412:30 pmGSO - MDW
1 stop4h 48mDelta
Sun 12/76:00 amMDW - GSO
1 stop4h 23mDelta
Deal found 10/27$229
This Delta deal was found by Cheapflights users on 10/27. 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.
Thu 11/206:05 amGSO - ORD
1 stop8h 12mDelta
Mon 11/245:23 amORD - GSO
1 stop5h 00mDelta
Deal found 10/27$229
This American Airlines deal was found by Cheapflights users on 10/27. 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 12/246:05 amGSO - ORD
Nonstop2h 16mAmerican Airlines
Mon 12/296:19 pmORD - GSO
Nonstop2h 03mAmerican Airlines
Deal found 10/27$233
This American Airlines deal was found by Cheapflights users on 10/26. 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.
Mon 11/246:15 amGSO - ORD
Nonstop2h 13mAmerican Airlines
Mon 12/16:34 pmORD - GSO
Nonstop2h 10mAmerican Airlines
Deal found 10/26$235
This American Airlines deal was found by Cheapflights users on 10/27. 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 12/311:42 amGSO - ORD
Nonstop2h 17mAmerican Airlines
Sat 12/67:10 amORD - GSO
1 stop5h 58mAmerican Airlines
Deal found 10/27$238
This Delta deal was found by Cheapflights users on 10/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/147:59 pmGSO - ORD
1 stop5h 02mDelta
Sun 11/165:23 amORD - GSO
1 stop5h 00mDelta
Deal found 10/26$239
This American Airlines deal was found by Cheapflights users on 10/27. 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 12/136:08 amGSO - ORD
Nonstop2h 17mAmerican Airlines
Sun 12/145:00 amORD - GSO
1 stop4h 53mAmerican Airlines
Deal found 10/27$240
This United Airlines deal was found by Cheapflights users on 10/27. 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.
Wed 11/56:30 amGSO - ORD
Nonstop2h 23mUnited Airlines
Thu 11/135:51 pmORD - GSO
Nonstop1h 54mUnited Airlines
Deal found 10/27$243

Cheap 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 October 28, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$209
(United Airlines)

One-way from

$100
(Kiwi.com)

Popular in

March

Cheapest in

July

Average price

$305

Good round-trip deal

$295 or less

Good one-way deal

$258 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. 4% potential increase in price ($16 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
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 October 28, 2025.
Use the filters below to find and compare flights from Greensboro to Chicago that are best for you.

Fly from

Greensboro

Fly to

Chicago

Route

Depart

Return

Price

GreensboroChicago

GSO - ORD

GSOORD

Greensboro/H. Point

Sat 2/7

2:46 pm-6:37 pm

1 stop4h 51m

Chicago O'Hare Intl

Tue 2/10

1:40 pm-4:44 pm

Nonstop2h 04m

$209

GreensboroChicago

GSO - ORD

GSOORD

Greensboro/H. Point

Sat 2/28

8:00 am-9:28 am

Nonstop2h 28m

Chicago O'Hare Intl

Sun 3/1

8:50 am-2:12 pm

1 stop4h 22m

$214

GreensboroChicago

GSO - ORD

GSOORD

Greensboro/H. Point

Sat 12/13

4:53 pm-10:43 pm

1 stop6h 50m

Chicago O'Hare Intl

Tue 1/6

2:30 pm-9:23 pm

1 stop5h 53m

$219

GreensboroChicago

GSO - ORD

GSOORD

Greensboro/H. Point

Thu 11/20

7:55 pm-11:43 pm

1 stop4h 48m

Chicago O'Hare Intl

Mon 11/24

1:47 pm-4:51 pm

Nonstop2h 04m

$219

GreensboroChicago

GSO - ORD

GSOORD

Greensboro/H. Point

Sat 12/13

4:53 pm-10:43 pm

1 stop6h 50m

Chicago O'Hare Intl

Sun 12/14

6:45 am-1:37 pm

1 stop5h 52m

$224

GreensboroChicago

GSO - ORD

GSOORD

Greensboro/H. Point

Thu 11/20

6:05 am-1:17 pm

1 stop8h 12m

Chicago O'Hare Intl

Mon 11/24

5:23 am-11:23 am

1 stop5h 00m

$229

GreensboroChicago

GSO - ORD

GSOORD

Greensboro/H. Point

Thu 11/13

6:30 am-7:53 am

Nonstop2h 23m

Chicago O'Hare Intl

Mon 11/17

8:50 am-2:13 pm

1 stop4h 23m

$229

GreensboroChicago

GSO - ORD

GSOORD

Greensboro/H. Point

Wed 12/3

11:42 am-12:59 pm

Nonstop2h 17m

Chicago O'Hare Intl

Sat 12/6

7:10 am-2:08 pm

1 stop5h 58m

$238

GreensboroChicago

GSO - ORD

GSOORD

Greensboro/H. Point

Sat 12/13

6:08 am-7:25 am

Nonstop2h 17m

Chicago O'Hare Intl

Sun 12/14

5:00 am-10:53 am

1 stop4h 53m

$240

GreensboroChicago

GSO - ORD

GSOORD

Greensboro/H. Point

Sat 11/8

5:32 pm-6:55 pm

Nonstop2h 23m

Chicago O'Hare Intl

Wed 11/12

5:51 pm-8:45 pm

Nonstop1h 54m

$243

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

Showing 1-10 of 43 results
1
2
3
...
5

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 October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust 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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Greensboro-Chicago flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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

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

Use this chart to determine the optimal time to book a round-trip flight from Greensboro to Chicago. Price data was last updated on October 24, 2025.

The best time to book flights from Greensboro to Chicago is 48 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 month to book a flight from Greensboro to Chicago?

Currently, February is the cheapest month in which you can book a flight from Greensboro to Chicago (average of $57). Flying from Greensboro to Chicago in July is currently the most expensive (average of $136). 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 October 28, 2025.

Unlike in the morning, when flights are generally more expensive, you can save up to 36% on flights from Greensboro to Chicago by exploring options for tickets in the evening.

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 December 16, 2024.

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

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

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 October 28, 2025.
Read reviews from past customers who have flown Delta, 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.
Delta
7.9
Good
7,994 reviews

Overall

7.9

Food

7.3

Entertainment

7.9

Comfort

7.9

Crew

8.5

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
Delta
7.9
Good
7,994 reviews
Delta
7.9
Good
7,994 reviews

Overall

7.9

Food

7.3

Entertainment

7.9

Comfort

7.9

Crew

8.5

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
United Airlines
7.4
Good
9,001 reviews
Delta
7.9
Good
7,994 reviews

Overall

7.9

Food

7.3

Entertainment

7.9

Comfort

7.9

Crew

8.5

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
American Airlines
7.2
Good
11,032 reviews
Delta
7.9
Good
7,994 reviews

Overall

7.9

Food

7.3

Entertainment

7.9

Comfort

7.9

Crew

8.5

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.

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 9 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 $209, United Airlines can have you in Chicago from Greensboro in 4h 51m. 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 $197, American Airlines will fly you from Greensboro to Chicago and back. In addition to American Airlines, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from United Airlines and Delta - these airlines can fly you to your destination from $204 and $218, respectively. These flights start at 36% lower than the current average price 3 months from now.

  • What are the cheapest airlines to fly from Greensboro to Chicago one-way?

    $134 is the cheapest one-way deal found within the past few days, from United Airlines. You may also be able to find cheap deals on American Airlines and Delta, with prices starting from $134 and $144, respectively.

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

    Consider Republic Airways (100%), Alaska Airlines (96%) or Qatar Airways (96%) 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 $1,068 for a flight from Greensboro to Chicago. The cheapest flight overall is $173 while the most popular route, (Greensboro/H. Point - Chicago O'Hare Intl) is currently priced at $199.

  • 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, February is the cheapest month in which you can book a flight from Greensboro to Chicago (average of $57). Flying from Greensboro to Chicago in July is currently the most expensive (average of $136). 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
Merrillville
Lansing
Hammond
Porter
Benton Harbor

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Greensboro to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Charlotte to O'Hare Intl flights
Raleigh to O'Hare Intl flights
Raleigh to Midway flights
Knoxville to O'Hare Intl flights
Charlotte to Midway flights
Norfolk to O'Hare Intl flights
Raleigh to St. Louis flights
Greensboro to O'Hare Intl flights
Knoxville to Midway flights
Asheville to O'Hare Intl flights
Charlotte to St. Louis flights
Norfolk to Midway flights
Norfolk to St. Louis flights
Wilmington to O'Hare Intl flights
Myrtle Beach to O'Hare Intl flights
Greensboro to Midway flights
Greensboro to St. Louis flights
Charlotte to Peoria flights
New Bern to O'Hare Intl flights
Myrtle Beach to Midway flights
Knoxville to St. Louis flights
Asheville to Midway flights
Wilmington to Midway flights
Fayetteville to O'Hare Intl flights
Charlotte to Moline flights
Charlotte to Bloomington flights
Raleigh to Evansville flights
Myrtle Beach to St. Louis flights
Fayetteville to Midway flights
Raleigh to Moline flights
Charlotte to Evansville flights
Raleigh to Peoria flights
Asheville to St. Louis flights
Greensboro to Moline flights
Norfolk to Moline flights
Wilmington to St. Louis flights
Jacksonville to Midway flights
Knoxville to Peoria flights
Blountville to O'Hare Intl flights
New Bern to St. Louis flights
Jacksonville to O'Hare Intl flights
Blountville to Midway flights
New Bern to Midway flights
Greensboro to Evansville flights
Norfolk to Peoria flights
Asheville to Moline flights
Raleigh to Bloomington flights
Knoxville to Moline flights
Knoxville to Bloomington flights

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 October 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$197Average$286FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$204Average$351FlexibilityNo cancel feeOn-time69%
DeltaCheapest$218Average$306FlexibilityNo cancel feeOn-timeN/A

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.