GSP - CHI

$92 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 8/17. 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
Travelers love KAYAK
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-$372
United Airlines
Wed 9/2Sun 9/6
GSP - ORD • Non-stop
Cheapest one-way
$92
Typical prices: $222-$329
Multiple Airlines
Mon 8/17
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
Insights
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
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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 - Sun, Sep 6
United Airlines Logo
6:30 am - 7:47 am
GSP
-
ORD
2h 17mnonstop
United Airlines Logo
5:59 pm - 9:07 pm
ORD
-
GSP
2h 08mnonstop
$269United Airlines
Tue, Aug 4 - Tue, Aug 11
American Airlines Logo
7:20 pm - 8:51 pm
GSP
-
ORD
2h 31mnonstop
American Airlines Logo
3:05 pm - 6:04 pm
ORD
-
GSP
1h 59mnonstop
$270American Airlines
Sat, Jul 4 - Sat, Jul 25
United Airlines Logo
6:10 am - 7:30 am
GSP
-
ORD
2h 20mnonstop
United Airlines Logo
6:55 am - 9:55 am
ORD
-
GSP
2h 00mnonstop
$272United Airlines
Fri, Aug 14 - Sun, Aug 16
Multiple Airlines Logo
4:57 pm - 12:15 pm
GSP
-
ORD
20h 18m
1 stop
Multiple Airlines Logo
8:05 am - 7:39 pm
ORD
-
GSP
10h 34m
2 stops
$273Multiple Airlines
Thu, Jul 30 - Sun, Aug 2
Multiple Airlines Logo
3:19 pm - 12:15 pm
GSP
-
ORD
21h 56m
1 stop
Multiple Airlines Logo
8:05 am - 8:12 pm
ORD
-
GSP
11h 07m
1 stop
$274Multiple 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
Wed, Sep 2 - Wed, Sep 9
Delta Logo
5:20 pm - 10:36 pm
GSP
-
MDW
6h 16m
1 stop
Delta Logo
6:05 am - 11:03 am
MDW
-
GSP
3h 58m
1 stop
$289Delta
Wed, Jul 22 - Sat, Jul 25
Southwest Logo
7:40 pm - 11:15 pm
GSP
-
MDW
4h 35m
1 stop
Southwest Logo
5:00 am - 1:20 pm
MDW
-
GSP
7h 20m
1 stop
$294Southwest
Tue, Aug 18 - Sat, Aug 22
Southwest Logo
11:00 am - 4:50 pm
GSP
-
MDW
6h 50m
2 stops
Southwest Logo
6:45 am - 5:30 pm
MDW
-
GSP
9h 45m
2 stops
$299Southwest
Sat, Jul 11 - Wed, Jul 15
Delta Logo
5:16 pm - 10:15 pm
GSP
-
MDW
5h 59m
1 stop
Delta Logo
11:05 am - 4:07 pm
MDW
-
GSP
4h 02m
1 stop
$309Delta
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.

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 $334 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 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$92
Best time to beat the crowds with an average 26% drop in price.
Most popular time to fly and prices are also 3% 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 5 days, the lowest price for a flight from Greenville to Chicago was $92 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 $322 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 $268 or less one-way and $330 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 8440 reviews
7.2Food
7.8Entertainment
8.1Boarding
8.5Crew
7.8Comfort
Airline reviews

FA was a bit strange and dodgy not very characteristic of Delta

6.0 GoodSaad, Jun 2026
LGA - ATL
Read more Delta reviews

FA was a bit strange and dodgy not very characteristic of Delta

Not really a “Delta” problem but worth mentioning: Boarding was a difficult process. TSA seemed understaffed and Pre-Check took longer than regular TSA. The supervisor was frazzled and yelled at travelers. Once through TSA, we had to put our carry-ons through another x-ray machine. Then queue up to board with both boarding pass and ID. Then, when we got to the stairs on the tarmac, we had to show our boarding pass again. Maybe this is just normal for Kona since the terminal is outdoors (but still a “secured” area).

flight was delayed 4+ hours. there was really no understanding of why? weather? the last hour of delay was post boarding. pilot seat was broken. was that the real reason? nonetheless, long day of inconveniences.

Love me some Delta. One of the few airlines to recognize and support veterans. Easy boarding, flight was on time and arrived early and the flight attendants were excellent on this flight.

I thought the service was very nice and pleasant. There were no hiccups and no issues so overall a good experience.

Very good flight. Crew was great. No issues and we even arrived early.

The flights are constantly late anymore, and they won't even give you a glass of water on the plane. For years, they were able to do a service on this flight from Atlanta to Knoxville and Knoxville Atlanta now they say it's too short of a flight. You can't even get a quick drink of water.

Flight got canceled 4 times, missed my connecting flight due to delays, have to wait to go home tomorrow

Third flight in two months where the crew was not there. Comfort seating does not guarantee overhead bin space. Passengers with children are allowed on the plane first - if you are flying to and from Orlando, this means half the plane has boarded before you get on. And somehow all the bin space is taken up. 3 out of 5 flights have had issues with equipment or procedure. Some of these instances caused the flight to be delayed because of a "nuisance" light. One time it was a bag that had been brought on board but did not belong to anyone so we had to return to the gate. Last night we were told the "AC" on the plane doesn't work well and we're 10th for take off- because the crew was late - and that it will get cool when we're in the air. Not sure if this is usual, but I didn't think flight crew could jump seat in first class. Movie and TV selection has not been refreshed for several months- flying one to two round trips each month easily exhausts the list of content.

Great experience nice pilot very soft and easy landing and take off

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!

These airplanes should be illegal. The seats are two tight, it is a safety issue. Wheelchair support was ridiculously slow. We almost missed our flight.

This flight is a quick way to get to Chicago, but a bit expensive.

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

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 ....

The flight was delayed significantly and we sat on runway after landing for awhile. Best thing was the flight attendant, Jenny, in first class, who was very professional and attentive. She was excellent - the rest of the flight was not.

The flight attendants were extremely sourly and borderline rude. I did not feel appreciated as an AA customer once.

The flight from LA to Chicago was smooth and service was very good overall.

The Mario was so helpful and provided amazing customer service however l have being waiting for a callback for almost a week now and have not heard anything further after l informed them l wanted to change my date of traveling because of my hospital appointment even send them proof and l was unable to use manag your booking on their website is a bit frustrating and l would appreciate an update on My request as soon as possible. And have called them times without numbers no response

Awful, tons of delays, I got into Chicago multiple hours late meaning I hit the very traffic I tried so desperately to avoid. Just empty apologies from American Airlines text alerts. Trash behavior from a trash airline.

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

Information on your arrival and departure airports