$92+ Cheap flights from Greenville (GSP) to Chicago (CHI)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/2. Fares are subject to change and may not be available on all flights or dates of travel.
GSP — CHI
Feb 7 — Feb 141
1 adult, Economy
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Find cheap flights from Greenville to Chicago with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from Greenville to Chicago are usually found in November or April, booked 60 days in advance, depart on a Thursday or Saturday and return on a Saturday
Cheap flight deals from Greenville to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Greenville (GSP) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 8, 2026.
Most accurate provider | eDreams 3 stars |
|---|---|
Most trusted provider | eDreams 3 stars |
Round-trip from | $180 (Kiwi.com) |
One-way from | $92 (Kiwi.com) |
Popular in | January |
Cheapest in | November |
Average price | $386 |
Good round-trip deal | $323 or less |
Good one-way deal | $201 or less |
Find flight deals from Greenville to Chicago
Cheapest flights from Greenville to ChicagoExplore the most affordable flight options available from Greenville to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 8, 2026.
Explore the most affordable flight options available from Greenville to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 8, 2026.
This Kiwi.com deal was found by Cheapflights users on 1/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/295:45 pmGSP - ORD
1 stop7h 01mMultiple Airlines
Wed 2/45:32 pmORD - GSP
1 stop22h 23mMultiple Airlines
Deal found 1/7![Multiple Airlines logo]()
$180
This Kiwi.com deal was found by Cheapflights users on 1/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/309:48 amGSP - ORD
1 stop26h 34mMultiple Airlines
Sun 2/13:05 pmORD - GSP
1 stop16h 53mMultiple Airlines
Deal found 1/8![Multiple Airlines logo]()
$181
This Kiwi.com deal was found by Cheapflights users on 1/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/309:48 amGSP - ORD
1 stop26h 34mMultiple Airlines
Wed 2/45:32 pmORD - GSP
1 stop22h 23mMultiple Airlines
Deal found 1/7![Multiple Airlines logo]()
$186
This Kiwi.com deal was found by Cheapflights users on 1/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/69:48 amGSP - ORD
1 stop26h 34mMultiple Airlines
Sun 2/88:43 pmORD - GSP
1 stop11h 15mMultiple Airlines
Deal found 1/7![Multiple Airlines logo]()
$196
This Mytrip deal was found by Cheapflights users on 1/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/295:45 pmGSP - ORD
1 stop7h 01mMultiple Airlines
Mon 2/210:07 amORD - GSP
1 stop9h 52mMultiple Airlines
Deal found 1/7![Multiple Airlines logo]()
$198
This United Airlines deal was found by Cheapflights users on 1/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/116:35 amGSP - ORD
Nonstop2h 21mUnited Airlines
Sun 2/157:05 amORD - GSP
Nonstop1h 56mUnited Airlines
Deal found 1/7![United Airlines logo]()
$202
This American Airlines deal was found by Cheapflights users on 1/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/217:14 amGSP - ORD
Nonstop2h 16mAmerican Airlines
Mon 3/238:50 pmORD - GSP
Nonstop1h 52mAmerican Airlines
Deal found 1/8![American Airlines logo]()
$203
This United Airlines deal was found by Cheapflights users on 1/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/76:35 amGSP - ORD
Nonstop2h 21mUnited Airlines
Wed 2/111:00 pmORD - GSP
1 stop5h 29mUnited Airlines
Deal found 1/8![United Airlines logo]()
$205
This Mytrip deal was found by Cheapflights users on 1/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/309:48 amGSP - ORD
1 stop10h 50mMultiple Airlines
Mon 2/210:07 amORD - GSP
1 stop9h 52mMultiple Airlines
Deal found 1/7![Multiple Airlines logo]()
$208
This Delta deal was found by Cheapflights users on 1/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/75:40 amGSP - MDW
1 stop5h 13mDelta
Wed 2/116:00 amMDW - GSP
1 stop4h 03mDelta
Deal found 1/8![Delta logo]()
$215
This Delta deal was found by Cheapflights users on 1/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/215:38 pmGSP - MDW
1 stop5h 53mDelta
Mon 3/235:40 pmMDW - GSP
1 stop5h 12mDelta
Deal found 1/7![Delta logo]()
$222
This Delta deal was found by Cheapflights users on 1/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/196:49 amGSP - MDW
1 stop6h 10mDelta
Sun 2/226:00 amMDW - GSP
1 stop4h 13mDelta
Deal found 1/7![Delta logo]()
$229
Cheapflights Fare Finder
Customize your flight search to find flights from Greenville to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated January 8, 2026.
Use the filters below to find and compare flights from Greenville to Chicago that are best for you.
Fly from
Greenville
Fly to
Chicago
Route
Depart
Return
Price
GreenvilleChicago
GSP - ORD
GSPORD
Greenville
Sat 3/21
6:30 am-7:53 am
Nonstop2h 23m
Chicago O'Hare Intl
Tue 3/24
6:10 pm-9:06 pm
Nonstop1h 56m
$195
GreenvilleChicago
GSP - ORD
GSPORD
Greenville
Wed 2/11
6:35 am-7:56 am
Nonstop2h 21m
Chicago O'Hare Intl
Sun 2/15
7:05 am-10:01 am
Nonstop1h 56m
$202
GreenvilleChicago
GSP - ORD
GSPORD
Greenville
Wed 2/4
10:37 am-11:55 am
Nonstop2h 18m
Chicago O'Hare Intl
Wed 2/11
7:10 am-10:16 am
Nonstop2h 06m
$202
GreenvilleChicago
GSP - ORD
GSPORD
Greenville
Wed 2/18
6:30 am-7:53 am
Nonstop2h 23m
Chicago O'Hare Intl
Sun 2/22
7:05 am-10:01 am
Nonstop1h 56m
$202
GreenvilleChicago
GSP - ORD
GSPORD
Greenville
Tue 2/10
6:35 am-7:56 am
Nonstop2h 21m
Chicago O'Hare Intl
Sun 2/15
7:05 am-10:01 am
Nonstop1h 56m
$202
GreenvilleChicago
GSP - ORD
GSPORD
Greenville
Sat 4/11
7:42 pm-11:43 pm
1 stop5h 01m
Chicago O'Hare Intl
Wed 4/15
7:00 am-9:56 am
Nonstop1h 56m
$205
GreenvilleChicago
GSP - ORD
GSPORD
Greenville
Fri 2/6
5:26 pm-6:50 pm
Nonstop2h 24m
Chicago O'Hare Intl
Sun 2/8
9:07 pm-11:59 pm
Nonstop1h 52m
$209
GreenvilleChicago
GSP - ORD
GSPORD
Greenville
Thu 2/19
6:30 am-7:53 am
Nonstop2h 23m
Chicago O'Hare Intl
Sun 2/22
7:05 am-10:01 am
Nonstop1h 56m
$209
GreenvilleChicago
GSP - ORD
GSPORD
Greenville
Fri 2/6
6:35 am-7:56 am
Nonstop2h 21m
Chicago O'Hare Intl
Sun 2/8
7:10 am-10:16 am
Nonstop2h 06m
$209
GreenvilleChicago
GSP - ORD
GSPORD
Greenville
Thu 2/12
6:30 am-7:53 am
Nonstop2h 23m
Chicago O'Hare Intl
Sun 2/15
7:05 am-10:01 am
Nonstop1h 56m
$209
Showing 1-10 of 36 results
Compare providers for flights from Greenville to Chicago
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Greenville to Chicago in January.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Greenville-Chicago flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Greenville-Chicago flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Greenville-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Greenville-Chicago flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Greenville-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Greenville to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Greenville with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Greenville to Chicago
How far ahead should I book a flight from Greenville to Chicago?
Use this chart to determine the optimal time to book a round-trip flight from Greenville to Chicago. Price data was last updated on January 2, 2026.
To ensure you get the cheapest price possible for a flight from Greenville to Chicago, you should look to book at least 60 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
What is the cheapest month to book a flight from Greenville to Chicago?
Currently, February is the cheapest month in which you can book a flight from Greenville to Chicago (average of $57). Flying from Greenville to Chicago in June is currently the most expensive (average of $161). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from GSP to CHI?
Find hourly flight availability from Greenville to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated January 8, 2026.
It’s typically best to fly out from Greenville to Chicago in the evening. Doing so could potentially save you 63% on the flight price compared to flying at noon, which is usually more expensive.
What is the cheapest day to fly from Greenville to Chicago?
Use this chart to determine the cheapest time to fly round-trip from Greenville to Chicago. Price data was last updated on January 3, 2026.
Travelers seeking maximum savings on their Greenville to Chicago flight should consider departing on Wednesday evenings when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
Weekly flight availability from Greenville to Chicago
Explore weekly flight availability from Greenville to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated January 8, 2026.
The most flights from GSP to CHI are scheduled on a Tuesday (19 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (13 on average).
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated January 8, 2026.
Read through reviews of airlines operating flights from Greenville to Chicago, such as Southwest, Delta, and United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Overall
8.0
Comfort
8.0
Boarding
8.1
Food
7.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Overall
8.0
Comfort
8.0
Boarding
8.1
Food
7.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Overall
8.0
Comfort
8.0
Boarding
8.1
Food
7.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Overall
8.0
Comfort
8.0
Boarding
8.1
Food
7.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Overall
8.0
Comfort
8.0
Boarding
8.1
Food
7.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Related info for your journey
Find useful and relevant information for your journey from Greenville to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsLansing
Merrillville
Hammond
Porter
Benton Harbor
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Alternative routes for Greenville to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Top 3 airlines flying from Greenville to Chicago
Discover the top 3 airlines that operate flights from Greenville to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated January 8, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$180 | Average$271 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$201 | Average$296 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$202 | Average$326 | FlexibilityNo cancel fee | On-time69% |