GSP - CHI

$90 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 8/28. 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
$269
Typical prices: $245-$417
American Airlines
Wed 9/2Wed 9/9
GSP - ORD • Non-stop
Cheapest one-way
$90
Typical prices: $222-$329
Multiple Airlines
Fri 8/28
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.
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
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Top airlines
Cheapest • from $269 (round-trip)
Best reviews • 7.8 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 18m
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 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 37% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 49% price drop
Most popular
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

Wed, Sep 2 - Wed, Sep 9
American Airlines Logo
11:31 am - 12:44 pm
GSP
-
ORD
2h 13mnonstop
American Airlines Logo
9:40 am - 12:41 pm
ORD
-
GSP
2h 01mnonstop
$269American Airlines
Thu, Jul 23 - Mon, Jul 27
American Airlines Logo
7:20 pm - 8:51 pm
GSP
-
ORD
2h 31mnonstop
American Airlines Logo
8:35 pm - 11:25 pm
ORD
-
GSP
1h 50mnonstop
$270American Airlines
Wed, Aug 12 - Wed, Aug 19
American Airlines Logo
11:31 am - 12:44 pm
GSP
-
ORD
2h 13mnonstop
American Airlines Logo
8:24 pm - 11:25 pm
ORD
-
GSP
2h 01mnonstop
$271American Airlines
Fri, Aug 7 - Tue, Aug 11
Multiple Airlines Logo
4:57 pm - 12:15 pm
GSP
-
ORD
20h 18m
1 stop
Multiple Airlines Logo
5:30 pm - 7:57 am
ORD
-
GSP
37h 27m
2 stops
$273Multiple Airlines
Sun, Aug 9 - Fri, Aug 14
Multiple Airlines Logo
8:37 am - 12:15 pm
GSP
-
ORD
28h 38m
1 stop
Multiple Airlines Logo
8:05 am - 4:07 pm
ORD
-
GSP
7h 02m
1 stop
$275Multiple Airlines
Mon, Jul 13 - Wed, Jul 22
Multiple Airlines Logo
12:06 pm - 12:15 pm
GSP
-
ORD
25h 09m
1 stop
Multiple Airlines Logo
8:05 am - 7:57 am
ORD
-
GSP
22h 52m
1 stop
$276Multiple Airlines
Wed, Sep 2 - Tue, Sep 8
American Airlines Logo
5:11 pm - 10:11 pm
GSP
-
ORD
6h 00m
1 stop
American Airlines Logo
8:00 am - 11:00 am
ORD
-
GSP
2h 00mnonstop
$279American Airlines
Fri, Aug 14 - Sun, Aug 16
Delta Logo
7:15 am - 12:39 pm
GSP
-
MDW
6h 24m
1 stop
Delta Logo
6:05 am - 10:35 am
MDW
-
GSP
3h 30m
1 stop
$289Delta
Wed, Jul 29 - Wed, Aug 5
Southwest Logo
7:40 pm - 11:15 pm
GSP
-
MDW
4h 35m
1 stop
Southwest Logo
6:30 am - 4:45 pm
MDW
-
GSP
9h 15m
2 stops
$294Southwest
Wed, Aug 19 - Fri, Aug 21
Southwest Logo
1:20 pm - 6:45 pm
GSP
-
MDW
6h 25m
1 stop
Southwest Logo
8:00 am - 12:30 pm
MDW
-
GSP
3h 30m
1 stop
$299Southwest
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 September.

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 $350, 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 37% 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$90
Best time to beat the crowds with an average 26% drop in price.
Most popular time to fly with an average 17% 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.

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 $90 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, Lufthansa, United Airlines, 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 $325 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 $263 or less one-way and $323 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.
7.8
DeltaOverall score based on 8452 reviews
8.5Crew
7.8Entertainment
8.1Boarding
7.2Food
7.8Comfort
Airline reviews

It was as good as it could be. Flying is not a pleasant experience these days.

8.0 ExcellentMark, Jun 2026
LAX - ORD
Read more Delta reviews

It was as good as it could be. Flying is not a pleasant experience these days.

There was an unruly family behind us that made the short flight miserable!!! The cabin crew did nothing to contain it.

Flight delay was frustrating, also you cannot checkin online without delta app, web browser check-in throw errors

Got on the plane and sat there for an hour before departure.

They ended up paying for the bag twice, but the counter wouldn't take my baggage receipt. Left it to me to resolve. Not sure how to resolve the issue.

Cramped seating for me. Luckily it wasn’t a long flight

5 hour delay. They blamed the weather but it was the computer issues they had been dealing with for days.

I usually have a positive experience with Delta. Complimentary upgrades are always nice!

The captain was amazing and kept us informed throughout that there would be some rough air. The flight also got delayed but we were able to actually leave on time, which was great.

The staff did not do a good job of getting everyone boarded quickly, so we missed our take off window and had to sit on the tarmac for 20+ min waiting for our turn. The plan was old. Pockets on the back of seats were torn and tearing off. One of the attendants was rude-she would ask a question but he walking away before you finished answering so she kept getting our drink orders wrong.

1 flight cancelled Had to fly out of different city Flight at new departure city was delayed 3 hours causing us to miss connecting flights. By the time we did make it to Prague our luggage did not. Had to wait day and a half for luggage to be delivered. Customer service was not good. Agents did not arrive at gate until 5-10 minutes before boarding

Awful. Delayed flights, missed connection to Toronto. Hotel vouchers were for already booked hotels x3. Giant waste of my time

Boarding was great, and the crew were very friendly. The seats must have been a bit on the older side and you could feel some of the seat components through the padding. Also, the plugs did not work on the row's entertainment screen or charging ports. Checked bag was transferred for connecting flight, and we appreciated how early we had the connecting gate information.

Very easy ! Use the kiosk and bag drop and right to security within 10 min

Over 5 hour delay with minimal updates or ability to standby for alternative flights. During boarding and 1 hr+ wait for takeoff, seats were drenched w water from air conditioning condensation and always leftover crumbs on carpet and seats

Even through the flight was delayed due to storms near IAH The flight was great! The crew was so hospitable and professional

Boarded early, left early, arrived 40 mins early! A win win for me!

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.

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

The flight and boarding were easy peasy. I was traveling with my 4-year-old, so a smooth boarding experience was especially appreciated. My only piece of feedback is really about where our gate was in O'Hare. They've shoved four gates into a tiny corner of the B terminal and there isn't early enough room or seating for everyone. Not United's problem, but did dent the overall experience.

The planes can use an actual cleaning. The armrest and seats do not appear to be cleaned on this one and most other planes.

Flight was delayed…once landed at ORD, no gates were available so made us wait for 56 minutes after we landed to let us out of the aircraft!

The flight de-boarded after being informed of a 3 hour delay. The gate agent said we could go to lounge. The flight ended up boarding 20 minutes later and I missed it.

We had a mechanical delay which made us 90 minutes late (9:30 PM) then land and put into the penalty box because a plane was in our gate? What the hell! We should get priority.Damn American.

The seats were extremely cramped, with very little legroom or personal space. There was no room left in the overhead bins for a backpack, and the space under the seat in front was so limited that I could barely fit my bag underneath. Overall, the seating arrangement felt very uncomfortable and overcrowded.

weather delay of almost 2 hours then we landed and our gate wasn't available so we waited another 30 min

Delayed flight more than I hour. When boarding we spent some additional time on the plane before takeoff ....

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

Everything was excellent and I enjoyed myself. Thank for everything

When my flight was delayed due to weather, I was rebooked to another flight since it showed that I would miss my connection. It was a lot of work to get back onto my originally connecting flight which was also delayed. That part caused a lot of stress and frustration. The ticketing agent at the desk was not very helpful.

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

Information on your arrival and departure airports