$109 Cheap flight deals from Anderson (GSP) to Chicago (CHI)

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This Weekend's Flight Deals from Anderson to Chicago

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sat, Jun 21 - Mon, Jul 7
GSP
Greenville-Spartanburg Intl.
ORD
O'Hare Intl.
$269 Roundtrip, found 4 days ago
$269
Roundtrip
found 4 days ago
Select Delta flight, departing Sat, Jun 21 from Greenville-Spartanburg Intl. to O'Hare Intl., returning Mon, Jul 7, priced at $269 found 4 days ago
Fri, Jun 20 - Fri, Jun 20
GSP
Greenville-Spartanburg Intl.
MDW
Midway Intl.
$668 Roundtrip, found 5 days ago
$668
Roundtrip
found 5 days ago
Select Delta flight, departing Fri, Jun 20 from Greenville-Spartanburg Intl. to Midway Intl., returning Fri, Jun 20, priced at $668 found 5 days ago

Airfares from $109 One Way, $196 Round Trip from Anderson to Chicago

Prices starting at $196 for return flights and $109 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.

Thu, Sep 4 - Sat, Sep 6
GSP
Greenville
ORD
Chicago
$196 Roundtrip, found 1 day ago
$196
Roundtrip
found 1 day ago
Select American Airlines flight, departing Thu, Sep 4 from Greenville to Chicago, returning Sat, Sep 6, priced at $196 found 1 day ago
Thu, Sep 4 - Sat, Sep 6
GSP
Greenville
ORD
Chicago
$203 Roundtrip, found 1 day ago
$203
Roundtrip
found 1 day ago
Select American Airlines flight, departing Thu, Sep 4 from Greenville to Chicago, returning Sat, Sep 6, priced at $203 found 1 day ago
Tue, Jul 1 - Fri, Jul 4
GSP
Greenville
ORD
Chicago
$206 Roundtrip, found 3 days ago
$206
Roundtrip
found 3 days ago
Select American Airlines flight, departing Tue, Jul 1 from Greenville to Chicago, returning Fri, Jul 4, priced at $206 found 3 days ago
Wed, Jul 23 - Sat, Jul 26
GSP
Greenville
ORD
Chicago
$209 Roundtrip, found 5 days ago
$209
Roundtrip
found 5 days ago
Select United flight, departing Wed, Jul 23 from Greenville to Chicago, returning Sat, Jul 26, priced at $209 found 5 days ago
Thu, Sep 4 - Sat, Sep 6
GSP
Greenville
ORD
Chicago
$209 Roundtrip, found 1 day ago
$209
Roundtrip
found 1 day ago
Select United flight, departing Thu, Sep 4 from Greenville to Chicago, returning Sat, Sep 6, priced at $209 found 1 day ago

Chicago economy flight packages

Price found within the past 48 hours. Click for updated prices.
Embassy Suites by Hilton Chicago Downtown River North
4.0-star property

Embassy Suites by Hilton Chicago Downtown River North

8.4/10 Very Good! (4,196 reviews)

Jul 26 - Jul 30

4 night stay

Greenville (GSP) to Chicago (ORD)

American Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
Excellent stay. Room was clean and well-designed for our family. Fantastic complimentary breakfast every morning.

Reviewed on Jun 13, 2025

Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

9.4/10 Exceptional! (1,609 reviews)

Jul 26 - Jul 30

4 night stay

Greenville (GSP) to Chicago (ORD)

American Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
This is the nicest hotel that I have ever stayed at. Everything was perfect!

Reviewed on Jun 16, 2025

Nobu Hotel Chicago
5.0-star property

Nobu Hotel Chicago

9.4/10 Exceptional! (678 reviews)

Jul 26 - Jul 30

4 night stay

Greenville (GSP) to Chicago (ORD)

American Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
Best hotel I ever been in

Reviewed on Jul 16, 2024

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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

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.

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.