GSP - CHI

$112 Find Cheap Flights from Greenville to Chicago

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 7/3. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Greenville to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Greenville to Chicago, as well as popular online travel agencies
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Everything you should know

Cheapest round-trip
$262
Typical prices: $364-$272
United Airlines
Sat 7/4Sat 7/11
GSP - ORD • Non-stop
Cheapest one-way
$112
Typical prices: $223-$329
Multiple Airlines
Fri 7/3
GSP - ORD • 1 stop
Advice from real travelers
AI-powered summary based on content written by travel experts and KAYAK users. AI can make mistakes.
United's Economy Plus offers extra legroom benefits.
American's Main Cabin Extra includes early boarding.
Expert advice
Expert advice
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Expert advice
Expert advice
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Top airlines
Cheapest • from $262 (round-trip)
Best reviews • 7.9 score
Airline reviews
Airline reviews
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Airline reviews
Airline reviews
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Nonstop flights
You can fly direct with American Airlines and United Airlines. Average duration is 2h 20m
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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Insights
Top layover airports
Cheapest • Avg $226 (round-trip)
Shortest trip • 4h 02m (one-way)
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 5 weeks in advance save around 30% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 46% price drop
Most popular
Good to know
Good to know
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Flight Deals
Booking Insights
Expert advice
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

Sat, Jul 4 - Sat, Jul 11
United Airlines Logo
5:43 pm - 7:00 pm
GSP
-
ORD
2h 17mnonstop
United Airlines Logo
1:55 pm - 5:00 pm
ORD
-
GSP
2h 05mnonstop
$262United Airlines
Thu, May 28 - Sun, May 31
American Airlines Logo
6:41 pm - 8:15 pm
GSP
-
ORD
2h 34mnonstop
American Airlines Logo
8:00 am - 11:04 am
ORD
-
GSP
2h 04mnonstop
$263American Airlines
Wed, May 27 - Sat, May 30
American Airlines Logo
6:41 pm - 8:15 pm
GSP
-
ORD
2h 34mnonstop
American Airlines Logo
7:23 pm - 10:26 pm
ORD
-
GSP
2h 03mnonstop
$267American Airlines
Sat, Jul 4 - Tue, Jul 7
American Airlines Logo
11:46 am - 12:55 pm
GSP
-
ORD
2h 09mnonstop
American Airlines Logo
8:59 pm - 11:58 pm
ORD
-
GSP
1h 59mnonstop
$268American Airlines
Wed, Sep 2 - Wed, Sep 9
American Airlines Logo
6:36 pm - 8:04 pm
GSP
-
ORD
2h 28mnonstop
American Airlines Logo
8:00 am - 10:49 am
ORD
-
GSP
1h 49mnonstop
$269American Airlines
Sat, Jul 4 - Mon, Jul 6
United Airlines Logo
10:30 am - 2:29 pm
GSP
-
ORD
4h 59m
1 stop
United Airlines Logo
6:10 pm - 9:17 pm
ORD
-
GSP
2h 07mnonstop
$272United Airlines
Thu, May 28 - Mon, Jun 1
Southwest Logo
6:25 pm - 11:30 pm
GSP
-
MDW
6h 05m
1 stop
Southwest Logo
6:15 pm - 10:35 pm
MDW
-
GSP
3h 20m
1 stop
$282Southwest
Thu, May 28 - Sat, Jun 6
Southwest Logo
1:50 pm - 8:05 pm
GSP
-
MDW
7h 15m
2 stops
Southwest Logo
3:30 pm - 8:00 pm
MDW
-
GSP
3h 30m
1 stop
$287Southwest
Thu, Aug 27 - Sun, Aug 30
Delta Logo
1:28 pm - 4:15 pm
GSP
-
MDW
3h 47m
1 stop
Delta Logo
6:05 am - 10:40 am
MDW
-
GSP
3h 35m
1 stop
$289Delta
Fri, Aug 7 - Mon, Aug 10
Delta Logo
11:25 am - 4:15 pm
GSP
-
MDW
5h 50m
1 stop
Delta Logo
6:05 am - 10:40 am
MDW
-
GSP
3h 35m
1 stop
$299Delta
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 July.

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.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $340 on average.

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 5 weeks before departure, which saves you about 30% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 25 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$112
Best time to beat the crowds with an average 22% drop in price.
Most popular time to fly and prices are also 4% lower on average.
Flight from Greenville to Chicago O'Hare 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 3 days, the lowest price for a flight from Greenville to Chicago was $112 for a one-way ticket and $262 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 $380 and an overall rating of 7.9, Delta is the most popular choice. United Airlines is also a great choice for the route, with an average price of $316 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 $260 or less one-way and $378 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

Reviews of the top 3 airlines serving from Greenville to Chicago

 
See real verified KAYAK customer reviews for airlines flying from Greenville to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Greenville to Chicago? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.9
DeltaOverall score based on 8448 reviews
8.1Boarding
8.5Crew
7.8Comfort
7.8Entertainment
7.2Food
Airline reviews

WiFi didn’t work on two of four planes. Flight attendants were not overly friendly or welcoming. Planes were extremely slow to board and deplane.

6.0 Goodrghinftl, May 2026
FWA - ATL
Read more Delta reviews

WiFi didn’t work on two of four planes. Flight attendants were not overly friendly or welcoming. Planes were extremely slow to board and deplane.

Delta does a great job with entertainment and free wifi. I can still be in touch with my colleagues while in the air.

Aside from a completely packed plane, I really have no complaints.

Bus to plane was delayed for no apparent reason and our luggage was still on the belt when they shut it off. Took about 20 minutes to turn it back on to get our luggage.

It was a pleasant surprise to have complimentary Wi-Fi on the flight

Much better than Latam, the worse airline company ever. I hope I don't have the need to fly Latam ever in my life again.

Seats in Delta Main are unbelievably close to the seat in front of. Hard to get a backpack under the seat.

The agent at check in and at the gate were less than thrilled to be at work. I'm not a fan of Kayak's placement on the plane. I got put in the middle seat and none of my preferences were used.

In ATL they have two sets of departure screens. Follow what is on your airline's departure board - the ATL Airport Authority departure board had completely incorrect details about the gate assignment for my flight, which would have made me miss boarding.

Flight was delayed it was hot while sitting on the plane, one engine was working on the plane until they had to do some jimmy rigging down the runway in order for the other engine to charge up. It was ridiculous

O’hsre taxi and deboarding took 40 minutes. Needed 20 minutes extra time between connecting flights to avoid running through terminal.

Standard flight with a drinks and a snack- overall very quick flight. The flight attendants were very strict, bordered on rude.

Delayed - weather wasn't bad at either end. Also sat on tarmac in ORD.

boarded early to only find out that flight would sit at gate for 45 min to an hour. Landed in chicago and sat on runway for over an hour before got to gate. Total delay was extensive for a 45 min flight door to door.

The flight was significantly delayed. The inbound flight from EWR was delayed departing because of mechanical problems. My original departure from CLT was 5:28 pm but due to the delay of the inbound flight, after arrival, deplaning, cleaning, boarding, we did not push back from the gate until 9:00 pm. Once in the air, the flight was smooth and what was originally supposed to be an arrival in ORD at 7:30 pm local time turned out to be 9:35 pm.

The flight I was supposed to be on was supposed to take off at 1:50 from State College. It was delayed over and over and over again until somehow I had to rebook on a flight that was supposed to have left State College at 8 am that morning but didn't end up taking off until almost 6 pm. Not only was this completely unacceptable, the "token from United" was a 15 dollar meal voucher that has to be used by today. I would personally like some miles added to my account for this inconvenience. I was in transit for 8 hours from the time I arrive at State College Aiport to when I got home. I was supposed to be home at 3 pm and I returned at 8 pm. Unacceptable. I have not been on an on Time united flight in nearly 5 years.

newer aircraft, ability to connect my headset via blue tooth for entertainment.

Very comfortable flight, snacks and drinks were good, good communication from crew. Could have used a little more information on timing of boarding for group 5

Great flight. Got to watch a movie. Smooth flight and early arrival at ORD.

It was better than excellent. The staff in Mason City were great. The young woman that pushed my wheelchair did more than could be expected of her. She came from India 17 years ago. I don't remember her name.

It was good, the staff was great, and the food, was as usual, tea and biscuit. Bathroom was clean, and the plane was clean as well.

Very good I can’t complain one bit. Thank you American Airlines for making my flight enjoyable and safe!

The staff and service on American Airlines were truly outstanding. I had requested wheelchair assistance for my mother due to her knee issues, and the team went above and beyond every step of the way—from boarding in Boston to our arrival in Chicago. Their care, professionalism, and attentiveness made the entire experience smooth and stress-free. I’m very grateful for the support they provided.

The new planes (American Eagle) are beautiful and especially comfortable. The flight attendants are consistently professional and courteous. And, while it may seem inconsequential, the new liquid tube of coffee creamer—in contrast to the powdered coffee creamer—makes all the difference in a cup of coffee.

Everything was excellent and I enjoyed myself. Thank for everything

I'm not sure American is capable of on-time arrivals and departures. When you land at ORD, you almost always get held on the tarmac because your gate is still occupied. I may have missed my connection, but that ended up up being significantly delayed as well. Once again, I finally got home well after midnight.

Crew at the gate was very crabby and not at all polite. The plane was very hot the entire flight. And the seat cushion was very worn out.

The staff are very, very professional. It's what flying should feel like.

Flight was delayed half hour before boarding, but when I checked flight aware the plane that would Pick us up had a delay of more than an hour. AA should let us know in advance to avoid waiting several hours in the airport

Delays with no explanation. It could have been handled better.

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

Information on your arrival and departure airports