Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Greensboro to Chicago from $144

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 1/18. 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

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Greensboro to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
6:00 am - 8:52 am
GSO
-
MDW
3h 52m1 stop
Delta Logo
6:25 am - 12:30 pm
MDW
-
GSO
5h 05m1 stop
$219Delta
Tue, Jan 20 - Sat, Jan 24
Delta Logo
6:00 am - 8:52 am
GSO
-
MDW
3h 52m1 stop
Delta Logo
6:00 am - 1:29 pm
MDW
-
GSO
6h 29m1 stop
$224Delta
Sat, Jan 24 - Mon, Jan 26
Delta Logo
12:40 pm - 5:29 pm
GSO
-
MDW
5h 49m1 stop
Delta Logo
6:00 am - 1:29 pm
MDW
-
GSO
6h 29m1 stop
$229Delta
Mon, Jan 19 - Sun, Jan 25
Delta Logo
5:25 am - 9:51 am
GSO
-
MDW
5h 26m1 stop
Delta Logo
10:35 am - 4:27 pm
MDW
-
GSO
4h 52m1 stop
$255Delta
Thu, Apr 16 - Sun, Apr 19
Delta Logo
2:18 pm - 5:29 pm
GSO
-
MDW
4h 11m1 stop
Delta Logo
6:35 pm - 11:16 pm
MDW
-
GSO
3h 41m1 stop
$287Delta
Mon, Jan 19 - Fri, Jan 23
Delta Logo
6:00 am - 8:52 am
GSO
-
MDW
3h 52m1 stop
Delta Logo
1:26 pm - 11:51 am
MDW
-
GSO
21h 25m2 stops
$304Delta
Sat, Jan 24 - Sat, Jan 24
Delta Logo
10:06 am - 4:20 pm
GSO
-
MDW
7h 14m1 stop
Delta Logo
6:45 am - 1:29 pm
MDW
-
GSO
5h 44m1 stop
$313Delta
Fri, Jan 2 - Mon, Jan 5
Delta Logo
7:20 am - 5:26 pm
GSO
-
MDW
11h 06m1 stop
Delta Logo
11:21 am - 7:02 pm
MDW
-
GSO
6h 41m1 stop
$331Delta
Wed, Dec 24 - Wed, Jan 7
Delta Logo
7:20 am - 5:26 pm
GSO
-
MDW
11h 06m1 stop
Delta Logo
9:32 am - 3:49 pm
MDW
-
GSO
5h 17m1 stop
$336Delta
Wed, Dec 24 - Tue, Jan 6
Delta Logo
5:15 pm - 9:45 pm
GSO
-
MDW
5h 30m1 stop
Delta Logo
4:30 pm - 11:57 pm
MDW
-
GSO
6h 27m1 stop
$346Delta
Mon, Apr 20 - Sat, Apr 25

Delta flights from Greensboro to Chicago Midway Airport

Our best Delta deals on Greensboro to Chicago Midway Airport flight tickets
Delta
Jan 20
GSO6:00 amGreensboro/H. Point
3h 52m
1 stop
MDW8:52 amChicago Midway
Jan 24
MDW6:25 amChicago Midway
5h 05m
1 stop
GSO12:30 pmGreensboro/H. Point
$219
Find similar
Delta
Jan 24
GSO5:20 amGreensboro/H. Point
5h 33m
1 stop
MDW9:53 amChicago Midway
Jan 26
MDW6:14 pmChicago Midway
4h 31m
1 stop
GSO11:45 pmGreensboro/H. Point
$224
Find similar
Delta
Jan 19
GSO12:40 pmGreensboro/H. Point
5h 49m
1 stop
MDW5:29 pmChicago Midway
Jan 26
MDW6:14 pmChicago Midway
4h 31m
1 stop
GSO11:45 pmGreensboro/H. Point
$229
Find similar

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 December 9, 2025.
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

Tue 1/20

6:00 am-8:52 am

1 stop3h 52m

Chicago Midway

Sat 1/24

6:25 am-12:30 pm

1 stop5h 05m

$219

GreensboroChicago

GSO - MDW

GSOMDW

Greensboro/H. Point

Sat 1/24

6:00 am-8:52 am

1 stop3h 52m

Chicago Midway

Mon 1/26

6:00 am-1:29 pm

1 stop6h 29m

$224

GreensboroChicago

GSO - MDW

GSOMDW

Greensboro/H. Point

Mon 1/19

12:40 pm-5:29 pm

1 stop5h 49m

Chicago Midway

Sun 1/25

6:00 am-1:29 pm

1 stop6h 29m

$229

GreensboroChicago

GSO - MDW

GSOMDW

Greensboro/H. Point

Thu 4/16

5:25 am-9:51 am

1 stop5h 26m

Chicago Midway

Sun 4/19

10:35 am-4:27 pm

1 stop4h 52m

$255

GreensboroChicago

GSO - MDW

GSOMDW

Greensboro/H. Point

Mon 1/19

2:18 pm-5:29 pm

1 stop4h 11m

Chicago Midway

Fri 1/23

6:35 pm-11:16 pm

1 stop3h 41m

$287

GreensboroChicago

GSO - MDW

GSOMDW

Greensboro/H. Point

Sat 1/24

6:00 am-8:52 am

1 stop3h 52m

Chicago Midway

Sat 1/24

1:26 pm-11:51 am

2 stops21h 25m

$304

GreensboroChicago

GSO - MDW

GSOMDW

Greensboro/H. Point

Fri 1/2

10:06 am-4:20 pm

1 stop7h 14m

Chicago Midway

Mon 1/5

6:45 am-1:29 pm

1 stop5h 44m

$313

GreensboroChicago

GSO - MDW

GSOMDW

Greensboro/H. Point

Wed 12/24

7:20 am-5:26 pm

1 stop11h 06m

Chicago Midway

Wed 1/7

11:21 am-7:02 pm

1 stop6h 41m

$331

GreensboroChicago

GSO - MDW

GSOMDW

Greensboro/H. Point

Wed 12/24

7:20 am-5:26 pm

1 stop11h 06m

Chicago Midway

Tue 1/6

9:32 am-3:49 pm

1 stop5h 17m

$336

GreensboroChicago

GSO - MDW

GSOMDW

Greensboro/H. Point

Mon 4/20

5:15 pm-9:45 pm

1 stop5h 30m

Chicago Midway

Sat 4/25

4:30 pm-11:57 pm

1 stop6h 27m

$346

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 day to depart on your flight to Chicago Midway Airport?

According to our data, Wednesday is the cheapest day to fly to Chicago Midway Airport from Greensboro. The lowest ticket price found for a Wednesday departure recently was $269. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Monday is the most expensive day to depart from Greensboro because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $478.

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

Flying to Chicago Midway Airport from Greensboro in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $343 when looking at flights departing in the afternoon. Try not to purchase tickets at noon because they tend to be around $483. Of course, these prices can vary depending on the time of year and what airport you fly to.

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
8,011 reviews
Search Delta flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
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.

An easier way to manage your Chicago Midway Airport 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.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Thu 1/8
Thu 1/15
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago