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Flights from Greenville to Chicago from $140

Find cheap flight tickets from Greenville (GSP) to Chicago (MDW). Cheapest fare starts from $302.
Greenville

GSP

→

Chicago

MDW

09/26/2025 – 10/03/2025

Cheap flight deals from Greenville to Chicago

Average price start from:
i

$302

Greenville to Chicago

One-way from:
i

$140

Greenville to Chicago

Cheapest day:
i

Wednesday

Cheapest flights to Chicago on this day

Cheapest In:
i

January

Cheapest prices for flights to Chicago this month

Find flight deals from Greenville to Chicago

Cheapest flights from Greenville to Chicago

ONEWAY FLIGHTS

LAST MINUTE

CHEAP FLIGHTS

BEST FLIGHTS

Explore the cheapest oneway flights from Greenville to Chicago spotted daily.

GSP

GSP

GSP - Greenville • 2025-09-26 • 09:00

Unknown

60 min

MDW

MDW

$140

Non-stop • 60 min

GSP

GSP

GSP - Greenville • 2025-09-26 • 09:00

Unknown

60 min

MDW

MDW

$149

Non-stop • 60 min

GSP

GSP

GSP - Greenville • 2025-09-26 • 09:00

Unknown

60 min

MDW

MDW

$190

Non-stop • 60 min

Price Trends & Analysis

Weekly Price Trends

If your flying dates are flexible, consider flying to Chicago on a Wednesday.

Monthly Price Trends

The cheapest month for flights from Greenville to Chicago is January.

Weather & Climate Information

Temperature

Plan your visit to Chicago with current temperature data. Chicago experiences varied weather throughout the year, with temperatures ranging from mild to warm depending on the season.

Rainfall

Stay prepared for your trip to Chicago with rainfall information. Understanding precipitation patterns helps you pack appropriately and plan outdoor activities during your visit.

Airlines at MDW

Experience seamless travel from Greenville to Chicago with trusted airlines like AERgO International, Aero, Aeroregional, Afriqiyah Airways. These carriers ensure reliable connections and flexible scheduling options for travelers. Flight duration typically ranges around 10-15 hours, with most routes including one stopover in major aviation hubs. For your trip from Greenville to Chicago, these airlines offer modern amenities and professional service to make your journey comfortable and enjoyable.

Places to Visit in Chicago

Chicago, the Windy City, captivates with its stunning skyline and vibrant neighborhoods, blending architectural marvels with rich cultural heritage. Visitors can explore world-class museums like the Art Institute, savor deep-dish pizza, and stroll along the scenic shores of Lake Michigan. Experience the pulse of the city through its lively jazz and blues scene, and delight in the dynamic fusion of cultures that make Chicago a true American gem.

About Chicago

Discover the beauty of Chicago when flying from Greenville. This captivating city combines rich heritage with contemporary charm, offering something special for every traveler. Plan your visit during off-peak periods for optimal savings and a more relaxed experience.

Airlines Flying from Greenville to Chicago

Experience seamless travel from Greenville to Chicago with trusted airlines like AERgO International, Aero, Aeroregional, Afriqiyah Airways. These carriers ensure reliable connections and flexible scheduling options for travelers. Flight duration typically ranges around 10-15 hours, with most routes including one stopover in major aviation hubs. For your trip from Greenville to Chicago, these airlines offer modern amenities and professional service to make your journey comfortable and enjoyable.

Hotels in Chicago

Explore excellent hotel options near MDW Airport for your Chicago visit: • undefined - distance not available These hotels near Chicago airport combine convenience with comfort, making them perfect for both short layovers and extended stays. Check for special offers and airport shuttle services.

Frequently Asked Questions

What's the lowest price for flights from Greenville to Chicago?

You can find flights starting from $140. For better deals, book during January and choose Wednesday departures.

How long is the journey from Greenville to Chicago?

The average flight time is about 10-15 hours, with most routes including one stopover for better pricing and comfort.

What airlines operate flights on this route?

Several airlines serve this route including AERgO International, Aero, Aeroregional. Research current schedules and compare prices for the best deal.

How far in advance should I book?

For the best prices, book 2-3 months ahead and consider traveling during January when prices are typically lower.

What accommodation options are near MDW Airport?

MDW Airport has several nearby hotels with shuttle services, making it convenient for travelers with early or late flights.

What attractions can I visit in Chicago?

Chicago features a wonderful combination of historical sites and modern attractions. The best time to visit is during pleasant weather months for optimal sightseeing.

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