Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Greensboro to Chicago from $177

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 9/21. 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
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Greensboro to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
6:08 am - 9:17 am
GSO
-
MDW
4h 09m
1 stop
Delta Logo
6:05 am - 1:29 pm
MDW
-
GSO
6h 24m
1 stop
$279Delta
Sat, Sep 5 - Sun, Sep 6
Delta Logo
6:08 am - 9:17 am
GSO
-
MDW
4h 09m
1 stop
Delta Logo
6:05 am - 1:29 pm
MDW
-
GSO
6h 24m
1 stop
$284Delta
Wed, Sep 2 - Sun, Sep 6
Delta Logo
6:08 am - 9:17 am
GSO
-
MDW
4h 09m
1 stop
Delta Logo
6:05 am - 11:38 am
MDW
-
GSO
4h 33m
1 stop
$289Delta
Sat, Sep 5 - Wed, Sep 9
Delta Logo
6:08 am - 9:17 am
GSO
-
MDW
4h 09m
1 stop
Delta Logo
6:05 am - 11:34 am
MDW
-
GSO
4h 29m
1 stop
$294Delta
Tue, Aug 25 - Thu, Sep 3
Delta Logo
12:27 pm - 4:15 pm
GSO
-
MDW
4h 48m
1 stop
Delta Logo
6:05 am - 1:53 pm
MDW
-
GSO
6h 48m
1 stop
$299Delta
Thu, Aug 13 - Mon, Aug 17
Delta Logo
4:30 pm - 10:36 pm
GSO
-
MDW
7h 06m
1 stop
Delta Logo
6:11 am - 1:29 pm
MDW
-
GSO
6h 18m
1 stop
$304Delta
Fri, Aug 28 - Sat, Aug 29
Delta Logo
6:51 pm - 10:36 pm
GSO
-
MDW
4h 45m
1 stop
Delta Logo
6:05 am - 11:34 am
MDW
-
GSO
4h 29m
1 stop
$309Delta
Fri, Aug 21 - Mon, Aug 24
Delta Logo
6:08 am - 9:17 am
GSO
-
MDW
4h 09m
1 stop
Delta Logo
6:05 am - 11:34 am
MDW
-
GSO
4h 29m
1 stop
$319Delta
Thu, Aug 6 - Thu, Aug 13
Delta Logo
6:08 am - 9:17 am
GSO
-
MDW
4h 09m
1 stop
Delta Logo
6:05 am - 1:53 pm
MDW
-
GSO
6h 48m
1 stop
$324Delta
Fri, Aug 14 - Sun, Aug 16
Delta Logo
6:00 am - 9:07 am
GSO
-
MDW
4h 07m
1 stop
Delta Logo
6:05 am - 2:04 pm
MDW
-
GSO
6h 59m
1 stop
$329Delta
Fri, Sep 11 - Sun, Sep 13

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

Delta flights from Greensboro to Chicago Midway Airport

Our best Delta deals on Greensboro to Chicago Midway Airport flight tickets
Delta
Sep 5
GSO6:08 amGreensboro/H. Point
4h 09m
1 stop
MDW9:17 amChicago Midway
Sep 6
MDW6:05 amChicago Midway
6h 24m
1 stop
GSO1:29 pmGreensboro/H. Point
$279
Delta
Sep 2
GSO6:08 amGreensboro/H. Point
4h 09m
1 stop
MDW9:17 amChicago Midway
Sep 6
MDW6:05 amChicago Midway
6h 24m
1 stop
GSO1:29 pmGreensboro/H. Point
$284
Delta
Sep 5
GSO6:08 amGreensboro/H. Point
4h 09m
1 stop
MDW9:17 amChicago Midway
Sep 9
MDW6:05 amChicago Midway
4h 33m
1 stop
GSO11:38 amGreensboro/H. Point
$289

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 July 25, 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

Cheapest round-trip

GreensboroChicago

GSO - MDW

GSOMDW

Greensboro/H. Point

Sat 9/5

6:08 am-9:17 am

1 stop4h 09m

Chicago Midway

Sun 9/6

6:05 am-1:29 pm

1 stop6h 24m

$279

GreensboroChicago

GSO - MDW

GSOMDW

Greensboro/H. Point

Wed 9/2

6:08 am-9:17 am

1 stop4h 09m

Chicago Midway

Sun 9/6

6:05 am-1:29 pm

1 stop6h 24m

$284

GreensboroChicago

GSO - MDW

GSOMDW

Greensboro/H. Point

Sat 9/5

6:08 am-9:17 am

1 stop4h 09m

Chicago Midway

Wed 9/9

6:05 am-11:38 am

1 stop4h 33m

$289
Quickest round-trip

GreensboroChicago

GSO - MDW

GSOMDW

Greensboro/H. Point

Tue 8/25

6:08 am-9:17 am

1 stop4h 09m

Chicago Midway

Thu 9/3

6:05 am-11:34 am

1 stop4h 29m

$294

GreensboroChicago

GSO - MDW

GSOMDW

Greensboro/H. Point

Thu 8/13

12:27 pm-4:15 pm

1 stop4h 48m

Chicago Midway

Mon 8/17

6:05 am-1:53 pm

1 stop6h 48m

$299

GreensboroChicago

GSO - MDW

GSOMDW

Greensboro/H. Point

Fri 8/28

4:30 pm-10:36 pm

1 stop7h 06m

Chicago Midway

Sat 8/29

6:11 am-1:29 pm

1 stop6h 18m

$304

GreensboroChicago

GSO - MDW

GSOMDW

Greensboro/H. Point

Fri 8/21

6:51 pm-10:36 pm

1 stop4h 45m

Chicago Midway

Mon 8/24

6:05 am-11:34 am

1 stop4h 29m

$309

GreensboroChicago

GSO - MDW

GSOMDW

Greensboro/H. Point

Thu 8/6

6:08 am-9:17 am

1 stop4h 09m

Chicago Midway

Thu 8/13

6:05 am-11:34 am

1 stop4h 29m

$319

GreensboroChicago

GSO - MDW

GSOMDW

Greensboro/H. Point

Fri 8/14

6:08 am-9:17 am

1 stop4h 09m

Chicago Midway

Sun 8/16

6:05 am-1:53 pm

1 stop6h 48m

$324

GreensboroChicago

GSO - MDW

GSOMDW

Greensboro/H. Point

Fri 9/11

6:00 am-9:07 am

1 stop4h 07m

Chicago Midway

Sun 9/13

6:05 am-2:04 pm

1 stop6h 59m

$329

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 typical price of a round-trip flight between Greensboro and Chicago Midway Airport?

Prices are currently low for flights on this route.

Typical prices usually range from $298 to $378.
The lowest price recently found on this route was $279.

What is the cheapest month to fly to Chicago Midway Airport?

The month of January is, on average, the cheapest month to fly to Chicago Midway Airport from Greensboro, with most prices found around $0. If you are unable to visit Chicago Midway Airport during the month of January, then departing from Greensboro during the month September is also very affordable. Most momondo users find prices during this month for around $232.

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

4h 00m

Direct flights

None
The fastest flight from Greensboro to Chicago Midway Airport takes 4h 00m
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

Frequently asked questions about flying from Greensboro to Chicago Midway Airport

  • 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 4h 00m.

  • 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 $249Free CancellationRating
7.8
8,486 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
Portage
Benton Harbor
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?

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
Mon 8/24
Mon 8/31
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago