$30 Cheap flight deals from Chicago (CHI) to Winchester (CHA)

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This Weekend's Flight Deals from Chicago to Winchester

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, Jul 11 - Mon, Jul 14
ORD
O'Hare Intl.
BNA
Nashville Intl.
$121 Roundtrip, just found
$121
Roundtrip
just found
Select Spirit Airlines flight, departing Fri, Jul 11 from O'Hare Intl. to Nashville Intl., returning Mon, Jul 14, priced at $121 just found
Fri, Jul 11 - Tue, Jul 22
ORD
O'Hare Intl.
CHA
Chattanooga Metropolitan
$239 Roundtrip, found 5 days ago
$239
Roundtrip
found 5 days ago
Select Delta flight, departing Fri, Jul 11 from O'Hare Intl. to Chattanooga Metropolitan, returning Tue, Jul 22, priced at $239 found 5 days ago
Sat, Jul 12 - Sun, Jul 27
MDW
Midway Intl.
HSV
Huntsville Intl.
$258 Roundtrip, found 13 hours ago
$258
Roundtrip
found 13 hours ago
Select Delta flight, departing Sat, Jul 12 from Midway Intl. to Huntsville Intl., returning Sun, Jul 27, priced at $258 found 13 hours ago
Sat, Jul 12 - Sun, Jul 20
ORD
O'Hare Intl.
HSV
Huntsville Intl.
$268 Roundtrip, found 1 day ago
$268
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Jul 12 from O'Hare Intl. to Huntsville Intl., returning Sun, Jul 20, priced at $268 found 1 day ago

Airfares from $30 One Way, $60 Round Trip from Chicago to Winchester

Prices starting at $60 for return flights and $30 for one-way flights to Winchester were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Mon, Jul 28 - Mon, Aug 4
ORD
Chicago
BNA
Nashville
$60 Roundtrip, just found
$60
Roundtrip
just found
Select Spirit Airlines flight, departing Mon, Jul 28 from Chicago to Nashville, returning Mon, Aug 4, priced at $60 just found
Wed, Oct 8 - Mon, Oct 13
MDW
Chicago
BNA
Nashville
$97 Roundtrip, found 1 day ago
$97
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Wed, Oct 8 from Chicago to Nashville, returning Mon, Oct 13, priced at $97 found 1 day ago
Thu, Sep 11 - Wed, Sep 17
ORD
Chicago
BNA
Nashville
$97 Roundtrip, found 21 hours ago
$97
Roundtrip
found 21 hours ago
Select United flight, departing Thu, Sep 11 from Chicago to Nashville, returning Wed, Sep 17, priced at $97 found 21 hours ago
Thu, Sep 11 - Wed, Sep 17
ORD
Chicago
BNA
Nashville
$97 Roundtrip, found 21 hours ago
$97
Roundtrip
found 21 hours ago
Select Southwest Airlines flight, departing Thu, Sep 11 from Chicago to Nashville, returning Wed, Sep 17, priced at $97 found 21 hours ago
Thu, Sep 11 - Wed, Sep 17
ORD
Chicago
BNA
Nashville
$97 Roundtrip, found 21 hours ago
$97
Roundtrip
found 21 hours ago
Select American Airlines flight, departing Thu, Sep 11 from Chicago to Nashville, returning Wed, Sep 17, priced at $97 found 21 hours ago

Winchester economy flight packages

Price found within the past 48 hours. Click for updated prices.
Virgin Hotels Nashville
4.5-star property

Virgin Hotels Nashville

9.4/10 Exceptional! (2,092 reviews)

Aug 18 - Aug 25

7 night stay

Chicago (CHI) to Nashville (BNA)

Southwest Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
The hotel is nice .Cleanliness was average .Alot of staff was around but no matter what we asked about they could not complete the task. The valet was excellent and fast. The Door greeter was entertaining .

Reviewed on Feb 15, 2025

Bobby Hotel
4.0-star property

Bobby Hotel

9.4/10 Exceptional! (1,000 reviews)

Aug 18 - Aug 25

7 night stay

Chicago (CHI) to Nashville (BNA)

Southwest Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
The location was very good and close to everything and the staff were excellent. I will say it was a little eclectic for my taste. The glass enclosed bathroom left a bit to be desired. There was a curtain to pull around it to give you some privacy but that did not work well with a bathroom sliding door that would not stay shut. I also found the layout could have been much better in my opinion. This was a room with over 500 square feet and it was all open with no divided spaces that would allow a person to sleep while you were up. One last thing the pool is small and only 3 feet deep. That being said this is a very clean nice hotel, just not my style

Reviewed on Sep 27, 2024

Noelle
4.0-star property

Noelle

9.4/10 Exceptional! (1,213 reviews)

Aug 18 - Aug 25

7 night stay

Chicago (CHI) to Nashville (BNA)

Southwest Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
This property was walkable to Broadway only a couple blocks away. King standard room was small but very quiet and clean. Love the Nespresso machine for coffee (its in the hall not in the room). Also, the bar in the hotel had live music.

Reviewed on Jan 31, 2025

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More About Flying To Winchester from Chicago

Route Information for Flights from Chicago to Winchester

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

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.