$102 Cheap flight deals from Chicago (CHI) to Winston-Salem (GSO)

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This Weekend's Flight Deals from Chicago to Winston-Salem

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, May 10 - Wed, May 28
ORD
O'Hare Intl.
GSO
Piedmont Triad Intl.
$246 Roundtrip, found 1 day ago
$246
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, May 10 from O'Hare Intl. to Piedmont Triad Intl., returning Wed, May 28, priced at $246 found 1 day ago
Fri, May 9 - Sat, May 17
MDW
Midway Intl.
GSO
Piedmont Triad Intl.
$308 Roundtrip, found 1 day ago
$308
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, May 9 from Midway Intl. to Piedmont Triad Intl., returning Sat, May 17, priced at $308 found 1 day ago

Airfares from $102 One Way, $203 Round Trip from Chicago to Winston-Salem

Prices starting at $203 for return flights and $102 for one-way flights to Winston-Salem 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, May 29 - Sat, May 31
ORD
Chicago
GSO
Greensboro
$203 Roundtrip, found 20 hours ago
$203
Roundtrip
found 20 hours ago
Select American Airlines flight, departing Thu, May 29 from Chicago to Greensboro, returning Sat, May 31, priced at $203 found 20 hours ago
Thu, Jun 5 - Tue, Jun 10
ORD
Chicago
GSO
Greensboro
$208 Roundtrip, found 6 days ago
$208
Roundtrip
found 6 days ago
Select American Airlines flight, departing Thu, Jun 5 from Chicago to Greensboro, returning Tue, Jun 10, priced at $208 found 6 days ago
Thu, May 29 - Sat, May 31
ORD
Chicago
GSO
Greensboro
$212 Roundtrip, found 20 hours ago
$212
Roundtrip
found 20 hours ago
Select American Airlines flight, departing Thu, May 29 from Chicago to Greensboro, returning Sat, May 31, priced at $212 found 20 hours ago
Sat, Jun 14 - Tue, Jul 1
MDW
Chicago
GSO
Greensboro
$219 Roundtrip, found 6 days ago
$219
Roundtrip
found 6 days ago
Select Delta flight, departing Sat, Jun 14 from Chicago to Greensboro, returning Tue, Jul 1, priced at $219 found 6 days ago
Wed, Jun 11 - Sat, Jun 21
ORD
Chicago
GSO
Greensboro
$219 Roundtrip, found 1 day ago
$219
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Jun 11 from Chicago to Greensboro, returning Sat, Jun 21, priced at $219 found 1 day ago

Winston-Salem economy flight packages

Price found within the past 48 hours. Click for updated prices.
Comfort Suites Whitsett - Greensboro East
2.5-star property

Comfort Suites Whitsett - Greensboro East

8.8/10 Excellent! (934 reviews)

Jun 27 - Jun 29

2 night stay

Chicago (ORD) to Greensboro (GSO)

United • Coach

Greensboro (GSO) to Chicago (ORD)

American Airlines • Coach
per person
found 1 day ago
Staff was friendly. The location was near the highway with restaurants close by

Reviewed on Mar 27, 2025

La Quinta Inn & Suites by Wyndham Greensboro NC
2.5-star property

La Quinta Inn & Suites by Wyndham Greensboro NC

8/10 Very Good! (1,003 reviews)

Jun 27 - Jun 29

2 night stay

Chicago (ORD) to Greensboro (GSO)

United • Coach

Greensboro (GSO) to Chicago (ORD)

American Airlines • Coach
per person
found 1 day ago
At first glance the hotel, lobby, and rooms looks very nice. Most things are updated and pleasantly colored. I was not a big fan of the check in process. Instead of just taking my card info for incidentals like every other hotel, they wanted a $100 deposit for each room so I had to swipe my credit card over and over. That's just odd to me. Again, instead of signing one agreement, they wanted me to sign 3 separate agreements, one for each room. Then they wanted my email, mailing address, phone number etc. Shouldn't they already have that? And if they don't, why do they need it? It just bogged down the check in process. Rooms were mostly clean, but there some small things they missed. For such a nice looking hotel, Breakfast seemed a little slim. All in all a decent experience, I would stay again, but just not enough for a "perfect" 5 star review.

Reviewed on Mar 16, 2025

The Historic Brookstown Inn, Trademark Collection by Wyndham
3.5-star property

The Historic Brookstown Inn, Trademark Collection by Wyndham

9.6/10 Exceptional! (1,003 reviews)

Jun 27 - Jun 29

2 night stay

Chicago (ORD) to Greensboro (GSO)

United • Coach

Greensboro (GSO) to Chicago (ORD)

American Airlines • Coach
per person
found 1 day ago
The friendliest staff I have ever encountered. When I walked in the door at check in the tone was set. I was greeted with a smile and the staff took the extra time to walk from behind the counter and actually show me around. This type of friendliness and human interaction is dying in the world we live in today so I don't give compliments like this often. Loved the place's history and the room was huge, but it was the staff that made if perfect.

Reviewed on Feb 2, 2025

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More About Flying To Winston-Salem from Chicago

Route Information for Flights from Chicago to Winston-Salem

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

Chicago to Winston-Salem

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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.