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$126+ 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 6/19. Fares are subject to change and may not be available on all flights or dates of travel.
GSO — CHI
May 6 — May 131
Tue 5/6
Tue 5/13
1 adult, Economy
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Cheapflights Tip: The best prices from Greensboro/H. Point to Chicago are usually found in September or August, booked 81 days in advance, depart on a Friday or Wednesday and return on a Tuesday

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 May 1, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$245
(Delta)

One-way from

$126
(American Airlines)

Popular in

March

Cheapest in

September

Average price

$329

Good round-trip deal

$309 or less

Good one-way deal

$165 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. 4% potential increase in price ($15 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in May 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 May 1, 2025.

This Delta deal was found by Cheapflights users on 4/30. 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.
Tue 6/1010:50 amGSO - ORD
1 stop6h 50mDelta
Fri 6/135:15 pmORD - GSO
1 stop4h 43mDelta
Deal found 4/30$245
This Delta deal was found by Cheapflights users on 4/30. 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.
Thu 5/297:30 amGSO - MDW
1 stop5h 58mDelta
Sat 5/316:00 amMDW - GSO
1 stop4h 28mDelta
Deal found 4/30$249
This American Airlines deal was found by Cheapflights users on 4/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/611:33 amGSO - ORD
Nonstop2h 08mAmerican Airlines
Mon 6/96:40 pmORD - GSO
Nonstop2h 12mAmerican Airlines
Deal found 4/30$251
This United Airlines deal was found by Cheapflights users on 4/29. 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.
Mon 10/136:15 amGSO - ORD
1 stop4h 21mUnited Airlines
Sun 10/265:55 pmORD - GSO
Nonstop2h 02mUnited Airlines
Deal found 4/29$276
This Mytrip deal was found by Cheapflights users on 4/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/169:26 pmGSO - ORD
1 stop23h 57mMultiple Airlines
Thu 6/1910:19 amORD - GSO
2 stops33h 44mMultiple Airlines
Deal found 4/30$368

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 May 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

Tue 6/10

2:42 pm-6:49 pm

1 stop5h 07m

Chicago O'Hare Intl

Fri 6/13

5:15 pm-10:58 pm

1 stop4h 43m

$245

GreensboroChicago

GSO - MDW

GSOMDW

Greensboro/H. Point

Thu 5/29

7:30 am-12:28 pm

1 stop5h 58m

Chicago Midway

Sat 5/31

6:00 am-11:28 am

1 stop4h 28m

$249

GreensboroChicago

GSO - ORD

GSOORD

Greensboro/H. Point

Fri 8/8

11:32 am-12:44 pm

Nonstop2h 12m

Chicago O'Hare Intl

Sun 8/10

8:05 am-11:02 am

Nonstop1h 57m

$251

GreensboroChicago

GSO - ORD

GSOORD

Greensboro/H. Point

Fri 5/16

7:30 pm-11:15 pm

1 stop4h 45m

Chicago O'Hare Intl

Sat 5/17

6:14 pm-9:17 pm

Nonstop2h 03m

$265

GreensboroChicago

GSO - ORD

GSOORD

Greensboro/H. Point

Mon 6/16

9:53 pm-8:23 pm

3 stops23h 30m

Chicago O'Hare Intl

Thu 6/19

10:19 am-9:03 pm

2 stops33h 44m

$408

GreensboroChicago

GSO - MDW

GSOMDW

Greensboro/H. Point

Thu 6/19

12:35 pm-6:41 pm

1 stop7h 06m

$136

GreensboroChicago

GSO - ORD

GSOORD

Greensboro/H. Point

Sun 7/6

6:05 am-10:03 am

1 stop4h 58m

$136

GreensboroChicago

GSO - ORD

GSOORD

Greensboro/H. Point

Thu 5/8

6:25 am-7:33 am

Nonstop2h 08m

$162

GreensboroChicago

GSO - ORD

GSOORD

Greensboro/H. Point

Fri 6/6

9:51 pm-11:29 pm

1 stop26h 38m

$183

GreensboroChicago

GSO - ORD

GSOORD

Greensboro/H. Point

Mon 5/5

5:34 pm-6:55 pm

Nonstop2h 21m

$197

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

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 May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy2 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 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 April 25, 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 May 1, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 2% on flights from Greensboro to Chicago by exploring options for tickets in the morning.

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 May 1, 2025.

The most flights from GSO to CHI are scheduled on a Thursday (14 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (9 on average).

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 May 1, 2025.
Read through reviews of airlines operating flights from Greensboro to Chicago, such as Delta, United Airlines and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,934 reviews

Boarding

8.2

Crew

8.5

Overall

8.0

Food

7.3

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Delta
8.0
Very good
7,934 reviews
Delta
8.0
Very good
7,934 reviews

Boarding

8.2

Crew

8.5

Overall

8.0

Food

7.3

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
United Airlines
7.4
Good
8,696 reviews
Delta
8.0
Very good
7,934 reviews

Boarding

8.2

Crew

8.5

Overall

8.0

Food

7.3

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,934 reviews

Boarding

8.2

Crew

8.5

Overall

8.0

Food

7.3

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

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 11 flights from Greensboro/H. Point to Chicago per day from 3 different airlines.

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

    Currently priced at $245, 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 American Airlines and United Airlines - these airlines can fly you to your destination from $251 and $276, respectively. These flights start at 22% lower than the current average price 3 months from now.

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

    $126 is the cheapest one-way deal found within the past few days, from American Airlines. You may also be able to find cheap deals on Delta and United Airlines, with prices starting from $136 and $224, respectively.

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

    Consider ANA (86%), GoJet (86%) or Republic Airways (83%) 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 $354 for a flight from Greensboro to Chicago. The cheapest flight overall is $124 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 Greensboro?

Book flights to Greensboro if you plan to visit one of these locations
Merrillville
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$187Average$302FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$198Average$372FlexibilityNo cancel feeOn-time69%
DeltaCheapest$226Average$340FlexibilityNo cancel feeOn-timeN/A

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