Lane · VAN · Oct 2026

Winchester, KY to Chicago, IL freight rate

$1,391dry van

+5.5% from last month

Per mile: $3.65
Distance: 381 mi
Typical range: $1,238–$1,544
Transit: 1 day

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Dry van · estimated all-in cost per load · monthly

Winchester to Chicago price history

3 months: +14.1%
1 year: +25.0%
5 years: +32.7%

Cost breakdown

Linehaul: $1,041
Fuel: $350
All-in estimate: $1,391

Return trip

Chicago → Winchester$1,872

This direction runs 26% below the return trip. Leaving KY prices above the national average and arriving in IL prices below it.

Winchester to Chicago by truck type

Estimated cost from Winchester, KY to Chicago, IL by truck type
Truck type	Estimate	Per mile	Typical range
53' dry van	$1,391	$3.65	$1,238 – $1,544
53' refrigerated	$1,660	$4.36	$1,444 – $1,876
48' flatbed	$1,736	$4.56	$1,493 – $1,979
Step deck	$1,903	$4.99	$1,598 – $2,207
Power only	$1,196	$3.14	$1,040 – $1,351
Hotshot	$901	$2.36	$748 – $1,054
26' box truck	$895	$2.35	$761 – $1,030
Sprinter van	$556	$1.46	$467 – $645

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The index is an estimate. For a price you can act on, ask connected freight providers for a live 53' dry van rate, or send the load details and get quoted for any truck type.

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More lanes from Winchester

53' dry van lanes from Winchester, KY
To	Miles	Estimate	Per mile	Typical range	Transit
New York, NY	681 mi	$2,788	$4.09	$2,481 – $3,095	2 d
Los Angeles, CA	2,267 mi	$5,598	$2.47	$4,982 – $6,214	5 d
Houston, TX	1,010 mi	$2,905	$2.88	$2,585 – $3,224	2 d
Phoenix, AZ	1,873 mi	$5,211	$2.78	$4,638 – $5,784	4 d
Philadelphia, PA	596 mi	$2,412	$4.05	$2,146 – $2,677	2 d
San Antonio, TX	1,193 mi	$3,325	$2.79	$2,959 – $3,691	3 d
San Diego, CA	2,218 mi	$5,489	$2.47	$4,885 – $6,093	5 d
Dallas, TX	936 mi	$2,735	$2.92	$2,434 – $3,036	2 d

More lanes into Chicago

53' dry van lanes into Chicago, IL
From	Miles	Estimate	Per mile	Typical range	Transit
New York, NY	847 mi	$2,447	$2.89	$2,178 – $2,716	2 d
Los Angeles, CA	2,063 mi	$6,880	$3.33	$6,123 – $7,637	4 d
Houston, TX	1,106 mi	$2,845	$2.57	$2,532 – $3,158	3 d
Phoenix, AZ	1,705 mi	$3,343	$1.96	$2,975 – $3,711	4 d
Philadelphia, PA	787 mi	$2,055	$2.61	$1,829 – $2,281	2 d
San Antonio, TX	1,236 mi	$3,117	$2.52	$2,774 – $3,460	3 d
San Diego, CA	2,034 mi	$6,794	$3.34	$6,046 – $7,541	4 d
Dallas, TX	942 mi	$2,503	$2.66	$2,227 – $2,778	2 d

About this lane

How much does it cost to ship a truckload from Winchester, KY to Chicago, IL?

A 53' dry van from Winchester, KY to Chicago, IL is estimated at $1,391 all-in in October 2026, or $3.65 a mile over about 381 mi. Quotes typically land between $1,238 and $1,544.

How far is Winchester, KY from Chicago, IL by truck?

About 381 mi by road, estimated from the straight-line distance. A solo driver covers it in roughly 1 day of transit.

How much of the price is fuel?

About $350 of the $1,391 estimate is fuel at the current national diesel price; the remaining $1,041 is linehaul.

Is it cheaper to ship from Chicago, IL to Winchester, KY?

The reverse direction is estimated at $1,872, which makes Winchester, KY to Chicago, IL 26% cheaper. Direction matters because trucks are scarcer leaving some markets than others.

Lane history applies the current origin and destination adjustments to the national series back to December 2003. Methodology