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$204+ 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 11/27. Fares are subject to change and may not be available on all flights or dates of travel.
GSO — CHI
Jul 5 — Jul 121
Sat 7/5
Sat 7/12
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 82 days in advance, depart on a Wednesday or Thursday 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 June 30, 2025.

Round-trip from

$219
(Delta)

One-way from

$204
(American Airlines)

Popular in

March

Cheapest in

September

Average price

$327

Good round-trip deal

$295 or less

Good one-way deal

$258 or less
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 ($16 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 June 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 June 30, 2025.

This Delta deal was found by Cheapflights users on 6/29. 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.
Tue 7/296:04 amGSO - MDW
1 stop3h 40mDelta
Tue 8/59:25 amMDW - GSO
1 stop5h 53mDelta
Deal found 6/29$219
This Delta deal was found by Cheapflights users on 6/30. 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 7/16:00 amGSO - ORD
1 stop5h 04mDelta
Sat 7/57:05 amORD - GSO
1 stop3h 50mDelta
Deal found 6/30$219
This American Airlines deal was found by Cheapflights users on 6/28. 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.
Tue 7/17:35 amGSO - ORD
Nonstop2h 14mAmerican Airlines
Sat 7/58:00 amORD - GSO
Nonstop1h 56mAmerican Airlines
Deal found 6/28$223
This United Airlines deal was found by Cheapflights users on 6/30. 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.
Thu 7/2410:25 amGSO - ORD
Nonstop2h 20mUnited Airlines
Tue 7/291:44 pmORD - GSO
Nonstop2h 07mUnited Airlines
Deal found 6/30$262

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 June 30, 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 - MDW

GSOMDW

Greensboro/H. Point

Tue 7/29

6:04 am-8:44 am

1 stop3h 40m

Chicago Midway

Tue 8/5

9:25 am-4:18 pm

1 stop5h 53m

$219

GreensboroChicago

GSO - ORD

GSOORD

Greensboro/H. Point

Wed 7/30

5:30 am-8:40 am

1 stop4h 10m

Chicago O'Hare Intl

Sat 8/2

9:50 am-4:12 pm

1 stop5h 22m

$219

GreensboroChicago

GSO - ORD

GSOORD

Greensboro/H. Point

Sat 7/26

11:26 am-12:37 pm

Nonstop2h 11m

Chicago O'Hare Intl

Sat 8/2

6:30 pm-9:46 pm

Nonstop2h 16m

$223

GreensboroChicago

GSO - ORD

GSOORD

Greensboro/H. Point

Tue 7/8

5:32 pm-6:55 pm

Nonstop2h 23m

Chicago O'Hare Intl

Wed 7/16

1:44 pm-4:51 pm

Nonstop2h 07m

$308

GreensboroChicago

GSO - ORD

GSOORD

Greensboro/H. Point

Fri 8/15

8:56 pm-10:31 am

2 stops14h 35m

$213

GreensboroChicago

GSO - ORD

GSOORD

Greensboro/H. Point

Sat 8/9

6:10 am-7:24 am

Nonstop2h 14m

$224

GreensboroChicago

GSO - ORD

GSOORD

Greensboro/H. Point

Tue 9/16

6:45 pm-7:48 am

2 stops14h 03m

$230

GreensboroChicago

GSO - MDW

GSOMDW

Greensboro/H. Point

Tue 9/16

5:02 pm-9:36 pm

1 stop5h 34m

$234

GreensboroChicago

GSO - ORD

GSOORD

Greensboro/H. Point

Sat 8/9

2:00 pm-7:16 pm

1 stop6h 16m

$234

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/29

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 June 27, 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 June 30, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 3% 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 June 30, 2025.

The most flights from GSO to CHI are scheduled on a Monday (14 on average). You will have fewer flight options on Tuesday, 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 June 30, 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
7,973 reviews

Crew

8.5

Overall

8.0

Entertainment

7.9

Comfort

7.9

Boarding

8.2

Food

7.3

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
7,973 reviews
Delta
8.0
Very good
7,973 reviews

Crew

8.5

Overall

8.0

Entertainment

7.9

Comfort

7.9

Boarding

8.2

Food

7.3

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
8,852 reviews
Delta
8.0
Very good
7,973 reviews

Crew

8.5

Overall

8.0

Entertainment

7.9

Comfort

7.9

Boarding

8.2

Food

7.3

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
10,000 reviews
Delta
8.0
Very good
7,973 reviews

Crew

8.5

Overall

8.0

Entertainment

7.9

Comfort

7.9

Boarding

8.2

Food

7.3

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 13 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 $219, 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 $223 and $262, respectively. These flights start at 30% lower than the current average price 3 months from now.

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

    $204 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 United Airlines and Delta, with prices starting from $230 and $234, respectively.

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

    Consider Japan Airlines (93%), Alaska Airlines (93%) or ANA (93%) 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 $1,950 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 $209.

  • 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
Lansing
Benton Harbor
Porter
Hammond
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 June 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$187Average$299FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$199Average$359FlexibilityNo cancel feeOn-time69%
DeltaCheapest$218Average$321FlexibilityNo cancel feeOn-timeN/A

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