How to Travel from

Chicago to Winchester

by Rideshare or Car

United States of America Chicago Winchester

Cheapest

By car (1 970 km)

19 h 38 min

1970 km.

from $108

Other

Rideshare

19 h 38 min

1970 km.

from $25.70

Airlines

American Airlines

Website:

aa.com/

Plane from Chicago O'Hare International Airport to Dayton

Ave. Duration:

1h 13m

Frequency:

Every day

Estimated price:

$89.17–$828.01

Plane from Chicago O'Hare International Airport to Fort

Ave. Duration:

1h 7m

Frequency:

Every day

Estimated price:

$121.02–$560.50

Plane from Chicago O'Hare International Airport to Indianapolis

Ave. Duration:

1h 5m

Frequency:

Every day

Estimated price:

$121.02–$382.16

United Airlines

Website:

united.com/

Plane from Chicago O'Hare International Airport to Dayton

Ave. Duration:

1h 19m

Frequency:

Every day

Estimated price:

$89.17–$828.01

Plane from Chicago O'Hare International Airport to Fort

Ave. Duration:

1h 12m

Frequency:

Every day

Estimated price:

$127.39–$573.24

Plane from Chicago O'Hare International Airport to Indianapolis

Ave. Duration:

1h 8m

Frequency:

Every day

Estimated price:

$121.02–$458.59

Train operators

Amtrak

Phone:

+1 800-872-7245

Website:

amtrak.com/home.html

Train from Chicago Union Station to Connersville

Ave. Duration:

6h 36m

Frequency:

3 times a week

Estimated price:

$34.39–$140.12

South Shore Line

Phone:

+1 219-926-5744

Website:

mysouthshoreline.com/

Train from Van Buren St. to Gary

Ave. Duration:

46 min

Frequency:

Every 30 minutes

Estimated price:

$4.20–$9.30

Bus operators

Miller Transportation

Phone:

+1 800-544-2383

Website:

ridewithmiller.com

Bus from Indianapolis Airport to Muncie,

Ave. Duration:

2h 15m

Frequency:

Once daily

Estimated price:

$17.83–$29.30

Barons Bus

Phone:

+1 888-378-3823

Email:

[email protected]

Website:

baronsbus.com/

Bus from Chicago to Portland,

Ave. Duration:

5h 25m

Frequency:

Once daily

Estimated price:

$24.20–$70.06

Bus from Gary, IN to Portland,

Ave. Duration:

4h 40m

Frequency:

Once daily

Estimated price:

$20.38–$70.06

Bus from Fort Wayne, IN to Portland,

Ave. Duration:

1h 10m

Frequency:

Once daily

Estimated price:

$5.48–$42.04

What is the cheapest way to get from Chicago to Winchester?

The cheapest way to get from Chicago to Winchester is to drive which costs $44.57 - $65.22 and takes 4h 29m.

What is the fastest way to get from Chicago to Winchester?

The fastest way to get from Chicago to Winchester is to fly and drive which takes 4h 8m and costs $86.96 - $760.87 .

How far is it from Chicago to Winchester?

The distance between Chicago and Winchester is 386 km. The road distance is 401.6 km.

How do I travel from Chicago to Winchester without a car?

The best way to get from Chicago to Winchester without a car is to bus which takes 5h 52m and costs $29.35 - $70.65 .

How long does it take to get from Chicago to Winchester?

It takes approximately 5h 52m to get from Chicago to Winchester, including transfers.

What is the time difference between Chicago and Winchester?

Winchester is 1h ahead of Chicago. It is currently 19:56 in Chicago and 20:56 in Winchester.

Can I drive from Chicago to Winchester?

Yes, the driving distance between Chicago to Winchester is 402 km. It takes approximately 4h 29m to drive from Chicago to Winchester.

Where can I stay near Winchester?

There are one+ hotels available in Winchester. Prices start at $98.26 per night.

Book in Winchester

The George Washington Hotel, A Wyndham Grand Hotel

103 E Piccadilly St, Winchester

Great

9.2

Holiday Inn Winchester Se-Historic Gateway by IHG

333 Front Royal Pike, Winchester

Fine

8.8

Holiday Inn Express Hotel & Suites Winchester by IHG

142 Foxridge Ln, Winchester

Fine

8.8

All accommodation options in WinchesterAll hotels

Winchester Residential Historic District

Winchester Residential Historic District is a national historic district located at Winchester, Randolph County, Indiana. The district encompasses 142 contributing buildings, 1 contributing site, and 1 contributing structure in a predominantly residential section of Winchester. The district developed between about 1837 and 1950 and includes notable examples of Greek Revival, Italianate, Romanesque Revival, Colonial Revival, Prairie School, and Classical Revival style architecture. Notable buildings include the First Presbyterian Church of Winchester (1903), Winchester Friends Church (1897), First United Methodist Church (1900), Main Street Christian Church (1912), First Church of the Nazarene (1929), Carey Goodrich House (1858), Kizer-Marsh House (c. 1870), and W. Miller House (1910).

Winchester Courthouse Square Historic District

Winchester Courthouse Square Historic District is a national historic district located at Winchester, Randolph County, Indiana. The district encompasses 52 contributing buildings and 10 contributing structures in the central business district of Winchester. The district developed between about 1875 and 1950 and includes notable examples of Italianate, Romanesque Revival, and Classical Revival style architecture. Notable buildings include the Randolph County Courthouse (1875), U. Post Office (1932), I. Hall (c. 1875), Winchester Community Library (1906), Masonic Lodge (c. 1925), Randolph Hotel (c. 1910), David Building (1927), and W. Miller Department Store (1883). Notable structures include the "Spirit of the Doughboy" monument (1928), Lamp of Freedom (c. 1950), Soldiers and Sailors monument (1892), and Laredo Taft Marker (c. 1936).

Levi Coffin House

The Coffin House is a National Historic Landmark located in the present-day town of Fountain City in Wayne County, Indiana. The two-story, eight room, brick home was constructed circa 1838–39 in the Federal style. The Coffin home became known as the "Grand Central Station" of the Underground Railroad because of its location where three of the escape routes to the North converged and the number of fleeing slaves who passed through it.

[{"selectedTransportType":"car","routePoints":[{"latitude":41.87567,"longitude":-87.62758,"title":"Chicago"},{"latitude":43.8622575244,"longitude":-108.1665802002,"title":"Winchester"}],"compositeRoutePoints":[],"transportTypes":{"car":{"title":"Car","color":"var(--color-transport-car)","icon":"\u003Ci class=\u0022icon iconmoon iconmoon-transport_car\u0022 style=\u0022color:var(--color-white)\u0022 aria-label=\u0027TRANSPORT_CAR\u0027\u003E\u003C\/i\u003E"},"taxi":{"title":"Taxi","color":"var(--color-transport-taxi)","icon":"\u003Ci class=\u0022icon iconmoon iconmoon-transport_taxi\u0022 style=\u0022color:var(--color-white)\u0022 aria-label=\u0027TRANSPORT_TAXI\u0027\u003E\u003C\/i\u003E"},"bus":{"title":"Bus","color":"var(--color-transport-bus)","icon":"\u003Ci class=\u0022icon iconmoon iconmoon-transport_bus\u0022 style=\u0022color:var(--color-white)\u0022 aria-label=\u0027TRANSPORT_BUS\u0027\u003E\u003C\/i\u003E"},"train":{"title":"Train","color":"var(--color-transport-train)","icon":"\u003Ci class=\u0022icon iconmoon iconmoon-transport_train\u0022 style=\u0022color:var(--color-white)\u0022 aria-label=\u0027TRANSPORT_TRAIN\u0027\u003E\u003C\/i\u003E"},"truck":{"title":"Truck","color":"var(--color-transport-truck)","icon":"\u003Ci class=\u0022icon iconmoon iconmoon-transport_truck\u0022 style=\u0022color:var(--color-white)\u0022 aria-label=\u0027TRANSPORT_TRUCK\u0027\u003E\u003C\/i\u003E"},"plane":{"title":"Plane","color":"var(--color-transport-plane)","icon":"\u003Ci class=\u0022icon iconmoon iconmoon-transport_plane\u0022 style=\u0022color:var(--color-white)\u0022 aria-label=\u0027TRANSPORT_PLANE\u0027\u003E\u003C\/i\u003E"},"ride_share":{"title":"Rideshare","color":"var(--color-transport-ride_share)","icon":"\u003Ci class=\u0022icon iconmoon iconmoon-transport_rideshare\u0022 style=\u0022color:var(--color-white)\u0022 aria-label=\u0027TRANSPORT_RIDE_SHARE\u0027\u003E\u003C\/i\u003E"},"people":{"title":"Person","color":"var(--color-transport-people)","icon":"\u003Ci class=\u0022icon iconmoon iconmoon-transport_people\u0022 style=\u0022color:var(--color-white)\u0022 aria-label=\u0027TRANSPORT_PEOPLE\u0027\u003E\u003C\/i\u003E"},"walk":{"title":"Walking","color":"var(--color-transport-walk)","icon":"\u003Ci class=\u0022icon iconmoon iconmoon-transport_walk\u0022 style=\u0022color:var(--color-white)\u0022 aria-label=\u0027TRANSPORT_WALK\u0027\u003E\u003C\/i\u003E"},"bike":{"title":"Bicycle","color":"var(--color-transport-bike)","icon":"\u003Ci class=\u0022icon iconmoon iconmoon-transport_bike\u0022 style=\u0022color:var(--color-white)\u0022 aria-label=\u0027TRANSPORT_BIKE\u0027\u003E\u003C\/i\u003E"},"transfer":{"title":"Transfer","color":"var(--color-transport-transfer)","icon":"\u003Ci class=\u0022icon iconmoon iconmoon-transport_transfer\u0022 style=\u0022color:var(--color-white)\u0022 aria-label=\u0027TRANSPORT_TRANSFER\u0027\u003E\u003C\/i\u003E"},"subway":{"title":"Subway","color":"var(--color-transport-subway)","icon":"\u003Ci class=\u0022icon iconmoon iconmoon-transport_subway\u0022 style=\u0022color:var(--color-white)\u0022 aria-label=\u0027TRANSPORT_SUBWAY\u0027\u003E\u003C\/i\u003E"},"composite":{"title":"Route","color":"var(--color-transport-composite)","icon":"\u003Ci class=\u0022icon iconmoon iconmoon-transport_transfer\u0022 style=\u0022color:var(--color-white)\u0022 aria-label=\u0027TRANSPORT_TRANSFER\u0027\u003E\u003C\/i\u003E"},"carsharing":{"title":"Carsharing","color":"var(--color-transport-carsharing)","icon":"\u003Ci class=\u0022icon iconmoon iconmoon-transport_carsharing\u0022 style=\u0022color:var(--color-white)\u0022 aria-label=\u0027TRANSPORT_CARSHARING\u0027\u003E\u003C\/i\u003E"},"suburban":{"title":"Electric Train","color":"var(--color-transport-suburban)","icon":"\u003Ci class=\u0022icon iconmoon iconmoon-transport_suburban\u0022 style=\u0022color:var(--color-white)\u0022 aria-label=\u0027TRANSPORT_SUBURBAN\u0027\u003E\u003C\/i\u003E"},"tram":{"title":"Tram","color":"var(--color-transport-tram)","icon":"\u003Ci class=\u0022icon iconmoon iconmoon-transport_tram\u0022 style=\u0022color:var(--color-white)\u0022 aria-label=\u0027TRANSPORT_TRAM\u0027\u003E\u003C\/i\u003E"},"trolleybus":{"title":"Trolleybus","color":"var(--color-transport-trolleybus)","icon":"\u003Ci class=\u0022icon iconmoon iconmoon-transport_trolleybus\u0022 style=\u0022color:var(--color-white)\u0022 aria-label=\u0027TRANSPORT_TROLLEYBUS\u0027\u003E\u003C\/i\u003E"},"cable_car":{"title":"Funicular","color":"var(--color-transport-cable_car)","icon":"\u003Ci class=\u0022icon iconmoon iconmoon-transport_funicular\u0022 style=\u0022color:var(--color-white)\u0022 aria-label=\u0027TRANSPORT_CABLE_CAR\u0027\u003E\u003C\/i\u003E"},"rail":{"title":"Rail","color":"var(--color-transport-rail)","icon":"\u003Ci class=\u0022icon iconmoon iconmoon-transport_train\u0022 style=\u0022color:var(--color-white)\u0022 aria-label=\u0027TRANSPORT_TRAIN\u0027\u003E\u003C\/i\u003E"},"ferry":{"title":"Ferry","color":"var(--color-transport-ferry)","icon":"\u003Ci class=\u0022icon iconmoon iconmoon-transport_ferry\u0022 style=\u0022color:var(--color-white)\u0022 aria-label=\u0027TRANSPORT_FERRY\u0027\u003E\u003C\/i\u003E"},"rent":{"title":"Rent auto","color":"var(--color-transport-rent)","icon":"\u003Ci class=\u0022icon iconmoon iconmoon-transport_rent\u0022 style=\u0022color:var(--color-white)\u0022 aria-label=\u0027TRANSPORT_RENT\u0027\u003E\u003C\/i\u003E"},"unknown":{"title":"Unknown","color":"var(--color-transport-unknown)","icon":"\u003Ci class=\u0022icon iconmoon iconmoon-transport_transfer\u0022 style=\u0022color:var(--color-white)\u0022 aria-label=\u0027TRANSPORT_TRANSFER\u0027\u003E\u003C\/i\u003E"}},"pointIcon":"\u003Ci class=\u0022icon iconmoon iconmoon-map_point\u0022 style=\u0022color:var(--color-primary)\u0022 aria-label=\u0027MAP_POINT\u0027\u003E\u003C\/i\u003E","routeId":52455284}, {"selectedTransportType":"ride_share","routePoints":[{"latitude":41.87567,"longitude":-87.62758,"title":"Chicago"},{"latitude":43.8622575244,"longitude":-108.1665802002,"title":"Winchester"}],"compositeRoutePoints":[],"transportTypes":{"car":{"title":"Car","color":"var(--color-transport-car)","icon":"\u003Ci class=\u0022icon iconmoon iconmoon-transport_car\u0022 style=\u0022color:var(--color-white)\u0022 aria-label=\u0027TRANSPORT_CAR\u0027\u003E\u003C\/i\u003E"},"taxi":{"title":"Taxi","color":"var(--color-transport-taxi)","icon":"\u003Ci class=\u0022icon iconmoon iconmoon-transport_taxi\u0022 style=\u0022color:var(--color-white)\u0022 aria-label=\u0027TRANSPORT_TAXI\u0027\u003E\u003C\/i\u003E"},"bus":{"title":"Bus","color":"var(--color-transport-bus)","icon":"\u003Ci class=\u0022icon iconmoon iconmoon-transport_bus\u0022 style=\u0022color:var(--color-white)\u0022 aria-label=\u0027TRANSPORT_BUS\u0027\u003E\u003C\/i\u003E"},"train":{"title":"Train","color":"var(--color-transport-train)","icon":"\u003Ci class=\u0022icon iconmoon iconmoon-transport_train\u0022 style=\u0022color:var(--color-white)\u0022 aria-label=\u0027TRANSPORT_TRAIN\u0027\u003E\u003C\/i\u003E"},"truck":{"title":"Truck","color":"var(--color-transport-truck)","icon":"\u003Ci class=\u0022icon iconmoon iconmoon-transport_truck\u0022 style=\u0022color:var(--color-white)\u0022 aria-label=\u0027TRANSPORT_TRUCK\u0027\u003E\u003C\/i\u003E"},"plane":{"title":"Plane","color":"var(--color-transport-plane)","icon":"\u003Ci class=\u0022icon iconmoon iconmoon-transport_plane\u0022 style=\u0022color:var(--color-white)\u0022 aria-label=\u0027TRANSPORT_PLANE\u0027\u003E\u003C\/i\u003E"},"ride_share":{"title":"Rideshare","color":"var(--color-transport-ride_share)","icon":"\u003Ci class=\u0022icon iconmoon iconmoon-transport_rideshare\u0022 style=\u0022color:var(--color-white)\u0022 aria-label=\u0027TRANSPORT_RIDE_SHARE\u0027\u003E\u003C\/i\u003E"},"people":{"title":"Person","color":"var(--color-transport-people)","icon":"\u003Ci class=\u0022icon iconmoon iconmoon-transport_people\u0022 style=\u0022color:var(--color-white)\u0022 aria-label=\u0027TRANSPORT_PEOPLE\u0027\u003E\u003C\/i\u003E"},"walk":{"title":"Walking","color":"var(--color-transport-walk)","icon":"\u003Ci class=\u0022icon iconmoon iconmoon-transport_walk\u0022 style=\u0022color:var(--color-white)\u0022 aria-label=\u0027TRANSPORT_WALK\u0027\u003E\u003C\/i\u003E"},"bike":{"title":"Bicycle","color":"var(--color-transport-bike)","icon":"\u003Ci class=\u0022icon iconmoon iconmoon-transport_bike\u0022 style=\u0022color:var(--color-white)\u0022 aria-label=\u0027TRANSPORT_BIKE\u0027\u003E\u003C\/i\u003E"},"transfer":{"title":"Transfer","color":"var(--color-transport-transfer)","icon":"\u003Ci class=\u0022icon iconmoon iconmoon-transport_transfer\u0022 style=\u0022color:var(--color-white)\u0022 aria-label=\u0027TRANSPORT_TRANSFER\u0027\u003E\u003C\/i\u003E"},"subway":{"title":"Subway","color":"var(--color-transport-subway)","icon":"\u003Ci class=\u0022icon iconmoon iconmoon-transport_subway\u0022 style=\u0022color:var(--color-white)\u0022 aria-label=\u0027TRANSPORT_SUBWAY\u0027\u003E\u003C\/i\u003E"},"composite":{"title":"Route","color":"var(--color-transport-composite)","icon":"\u003Ci class=\u0022icon iconmoon iconmoon-transport_transfer\u0022 style=\u0022color:var(--color-white)\u0022 aria-label=\u0027TRANSPORT_TRANSFER\u0027\u003E\u003C\/i\u003E"},"carsharing":{"title":"Carsharing","color":"var(--color-transport-carsharing)","icon":"\u003Ci class=\u0022icon iconmoon iconmoon-transport_carsharing\u0022 style=\u0022color:var(--color-white)\u0022 aria-label=\u0027TRANSPORT_CARSHARING\u0027\u003E\u003C\/i\u003E"},"suburban":{"title":"Electric Train","color":"var(--color-transport-suburban)","icon":"\u003Ci class=\u0022icon iconmoon iconmoon-transport_suburban\u0022 style=\u0022color:var(--color-white)\u0022 aria-label=\u0027TRANSPORT_SUBURBAN\u0027\u003E\u003C\/i\u003E"},"tram":{"title":"Tram","color":"var(--color-transport-tram)","icon":"\u003Ci class=\u0022icon iconmoon iconmoon-transport_tram\u0022 style=\u0022color:var(--color-white)\u0022 aria-label=\u0027TRANSPORT_TRAM\u0027\u003E\u003C\/i\u003E"},"trolleybus":{"title":"Trolleybus","color":"var(--color-transport-trolleybus)","icon":"\u003Ci class=\u0022icon iconmoon iconmoon-transport_trolleybus\u0022 style=\u0022color:var(--color-white)\u0022 aria-label=\u0027TRANSPORT_TROLLEYBUS\u0027\u003E\u003C\/i\u003E"},"cable_car":{"title":"Funicular","color":"var(--color-transport-cable_car)","icon":"\u003Ci class=\u0022icon iconmoon iconmoon-transport_funicular\u0022 style=\u0022color:var(--color-white)\u0022 aria-label=\u0027TRANSPORT_CABLE_CAR\u0027\u003E\u003C\/i\u003E"},"rail":{"title":"Rail","color":"var(--color-transport-rail)","icon":"\u003Ci class=\u0022icon iconmoon iconmoon-transport_train\u0022 style=\u0022color:var(--color-white)\u0022 aria-label=\u0027TRANSPORT_TRAIN\u0027\u003E\u003C\/i\u003E"},"ferry":{"title":"Ferry","color":"var(--color-transport-ferry)","icon":"\u003Ci class=\u0022icon iconmoon iconmoon-transport_ferry\u0022 style=\u0022color:var(--color-white)\u0022 aria-label=\u0027TRANSPORT_FERRY\u0027\u003E\u003C\/i\u003E"},"rent":{"title":"Rent auto","color":"var(--color-transport-rent)","icon":"\u003Ci class=\u0022icon iconmoon iconmoon-transport_rent\u0022 style=\u0022color:var(--color-white)\u0022 aria-label=\u0027TRANSPORT_RENT\u0027\u003E\u003C\/i\u003E"},"unknown":{"title":"Unknown","color":"var(--color-transport-unknown)","icon":"\u003Ci class=\u0022icon iconmoon iconmoon-transport_transfer\u0022 style=\u0022color:var(--color-white)\u0022 aria-label=\u0027TRANSPORT_TRANSFER\u0027\u003E\u003C\/i\u003E"}},"pointIcon":"\u003Ci class=\u0022icon iconmoon iconmoon-map_point\u0022 style=\u0022color:var(--color-primary)\u0022 aria-label=\u0027MAP_POINT\u0027\u003E\u003C\/i\u003E","routeId":52455284}]

Two ways to Travel from Chicago to Winchester

Transport providers

Airlines

American Airlines

United Airlines

Train operators

Amtrak

South Shore Line

Bus operators

Miller Transportation

Barons Bus

Questions and Answers

What is the cheapest way to get from Chicago to Winchester?

What is the fastest way to get from Chicago to Winchester?

How far is it from Chicago to Winchester?

How do I travel from Chicago to Winchester without a car?

How long does it take to get from Chicago to Winchester?

What is the time difference between Chicago and Winchester?

Can I drive from Chicago to Winchester?

Where can I stay near Winchester?