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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 9/19. 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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0 bags

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Find the cheapest flights from Greensboro to Chicago (GSO-MDW)

Cheap round-trip flights

Delta Logo
6:55 am - 9:56 amGSO-MDW
4h 01m1 stop
Delta Logo
9:30 am - 4:34 pmMDW-GSO
6h 04m1 stop
$189Delta
Find Deal
Thu, Jan 29 - Sat, Jan 31
Delta Logo
5:00 pm - 9:36 pmGSO-MDW
5h 36m1 stop
Delta Logo
10:35 am - 3:55 pmMDW-GSO
4h 20m1 stop
$199Delta
Find Deal
Fri, Sep 12 - Tue, Sep 16
Delta Logo
5:00 pm - 9:36 pmGSO-MDW
5h 36m1 stop
Delta Logo
6:15 pm - 11:07 pmMDW-GSO
3h 52m1 stop
$209Delta
Find Deal
Fri, Sep 26 - Fri, Oct 3
Delta Logo
6:04 am - 8:40 amGSO-MDW
3h 36m1 stop
Delta Logo
4:25 pm - 11:59 pmMDW-GSO
6h 34m1 stop
$219Delta
Find Deal
Fri, Oct 3 - Sat, Oct 4
Delta Logo
6:35 am - 9:40 amGSO-MDW
4h 05m1 stop
Delta Logo
10:35 am - 5:39 pmMDW-GSO
6h 04m1 stop
$224Delta
Find Deal
Tue, Sep 23 - Tue, Sep 30
Delta Logo
5:00 pm - 9:36 pmGSO-MDW
5h 36m1 stop
Delta Logo
6:15 pm - 11:07 pmMDW-GSO
3h 52m1 stop
$229Delta
Find Deal
Fri, Sep 26 - Mon, Sep 29
Delta Logo
6:04 am - 8:40 amGSO-MDW
3h 36m1 stop
Delta Logo
6:15 pm - 11:07 pmMDW-GSO
3h 52m1 stop
$254Delta
Find Deal
Wed, Sep 17 - Mon, Sep 22
Delta Logo
6:37 pm - 8:40 amGSO-MDW
15h 03m2 stops
Delta Logo
6:23 pm - 11:06 pmMDW-GSO
3h 43m1 stop
$257Delta
Find Deal
Fri, Oct 3 - Tue, Oct 7
Delta Logo
5:19 pm - 6:35 pmGSO-MDW
26h 16m1 stop
Delta Logo
9:35 am - 4:39 pmMDW-GSO
6h 04m1 stop
$285Delta
Find Deal
Tue, Sep 30 - Thu, Oct 2
Delta Logo
5:00 pm - 9:36 pmGSO-MDW
5h 36m1 stop
Delta Logo
12:43 pm - 7:02 pmMDW-GSO
5h 19m1 stop
$287Delta
Find Deal
Mon, Sep 29 - Tue, Sep 30

Delta flights from Greensboro to Chicago Midway Airport

Our best Delta deals on Greensboro to Chicago Midway Airport flight tickets
Delta
Jan 29
GSO6:55 amGreensboro/H. Point
4h 01m
1 stop
MDW9:56 amChicago Midway
Jan 31
MDW9:30 amChicago Midway
6h 04m
1 stop
GSO4:34 pmGreensboro/H. Point
$189
Find similar
Delta
Sep 12
GSO5:00 pmGreensboro/H. Point
5h 36m
1 stop
MDW9:36 pmChicago Midway
Sep 16
MDW10:35 amChicago Midway
4h 20m
1 stop
GSO3:55 pmGreensboro/H. Point
$199
Find similar
Delta
Sep 26
GSO5:00 pmGreensboro/H. Point
5h 36m
1 stop
MDW9:36 pmChicago Midway
Oct 3
MDW6:15 pmChicago Midway
3h 52m
1 stop
GSO11:07 pmGreensboro/H. Point
$209
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 August 28, 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

Thu 1/29

6:55 am-9:56 am

1 stop4h 01m

Chicago Midway

Sat 1/31

9:30 am-4:34 pm

1 stop6h 04m

$189

GreensboroChicago

GSO - MDW

GSOMDW

Greensboro/H. Point

Fri 9/12

5:00 pm-9:36 pm

1 stop5h 36m

Chicago Midway

Tue 9/16

10:35 am-3:55 pm

1 stop4h 20m

$199

GreensboroChicago

GSO - MDW

GSOMDW

Greensboro/H. Point

Fri 9/26

5:00 pm-9:36 pm

1 stop5h 36m

Chicago Midway

Fri 10/3

6:15 pm-11:07 pm

1 stop3h 52m

$209

GreensboroChicago

GSO - MDW

GSOMDW

Greensboro/H. Point

Fri 10/3

6:04 am-8:40 am

1 stop3h 36m

Chicago Midway

Sat 10/4

4:25 pm-11:59 pm

1 stop6h 34m

$219

GreensboroChicago

GSO - MDW

GSOMDW

Greensboro/H. Point

Tue 9/23

6:35 am-9:40 am

1 stop4h 05m

Chicago Midway

Tue 9/30

10:35 am-5:39 pm

1 stop6h 04m

$224

GreensboroChicago

GSO - MDW

GSOMDW

Greensboro/H. Point

Fri 9/26

5:00 pm-9:36 pm

1 stop5h 36m

Chicago Midway

Mon 9/29

6:15 pm-11:07 pm

1 stop3h 52m

$229

GreensboroChicago

GSO - MDW

GSOMDW

Greensboro/H. Point

Wed 9/17

6:04 am-8:40 am

1 stop3h 36m

Chicago Midway

Mon 9/22

6:15 pm-11:07 pm

1 stop3h 52m

$254

GreensboroChicago

GSO - MDW

GSOMDW

Greensboro/H. Point

Fri 10/3

6:37 pm-8:40 am

2 stops15h 03m

Chicago Midway

Tue 10/7

6:23 pm-11:06 pm

1 stop3h 43m

$257

GreensboroChicago

GSO - MDW

GSOMDW

Greensboro/H. Point

Tue 9/30

5:19 pm-6:35 pm

1 stop26h 16m

Chicago Midway

Thu 10/2

9:35 am-4:39 pm

1 stop6h 04m

$285

GreensboroChicago

GSO - MDW

GSOMDW

Greensboro/H. Point

Mon 9/29

5:00 pm-9:36 pm

1 stop5h 36m

Chicago Midway

Tue 9/30

12:43 pm-7:02 pm

1 stop5h 19m

$287

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 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

Direct flights

None
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 23m.

  • 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 $223Free CancellationRating
7.9
7,977 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
Lansing
Portage
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.

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