GSP - CHI

$104 Find Cheap Flights from Greenville to Chicago - Compare and Save

1 adult
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$279
Typical prices: $270-$400
Multiple Airlines
Mon 12/17Sat 1/13
GSP - ORD • 1 stop
Cheapest non-stop
$318
Typical prices: $269-$399
American Airlines
Mon 10/29Thu 11/1
GSP - ORD • Non-stop
Advice from real travelers
Greenville Airport is small, so security is usually quick, especially with PreCheck.
At O'Hare, expect long walks; some transfers need the terminal train.
Expert advice
+1
Expert advice
+1
Nonstop flights
You can fly direct with United Airlines and American Airlines. Average duration is 2h 21m
Direct flights
+1
Direct flights
+1
Top routes
Cheapest • 8% 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 39% compared to booking last minute.
Insights
Insights
When to travel
Cheapest • 14% price drop
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Cheapest • Avg $226 (round-trip)
Shortest trip • 4h 25m (one-way)
Insights
Insights
Start a new search
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We hope you love your trip to Chicago!

Cheap Flights from Greenville to Chicago (GSP-CHI)

 

Cheap flights from Greenville to Chicago with top airlines, updated regularly. Compare round-trip, one-way, direct and last-minute deals.

Thu, Dec 17 - Wed, Jan 13
Multiple Airlines Logo
8:43 am - 12:50 pmGSP  Greenville-ORD Chicago O'Hare Intl
29h 07m1 stop Fort Lauderdale
Multiple Airlines Logo
8:25 am - 9:32 amORD  Chicago O'Hare Intl-GSP Greenville
24h 07m2 stops Fort Lauderdale Tampa
$279Multiple Airlines
Sat, Nov 7 - Sat, Nov 14
Southwest Logo
4:55 pm - 7:40 pmGSP  Greenville-MDW Chicago Midway
3h 45m1 stop Nashville Intl
Southwest Logo
1:25 pm - 7:35 pmMDW  Chicago Midway-GSP Greenville
5h 10m1 stop Baltimore/Washington
$281Southwest
Mon, Dec 14 - Mon, Jan 11
Multiple Airlines Logo
8:32 pm - 7:20 amGSP  Greenville-ORD Chicago O'Hare Intl
35h 48m2 stops Orlando Atlanta Hartsfield-Jackson
Multiple Airlines Logo
8:25 am - 5:26 pmORD  Chicago O'Hare Intl-GSP Greenville
8h 01m1 stop Fort Lauderdale
$282Multiple Airlines
Thu, Oct 29 - Sun, Nov 1
American Airlines Logo
6:01 am - 7:22 amGSP  Greenville-ORD Chicago O'Hare Intl
2h 21mnonstop
American Airlines Logo
6:55 pm - 9:59 pmORD  Chicago O'Hare Intl-GSP Greenville
2h 04mnonstop
$318American Airlines
Sun, Nov 1 - Sun, Nov 8
American Airlines Logo
7:06 am - 8:34 amGSP  Greenville-ORD Chicago O'Hare Intl
2h 28mnonstop
American Airlines Logo
8:00 am - 11:07 amORD  Chicago O'Hare Intl-GSP Greenville
2h 07mnonstop
$319American Airlines
Wed, Dec 2 - Sat, Dec 5
United Airlines Logo
6:30 am - 7:46 amGSP  Greenville-ORD Chicago O'Hare Intl
2h 16mnonstop
United Airlines Logo
6:50 am - 9:52 amORD  Chicago O'Hare Intl-GSP Greenville
2h 02mnonstop
$319United Airlines
Fri, Nov 6 - Sun, Nov 8
United Airlines Logo
5:37 pm - 7:00 pmGSP  Greenville-ORD Chicago O'Hare Intl
2h 23mnonstop
United Airlines Logo
6:29 am - 9:30 amORD  Chicago O'Hare Intl-GSP Greenville
2h 01mnonstop
$319United Airlines
Fri, Nov 13 - Mon, Nov 16
American Airlines Logo
6:42 pm - 8:13 pmGSP  Greenville-ORD Chicago O'Hare Intl
2h 31mnonstop
American Airlines Logo
1:10 pm - 4:07 pmORD  Chicago O'Hare Intl-GSP Greenville
1h 57mnonstop
$319American Airlines
Thu, Dec 17 - Wed, Jan 13
Delta Logo
10:57 am - 1:56 pmGSP  Greenville-ORD Chicago O'Hare Intl
3h 59m1 stop Detroit Metropolitan Wayne County
Delta Logo
9:30 am - 2:49 pmORD  Chicago O'Hare Intl-GSP Greenville
4h 19m1 stop Atlanta Hartsfield-Jackson
$339Delta
Mon, Dec 14 - Mon, Jan 11
Delta Logo
12:18 pm - 5:06 pmGSP  Greenville-ORD Chicago O'Hare Intl
5h 48m1 stop Atlanta Hartsfield-Jackson
Delta Logo
9:30 am - 4:09 pmORD  Chicago O'Hare Intl-GSP Greenville
5h 39m1 stop Atlanta Hartsfield-Jackson
$339Delta

Price, demand and travel trends for Greenville to Chicago flights

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

What is the cheapest Greenville to Chicago flight route?

Greenville (GSP) to Chicago O'Hare Intl Airport (ORD) is the cheapest Greenville to Chicago route, averaging $319 round-trip. Other Greenville to Chicago routes average $376, based on KAYAK data over the past 12 months.

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

Based on deals KAYAK users found in the last 12 months, Saturday is the cheapest day of the week to fly from Greenville to Chicago. It’s 10% cheaper than the average day, while Sunday is the most expensive, with prices 48% higher.

What’s the cheapest month to fly from Greenville to Chicago?

•March is the cheapest month to fly from Greenville to Chicago at $276 round-trip.
•June ($370) and July ($349) are the most expensive months.
•The price difference between flying in the cheapest and most expensive months is 34% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

When are flights from Greenville to Chicago the cheapest?

Flights from Greenville to Chicago are cheapest 22 weeks before departure. Booking in this window typically costs about 39% less than the average last-minute fare (within 2 weeks of the flight), based on KAYAK data.

Expert advice for your flight from Greenville 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 Greenville to Chicago flights

Low season

January

Cheapest flight

$104
Beat the crowds with an average 46% drop in travelers.
The most popular month to fly with an average 68% increase in travelers.
One-way flight from Greenville to Chicago O'Hare Intl Airport

When to book flights from Greenville to Chicago

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

Flights from Greenville to Chicago: the best tips from KAYAK users' own experiences

Insights shared by verified travelers who flew the route from Greenville to Chicago 
Verified travelerFlew with American Airlines-Apr 2026
Chicago has a enormous airport so be ready to walk and transfer to international flights by train via terminal
EllenFlew with United Airlines-May 2024
Greenville airport is small, getting through security won't take too long (particularly if you have Precheck). Be prepared to walk for 10-15 minutes from your arrival gate in O'Hare to your next departure gate, if you have one. Sometimes those gates are really close together, but my experience is that they are typically farther apart and require a solid walk.

Your Greenville to Chicago flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

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

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

    • Earliest: departs at 6:00 am and lands at 8:21 am
    • Latest: departs at 8:36 pm and lands at 10:57 pm.

    The flight takes about 2h 21m.

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

    Two cabin classes are available on flights from Greenville to Chicago:

    • Economy Class
    • First Class

  • How long is a flight from Greenville to Chicago?

    A nonstop flight from Greenville to Chicago takes 2h 21m, covering 564 miles.

  • Do I need a passport to fly from Greenville 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.

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

    Round-trip flights from Greenville to Chicago range from $270 to $400, with an average of $320 over the past 12 months. Anything below $270 counts as a good deal.

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

    Last-minute fares on this route (booked within two weeks of departure) run 39% above the $320 route average. Book 22 weeks before departure for the lowest fares.

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

    On this route, layover flights are cheaper than nonstop options on average. Layover fares average $226 round-trip via New York LaGuardia (LGA), compared to $319 for nonstop.

  • What is the standard checked-bag allowance on flights from Greenville 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.

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

    Morning is the busiest departure period on Greenville to Chicago flights, with 58% of flights leaving in that window. Evening departures account for 28%, afternoon flights for 14%, and night flights for 0%.

  • Have flight prices from Greenville 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 $279 to $2,075. That means the highest observed fare was about 7x higher than the lowest one.

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

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

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

    One-way fares from Greenville to Chicago are currently lower than usual. Average one-way flight prices are about $188, which is 25% below the typical average for this route.

  • 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
    • Ace
    • Dollar

    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 $28:

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

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

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

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

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

    • Atlanta Hartsfield-Jackson (ATL) - 61% of one-stop connections
    • Nashville Intl (BNA) - 25% of one-stop connections
    • New York LaGuardia (LGA) - 5% of one-stop connections
    • Baltimore/Washington (BWI) - 2% of one-stop connections

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

    Yes. Flexible dates can save you up to 40% on flights from Greenville to Chicago. Saturday is the cheapest departure day at $288 round-trip on average, while Sunday is the most expensive at $475, a difference of $187.

    Cheaper weekend fares like these are typical of routes dominated by weekday business travel.

  • What airlines fly from Greenville to Chicago?

    2 airlines operate flights between Greenville and Chicago. The airlines offering nonstop flights on this route include:

    • United Airlines
    • American Airlines

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

    Flying via Nashville Intl (BNA) gives the shortest average 1-stop total travel time at 4h 25m, compared with 4h 44m via Baltimore/Washington (BWI) and 4h 50m via Atlanta Hartsfield-Jackson (ATL).

  • What is the time difference between Greenville and Chicago?

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

  • What popular places can I visit in Chicago?

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

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

    Among airlines operating Greenville to Chicago flights:

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

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

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

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

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

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

Your guide to booking Greenville to Chicago flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates are flexible, aim for a Saturday departure and avoid flying on Sunday. On this route, Saturday flights average $288, about $187 less than Sunday fares (39% 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 39% versus last-minute pricing (KAYAK booking data, last 12 months).
  • If you can choose when to travel, plan your Greenville to Chicago trip for March. Fares historically average $276 round-trip in that month - typically $94 less than the most expensive month, which is June (based on the last 12 months).
  • If you have the time, taking a 1-stop flight through New York LaGuardia Airport (LGA) can be cheaper than flying direct. The cheapest layover option averages $226 round-trip on this route - about $93 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
    • Skylark Motel

Prefer to fly direct from Greenville to Chicago?

 
Find which airlines fly direct from Greenville Airport to Chicago, which days they fly and book direct flights.

Direct departures

Greenville 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 Greenville

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

More options for your flight from Greenville to Chicago

Complete your trip to Chicago with a hotel stay or car rental