When is the cheapest time of year to fly from Greenville to Chicago?

Based on statistics over the past years, the lowest prices for flights from Greenville to Chicago can be found flying in these months: .

Cheap Flights from Greenville to Chicago

Cheapest flights from Greenville to Chicago

Flaut.Travel was designed and developed by a team dedicated to making the process of searching, comparing and booking airline tickets as easy and convenient as possible. Our service helps travelers to find and buy the cheapest flights from Greenville to Chicago. We have connected more than 40 airlines and airline ticketing agencies to help you find the most suitable and affordable flight option.

Cheapest one way flight

$134

United Airlines

1 transfer

5h 33m

10/12/2025

The cheapest one-way flight from Greenville to Chicago departs on 10/12/2025, is operated by United Airlines and costs $134

Cheapest round trip flight

$233

American Airlines

Direct flight

4h 5m

10/25/2025

The cheapest roundtrip flight from Greenville to Chicago departs on 10/25/2025, is operated by American Airlines and costs $233

The fastest flight

5h 33m

Fastest flight from Greenville to Chicago takes 5h 33m

Direct flights

No direct flights

There are no direct flights on this route.

Earliest flight

7:20 AM

Latest flight

8:04 PM

Direct flights count

56

Distance

904km

Timezone difference

1h

The distance between Greenville and Chicago is 904km (560 miles). There are 56 direct flights from Greenville to Chicago. The time difference between Greenville and Chicago is 1h. Flights from Greenville begin at 7:20 AM. The latest flight from Greenville departs at 8:04 PM

Remember that on average the ideal time to book flights is 2 months before departure!

Airfare from Greenville to Chicago by month

We carefully collect statistics on the search and pricing of airlines and, based on these data, we make an assumption about future prices. Thus, you can better understand which season is the cheapest to fly from Greenville to Chicago

Avg Price

Airlines operating on route

The route Greenville — Chicago is served by a single airline — United Airlines. This means that when planning your trip, you won’t need to spend time choosing between dozens of carriers: all flights are operated by one provider, which simplifies the booking process. Despite the limited choice, passengers can still plan ahead, select optimal departure dates, and buy tickets at the lowest price — from $134. Using our service, you can quickly compare available United Airlines flights and book a seat in advance at a favorable rate.

United Airlines

Starting at $134

Direct Flights from Greenville to Chicago

A direct flight is the most convenient and comfortable way to fly from Greenville to Chicago, despite the fact that sometimes flights with transfers can cost significantly less.

Greenville — Chicago

GSP — CHI

10/12/2025

Departure

Direct flight

UA4468

Starting at $613

Schedule of direct flights from Greenville to Chicago

A direct flight is the easiest way to get to your destination. The following airlines operate non-stop flights from Greenville to Chicago:

Unable to find information about the schedule of direct flights from

Greenville airports overview

GSP

Greenville-Spartanburg International Airport

Airlines flying to this airport

$134

Starting at

$374

on average

Chicago airports overview

ORD

O'Hare International Airport

Airlines flying to this airport

$134

Starting at

$374

on average

Frequently asked questions (FAQ)

Answers to questions about the route that travelers are most interested in.

How much is the cheapest flight ticket from Greenville to Chicago?

The cheapest flight ticket from Greenville to Chicago according to data for the last 48 hours costs $134

When is the best time to buy air tickets on the route Greenville — Chicago?

Often the best time to buy tickets from Greenville to Chicago is 2 months before departure.

How long does it take to fly from Greenville to Chicago?

The fastest flights from Greenville to Chicago start from 5 hours 33 minutes in the air.

Which airline can fly direct from Greenville to Chicago?

The following airlines operate direct flights on the route Greenville — Chicago: United Airlines

Special offers and sales on air tickets from Greenville to Chicago

We keep tight track on airlines' pre-holidays sales and other special offers occurences all the time to let you save maximum amount of funds while traveling to your family or just going out on vacation.

We couldn't find any special offers for flights from Greenville to Chicago

Alternative routes

Atlanta ➜ Chicago•Asheville ➜ Chicago•Chattanooga ➜ Chicago•Charlotte ➜ Chicago•Winston-Salem ➜ Chicago•Myrtle Beach ➜ Chicago•Savannah ➜ Chicago•Knoxville ➜ Chicago•Greenville ➜ Appleton•Greenville ➜ Kalamazoo•Greenville ➜ Champaign•Greenville ➜ Fort Wayne•Greenville ➜ Indianapolis•Greenville ➜ Lansing•Greenville ➜ Milwaukee•Greenville ➜ Muskegon•Greenville ➜ South Bend

•••••••••••••••••••

Cheapest one way flight

$134

United Airlines

1 transfer

5h 33m

10/12/2025

The cheapest one-way flight from Greenville to Chicago departs on 10/12/2025, is operated by United Airlines and costs $134

Cheapest round trip flight

$233

American Airlines

Direct flight

4h 5m

10/25/2025

The cheapest roundtrip flight from Greenville to Chicago departs on 10/25/2025, is operated by American Airlines and costs $233

The fastest flight