GSO - CHI

$128 Find Cheap Flights from Greensboro to Chicago - Compare and Save

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Everything you should know

Cheapest round-trip
$269
Typical prices: $267-$384
United Airlines
Sun 9/16Wed 9/19
GSO - ORD • Non-stop
Cheapest non-stop
$269
Typical prices: $265-$377
United Airlines
Wed 10/31Sat 11/3
GSO - ORD • Non-stop
Nonstop flights
You can fly direct with American Airlines and United Airlines. Average duration is 2h 22m
Direct flights
+1
Direct flights
+1
Top routes
Cheapest • 4% average savings
Most popular
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 22 weeks in advance save around 44% compared to booking last minute.
Insights
Insights
When to travel
Cheapest • 15% price drop
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Cheapest • Avg $223 (round-trip)
Shortest trip • 4h 24m (one-way)
Insights
Insights
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Flight Deals
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Expert advice
Flight Deals

Cheap Flights from Greensboro to Chicago (GSO-CHI)

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Greensboro to Chicago

Sat, Oct 31 - Tue, Nov 3
United Airlines Logo
5:40 pm - 7:00 pmGSO  Greensboro/H. Point-ORD Chicago O'Hare Intl
2h 20mnonstop
United Airlines Logo
2:05 pm - 5:02 pmORD  Chicago O'Hare Intl-GSO Greensboro/H. Point
1h 57mnonstop
$269United Airlines
Thu, Sep 10 - Tue, Sep 22
United Airlines Logo
6:35 am - 7:52 amGSO  Greensboro/H. Point-ORD Chicago O'Hare Intl
2h 17mnonstop
United Airlines Logo
6:18 pm - 9:23 pmORD  Chicago O'Hare Intl-GSO Greensboro/H. Point
2h 05mnonstop
$269United Airlines
Sat, Oct 17 - Sat, Oct 24
American Airlines Logo
7:41 pm - 9:13 pmGSO  Greensboro/H. Point-ORD Chicago O'Hare Intl
2h 32mnonstop
American Airlines Logo
7:26 pm - 10:35 pmORD  Chicago O'Hare Intl-GSO Greensboro/H. Point
2h 09mnonstop
$269American Airlines
Tue, Sep 22 - Sat, Sep 26
American Airlines Logo
7:20 am - 8:45 amGSO  Greensboro/H. Point-ORD Chicago O'Hare Intl
2h 25mnonstop
American Airlines Logo
3:26 pm - 6:34 pmORD  Chicago O'Hare Intl-GSO Greensboro/H. Point
2h 08mnonstop
$269American Airlines
Sat, Sep 12 - Sat, Sep 19
United Airlines Logo
5:51 pm - 7:05 pmGSO  Greensboro/H. Point-ORD Chicago O'Hare Intl
2h 14mnonstop
United Airlines Logo
6:18 pm - 9:23 pmORD  Chicago O'Hare Intl-GSO Greensboro/H. Point
2h 05mnonstop
$269United Airlines
Sat, Nov 7 - Tue, Nov 10
American Airlines Logo
7:30 pm - 9:04 pmGSO  Greensboro/H. Point-ORD Chicago O'Hare Intl
2h 34mnonstop
American Airlines Logo
3:04 pm - 6:04 pmORD  Chicago O'Hare Intl-GSO Greensboro/H. Point
2h 00mnonstop
$269American Airlines
Wed, Nov 11 - Wed, Nov 18
Delta Logo
7:00 am - 10:33 amGSO  Greensboro/H. Point-MDW Chicago Midway
4h 33m1 stop Atlanta Hartsfield-Jackson
Delta Logo
1:00 pm - 8:00 pmMDW  Chicago Midway-GSO Greensboro/H. Point
6h 00m1 stop Atlanta Hartsfield-Jackson
$289Delta
Sat, Oct 31 - Tue, Nov 3
Delta Logo
5:00 pm - 10:33 pmGSO  Greensboro/H. Point-MDW Chicago Midway
6h 33m1 stop Atlanta Hartsfield-Jackson
Delta Logo
4:19 pm - 11:59 pmMDW  Chicago Midway-GSO Greensboro/H. Point
6h 40m1 stop Atlanta Hartsfield-Jackson
$289Delta
Mon, Oct 26 - Thu, Oct 29
Multiple Airlines Logo
5:54 pm - 12:02 pmGSO  Greensboro/H. Point-ORD Chicago O'Hare Intl
19h 08m2 stops Orlando Atlanta Hartsfield-Jackson
Multiple Airlines Logo
9:26 am - 12:08 pmORD  Chicago O'Hare Intl-GSO Greensboro/H. Point
25h 42m1 stop Orlando
$323Multiple Airlines
Fri, Oct 23 - Sun, Oct 25
Multiple Airlines Logo
5:54 pm - 7:31 amGSO  Greensboro/H. Point-ORD Chicago O'Hare Intl
14h 37m1 stop Orlando
Multiple Airlines Logo
7:44 pm - 12:08 pmORD  Chicago O'Hare Intl-GSO Greensboro/H. Point
15h 24m2 stops Atlanta Hartsfield-Jackson Orlando
$378Multiple Airlines
Booking Insights

Price, demand and travel trends for Greensboro to Chicago flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights from Greensboro to Chicago with more confidence.

How much is a round-trip flight from Greensboro to Chicago?

Round-trip flights from Greensboro to Chicago start at $269. Prices are typical for this route right now, with typical round-trip fares ranging from $267 to $384. The lowest price found in the past 5 days was $269 on United Airlines.

What is the cheapest Greensboro to Chicago flight route?

There's little price difference between Greensboro to Chicago routes. They average around $327 round-trip, based on KAYAK data over the past 12 months.

What's the cheapest day of the week to fly from Greensboro to Chicago?

Saturday is the cheapest day of the week to fly from Greensboro to Chicago, it is 6% cheaper than the average day. Sunday is the most expensive day with flight prices 14% higher than average. Based on deals found by KAYAK users in the last 12 months.

What is the cheapest month to fly from Greensboro to Chicago?

  • November is the cheapest month to fly from Greensboro to Chicago at $269 round-trip.
  • July ($369) and June ($345) are the most expensive months.
  • The price difference between flying in the cheapest and most expensive months is 37% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

When are prices from Greensboro to Chicago the cheapest?

Flights from Greensboro to Chicago are cheapest 22 weeks before departure. Booking in this window typically costs about 44% less than the average last-minute fare (within 2 weeks of the flight), based on KAYAK data.

Expert advice

Expert advice for your flight from Greensboro to Chicago

 
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Harriet Baskas

Harriet Baskas

Expert on American Airlines

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Stefanie Waldek

Stefanie Waldek

Expert on United Airlines

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Key details for Greensboro to Chicago flights

Low season

January

Cheapest flight

$128
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly with an average 7% increase in price.
Flight from Greensboro to Chicago O'Hare Intl Airport

When to book flights from Greensboro to Chicago

Are your dates flexible? Find out the best times to travel from Greensboro to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

Your Greensboro to Chicago flight questions, answered

Find helpful route details based on KAYAK data, including flight times, airports, airlines and booking questions.

  • Which airlines offer extra legroom and free seat selection on Greensboro to Chicago flights?

    Among airlines operating Greensboro to Chicago flights:

    • American Airlines: offers extra legroom; offers free seat selection
    • United Airlines: offers extra legroom; offers free seat selection

    Extra legroom and free seat selection availability depends on fare class and route.

  • What airlines are available from Greensboro to Chicago?

    2 airlines operate flights between Greensboro and Chicago. The airlines offering nonstop flights on this route include:
    • American Airlines
    • United Airlines

  • Which airports can I use when flying from Greensboro to Chicago?

    Flights from Greensboro to Chicago usually depart from Greensboro/H. Point (GSO) and may arrive at several airports in Chicago area, including Chicago Midway (MDW), Chicago O'Hare Intl (ORD) and Chicago Greater Rockford (RFD).

  • Which airlines include bags at no extra cost on Greensboro to Chicago flights?

    Here are some options for this route, based on selected ticket types and cabin classes:

    • American Airlines: a cabin bag and a checked bag in Economy Class
    • United Airlines: a cabin bag and a checked bag in Economy Class

    Bag allowance can vary by ticket type, cabin class, route and airline, so travelers should check the fare details before booking.

  • What cabin classes can I book on flights from Greensboro to Chicago?

    Three cabin classes are available on flights from Greensboro to Chicago:

    • Economy Class
    • Premium Economy Class
    • First Class

  • How much can I save by taking a layover when flying from Greensboro to Chicago?

    On this route, layover flights are cheaper than nonstop options on average. Layover fares average $223 round-trip via Washington, D.C. Dulles Intl (IAD), compared to $314 for nonstop.

  • What is the standard checked-bag allowance on flights from Greensboro to Chicago?

    There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $40–$100 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

  • Which airports do connecting flights from Greensboro to Chicago pass through?

    One-stop flights from Greensboro to Chicago most commonly connect through:

    • Atlanta Hartsfield-Jackson (ATL) - 60% of one-stop connections
    • Detroit Metropolitan Wayne County (DTW) - 15% of one-stop connections
    • Charlotte Douglas (CLT) - 13% of one-stop connections
    • Chicago O'Hare Intl (ORD) - 10% of one-stop connections

    Atlanta Hartsfield-Jackson (ATL) handles the largest share of one-stop connections on this route.

  • Can I save money by using flexible dates for flights from Greensboro to Chicago?

    On the Greensboro to Chicago route, being flexible with your departure day can save you up to 18%. Saturday is the cheapest day at $299 round-trip on average, while Sunday is the most expensive at $362: a $63 difference. Cheaper weekend fares like these are typical of routes dominated by weekday business travel.

  • How are flight departures from Greensboro to Chicago spread across the day?

    Morning is the busiest departure period on Greensboro to Chicago flights, with 51% of flights leaving in that window. Evening departures account for 33%, afternoon flights for 16%, and night flights for 0%.

  • What popular places can I visit in Chicago?

    Some of the most popular sights in Chicago are Magnificent Mile, Grant Park and River North. These are among the most viewed places in Chicago on KAYAK.

  • How long is a flight from Greensboro to Chicago?

    A nonstop flight from Greensboro to Chicago takes 2h 22m, covering 573 miles.

  • What are the earliest and latest flights from Greensboro to Chicago?

    These are the earliest and latest flight times available from Greensboro to Chicago:

    • Earliest: departs at 6:15 am and lands at 8:37 am
    • Latest: departs at 7:43 pm and lands at 10:05 pm.

    The flight takes about 2h 22m.

  • How expensive are last-minute Greensboro to Chicago flights?

    Last-minute fares on this route - booked within 2 weeks of departure - run 16% above the route average of $315. Book 22 weeks before departure for the lowest fares.

  • Do I need a passport to fly from Greensboro to Chicago?

    No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID, or another TSA-accepted form of identification.

  • Have flight prices from Greensboro to Chicago changed much recently?

    Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $269 to $1,686. That means the highest observed fare was about 6x higher than the lowest one.

  • How are flight prices from Greensboro to Chicago looking right now?

    One-way fares from Greensboro to Chicago are currently lower than usual. Average one-way flight prices are about $198, which is 29% below the typical average for this route.

  • How much time can I save by choosing a different layover airport from Greensboro to Chicago?

    Flying via Detroit Metropolitan Wayne County (DTW) gives the shortest average 1-stop total travel time at 4h 24m, compared with 4h 35m via Washington, D.C. Dulles Intl (IAD) and 4h 50m via Charlotte Douglas (CLT).

  • What is the time difference between Greensboro and Chicago?

    Chicago is 1 hour behind Greensboro (Central Time vs Eastern Time). Plan for the time shift when scheduling connections or first-day activities.

  • What car rental options are available in Chicago?

    Since Chicago is served by multiple airports, car rental options and rates can vary depending on which one you fly into.
    Near Chicago O'Hare Intl Airport (ORD) — daily rates from around $17:

    · Routes Car & Truck Rentals
    · Europcar
    · Hertz
    · Dollar
    · Ace

    Near Chicago Midway Airport (MDW) — daily rates from around $32:

    · Hertz
    · Dollar
    · Budget
    · Alamo
    · Rent-A-Wreck

    Near Chicago Greater Rockford Airport (RFD) — daily rates from around $30:

    · Alamo
    · Enterprise Rent-A-Car
    · Budget
    · Avis
    · National

  • How much should I expect to pay for a Greensboro to Chicago flight?

    Round-trip flights from Greensboro to Chicago range from $267 to $384, with an average of $315 over the past 12 months. Anything below $267 counts as a good deal.

  • Which airlines offer Wi-Fi on Greensboro to Chicago flights?

    American Airlines is the only airline on the Greensboro to Chicago route offering in-flight Wi-Fi. Pricing depends on fare class.

Your guide to booking Greensboro to Chicago flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates can be flexible, aim for a Saturday departure instead of Sunday. On this route, Saturday flights average $299 - about $63 less than Sunday (17% savings) based on the last 12 months.
  • For the best chance at a low fare, aim to book around 22 weeks before you fly. On this route, that window historically saves about 44% versus last-minute pricing (KAYAK booking data, last 12 months).
  • If you can choose when to travel, plan your Greensboro to Chicago trip for November. Fares historically average $269 round-trip in that month - typically $100 less than the most expensive month, which is July (based on the last 12 months).
  • If you have the time, taking a 1-stop flight through Washington, D.C. Dulles Intl Airport (IAD) can be cheaper than flying direct. The cheapest layover option averages $223 round-trip on this route - about $91 less than direct flights (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to Chicago Midway Airport.
    - DoubleTree by Hilton Chicago Midway Airport
    - Holiday Inn Chicago - Midway Airport S by IHG

Prefer to fly direct from Greensboro to Chicago?

 
Find which airlines fly direct from Greensboro/H. Point Airport to Chicago, which days they fly and book direct flights.

Direct departures

Greensboro/H. Point to Chicago

Monday

American Airlines,United Airlines

American Airlines,United Airlines

Tuesday

American Airlines,United Airlines

American Airlines,United Airlines

Wednesday

American Airlines,United Airlines

American Airlines,United Airlines

Thursday

American Airlines,United Airlines

American Airlines,United Airlines

Friday

American Airlines,United Airlines

American Airlines,United Airlines

Saturday

American Airlines,United Airlines

American Airlines,United Airlines

Sunday

American Airlines,United Airlines

American Airlines,United Airlines

See more direct flights

Direct returns

Chicago to Greensboro/H. Point

Monday

American Airlines,United Airlines

American Airlines,United Airlines

Tuesday

American Airlines,United Airlines

American Airlines,United Airlines

Wednesday

American Airlines,United Airlines

American Airlines,United Airlines

Thursday

American Airlines,United Airlines

American Airlines,United Airlines

Friday

American Airlines,United Airlines

American Airlines,United Airlines

Saturday

American Airlines,United Airlines

American Airlines,United Airlines

Sunday

American Airlines,United Airlines

American Airlines,United Airlines

See more direct flights

Everything you need to know for your flight from Greensboro to Chicago

Information on your arrival and departure airports