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$118+ 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 12/8. Fares are subject to change and may not be available on all flights or dates of travel.
GSO — CHI
oct. 31 — nov. 71
vie. 10/31
vie. 11/7
1 adult, Economy
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Cheapflights Tip: The best prices from Greensboro/H. Point to Chicago are usually found in July or May, booked 81 days in advance, depart on a Friday or Wednesday and return on a Saturday

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 octubre 1, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$209
(American Airlines)

One-way from

$118
(Kiwi.com)

Popular in

March

Cheapest in

July

Average price

$300

Good round-trip deal

$293 or less

Good one-way deal

$208 or less
Provider with most accurate pricing for Greensboro/H. Point-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Greensboro/H. Point-Chicago (CHI) flights.
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From Greensboro/H. Point to Chicago (CHI)
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One-way flight from Greensboro/H. Point to Chicago (CHI)
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Highest demand for flights based on searches. 5% potential increase in price ($17 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Price to beat on a round-trip flight from Greensboro/H. Point to Chicago (CHI).
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Price to beat on a one-way flight from Greensboro/H. Point to Chicago (CHI).
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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 octubre 1, 2025.

This United Airlines deal was found by Cheapflights users on 9/29. 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.
vie. 10/245:28 pmGSO - ORD
Nonstop2h 27mUnited Airlines
lun. 10/271:47 pmORD - GSO
Nonstop2h 04mUnited Airlines
Deal found 9/29$209
This United Airlines deal was found by Cheapflights users on 9/30. 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.
vie. 10/317:55 pmGSO - ORD
1 stop4h 48mUnited Airlines
mié. 11/55:51 pmORD - GSO
Nonstop1h 54mUnited Airlines
Deal found 9/30$214
This United Airlines deal was found by Cheapflights users on 10/1. 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.
jue. 10/2310:48 amGSO - ORD
Nonstop2h 12mUnited Airlines
mar. 10/288:50 amORD - GSO
1 stop4h 23mUnited Airlines
Deal found 10/1$219
This Delta deal was found by Cheapflights users on 9/29. 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.
sáb. 11/111:30 amGSO - MDW
1 stop4h 56mDelta
lun. 11/36:00 amMDW - GSO
1 stop6h 53mDelta
Deal found 9/29$224
This United Airlines deal was found by Cheapflights users on 10/1. 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.
vie. 11/77:55 pmGSO - ORD
1 stop4h 48mUnited Airlines
sáb. 11/81:00 pmORD - GSO
1 stop4h 46mUnited Airlines
Deal found 10/1$224
This United Airlines deal was found by Cheapflights users on 9/30. 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.
vie. 10/245:28 pmGSO - ORD
Nonstop2h 27mUnited Airlines
dom. 10/261:47 pmORD - GSO
Nonstop2h 04mUnited Airlines
Deal found 9/30$227
This Delta deal was found by Cheapflights users on 9/30. 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.
mar. 10/216:59 pmGSO - MDW
1 stop4h 15mDelta
mié. 10/296:00 amMDW - GSO
1 stop4h 43mDelta
Deal found 9/30$229
This Delta deal was found by Cheapflights users on 10/1. 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.
vie. 10/246:59 pmGSO - ORD
1 stop5h 59mDelta
lun. 10/275:51 pmORD - GSO
1 stop3h 59mDelta
Deal found 10/1$229
This United Airlines deal was found by Cheapflights users on 9/30. 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.
mié. 11/127:55 pmGSO - ORD
1 stop4h 48mUnited Airlines
lun. 11/175:51 pmORD - GSO
Nonstop1h 54mUnited Airlines
Deal found 9/30$231
This American Airlines deal was found by Cheapflights users on 9/29. 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.
vie. 10/317:30 amGSO - ORD
Nonstop2h 08mAmerican Airlines
dom. 11/26:34 pmORD - GSO
Nonstop2h 10mAmerican Airlines
Deal found 9/29$235
This American Airlines deal was found by Cheapflights users on 9/28. 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.
vie. 10/317:30 amGSO - ORD
Nonstop2h 08mAmerican Airlines
lun. 11/36:34 pmORD - GSO
Nonstop2h 10mAmerican Airlines
Deal found 9/28$236
This American Airlines deal was found by Cheapflights users on 9/28. 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.
sáb. 12/137:43 amGSO - ORD
1 stop5h 57mAmerican Airlines
dom. 12/148:11 pmORD - GSO
Nonstop2h 07mAmerican Airlines
Deal found 9/28$238

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 octubre 1, 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

vie. 10/31

6:30 am-7:53 am

Nonstop2h 23m

Chicago O'Hare Intl

lun. 11/3

5:51 pm-8:45 pm

Nonstop1h 54m

$209

GreensboroChicago

GSO - ORD

GSOORD

Greensboro/H. Point

sáb. 11/8

7:55 pm-11:43 pm

1 stop4h 48m

Chicago O'Hare Intl

sáb. 11/15

5:51 pm-8:45 pm

Nonstop1h 54m

$209

GreensboroChicago

GSO - ORD

GSOORD

Greensboro/H. Point

vie. 11/7

7:55 pm-11:43 pm

1 stop4h 48m

Chicago O'Hare Intl

sáb. 11/8

1:47 pm-4:51 pm

Nonstop2h 04m

$214

GreensboroChicago

GSO - ORD

GSOORD

Greensboro/H. Point

sáb. 11/1

7:55 pm-11:43 pm

1 stop4h 48m

Chicago O'Hare Intl

lun. 11/3

5:51 pm-8:45 pm

Nonstop1h 54m

$214

GreensboroChicago

GSO - ORD

GSOORD

Greensboro/H. Point

vie. 10/24

6:15 am-9:36 am

1 stop4h 21m

Chicago O'Hare Intl

lun. 10/27

1:47 pm-4:51 pm

Nonstop2h 04m

$219

GreensboroChicago

GSO - ORD

GSOORD

Greensboro/H. Point

vie. 1/16

8:00 pm-11:39 pm

1 stop4h 39m

Chicago O'Hare Intl

lun. 1/19

5:50 pm-8:51 pm

Nonstop2h 01m

$219

GreensboroChicago

GSO - ORD

GSOORD

Greensboro/H. Point

sáb. 10/18

6:35 am-7:47 am

Nonstop2h 12m

Chicago O'Hare Intl

mar. 10/21

8:45 am-11:49 am

Nonstop2h 04m

$219

GreensboroChicago

GSO - ORD

GSOORD

Greensboro/H. Point

vie. 10/31

6:30 am-7:53 am

Nonstop2h 23m

Chicago O'Hare Intl

dom. 11/2

8:50 am-2:13 pm

1 stop4h 23m

$219

GreensboroChicago

GSO - MDW

GSOMDW

Greensboro/H. Point

sáb. 11/1

11:30 am-3:26 pm

1 stop4h 56m

Chicago Midway

lun. 11/3

5:09 pm-11:56 pm

1 stop5h 47m

$224

GreensboroChicago

GSO - ORD

GSOORD

Greensboro/H. Point

sáb. 11/22

12:28 pm-5:17 pm

1 stop5h 49m

Chicago O'Hare Intl

vie. 11/28

6:45 am-1:40 pm

1 stop5h 55m

$224

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/1

Showing 1-10 of 38 results
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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 October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
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 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

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 September 26, 2025.

The best time to book flights from Greensboro to Chicago is 80 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, August is the cheapest month in which you can book a flight from Greensboro to Chicago (average of $245). Flying from Greensboro to Chicago in March is currently the most expensive (average of $321). 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 octubre 1, 2025.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 47% on flights from Greensboro to Chicago by exploring options for tickets at noon.

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 Thursday evenings when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

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 octubre 1, 2025.

The most flights from GSO to CHI are scheduled on a Tuesday (18 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (11 on average).

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 octubre 1, 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
8.0
Very good
7,961 reviews

Entertainment

7.9

Boarding

8.2

Comfort

7.9

Food

7.3

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,961 reviews
Delta
8.0
Very good
7,961 reviews

Entertainment

7.9

Boarding

8.2

Comfort

7.9

Food

7.3

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,929 reviews
Delta
8.0
Very good
7,961 reviews

Entertainment

7.9

Boarding

8.2

Comfort

7.9

Food

7.3

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
11,030 reviews
Delta
8.0
Very good
7,961 reviews

Entertainment

7.9

Boarding

8.2

Comfort

7.9

Food

7.3

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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 15 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 2h 23m. 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 $191, 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 $208 and $218, respectively. These flights start at 39% lower than the current average price 3 months from now.

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

    Consider Republic Airways (100%), Alaska Airlines (96%) or Qatar Airways (95%) 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 $886 for a flight from Greensboro to Chicago. The cheapest flight overall is $148 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, August is the cheapest month in which you can book a flight from Greensboro to Chicago (average of $245). Flying from Greensboro to Chicago in March is currently the most expensive (average of $321). 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
Benton Harbor
Porter
Chesterton

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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 octubre 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$191Average$290FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$208Average$363FlexibilityNo cancel feeOn-time69%
DeltaCheapest$218Average$301FlexibilityNo cancel feeOn-timeN/A

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