GSP - CHI

$90 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 4/20. 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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41.299.237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$157
Overall average: $279
Delta
vie. 5/1lun. 5/4
GSP - ORD • 1 stop
Cheapest non-stop
$209
Typical prices: $243-$376
United Airlines
mié. 4/1dom. 4/5
GSP - ORD • Non-stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
United's Economy Plus offers extra legroom benefits.
American's Main Cabin Extra includes early boarding.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Delta
Cheapest • from $157 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Every day
You can fly direct with American Airlines and United Airlines. Average duration is 2h 19m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
GSP
-
ORD
Cheapest
GSP
-
ORD
Most popular
Insights
Insights
Insights
Insights
Top layover airports
Baltimore (BWI)
Cheapest • Avg $232 (round-trip)
Charlotte (CLT)
Shortest trip • 3h 58m (one-way)
Insights
Insights
Insights
Insights
When to book
5 weeks
in advance
Our data shows that travelers who book at least 5 weeks in advance save around 18% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
February
Cheapest • 16% price drop
October
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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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

vie., may. 1 - lun., may. 4
Delta Logo
5:23 pm - 9:25 pm
GSP
-
ORD
5h 02m
1 stop
Delta Logo
6:00 am - 3:14 pm
ORD
-
GSP
8h 14m
1 stop
$157Delta
mié., abr. 1 - dom., abr. 5
Delta Logo
7:30 am - 12:29 pm
GSP
-
MDW
5h 59m
1 stop
Delta Logo
1:10 pm - 5:29 pm
MDW
-
GSP
3h 19m
1 stop
$157Delta
mié., abr. 1 - dom., abr. 5
United Airlines Logo
6:30 am - 7:54 am
GSP
-
ORD
2h 24mnonstop
United Airlines Logo
7:00 am - 9:56 am
ORD
-
GSP
1h 56mnonstop
$209United Airlines
sáb., mar. 21 - lun., mar. 23
American Airlines Logo
7:40 am - 8:56 am
GSP
-
ORD
2h 16mnonstop
American Airlines Logo
8:50 pm - 11:42 pm
ORD
-
GSP
1h 52mnonstop
$210American Airlines
vie., may. 1 - mié., may. 6
American Airlines Logo
8:16 pm - 9:38 pm
GSP
-
ORD
2h 22mnonstop
American Airlines Logo
9:00 pm - 11:59 pm
ORD
-
GSP
1h 59mnonstop
$212American Airlines
sáb., mar. 7 - mar., mar. 10
Delta Logo
1:00 pm - 6:55 pm
GSP
-
ORD
6h 55m
1 stop
Delta Logo
7:10 am - 2:56 pm
ORD
-
GSP
6h 46m
1 stop
$213Delta
mar., mar. 10 - mar., mar. 17
United Airlines Logo
10:00 am - 2:34 pm
GSP
-
ORD
5h 34m
1 stop
United Airlines Logo
7:05 am - 10:01 am
ORD
-
GSP
1h 56mnonstop
$219United Airlines
lun., abr. 20 - jue., abr. 23
Multiple Airlines Logo
5:43 pm - 11:22 am
GSP
-
ORD
18h 39m
1 stop
Multiple Airlines Logo
3:15 pm - 4:53 pm
ORD
-
GSP
24h 38m
2 stops
$223Multiple Airlines
mar., abr. 7 - vie., abr. 10
Southwest Logo
5:10 pm - 10:15 pm
GSP
-
MDW
6h 05m
1 stop
Southwest Logo
5:55 pm - 10:15 pm
MDW
-
GSP
3h 20m
1 stop
$244Southwest
jue., abr. 9 - dom., abr. 12
Southwest Logo
6:25 am - 12:10 pm
GSP
-
MDW
6h 45m
1 stop
Southwest Logo
5:15 am - 1:10 pm
MDW
-
GSP
6h 55m
1 stop
$260Southwest
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.

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 $209 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 February, where tickets cost $239 (return) on average. On the other hand, the most expensive months are January and March, where the average cost of round-trip tickets is $331 and $319 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 $283, 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 5 weeks before departure, which saves you about 18% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 19 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$90
Best time to beat the crowds with an average 16% drop in price.
Most popular time to fly with an average 1% increase in price.
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.

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 $90 for a one-way ticket and $157 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, Southwest or Delta?

    The two airlines most popular with KAYAK users for flights from Greenville to Chicago are Southwest and Delta. With an average price for the route of $319 and an overall rating of 8.0, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $268 and an overall rating of 7.9.

  • 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 $233 or less one-way and $346 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 4 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.
8.0
SouthwestOverall score based on 4295 reviews
8.1Boarding
7.5Entertainment
8.0Comfort
7.0Food
8.6Crew
Airline reviews

The WiFi and crew on the plane were good, however, the boarding experience was awful. I paid for the Choice Preferred and was boarded in group 5 so all overhead storage was full. They found room for our luggage, but further back making getting off the plane a nightmare. Also, we were in row 6 and the seats were extremely uncomfortable. Both my daughter and I had no leg room and couldn’t wait to get off the plane.

4.0 OkayAnonymous, Feb 2026
BOI - LAS
Read more Southwest reviews

The WiFi and crew on the plane were good, however, the boarding experience was awful. I paid for the Choice Preferred and was boarded in group 5 so all overhead storage was full. They found room for our luggage, but further back making getting off the plane a nightmare. Also, we were in row 6 and the seats were extremely uncomfortable. Both my daughter and I had no leg room and couldn’t wait to get off the plane.

The charges were ridiculous for an hour flight and the turbulence was very scary.

Still need to work out the kinks on the new assigned seating boarding process. Otherwise, a very good flight.

WiFi did not work. Boarding with the new seating assignments took too long. The temperature in the terminal was obnoxious. +/- 80°

The seats are now more narrow. I paid for front row the seats in the front are even more narrow than before.

Only downside was the legroom and seat width, which is always a problem unless I spend more for a premium seat.

My flight from Denver to Minneapolis was excellent. My flight from Minneapolis to Denver was one of the worst I flights I have ever experienced. I had a window seat, the gentleman in the middle seat was morbidly obese and SW should have made him purchase two seats. His elbow dug into my arm most of the way even after I asked to please be careful. I was literally squashed between the him and the window with no wiggle room. The plane was full so it was not possible to ask for a different seat. I realize I should have complained to the flight attendant but I didn't feel anything could be done to rectify the situation. I fly SW often, I will continue to do so as this was my first negative experience.

I was assigned seat 7E, yet my boarding was Group 5, which caused me to have to put my luggage in the back of the plance above `19 or 20 aisle, as passengers who had boarded earlier took the overhead bins in the front. SW needs to monitor bin space and ensure that bin space above the seat are aligned to those sitting near their seats. Also the seating assignments needs to align with group number. Maybe board those last first and so on? Having said the ALL the passengers on the plane were gracious enough to allow me and other passengers in this dilema to retrieve our luggage and helped us along the way. I always love the flight staff, as always their fantastic and I can't rave about them enough!

I appreciate the staff who allowed me to board though I arrived a little late! Regarding the assigned seating, I had booked my flight before this change and wasn't aware of the change at the time, and so I didn't select a seat at booking as I didn't realize it was relevant. Better communication about the change would have been helpful for preparing.

Flight attendants very hospitable and friendly. Pilot flew a smooth take off and landing.

Boarding and crew were fantastic, but I paid for a window seat with no window. Seat 11D on a CRJ-900 apparently does not have a window. Lesson learned.

Terrible. Four hour delay because Delta could not find crew to man the aircraft. Terrible communication. Terrible insight into the delays. One of the worst flight experiences I’ve had.

The landing was the worst I’ve experienced with a flight.

The crew, and fellow passengers, were super gracious and kind. There seemed to be plenty of bin space even though the plane was full. It’s nice to get a glass of wine with dinner in Premiere seating, and there was a lot of food.

First flight out and was 85 minutes delayed. Notification came out way too late

Delta flights recently are always delayed AND at jfk tney get the gates further away (need To walk 20’ to get to them/all the way at the end of the terminal). Not sure whats happening but price doesnt match experience!

Everything I mentioned earlier - the airbus was more comfortable indeed and the experience was further enhanced.

Delta continues to set the benchmark for traveler-friendly service with minimal disruption and clear communication within the mainland US (coast to coast). I am consistently pleased to be a Delta customer, and this experience once again met my expectations. There was a brief delay departing from MIA due to a technical issue that required the aircraft to return to the gate. However, the situation was handled professionally and transparently. Fortunately, my planned layover allowed ample buffer time, so the adjustment caused no stress. Overall, another smooth and reassuring experience.

Good experience and the flight landed early. There was no food I had or entertainment.

Flight was delayed and no reasons provided. After the passengers were boarded, the crew made announcement that the captain has jot arrived and he would take another 15 mins. All passengers patiently sat until the captain came and started. Terrible experience!

Crew was great (professional, attentive, prompt). Snacks for 4 hrs flight is deplorable.

United Airlines is my preferred airlines and I am thankful for Gary who also help support me on the phone to switch my flight literally last min.

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

It was a pretty standard flight... until the almost hour and a half spent on the taxi way. I get that the weather has been poor but the delay had nothing to do with the weather and more to do with a plane with several issues tying up the gate. I get that that happens from time to time but this has been EVERY flight I've been on for the past 5 years and I fly 3 to 5 times a year. This isn't just United... it's American, it's Delta. It's an issue with the entire industry. I work for UPS and packages on a cargo plane get better service than people do these days. Anymore I HATE flying.

Perfect flight. Smooth flight. Arrived 20 minutes early at destination. Excellent service.

The flights were on time which was great give. It was holiday travel season and there’d been some weather issues. The only complaint and this is every time with United is the terrible seat design. The head rest is not built for comfort and having my neck bent forward for a cross country trip reminded me while I try not to take United flights as a rule.

Everything was absolutely wonderful from check in to baggage claim. Staff was very professional and sweet. Will definitely recommend United to family and friends.

They did the one thing that really matters - got to Chicago early.

The flight was on time. I generally don’t drink or eat on short flights and the seats were good and the flight attendants were friendly. That’s all I expect

It was nice to have gotten up upgraded to first class with a meal on a three hour flight

American Airlines was great and worked very hard to change my ticket so I could get an earlier, direct flight back to Dallas. However, I was informed that Kayak made mistakes with my itinerary and classified my ticket as desiring to be on the earlier flight instead of taking the necessary step of calling AA to get me on the standby list. This ended up keeping me from being added to the standby list and delayed me getting home by 6 hours. I am happy to discuss this further with Kayak so they can correct their procedures so this won't happen again.

Waited for oxygen tanks for 30 minutes after boarding was complete.

We flew in first class. The crew did not offer drinks before the flight took off, but they treated us well during the flight. The food was excellent. There was actually too much food served, but it was nice to have all the options.

Update to handle the delay was very bad, crews no smiles or welcome or thanks. Don’t care attitude

Pilot navigated severe weather/snow storm with skill. Described his intentions clearly

Little warm on the plane and delayed for an hour

So excited very proud first of all I wanna thank kayak all updates very professional and fast alart And amazing cabin crew so nice to me they deserve big salute

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

Awful. They won’t help me with anything. I booked on American but they abdicated to Iberia. The ticket was overpriced. Everything negative

I enjoyed the extra leg room compared to other airlines. The first stewards made my daughter’s birthday special by giving her an extra snack. Then the last one coming home from Chicago to Appleton made our night really enjoyable Thanks for making our trip enjoyable

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

Information on your arrival and departure airports