
$49 Cheap flight deals from Chicago (CHI) to Winchester (CHA)
Earn rewards on top of your airline miles with Orbitz Rewards
Many airlines offer flexible change policies
Sign up to receive text alerts about your trip
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.
Airfares from $49 One Way, $97 Round Trip from Chicago to Winchester
Prices starting at $97 for return flights and $49 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.
Winchester economy flight packages

Nashville Airport Marriott
Jan 16 - Jan 19
Chicago (CHI) to Nashville (BNA)
Nashville (BNA) to Chicago (CHI)
Reviewed on Oct 26, 2025

Memoir Wedgewood Houston
Dec 30 - Jan 4
Chicago (CHI) to Nashville (BNA)
Reviewed on Mar 22, 2025

Sleeps 8 Walkable Sobro Suites w/ Local Art & Vibes by Avantstay
Jan 19 - Jan 24
Chicago (ORD) to Nashville (BNA)
Nashville (BNA) to Chicago (ORD)
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 |
Chicago to Winchester
Smart business means on-the-spot travel planning at budget prices. Orbitz On-the-Go can help by using cutting-edge mobile tools and guaranteed low prices. Orbitz On-the-Go is your go-to for bargain flights from Chicago to Winchester, and discount Chicago to Winchester flights.
Business Development
Boosting sales with multiple presentations within a day or week? Then easily book cheap domestic flights from Chicago to Winchester. Are you expanding into emerging markets? Find low-fare deals on international Chicago to Winchester flights. Orbitz On-the-Go mobile apps keep it simple.
Continuing Education
Successful business people know that keeping your edge in business means staying in training. Find a low-cost air ticket for your next workshop with Orbitz flights from Chicago to Winchester. Move to the head of the seminar with Orbitz On-the-Go’s guaranteed low prices on Chicago to Winchester flights.
Budget Planning
Orbitz allows you to focus on the income, while we reduce your expenses with guaranteed low prices. Your bottom line is bound to improve with our bargain flights from Chicago to Winchester and discount Chicago to Winchester flights. Watch your business thrive.
Time Management
Time is money, and Orbitz On-the-Go saves both. Our cutting-edge mobile tools make business travel planning quick and easy, even for same-day reservations. It’s not unusual for our clients to save big on same-day tickets for Chicago to {destination.name} flights. Free alerts keep you on time with flight, gate and baggage updates, plus other time-saving features.
Flights from Chicago
- Chicago to Orlando
- Chicago to Houston
- Chicago to New York
- Chicago to Phoenix
- Chicago to Dallas
- Chicago to Los Angeles
- Chicago to London
- Chicago to New Orleans
- Chicago to Washington
- Chicago to Rome
- Chicago to Paris
- Chicago to Toronto
- Chicago to San Francisco
- Chicago to Cleveland
- Chicago to Detroit
- Chicago to Montreal
- Chicago to Sacramento
- Chicago to Kansas City
- Chicago to Hartford
- Chicago to Atlantic City
More Destinations
- Flights from Duluth to Sewanee
- Flights from Green Bay to Sewanee
- Flights from Wilmington to Sewanee
- Flights from Baltimore to Sewanee
- Flights from Charlotte to Sewanee
- Flights from Chicago to Sewanee
- Flights from Dallas to Sewanee
- Flights from Detroit to Sewanee
- Flights from Houston to Sewanee
- Flights from Indianapolis to Sewanee
- Flights from Miami to Sewanee
- Flights from New Orleans to Sewanee
- Flights from New York to Sewanee
- Flights from Philadelphia to Sewanee
- Flights from Phoenix to Sewanee
- Flights from Raleigh to Sewanee
- Flights from Seattle to Sewanee
- Flights from Charleston to Sewanee
- Flights from Lynchburg to Sewanee
- Flights from Redding to Sewanee
- Flights from Augusta to Sewanee
- Flights from Pittsburgh to Sewanee
- Flights from Newark to Sewanee
- Flights from Richmond to Sewanee
- Flights from Pensacola to Sewanee
- Flights from Bentonville - Fayetteville to Sewanee
- Flights from Buffalo to Sewanee
- Flights from Norfolk - Virginia Beach to Sewanee
- Flights from Jacksonville to Sewanee
- Flights from Baton Rouge to Sewanee
- Flights from Greenville - Spartanburg to Sewanee
- Flights from Gainesville to Sewanee
- Flights from Charlottesville to Sewanee
- Flights from El Paso to Manchester
- Flights from Longview to Manchester
- Flights from Austin to Manchester
- Flights from Bangkok to Manchester
- Flights from Helsinki to Manchester
- Flights from Lisbon District to Manchester
- Flights from Oslo to Manchester
- Flights from Portland to Manchester
- Flights from Rio de Janeiro to Manchester
- Flights from Vancouver to Manchester
- Flights from Frankfurt to Manchester
- Flights from Hartford to Manchester
- Flights from Mazatlán to Manchester
- Flights from Tel Aviv to Manchester
- Flights from Portland to Manchester
- Flights from Montrose to Manchester
- Flights from Omaha to Manchester
- Flights from Saginaw to Manchester
- Flights from Bentonville - Fayetteville to Manchester
- Flights from Reno to Manchester
- Flights from Peoria to Manchester
- Flights from Lexington to Manchester
- Flights from Savannah to Manchester
- Flights from Bangor to Manchester
- Flights from Adelaide to Manchester
- Flights from Weston to Manchester
- Flights from Bridgeport to Manchester
- Flights from Wichita to Manchester
- Flights from Brownsville to Manchester
- Flights from Corpus Christi to Manchester
- Flights from Anchorage to Fayetteville
- Flights from Monterey to Fayetteville
- Flights from Roanoke to Fayetteville
- Flights from Hilton Head Island to Fayetteville
- Flights from Burlington to Fayetteville
- Flights from Manchester to Fayetteville
- Flights from Las Vegas to Lynchburg
- Flights from London to Lynchburg
- Flights from Minneapolis - St. Paul to Lynchburg
- Flights from Philadelphia to Lynchburg
- Flights from Lincoln to Lynchburg
- Flights from Atlanta to Shelbyville
- Flights from Baltimore to Shelbyville
- Flights from Charlotte to Shelbyville
- Flights from Chicago to Shelbyville
- Flights from Dallas to Shelbyville
- Flights from Houston to Shelbyville
- Flights from Memphis to Shelbyville
- Flights from Miami to Shelbyville
- Flights from Minneapolis - St. Paul to Shelbyville
- Flights from Portland to Shelbyville
- Flights from Toronto to Shelbyville
- Flights from Durango to Shelbyville
- Flights from Albany to Shelbyville
- Flights from Fort Lauderdale to Shelbyville
- Flights from Syracuse to Shelbyville
- Flights from Manchester to Shelbyville
- Flights from Albuquerque to Shelbyville
- Flights from Fort Myers to Shelbyville
- Flights from Dayton to Shelbyville
- Flights from Tampa to Shelbyville
- Flights from Baton Rouge to Shelbyville
- Flights from Biloxi to Shelbyville
- Flights from Fayetteville to Shelbyville
- Flights from Tallahassee to Shelbyville
- Flights from Charleston to Shelbyville
- Flights from College Station to Shelbyville
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.




