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Cheap flights from Greensboro to Chicago from $146

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 2/2. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Greensboro to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
6:10 am - 8:53 am
GSO
-
MDW
3h 43m
1 stop
Delta Logo
6:00 am - 2:11 pm
MDW
-
GSO
7h 11m
1 stop
$229Delta
Sat, Apr 11 - Tue, Apr 14
Delta Logo
6:00 am - 8:54 am
GSO
-
MDW
3h 54m
1 stop
Delta Logo
9:34 am - 4:36 pm
MDW
-
GSO
6h 02m
1 stop
$249Delta
Sat, Feb 14 - Mon, Feb 16
Delta Logo
6:00 am - 8:54 am
GSO
-
MDW
3h 54m
1 stop
Delta Logo
6:20 pm - 11:14 pm
MDW
-
GSO
3h 54m
1 stop
$254Delta
Thu, Feb 26 - Sun, Mar 1
Delta Logo
6:00 am - 8:54 am
GSO
-
MDW
3h 54m
1 stop
Delta Logo
6:00 am - 11:35 am
MDW
-
GSO
4h 35m
1 stop
$284Delta
Sat, Mar 7 - Tue, Mar 10
Delta Logo
2:18 pm - 5:45 pm
GSO
-
MDW
4h 27m
1 stop
Delta Logo
9:34 am - 4:36 pm
MDW
-
GSO
6h 02m
1 stop
$307Delta
Wed, Feb 18 - Fri, Feb 20
Delta Logo
5:19 pm - 10:31 pm
GSO
-
MDW
6h 12m
1 stop
Delta Logo
12:45 pm - 8:46 pm
MDW
-
GSO
7h 01m
1 stop
$333Delta
Mon, Mar 2 - Thu, Mar 5
Delta Logo
12:40 pm - 5:29 pm
GSO
-
MDW
5h 49m
1 stop
Delta Logo
6:20 pm - 11:14 pm
MDW
-
GSO
3h 54m
1 stop
$387Delta
Mon, Feb 9 - Fri, Feb 13
Delta Logo
8:19 am - 11:59 am
GSO
-
MDW
4h 40m
1 stop
Delta Logo
9:34 am - 4:36 pm
MDW
-
GSO
6h 02m
1 stop
$442Delta
Tue, Feb 10 - Thu, Feb 12
Delta Logo
6:15 am - 8:42 am
GSO
-
MDW
3h 27m
1 stop
Delta Logo
5:59 pm - 10:56 pm
MDW
-
GSO
3h 57m
1 stop
$449Delta
Thu, Jun 4 - Sun, Jun 7
Multiple Airlines Logo
10:01 pm - 7:07 pm
GSO
-
MDW
22h 06m
2 stops
Multiple Airlines Logo
7:30 am - 4:02 pm
MDW
-
GSO
7h 32m
1 stop
$466Multiple Airlines
Mon, Feb 9 - Fri, Feb 13

Delta flights from Greensboro to Chicago Midway Airport

Our best Delta deals on Greensboro to Chicago Midway Airport flight tickets
Delta
Apr 11
GSO6:10 amGreensboro/H. Point
3h 43m
1 stop
MDW8:53 amChicago Midway
Apr 14
MDW6:00 amChicago Midway
7h 11m
1 stop
GSO2:11 pmGreensboro/H. Point
$229
Delta
Feb 26
GSO6:00 amGreensboro/H. Point
3h 54m
1 stop
MDW8:54 amChicago Midway
Mar 1
MDW6:20 pmChicago Midway
3h 54m
1 stop
GSO11:14 pmGreensboro/H. Point
$254
Delta
Mar 7
GSO6:00 amGreensboro/H. Point
3h 54m
1 stop
MDW8:54 amChicago Midway
Mar 10
MDW6:00 amChicago Midway
4h 35m
1 stop
GSO11:35 amGreensboro/H. Point
$284

momondo Fare Finder

 
Customize your flight search to find flights from Greensboro to Chicago Midway Airport 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, momondo users made 832,500 searches. Data last updated January 26, 2026.
Use the filters below to find and compare flights from Greensboro to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

GreensboroChicago

GSO - MDW

GSOMDW

Greensboro/H. Point

Sat 4/11

6:10 am-8:53 am

1 stop3h 43m

Chicago Midway

Tue 4/14

6:00 am-2:11 pm

1 stop7h 11m

$229

GreensboroChicago

GSO - MDW

GSOMDW

Greensboro/H. Point

Sat 2/14

6:00 am-8:54 am

1 stop3h 54m

Chicago Midway

Mon 2/16

9:34 am-4:36 pm

1 stop6h 02m

$249

GreensboroChicago

GSO - MDW

GSOMDW

Greensboro/H. Point

Thu 2/26

6:00 am-8:54 am

1 stop3h 54m

Chicago Midway

Sun 3/1

6:20 pm-11:14 pm

1 stop3h 54m

$254

GreensboroChicago

GSO - MDW

GSOMDW

Greensboro/H. Point

Sat 3/7

6:00 am-8:54 am

1 stop3h 54m

Chicago Midway

Tue 3/10

6:00 am-11:35 am

1 stop4h 35m

$284

GreensboroChicago

GSO - MDW

GSOMDW

Greensboro/H. Point

Wed 2/18

2:18 pm-5:45 pm

1 stop4h 27m

Chicago Midway

Fri 2/20

9:34 am-4:36 pm

1 stop6h 02m

$307

GreensboroChicago

GSO - MDW

GSOMDW

Greensboro/H. Point

Mon 3/2

5:19 pm-10:31 pm

1 stop6h 12m

Chicago Midway

Thu 3/5

12:45 pm-8:46 pm

1 stop7h 01m

$333

GreensboroChicago

GSO - MDW

GSOMDW

Greensboro/H. Point

Mon 2/9

12:40 pm-5:29 pm

1 stop5h 49m

Chicago Midway

Fri 2/13

6:20 pm-11:14 pm

1 stop3h 54m

$387

GreensboroChicago

GSO - MDW

GSOMDW

Greensboro/H. Point

Tue 2/10

8:19 am-11:59 am

1 stop4h 40m

Chicago Midway

Thu 2/12

9:34 am-4:36 pm

1 stop6h 02m

$442

GreensboroChicago

GSO - MDW

GSOMDW

Greensboro/H. Point

Thu 6/4

6:15 am-8:42 am

1 stop3h 27m

Chicago Midway

Sun 6/7

5:59 pm-10:56 pm

1 stop3h 57m

$449

GreensboroChicago

GSO - MDW

GSOMDW

Greensboro/H. Point

Mon 2/9

10:01 pm-7:07 pm

2 stops22h 06m

Chicago Midway

Fri 2/13

7:30 am-4:02 pm

1 stop7h 32m

$466

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Greensboro to Chicago Midway Airport

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

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

Delta is the most popular carrier operating from Greensboro/H. Point to Chicago Midway

What airlines fly to Chicago Midway Airport?

Southwest, Delta and Frontier are the top three most popular airlines that fly to Chicago Midway Airport from Greensboro according to our data. Southwest is the first choice among our users, with 75% of people opting to fly with this airline when traveling to Chicago Midway Airport. Keep in mind that there are 3 different airlines that fly to Chicago Midway Airport on a routine basis, so you have a few additional options to choose from.

When to book flights from Greensboro to Chicago Midway Airport

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

Cheap Greensboro to Chicago Midway Airport (GSO to MDW) flight deals and tips

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

Fastest flight time

3h 27m

Direct flights

None
The fastest flight from Greensboro to Chicago Midway Airport takes 3h 27m
There are no direct flights from Greensboro to Chicago Midway Airport. There are no popular flight routes from Greensboro to Chicago Midway Airport.
Search flight deals

  • How far is Greensboro/H. Point to Chicago Midway by plane?

    A flight from Greensboro/H. Point to Chicago Midway will travel around 581.0 mi. By plane, this route typically takes 3h 27m.

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

    Prices for flights from Greensboro/H. Point Airport to Chicago Midway Airport refresh daily.

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

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

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Greensboro/H. Point Airport to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The necessary travel and health documents for your Chicago Midway Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular airline from Greensboro to Chicago Midway Airport?

Best airlines flying from Greensboro to Chicago Midway Airport

Compare and see reviews for airlines that fly from Greensboro to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $196Free CancellationRating
7.9
8,111 reviews
Search Delta flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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Portage
Lansing
Schererville
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Munster
Crown Point
Chesterton
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Porter
Griffith
Saint John

Why use momondo?

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

It is quick and easy to find Greensboro to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

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

Flights from Greensboro to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

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

Once all potential Greensboro to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

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

If you are not ready to book a flight from Greensboro to Chicago now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Chicago and let you know when they change.

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