GSP - CHI

$97 Find Cheap Flights from Greenville to Chicago - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Greenville to Chicago departing on 8/6. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$269
Typical prices: $271-$394
United Airlines
Thu 8/6Thu 8/13
GSP - ORD • Non-stop
Cheapest one-way
$97
Southwest
Thu 8/6
GSP - MDW • 1 stop
Advice from real travelers
AI-powered summary based on content written by travel experts and KAYAK users. AI can make mistakes.
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
Expert advice
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Expert advice
Expert advice
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Nonstop flights
You can fly direct with American Airlines and United Airlines. Average duration is 2h 19m
Direct flights
Direct flights
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Direct flights
Direct flights
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Top routes
Cheapest
Most popular
Insights
Insights
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Top layover airports
Cheapest • Avg $226 (round-trip)
Shortest trip • 4h 11m (one-way)
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 4 weeks in advance save around 38% compared to booking last minute.
Insights
Insights
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Insights
When to travel
Cheapest • 49% price drop
Most popular
Good to know
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Flight Deals

Cheap Flights from Greenville to Chicago (GSP-CHI)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Greenville to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Greenville to Chicago

Thu, Aug 6 - Thu, Aug 13
United Airlines Logo
6:10 am - 7:30 am
GSP
-
ORD
2h 20mnonstop
United Airlines Logo
1:55 pm - 5:02 pm
ORD
-
GSP
2h 07mnonstop
$269United Airlines
Thu, Aug 6 - Sun, Aug 9
American Airlines Logo
6:34 pm - 8:04 pm
GSP
-
ORD
2h 30mnonstop
American Airlines Logo
8:00 am - 11:00 am
ORD
-
GSP
2h 00mnonstop
$270American Airlines
Thu, Aug 13 - Sun, Aug 16
Southwest Logo
4:40 pm - 10:20 pm
GSP
-
MDW
6h 40m
2 stops
Southwest Logo
5:00 am - 10:10 am
MDW
-
GSP
4h 10m
1 stop
$271Southwest
Mon, Aug 3 - Mon, Aug 10
Multiple Airlines Logo
12:06 pm - 12:15 pm
GSP
-
ORD
25h 09m
1 stop
Multiple Airlines Logo
8:05 am - 4:07 pm
ORD
-
GSP
7h 02m
1 stop
$271Multiple Airlines
Thu, Oct 8 - Tue, Oct 13
Southwest Logo
6:25 am - 2:55 pm
GSP
-
MDW
9h 30m
2 stops
Southwest Logo
9:40 am - 6:30 pm
MDW
-
GSP
7h 50m
2 stops
$272Southwest
Fri, Oct 30 - Tue, Nov 3
Southwest Logo
8:25 am - 1:25 pm
GSP
-
MDW
6h 00m
2 stops
Southwest Logo
6:05 am - 2:10 pm
MDW
-
GSP
7h 05m
2 stops
$273Southwest
Mon, Aug 24 - Thu, Aug 27
Multiple Airlines Logo
4:55 pm - 12:50 pm
GSP
-
ORD
20h 55m
1 stop
Multiple Airlines Logo
8:05 am - 7:39 pm
ORD
-
GSP
10h 34m
2 stops
$278Multiple Airlines
Thu, Aug 6 - Sun, Aug 9
United Airlines Logo
7:40 pm - 11:31 pm
GSP
-
ORD
4h 51m
1 stop
United Airlines Logo
6:17 pm - 9:26 pm
ORD
-
GSP
2h 09mnonstop
$279United Airlines
Thu, Aug 6 - Sun, Aug 9
American Airlines Logo
1:37 pm - 4:48 pm
GSP
-
ORD
4h 11m
1 stop
American Airlines Logo
8:00 am - 11:00 am
ORD
-
GSP
2h 00mnonstop
$280American Airlines
Fri, Oct 30 - Tue, Nov 3
Delta Logo
6:45 am - 12:05 pm
GSP
-
MDW
6h 20m
1 stop
Delta Logo
5:15 pm - 11:37 pm
MDW
-
GSP
5h 22m
1 stop
$289Delta
Booking Insights

KAYAK's insights & trends for Greenville to Chicago flights

Get data-powered insights and trends into flights from Greenville to Chicago to help you find the cheapest flights, the best time to fly and much more.

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

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Greenville to Chicago departing in August.

What is the cheapest Greenville to Chicago flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest return flight from Greenville to Chicago costs $269 on the route between Greenville (GSP) and Chicago O'Hare Intl Airport (ORD). It is also the most popular route.

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

The average price of all round-trip flights from Greenville to Chicago clicked on KAYAK for each day over the last 12 months.

Your flight ticket price will generally be cheaper if you fly to Chicago on a Thursday and more expensive on a Sunday. On your return trip to Greenville, you should consider flying back on a Saturday, and avoid Sundays for better deals.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Greenville to Chicago, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Greenville to Chicago is November, where tickets cost $81 (return) on average. On the other hand, the most expensive months are January and February, where the average cost of round-trip tickets is $195 and $195 respectively.

Can I save money by flying with a layover from Greenville to Chicago?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $348, prices are generally cheapest when you fly direct.

How far in advance should I book a flight from Greenville to Chicago?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Greenville to Chicago, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Greenville to Chicago, you should book around 4 weeks before departure, which saves you about 38% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 16 weeks before departure.

Expert advice

Expert advice for your flight from Greenville to Chicago

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
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.

Good to know

Low seasonFebruary
Cheapest flight$97
Best time to beat the crowds with an average 27% drop in price.
Most popular time to fly with an average 20% increase in price.
Flight from Greenville to Chicago Midway 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
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

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
GSP
-
ORD
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
GSP
-
ORD
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.

FAQs for booking flights from Greenville to Chicago

  • What is the cheapest flight from Greenville to Chicago?

    In the last 5 days, the lowest price for a flight from Greenville to Chicago was $97 for a one-way ticket and $269 for a round-trip.

  • Do I need a passport to fly between Greenville and Chicago?

    A passport is not required to fly from Greenville to Chicago.

  • Which airports will I be using when flying from Greenville to Chicago?

    When flying out of Greenville you will be using Greenville. You will be landing at one of these airports: Chicago Midway or Chicago O'Hare Intl.

  • Which airlines offer Wi-Fi service onboard planes from Greenville to Chicago?

    American Airlines, United Airlines, Lufthansa, and Delta offer inflight Wi-Fi service on the Greenville to Chicago flight route.

  • Which aircraft models fly most regularly from Greenville to Chicago?

    The Embraer 175 (Enhanced Winglets) is the aircraft model that flies most regularly on the Greenville to Chicago flight route.

  • Which airline alliances offer flights from Greenville to Chicago?

    SkyTeam, Star Alliance, and oneworld are the airline alliances operating flights between Greenville and Chicago, with SkyTeam being the most commonly used for this route.

  • On which days can I fly direct from Greenville to Chicago?

    There are nonstop flights from Greenville to Chicago on a daily basis.

  • Which is the best airline for flights from Greenville to Chicago, Delta or United Airlines?

    The two airlines most popular with KAYAK users for flights from Greenville to Chicago are Delta and United Airlines. With an average price for the route of $384 and an overall rating of 7.8, Delta is the most popular choice. United Airlines is also a great choice for the route, with an average price of $336 and an overall rating of 7.4.

  • How does KAYAK find such low prices on flights from Greenville to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Greenville to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Greenville to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Greenville is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Greenville to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Greenville with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Greenville to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Greenville up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Greenville to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $258 or less one-way and $328 or less round-trip.

Prefer to fly direct from Greenville to Chicago?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying 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

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

Information on your arrival and departure airports