$110 Cheap flight deals from Chicago (CHI) to Simpsonville (GSP)

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This Weekend's Flight Deals from Chicago to Simpsonville

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, Nov 15 - Mon, Nov 24
MDW
Midway Intl.
GSP
Greenville-Spartanburg Intl.
$258 Roundtrip, found 5 days ago
$258
Roundtrip
found 5 days ago
Select Delta flight, departing Sat, Nov 15 from Midway Intl. to Greenville-Spartanburg Intl., returning Mon, Nov 24, priced at $258 found 5 days ago
Sat, Nov 15 - Tue, Dec 2
ORD
O'Hare Intl.
GSP
Greenville-Spartanburg Intl.
$264 Roundtrip, found 23 hours ago
$264
Roundtrip
found 23 hours ago
Select Delta flight, departing Sat, Nov 15 from O'Hare Intl. to Greenville-Spartanburg Intl., returning Tue, Dec 2, priced at $264 found 23 hours ago
Fri, Nov 14 - Sat, Nov 15
RFD
Greater Rockford
GSP
Greenville-Spartanburg Intl.
$321 Roundtrip, found 23 hours ago
$321
Roundtrip
found 23 hours ago
Select American Airlines flight, departing Fri, Nov 14 from Greater Rockford to Greenville-Spartanburg Intl., returning Sat, Nov 15, priced at $321 found 23 hours ago

Airfares from $110 One Way, $205 Round Trip from Chicago to Simpsonville

Prices starting at $205 for return flights and $110 for one-way flights to Simpsonville 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, Dec 13 - Mon, Dec 15
RFD
Rockford
GSP
Greenville
$205 Roundtrip, found 3 days ago
$205
Roundtrip
found 3 days ago
Select American Airlines flight, departing Sat, Dec 13 from Rockford to Greenville, returning Mon, Dec 15, priced at $205 found 3 days ago
Sat, Dec 13 - Mon, Dec 15
ORD
Chicago
GSP
Greenville
$206 Roundtrip, found 3 days ago
$206
Roundtrip
found 3 days ago
Select American Airlines flight, departing Sat, Dec 13 from Chicago to Greenville, returning Mon, Dec 15, priced at $206 found 3 days ago
Fri, Dec 12 - Mon, Dec 15
ORD
Chicago
GSP
Greenville
$209 Roundtrip, just found
$209
Roundtrip
just found
Select American Airlines flight, departing Fri, Dec 12 from Chicago to Greenville, returning Mon, Dec 15, priced at $209 just found
Fri, Dec 5 - Sun, Dec 7
RFD
Rockford
GSP
Greenville
$212 Roundtrip, found 2 days ago
$212
Roundtrip
found 2 days ago
Select American Airlines flight, departing Fri, Dec 5 from Rockford to Greenville, returning Sun, Dec 7, priced at $212 found 2 days ago
Fri, Dec 12 - Sun, Dec 14
ORD
Chicago
GSP
Greenville
$213 Roundtrip, found 2 days ago
$213
Roundtrip
found 2 days ago
Select American Airlines flight, departing Fri, Dec 12 from Chicago to Greenville, returning Sun, Dec 14, priced at $213 found 2 days ago

Simpsonville economy flight packages

Price found within the past 48 hours. Click for updated prices.
Crowne Plaza Hotel Greenville-I-385-Roper Mtn Rd by IHG
3.5-star property

Crowne Plaza Hotel Greenville-I-385-Roper Mtn Rd by IHG

8.6/10 Excellent! (1,008 reviews)

Dec 27 - Dec 30

3 night stay

Chicago (ORD) to Greenville (GSP)

Spirit Airlines • Non-stop roundtrip • Coach
Price was $604, price is now $556 per person
$556
per person
found 13 hours ago
Very firm bed. Excellent accessibility options.

Reviewed on Aug 16, 2025

Best Western Plus Clemson Hotel & Conference Center
2.5-star property

Best Western Plus Clemson Hotel & Conference Center

8.2/10 Very Good! (1,013 reviews)

Dec 27 - Dec 30

3 night stay

Chicago (ORD) to Greenville (GSP)

Spirit Airlines • Non-stop roundtrip • Coach
Price was $622, price is now $571 per person
$571
per person
found 13 hours ago
on our arrival we were early, we were told we had to pay for an early check in fee, we didn’t have a problem with that if the lady was nice about it and looked at us and welcomed us to the hotel. instead she sat at the desk didn’t look at us and we abrupt about it. Then we went to take a shower and the curtain in the shower had mold all on the bottom of it. The cleaning lady was very nice about it but i had to put up the new curtain because she didn’t know how to put it up. Then that night at 10:30 the TV goes out, we had no TV until the next afternoon. Then the same thing happens with the TV before we went out for dinner. Then on top of everything the electric goes out, which we understand it wasn’t there fault, but they put out the breakfast food it was hot, they decided to take it away then the lights go back on at 8:00 and they decided to not put out any hot food but the lady that was working it decide to eat her eggs in front of everyone that she heated up. unbelievable!!! We went to use the waffle machine and the decided to not plug it in. I never seen anything like this before and this wasn’t our first time staying there and we will not be staying there moving forward.

Reviewed on Aug 12, 2025

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More About Flying To Simpsonville from Chicago

Route Information for Flights from Chicago to Simpsonville

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

Chicago to Simpsonville

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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.