What airlines fly to Chicago?

American Airlines, United Airlines and Frontier are the top three most popular airlines that fly to Chicago from Greensboro according to our data. American Airlines is the first choice among our users, with 45% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 6 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

How many flights depart from Greensboro to Chicago on average per day?

As of July 2026, 13 flights take off from Greensboro and land in Chicago each day. The most common flight departure time for this route is 10:00AM, with 53% of daily flights taking off at noon.

What is the cheapest airline that flies from Greensboro/H. Point to Chicago?

United Airlines and Delta are the most popular carriers operating from Greensboro/H. Point to Chicago

How many flights depart from Greensboro to Chicago on average per week?

As of July 2026, there are 97 flights per week flying from Greensboro to Chicago. The most common day of the week flights depart is Mon, with 18% of flights taking off on this day.

When did momondo last update prices for flights from Greensboro/H. Point Airport to Chicago?

Prices for flights from Greensboro/H. Point Airport to Chicago are updated daily.

How many operators does momondo search for flights from Greensboro/H. Point Airport to Chicago?

As of July 2026, there are 3 operators available to choose from for flights from Greensboro/H. Point Airport to Chicago.

How old do you have to be to fly from Greensboro/H. Point Airport to Chicago?

The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Greensboro/H. Point Airport to Chicago.

What documentation or ID do you need to fly to Chicago?

The travel and health documents required for your trip to Chicago can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$132 Cheap Flights from Greensboro to Chicago in 2026

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Greensboro to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

7:25 am - 8:49 am

GSO

ORD

2h 24mnonstop

8:09 am - 11:10 am

ORD

GSO

2h 01mnonstop

$269American Airlines

Tue, Dec 22 - Tue, Dec 29

6:46 pm - 8:24 pm

GSO

ORD

2h 38mnonstop

10:30 am - 1:37 pm

ORD

GSO

2h 07mnonstop

$269American Airlines

Fri, Sep 11 - Sat, Sep 12

7:20 am - 8:45 am

GSO

ORD

2h 25mnonstop

7:39 pm - 10:49 pm

ORD

GSO

2h 10mnonstop

$269American Airlines

Fri, Sep 11 - Fri, Sep 11

5:51 pm - 7:05 pm

GSO

ORD

2h 14mnonstop

6:59 am - 10:04 am

ORD

GSO

2h 05mnonstop

$274United Airlines

Sat, Aug 29 - Sun, Aug 30

6:35 am - 7:52 am

GSO

ORD

2h 17mnonstop

6:55 am - 10:01 am

ORD

GSO

2h 06mnonstop

$274United Airlines

Wed, Sep 23 - Sun, Sep 27

10:40 am - 11:52 am

GSO

ORD

2h 12mnonstop

2:10 pm - 5:15 pm

ORD

GSO

2h 05mnonstop

$274United Airlines

Tue, Aug 25 - Tue, Sep 1

5:00 pm - 10:33 pm

GSO

MDW

6h 33m

1 stop

6:04 am - 11:08 am

MDW

GSO

4h 04m

1 stop

$289Delta

Sat, Oct 17 - Wed, Oct 21

10:45 am - 4:22 pm

GSO

MDW

6h 37m

1 stop

6:00 am - 11:23 am

MDW

GSO

4h 23m

1 stop

$289Delta

Tue, Dec 22 - Tue, Dec 29

9:50 pm - 11:08 pm

GSO

ORD

26h 18m

1 stop

7:44 pm - 4:02 pm

ORD

GSO

19h 18m

1 stop

$309Multiple Airlines

Mon, Aug 24 - Thu, Aug 27

9:50 pm - 11:08 pm

GSO

ORD

26h 18m

1 stop

7:28 pm - 12:08 pm

ORD

GSO

15h 40m

2 stops

$334Multiple Airlines

Mon, Aug 31 - Sun, Sep 13

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American Airlines flights from Greensboro to Chicago

Our best American Airlines deals on Greensboro to Chicago flight tickets

American Airlines

Aug 29

GSO7:49 amGreensboro/H. Point

2h 21m

ORD9:10 amChicago O'Hare Intl

Sep 5

ORD3:18 pmChicago O'Hare Intl

2h 01m

GSO6:19 pmGreensboro/H. Point

$269

American Airlines

Sep 11

GSO6:46 pmGreensboro/H. Point

2h 38m

ORD8:24 pmChicago O'Hare Intl

Sep 13

ORD9:59 amChicago O'Hare Intl

2h 07m

GSO1:06 pmGreensboro/H. Point

$274

American Airlines

Sep 3

GSO6:55 pmGreensboro/H. Point

2h 35m

ORD8:30 pmChicago O'Hare Intl

Sep 10

ORD3:08 pmChicago O'Hare Intl

2h 08m

GSO6:16 pmGreensboro/H. Point

$279

Delta flights from Greensboro to Chicago

Our best Delta deals on Greensboro to Chicago flight tickets

Delta

Sep 5

GSO5:03 pmGreensboro/H. Point

4h 52m

1 stop

ORD8:55 pmChicago O'Hare Intl

Sep 10

ORD3:40 pmChicago O'Hare Intl

4h 17m

1 stop

GSO8:57 pmGreensboro/H. Point

$289

Delta

Sep 11

GSO2:49 pmGreensboro/H. Point

7h 07m

1 stop

ORD8:56 pmChicago O'Hare Intl

Sep 13

ORD6:40 amChicago O'Hare Intl

6h 24m

1 stop

GSO2:04 pmGreensboro/H. Point

$294

Delta

Aug 20

GSO2:50 pmGreensboro/H. Point

4h 59m

1 stop

ORD6:49 pmChicago O'Hare Intl

Aug 23

ORD5:30 amChicago O'Hare Intl

3h 55m

1 stop

GSO10:25 amGreensboro/H. Point

$299

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

GreensboroChicago

GSO - ORD

GSOORD

Greensboro/H. Point

Tue 12/22

7:25 am-8:49 am

Nonstop2h 24m

Chicago O'Hare Intl

Tue 12/29

8:09 am-11:10 am

Nonstop2h 01m

$269

GreensboroChicago

GSO - ORD

GSOORD

Greensboro/H. Point

Fri 9/11

6:46 pm-8:24 pm

Nonstop2h 38m

Chicago O'Hare Intl

Sat 9/12

10:30 am-1:37 pm

Nonstop2h 07m

$269

GreensboroChicago

GSO - ORD

GSOORD

Greensboro/H. Point

Fri 9/11

7:20 am-8:45 am

Nonstop2h 25m

Chicago O'Hare Intl

Fri 9/11

7:39 pm-10:49 pm

Nonstop2h 10m

$269

GreensboroChicago

GSO - ORD

GSOORD

Greensboro/H. Point

Sat 8/29

5:51 pm-7:05 pm

Nonstop2h 14m

Chicago O'Hare Intl

Sun 8/30

6:59 am-10:04 am

Nonstop2h 05m

$274

GreensboroChicago

GSO - ORD

GSOORD

Greensboro/H. Point

Wed 9/23

6:35 am-7:52 am

Nonstop2h 17m

Chicago O'Hare Intl

Sun 9/27

6:55 am-10:01 am

Nonstop2h 06m

$274

Quickest round-trip

GreensboroChicago

GSO - ORD

GSOORD

Greensboro/H. Point

Tue 8/25

10:40 am-11:52 am

Nonstop2h 12m

Chicago O'Hare Intl

Tue 9/1

2:10 pm-5:15 pm

Nonstop2h 05m

$274

GreensboroChicago

GSO - MDW

GSOMDW

Greensboro/H. Point

Sat 10/17

5:00 pm-10:33 pm

1 stop6h 33m

Chicago Midway

Wed 10/21

6:04 am-11:08 am

1 stop4h 04m

$289

GreensboroChicago

GSO - MDW

GSOMDW

Greensboro/H. Point

Tue 12/22

10:45 am-4:22 pm

1 stop6h 37m

Chicago Midway

Tue 12/29

6:00 am-11:23 am

1 stop4h 23m

$289

GreensboroChicago

GSO - ORD

GSOORD

Greensboro/H. Point

Mon 8/24

9:50 pm-11:08 pm

1 stop26h 18m

Chicago O'Hare Intl

Thu 8/27

7:44 pm-4:02 pm

1 stop19h 18m

$309

GreensboroChicago

GSO - ORD

GSOORD

Greensboro/H. Point

Mon 8/31

9:50 pm-11:08 pm

1 stop26h 18m

Chicago O'Hare Intl

Sun 9/13

7:28 pm-12:08 pm

2 stops15h 40m

$334

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Greensboro to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Other information

What is the typical price of a round-trip flight between Greensboro and Chicago?

Prices are currently low for flights on this route.

Typical prices usually range from $287 to $426.
The lowest price recently found on this route was $269.

What is the cheapest month to fly to Chicago?

The month of November is, on average, the cheapest month to fly to Chicago from Greensboro, with most prices found around $255. If you’re not able to fly to Chicago in November, then February is your next best option. Flight prices from Greensboro to Chicago during February average around $279.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $361. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Greensboro to Chicago for around $623.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Greensboro to Chicago during this time can be as low as $340. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $457.

What is the cheapest Greensboro/H. Point to Chicago flight route?

Fly from Greensboro/H. Point to Chicago O'Hare Intl for the best Greensboro/H. Point - Chicago flight prices

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

You are more likely to see cheaper flights to Chicago from Greensboro when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $302 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Greensboro for as low as $239 on momondo.

What cabin class options are available on Greensboro to Chicago flights?

There are 4 cabin classes available to choose from on Greensboro to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Greensboro to Chicago flights?

No. A direct flight is the cheapest option for a flight between Greensboro to Chicago.

How have Greensboro to Chicago flight prices changed over time?

As of July 2026, prices for Greensboro to Chicago flights are approximately 21% more expensive when compared to flights at the same time last year.

When to book flights from Greensboro to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Greensboro to Chicago according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap Greensboro to Chicago (GSO to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Greensboro to Chicago

Best Price Found	$309
Fastest flight time	2h 06m
Direct flights	Every day
Airports in Chicago	3 airports

The best one-way flight to Chicago from Greensboro in the past 72 hours is $309. The best round-trip flight deal from Greensboro to Chicago found on momondo in the last 72 hours is $348.

The fastest flight from Greensboro to Chicago takes 2h 06m

Direct flights go from Greensboro to Chicago every day.

There are 3 airports in Chicago. From Greensboro there are direct flights to Chicago O'Hare Intl (ORD).

Search flight deals

Frequently asked questions about flying from Greensboro to Chicago

How far is Greensboro/H. Point to Chicago by plane?
There are 580.4 mi between Greensboro/H. Point and Chicago. A reasonable flight in good conditions will take 2h 06m.
When did momondo last update prices for flights from Greensboro/H. Point Airport to Chicago?
Prices for flights from Greensboro/H. Point Airport to Chicago are updated daily.
How many operators does momondo search for flights from Greensboro/H. Point Airport to Chicago?
As of July 2026, there are 3 operators available to choose from for flights from Greensboro/H. Point Airport to Chicago.
How old do you have to be to fly from Greensboro/H. Point Airport to Chicago?
The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Greensboro/H. Point Airport to Chicago.
What documentation or ID do you need to fly to Chicago?
The travel and health documents required for your trip to Chicago can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from Greensboro to Chicago?
Based on momondo bookings for flights between Greensboro and Chicago, the leading plane model is Embraer 175, making up 29.60% of the total bookings. Other popular models include Canadair (Bombardier) Regional Jet CRJ-550 with 27.67%, Embraer 170 with 23.50%, and Embraer 175 (Enhanced Winglets) with 5.60%.
What is the most popular airline from Greensboro to Chicago?
momondo data reveals that the most frequently booked airline on the route from Greensboro to Chicago is American Airlines, representing 69% of all bookings. The subsequent popular airline is United Airlines at 31%.

Best airlines flying from Greensboro to Chicago

Compare and see reviews for airlines that fly from Greensboro to Chicago with momondo

Airline	Rating	Free Cancellation	Price
Delta	PriceFrom $188	Free Cancellation	Rating 7.8 8,482 reviews	Search Delta flights
United Airlines	PriceFrom $199	Free Cancellation	Rating 7.4 10,046 reviews	Search United Airlines flights
American Airlines	PriceFrom $209	Free Cancellation	Rating 7.1 11,839 reviews	Search American Airlines flights

United Airlines Flights From Greensboro to Chicago
Across 14 United Airlines flights from Greensboro to Chicago this week, the average price was $302, with the best United Airlines deals starting from $199 round-trip. 10,046 users have rated United Airlines on momondo, with an average score of 7.4/10.
American Airlines Flights From Greensboro to Chicago
American Airlines is also a popular choice for this route. American Airlines flight deals for Greensboro to Chicago start from as low as $209 round-trip, depending on your selected dates, with average American Airlines deals seen on momondo around $308. American Airlines operates 9 flights to Chicago from Greensboro in an average week. Users have rated it 7.1/10 across 11,839 reviews.

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Portage

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Lansing

Saint Joseph

Valparaiso

Schererville

Munster

Chesterton

Monticello

Crown Point

Porter

Griffith

Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Greensboro to Chicago?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Greensboro to Chicago for you.

Can I find flights from Greensboro to Chicago with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Greensboro to Chicago flights to just show those with flexible booking policies.

How can momondo help me find flights from Greensboro to Chicago?

momondo helps you find the best flight between Greensboro and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Greensboro to Chicago right now. Can momondo alert me if prices change?

Price alerts on flights to Chicago from Greensboro are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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Cheap flights from Greensboro to Chicago from $132

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Greensboro to Chicago departing on 8/24. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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American Airlines flights from Greensboro to Chicago

Our best American Airlines deals on Greensboro to Chicago flight tickets

Delta flights from Greensboro to Chicago

Our best Delta deals on Greensboro to Chicago flight tickets

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See travel insights to Chicago from

How to get the cheapest flight ticket from Greensboro to Chicago

What is the typical price of a round-trip flight between Greensboro and Chicago?

What is the cheapest month to fly to Chicago?

What is the cheapest day to depart on your flight to Chicago?

What is the cheapest time of day to depart on your flight to Chicago?

What is the cheapest Greensboro/H. Point to Chicago flight route?

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

What cabin class options are available on Greensboro to Chicago flights?

Can stopping save me money on Greensboro to Chicago flights?

How have Greensboro to Chicago flight prices changed over time?

What is the cheapest airline that flies from Greensboro/H. Point to Chicago?

What airlines fly to Chicago?

How many flights depart from Greensboro to Chicago on average per day?

How many flights depart from Greensboro to Chicago on average per week?

When to book flights from Greensboro to Chicago

Cheap Greensboro to Chicago (GSO to CHI) flight deals and tips

Best Price Found

Fastest flight time

Direct flights

Airports in Chicago

Frequently asked questions about flying from Greensboro to Chicago

Best airlines flying from Greensboro to Chicago

Compare and see reviews for airlines that fly from Greensboro to Chicago with momondo

Traveling to a place near Chicago?

Why use momondo?

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago

Fly your favorite airline to Chicago

Airlines are sorted and displayed according to clicks in the past 7 days on momondo

Cabin classes currently available on flights to Chicago

List of cabin classes available on flights landing in Chicago. Availability may vary depending on flight origin and airline.

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