CHI - GSP

$93 Find Cheap Flights from Chicago to Greenville

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Greenville departing on 4/28. 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 Greenville

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Greenville, 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 Chicago to Greenville, 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
$225
Southwest
Fri 4/17Wed 4/22
MDW - GSP • 1 stop
Cheapest non-stop
$249
Typical prices: $283-$385
American Airlines
Tue 4/21Tue 4/21
ORD - GSP • Non-stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
American's Basic Economy is carry-on only with late boarding.
United's Priority Boarding helps secure overhead space.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Cheapest • from $225 (round-trip)
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with American Airlines and United Airlines. Average duration is 1h 57m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
Cheapest
Most popular
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $201 (round-trip)
Shortest trip • 3h 20m (one-way)
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 3 weeks in advance save around 23% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 23% price drop
Most popular
Good to know
Good to know
+1
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Greenville!
Flight Deals
Booking Insights
Expert advice
Flight Deals

Cheap Flights from Chicago to Greenville (CHI-GSP)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Greenville 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 Chicago to Greenville

Fri, Apr 17 - Wed, Apr 22
Southwest Logo
5:55 pm - 10:15 pm
MDW
-
GSP
3h 20m
1 stop
Southwest Logo
5:05 pm - 8:00 pm
GSP
-
MDW
3h 55m
1 stop
$225Southwest
Fri, Apr 17 - Wed, Apr 22
Southwest Logo
2:40 pm - 10:15 pm
ORD
-
GSP
6h 35m
1 stop
Southwest Logo
6:45 am - 12:50 pm
GSP
-
ORD
7h 05m
1 stop
$225Southwest
Mon, Apr 13 - Wed, Apr 15
Southwest Logo
5:55 pm - 10:15 pm
MDW
-
GSP
3h 20m
1 stop
Southwest Logo
5:05 pm - 8:00 pm
GSP
-
MDW
3h 55m
1 stop
$227Southwest
Mon, Apr 13 - Tue, Apr 14
Southwest Logo
2:40 pm - 10:15 pm
ORD
-
GSP
6h 35m
1 stop
Southwest Logo
6:45 am - 12:50 pm
GSP
-
ORD
7h 05m
1 stop
$227Southwest
Tue, Apr 14 - Tue, Apr 28
United Airlines Logo
5:45 pm - 8:47 pm
ORD
-
GSP
2h 02mnonstop
United Airlines Logo
10:36 am - 11:53 am
GSP
-
ORD
2h 17mnonstop
$249United Airlines
Thu, Apr 30 - Mon, May 4
Multiple Airlines Logo
7:15 pm - 4:53 pm
ORD
-
GSP
20h 38m
1 stop
Multiple Airlines Logo
5:43 pm - 11:55 pm
GSP
-
ORD
7h 12m
1 stop
$250Multiple Airlines
Sat, Aug 29 - Sat, Sep 5
American Airlines Logo
4:18 pm - 7:09 pm
ORD
-
GSP
1h 51mnonstop
American Airlines Logo
7:39 pm - 8:49 pm
GSP
-
ORD
2h 10mnonstop
$255American Airlines
Tue, Apr 14 - Tue, Apr 28
United Airlines Logo
8:45 am - 2:12 pm
ORD
-
GSP
4h 27m
1 stop
United Airlines Logo
6:30 am - 7:54 am
GSP
-
ORD
2h 24mnonstop
$259United Airlines
Thu, Apr 16 - Mon, Apr 20
Multiple Airlines Logo
5:50 am - 4:53 pm
ORD
-
GSP
34h 03m
2 stops
Multiple Airlines Logo
5:43 pm - 9:36 am
GSP
-
ORD
16h 53m
1 stop
$261Multiple Airlines
Sat, May 2 - Mon, May 4
American Airlines Logo
8:00 am - 11:01 am
ORD
-
GSP
2h 01mnonstop
American Airlines Logo
8:16 pm - 9:38 pm
GSP
-
ORD
2h 22mnonstop
$262American Airlines
Booking Insights

KAYAK's insights & trends for Chicago to Greenville flights

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

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

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

What is the cheapest Chicago to Greenville flight route?

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

The cheapest return flight from Chicago to Greenville costs $209 on the route between Chicago O'Hare Intl Airport (ORD) and Greenville (GSP). It is also the most popular route.

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

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

If you are looking for a flight deal from Chicago to Greenville, look for departures on Saturdays and avoid leaving on a Sunday, as it's usually the priciest day. When flying back from Greenville, Thursday is the cheapest day to fly and Sunday is the most expensive.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Greenville, 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 Chicago to Greenville is January, where tickets cost $223 (return) on average. On the other hand, the most expensive months are May and March, where the average cost of round-trip tickets is $359 and $332 respectively.

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

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 $277, prices are generally cheapest when you fly direct.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago to Greenville, 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 Chicago to Greenville, you should book around 3 weeks before departure, which saves you about 23% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 22 weeks before departure.

Expert advice

Expert advice for your flight from Chicago to Greenville

 
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 seasonJanuary
Cheapest flight$93
Best time to beat the crowds with an average 24% drop in price.
Most popular time to fly with an average 23% increase in price.
Flight from Chicago Midway Airport to Greenville

When to book flights from Chicago to Greenville

Are your dates flexible? Find out the best times to travel from Chicago to Greenville 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 Chicago to Greenville

  • What is the cheapest flight from Chicago to Greenville?

    In the last 3 days, the lowest price for a flight from Chicago to Greenville was $93 for a one-way ticket and $225 for a round-trip.

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

    Even though you are not required to have a passport, keep in mind that an official ID is needed to board the airplane.

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

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

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

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

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

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

  • Which airline alliances offer flights from Chicago to Greenville?

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

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

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

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

    The two airlines most popular with KAYAK users for flights from Chicago to Greenville are Delta and United Airlines. With an average price for the route of $241 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 $309 and an overall rating of 7.4.

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

    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 Chicago to Greenville.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Greenville from Chicago 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 Chicago to Greenville?

    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 Greenville with an airline and back to Chicago with another airline.

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

    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 Greenville from Chicago 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 Chicago to Greenville

  • Looking for a cheap flight? 25% of our users found flights on this route for $178 or less one-way and $267 or less round-trip.

Prefer to fly direct from Chicago to Greenville?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Chicago to Greenville.
Find which airlines fly direct from Chicago to Greenville Airport, which days they fly and book direct flights.

Direct departures

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

Direct returns

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

Reviews of the top 3 airlines serving from Chicago to Greenville

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Greenville. 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 Chicago to Greenville? 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 8327 reviews
7.8Entertainment
7.9Comfort
8.1Boarding
8.5Crew
7.2Food
Airline reviews

The cabin temperature was nice and cool. The wifi was not working.

8.0 ExcellentMatt, Mar 2026
SEA - SJC
Read more Delta reviews

The cabin temperature was nice and cool. The wifi was not working.

Flight late, the waited for a long time for “personal” to arrive at gate to dock the plane in Rochester. So annoying. This flight was expected, why aren’t personel available for the jet bridge?

As previously noted, this flight was great: departure was timely, the crew was friendly and attentive, and wifi connectivity was seamless. In particular, I appreciated that the flight attendant just told me to stow the laptop right before takeoff/landing, and trusted me to do so (which I did!).

Kayak botched up the booking, i had to call delta and fix. In the process Delta failed to honor my comfort plus seat assignment that i had previously.

Entertainment is ok! Boarding and seat with zone is terrible. I paid for the seats but you didn’t give me what I paid for which is exit isles.

the crew cancel the morning service due to the weather. Then the flight got deverted to Nashville . we were on the ground for over two hours the only gave us water once... no food or any snacks.... the crew should have handled better and offered something to passengers.

My recent experience was excellent on Delta! I flew with Delta Comfort and I was really comfortable in my seat. I enjoyed the in-flight service. The flight attendants were so friendly and hospitable. I love the snack on the flight as well. This was my first time flying on Delta and I will definitely consider flying with them again.

My flight was cencaled due with the bad weather on Sunday the crew was poorly mistaken my luggage supposed depart with my flight instead I didn’t have my luggage for almost 3 days the website is poorly respond to my complain until I have someone to do it my connection smooth their not even respon or email me even the have my luggage

Delta needs to step its game up get a more reliable internet service. Internet service was non-existent for this flight.

Mechanical Delay of over an hour with multiple gate changes. Entertainment system down for rejuvenation.

This trip did not start off well. The inbound flight was delayed about 20 minutes. Then, after initial onboarding, the passengers had to deplane due to a mechanical problem. That took about 30 minutes to fix and be cleared. Then, reboarding was chaotic. It took a long time to sort passengers and two passengers on standby were ticketed but there was no seat. So, they had to deplane. One of the flight crew was trying to help passengers figure out a place to put their carry-on bags and that took more time. In the end, our scheduled 10:30 am departure did not actually take off until about 12:05 pm CST. The flight itself was long but we got to Houston. Some passengers missed their connecting flights and had to rebook. Not the best of flights I've had.

We were delayed for about an hour from taking off due to traffic control procedures at the destination airport. But once in the air, the flight went well. The crew members were great and provided cabin service despite moderate turbulence during much of the flight.

Short flight, but no drink/snack service. The flights both going and coming were delayed.

Not being stranded in Chicago for her airport to 11:30 tomorrow morning the 3rd

I was fully checked in the prior night and i was unchecked and then didn’t have a seat when I boarded. Instead of an aisle seat, I was out in the middle seat of the very last row of the plane.

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!

I understand weather is an issue, but making us chase our plane down at five scheduled gates across three terminals in an airport the size of O'Hare was unfair. They'd have probably been better off to leave gates as TBD until the inbound plane is in final approach instead of running us all over the place. Also, props to the consistently-unprepared ground crew in Richmond for once again leaving my lane parked short of the gate because they couldn't have a crew in place on time with 2 hours notice...

cabin crew was OK, food was OK, the trip from the US to Munich was actually pretty bad comfort wise. Noisy aircraft, lights never dimmed even in Business class (night flight) barely sufficient amenities for the price. I have millions of miles with United but TBH American is gaining ground and Delta has always been marginally better then United although on paper United has more longes and cheaper upgrades.

Essy to get on. The hostess gave very little pop, the plane was late getting in, and we are still waiting for our bags. This sucks. :/

The gate got changed several times and the flight was delayed over an hour. Awful experience

American continues to decline in their customer service and its beyond disappointing.

It was an older plane. First Class was not especially roomy or comfortable. It was a short flight so there were no meal but they did offer mixed nuts which used to be normal but now is rare. Crew member was very polite and professional.

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

As previously stated the delay I experienced flying from Wichita to Chicago caused a host of issues. When I finally was able to be booked on the last remaining American flight from Chicago to Cincinnati, the gate changed four times with the last change occurring very near the scheduled boarding time. While I didn't have a problem moving from gate to gate, I did notice and make note of others that had mobility issues and had to move each time for the gate change.

Maintenance took a very long time and then we were in a holding pattern. While a one-off maintenance issue is standard, there were delays on both of my flights for this trip based on maintenance issues with the planes, which delayed both flights over 45 minutes. Thankfully, I didn't have any connections but it wasn't an experience that would make me pick AA if I have other options.

No Snacks or Entertainment. The flight was short, snacks should still be given.

See prior comment about how Kayak mishandled my reservation and delayed my arrival by 6 hours.

Boarding delayed 20 minutes for no reason, no wifi, in flight entertainment, or snacks / waters?

Delayed an hour due to operational issues. Minimal apologies or care for the significant inconvenience caused. Landed at nearly 1am and they still couldn’t find ground staff to get us off the plane promptly.

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

Information on your arrival and departure airports