Cheap flights from Greenville to Chicago

One-way fares from $167 · GSP → CHI · prices found by travellers in the last 48 hours

Compare all dates Chicago → Greenville
Cheapest fare
$167

United Airlines · Sat, Nov 14

Cheapest month
November

from $167

Direct flights
Yes

United Airlines

Flight time
2h 15m

900 km

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Cheapest month to fly from Greenville to Chicago

Lowest one-way fare per person in each month. Choose a month to see every date.

  1. November 2026 Cheapest $167

Cheapest dates in November 2026

The lowest fares we've seen for each day, cheapest first.

United Airlines
Depart06:00 Sat, Nov 14GSP → ORD 2h 15m · Direct
$167one way, per person
View deal
See every date in November 2026 →

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About flights from Greenville to Chicago

Greenville (GSP) and Chicago (CHI) are about 900 km apart. Direct flights take around 2h 15m, and recent direct fares were with United Airlines. Over the next few months, one-way fares start from $167, and November 2026 is currently the cheapest month to fly.

These prices come from searches travellers made in the last 48 hours, so they move quickly. If you see a good fare, it's worth booking soon. FlightsExp is free to use: you book directly with our travel partner.

Frequently asked questions

How much is a flight from Greenville to Chicago?

The cheapest one-way fare we've seen recently is $167 with United Airlines, departing Saturday, November 14, 2026.

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

November 2026 currently has the lowest fares, from $167 one way.

Are there direct flights from Greenville to Chicago?

Yes. Recent direct fares were with United Airlines.

How long is the flight from Greenville to Chicago?

A direct flight takes about 2h 15m. Greenville and Chicago are around 900 km apart.

Which airlines fly from Greenville to Chicago?

Recent fares on this route were with United Airlines.

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