$132 Cheap flight deals from Anderson (GSP) to Chicago (CHI)

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Airfares from $132 One Way, $254 Round Trip from Anderson to Chicago

Prices starting at $254 for return flights and $132 for one-way flights to Chicago were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sat, Sep 5 - Tue, Sep 15
GSP
Greenville
RFD
Rockford
$254 Roundtrip, found 4 days ago
$254
Roundtrip
found 4 days ago
Select American Airlines flight, departing Sat, Sep 5 from Greenville to Rockford, returning Tue, Sep 15, priced at $254 found 4 days ago
Sat, Sep 5 - Tue, Sep 15
GSP
Greenville
ORD
Chicago
$255 Roundtrip, found 3 days ago
$255
Roundtrip
found 3 days ago
Select American Airlines flight, departing Sat, Sep 5 from Greenville to Chicago, returning Tue, Sep 15, priced at $255 found 3 days ago
Sat, Sep 5 - Tue, Sep 15
GSP
Greenville
RFD
Rockford
$261 Roundtrip, found 14 hours ago
$261
Roundtrip
found 14 hours ago
Select American Airlines flight, departing Sat, Sep 5 from Greenville to Rockford, returning Tue, Sep 15, priced at $261 found 14 hours ago
Fri, Sep 25 - Wed, Sep 30
GSP
Greenville
ORD
Chicago
$262 Roundtrip, found 12 hours ago
$262
Roundtrip
found 12 hours ago
Select United flight, departing Fri, Sep 25 from Greenville to Chicago, returning Wed, Sep 30, priced at $262 found 12 hours ago
Tue, Jun 9 - Wed, Jun 10
GSP
Greenville
ORD
Chicago
$265 Roundtrip, found 1 day ago
$265
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Jun 9 from Greenville to Chicago, returning Wed, Jun 10, priced at $265 found 1 day ago

Chicago economy flight packages

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

9.4/10 Exceptional! (3,991 reviews)

Jun 3 - Jun 5

2 night stay

Greenville (GSP) to Chicago (ORD)

American Airlines • Non-stop • Coach

Chicago (ORD) to Greenville (GSP)

Southwest Airlines • Non-stop • Coach
Save 100% on your flight
Price was $906, price is now $613 per person
$613
per person
found 11 hours ago
Great location, clean, and great breakfast buffet

Reviewed on Mar 8, 2026

Swissotel - Chicago
4.5-star property

Swissotel - Chicago

9/10 Wonderful! (3,293 reviews)

Jun 18 - Jun 21

3 night stay

Greenville (GSP) to Chicago (ORD)

American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,137, price is now $752 per person
$752
per person
found 1 day ago
Great stay and we highly recommend. We will be back.

Reviewed on Apr 21, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0-star property

Sable at Navy Pier Chicago, Curio Collection by Hilton

9.4/10 Exceptional! (2,478 reviews)

Jun 18 - Jun 21

3 night stay

Greenville (GSP) to Chicago (ORD)

American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,445, price is now $974 per person
$974
per person
found 1 day ago
Courteous staff, clean room, conveniently located right on the pier.

Reviewed on Nov 3, 2025

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More About Flying To Chicago from Anderson

Route Information for Flights from Anderson to Chicago

Origin Airport IATA Code
GSP
Destination Airport IATA Code
CHI
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Anderson to Chicago

Looking for cheap Anderson to Chicago flights? Orbitz has the cheapest air fares for flights from Anderson to Chicago. Plus, with our cutting-edge mobile tools, travel planning has never been easier or more wallet-friendly.

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Use the Orbitz app or the mobile Orbitz site, m.orbtiz.com, to see information about your Anderson to Chicago flights anytime you need it. Your itinerary is also sent to your email address for reference. Access updates on your flights from Anderson to Chicago on your mobile device too, including delays and baggage claim details.

Cheap Air Ticket Prices Guaranteed

Orbitz is your number one source for low fares for Anderson to Chicago flights. Our low price guarantee on domestic and international air tickets give you great savings for a perfect trip to Chicago. Need hotels too? You can book them last minute on your mobile phone.

Frequently asked questions

Are there non-stop flights from Anderson to Chicago?
Yes, you'll be pleased to hear that you can jet straight from Roger Milliken Field to O'Hare Intl. Airport (ORD). Direct flights can be booked with United Airlines and American Airlines.
What is the shortest flight from Anderson to Chicago?
If the weather is good and there are no unexpected hiccups, you could be jetting into MDW from GSP in just 2 hours and 42 minutes. With such a fast flight time, think about taking carry-on luggage only.
What airlines fly from Anderson to Chicago most frequently?
Take a look at United Airlines (UA). This airline offers some of the most frequent flights from Roger Milliken Field to ORD. It operates 91 services on this route each month and is popular with passengers. American Airlines (AA) will also take you to your destination in style and comfort. Offering 52 monthly flights between Anderson and Chicago, it's another popular airline to look into.
What is the cheapest day of the week to fly?
Consider flying out early in the week to save on your airfare. Orbitz data from 2021 shows that Monday is the cheapest day to depart, followed by Tuesday. Saturday showed the highest average ticket prices likely because many travelers prefer to start their vacation on a weekend.
What is the cheapest month to fly?
We won't keep you guessing, according to Orbitz data from 2021, the cheapest month to fly is February. Perfect for those who need a weekend getaway, or just a break from it all in the shortest month of the year. Be aware that the most expensive time to fly is during the height of summer in July, and in the holiday month of December.*According to flight demand on Orbitz.com from January to December 2021. Savings are subject to change based on departure location, date and destination.

More Destinations

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.