$153 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.

Fri, Sep 11 - Sun, Sep 13
GSP
Greenville-Spartanburg Intl.
ORD
O'Hare Intl.
$663 Roundtrip, found 6 days ago
$663
Roundtrip
found 6 days ago
Select American Airlines flight, departing Fri, Sep 11 from Greenville-Spartanburg Intl. to O'Hare Intl., returning Sun, Sep 13, priced at $663 found 6 days ago
Fri, Sep 11 - Sun, Sep 13
GSP
Greenville-Spartanburg Intl.
MDW
Midway Intl.
$696 Roundtrip, found 6 days ago
$696
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Fri, Sep 11 from Greenville-Spartanburg Intl. to Midway Intl., returning Sun, Sep 13, priced at $696 found 6 days ago

Airfares from $153 One Way, $299 Round Trip from Anderson to Chicago

Prices starting at $299 for return flights and $153 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.

Wed, Mar 10 - Sat, Mar 13
GSP
Greenville
ORD
Chicago
$299 Roundtrip, found 2 days ago
$299
Roundtrip
found 2 days ago
Select United flight, departing Wed, Mar 10 from Greenville to Chicago, returning Sat, Mar 13, priced at $299 found 2 days ago
Thu, Nov 5 - Mon, Nov 9
GSP
Greenville
ORD
Chicago
$303 Roundtrip, found 9 hours ago
$303
Roundtrip
found 9 hours ago
Select American Airlines flight, departing Thu, Nov 5 from Greenville to Chicago, returning Mon, Nov 9, priced at $303 found 9 hours ago
Fri, Nov 6 - Thu, Nov 19
GSP
Greenville
ORD
Chicago
$309 Roundtrip, found 3 days ago
$309
Roundtrip
found 3 days ago
Select American Airlines flight, departing Fri, Nov 6 from Greenville to Chicago, returning Thu, Nov 19, priced at $309 found 3 days ago
Tue, Oct 20 - Wed, Oct 21
GSP
Greenville
ORD
Chicago
$310 Roundtrip, found 4 days ago
$310
Roundtrip
found 4 days ago
Select United flight, departing Tue, Oct 20 from Greenville to Chicago, returning Wed, Oct 21, priced at $310 found 4 days ago
Thu, Nov 5 - Mon, Nov 9
GSP
Greenville
ORD
Chicago
$313 Roundtrip, found 9 hours ago
$313
Roundtrip
found 9 hours ago
Select American Airlines flight, departing Thu, Nov 5 from Greenville to Chicago, returning Mon, Nov 9, priced at $313 found 9 hours ago

Chicago economy flight packages

Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago
4.5-star property

Swissotel - Chicago

9/10 Wonderful! (3,512 reviews)

Oct 30 - Nov 1

2 night stay

Greenville (GSP) to Chicago (ORD)

American Airlines • Roundtrip • Coach
Price was $698, price is now $539 per person
$539
per person
found 1 day ago
The hotel was perfectly fine for a room price half the cost we paid

Reviewed on Sep 6, 2026

Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

9.4/10 Exceptional! (5,106 reviews)

Oct 29 - Nov 1

3 night stay

Greenville (GSP) to Chicago (ORD)

American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,157, price is now $767 per person
$767
per person
found 1 day ago

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! (2,685 reviews)

Oct 29 - Nov 1

3 night stay

Greenville (GSP) to Chicago (ORD)

American Airlines • Roundtrip • Coach
Price was $980, price is now $743 per person
$743
per person
found 1 day ago
.

Reviewed on Sep 7, 2026

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Chicago first class flight packages

Price found within the past 48 hours. Click for updated prices.
Sofitel Chicago Magnificent Mile
4.5-star property

Sofitel Chicago Magnificent Mile

9.4/10 Exceptional! (2,618 reviews)

Oct 8 - Oct 11

3 night stay

Greenville (GSP) to Chicago (ORD)

United • Roundtrip • FirstClass
Price was $2,246, price is now $2,057 per person
$2,057
per person
found 11 hours ago
This is not a five star hotel. Splatter on the shades, water damage on the ceiling bathroom, broken in controls for the shades, etc. A resort fee on top is an insulant. It allegedly included water and wifi as I was told. No minibar either. The water in question wasn’t replaced. When I had to call to ask for coffee because the cups weren’t washed and coffee wasn’t replaced - it was fixed promptly. But should I have to call to ask for coffee to begin with?

Reviewed on Sep 6, 2026

Pendry Chicago
4.5-star property

Pendry Chicago

9.2/10 Wonderful! (1,162 reviews)

Oct 8 - Oct 11

3 night stay

Greenville (GSP) to Chicago (ORD)

United • Roundtrip • FirstClass
Price was $2,387, price is now $2,120 per person
$2,120
per person
found 11 hours ago

The Langham, Chicago
5.0-star property

The Langham, Chicago

9.8/10 Exceptional! (1,018 reviews)

Oct 8 - Oct 11

3 night stay

Greenville (GSP) to Chicago (ORD)

United • Roundtrip • FirstClass
Price was $3,349, price is now $2,991 per person
$2,991
per person
found 11 hours ago
Great property all around. No complaints!

Reviewed on Sep 6, 2026

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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

Great Deals on Flights From Anderson to Chicago

Spend more of your time and money at Chicago instead of sitting at your computer, searching for discount Anderson to Chicago flights. This is why Orbitz makes it easy for you to check out destinations, plan your trip, and book your air fare, hotel, car rental, and more in just one place. Our low price guarantee means that you get great deals on flights from Anderson to Chicago.

Flights That Fit Your Budget

Traveling on a budget? Not to worry if you are using Orbitz. We monitor thousands of fares to make sure we show you the best air ticket prices available for your travel dates. Besides amazing prices on Anderson to Chicago flights, we offer you great deals on hotels, vacation packages, and last-minute getaways for the perfect trip.

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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.

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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.