Lane · VAN · Oct 2026

Chicago, IL to Winchester, KY freight rate

$1,872dry van

+5.6% from last month

Per mile: $4.91
Distance: 381 mi
Typical range: $1,667–$2,078
Transit: 1 day

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

Chicago to Winchester price history

3 months: +13.9%
1 year: +25.0%
5 years: +32.7%

Cost breakdown

Linehaul: $1,522
Fuel: $350
All-in estimate: $1,872

Return trip

Winchester → Chicago$1,391

This direction runs 35% above the return trip. Leaving IL prices above the national average and arriving in KY prices below it.

Chicago to Winchester by truck type

Estimated cost from Chicago, IL to Winchester, KY by truck type
Truck type	Estimate	Per mile	Typical range
53' dry van	$1,872	$4.91	$1,667 – $2,078
53' refrigerated	$2,236	$5.87	$1,945 – $2,526
48' flatbed	$2,337	$6.13	$2,010 – $2,665
Step deck	$2,562	$6.72	$2,152 – $2,972
Power only	$1,610	$4.23	$1,401 – $1,819
Hotshot	$1,213	$3.18	$1,007 – $1,419
26' box truck	$1,206	$3.16	$1,025 – $1,387
Sprinter van	$749	$1.97	$629 – $869

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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 Chicago

53' dry van lanes from Chicago, IL
To	Miles	Estimate	Per mile	Typical range	Transit
New York, NY	847 mi	$4,023	$4.75	$3,580 – $4,465	2 d
Los Angeles, CA	2,063 mi	$6,306	$3.06	$5,612 – $6,999	4 d
Houston, TX	1,106 mi	$3,830	$3.46	$3,409 – $4,251	3 d
Phoenix, AZ	1,705 mi	$5,882	$3.45	$5,235 – $6,529	4 d
Philadelphia, PA	787 mi	$3,619	$4.60	$3,221 – $4,017	2 d
San Antonio, TX	1,236 mi	$4,196	$3.39	$3,734 – $4,657	3 d
San Diego, CA	2,034 mi	$6,227	$3.06	$5,542 – $6,912	4 d
Dallas, TX	942 mi	$3,369	$3.58	$2,998 – $3,739	2 d

More lanes into Winchester

53' dry van lanes into Winchester, KY
From	Miles	Estimate	Per mile	Typical range	Transit
New York, NY	681 mi	$2,284	$3.35	$2,033 – $2,535	2 d
Los Angeles, CA	2,267 mi	$8,225	$3.63	$7,320 – $9,129	5 d
Houston, TX	1,010 mi	$2,906	$2.88	$2,586 – $3,226	2 d
Phoenix, AZ	1,873 mi	$3,988	$2.13	$3,549 – $4,427	4 d
Philadelphia, PA	596 mi	$1,844	$3.09	$1,641 – $2,047	2 d
San Antonio, TX	1,193 mi	$3,326	$2.79	$2,960 – $3,692	3 d
San Diego, CA	2,218 mi	$8,065	$3.64	$7,178 – $8,952	5 d
Dallas, TX	936 mi	$2,736	$2.92	$2,435 – $3,037	2 d

About this lane

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

A 53' dry van from Chicago, IL to Winchester, KY is estimated at $1,872 all-in in October 2026, or $4.91 a mile over about 381 mi. Quotes typically land between $1,667 and $2,078.

How far is Chicago, IL from Winchester, KY 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 $1,872 estimate is fuel at the current national diesel price; the remaining $1,522 is linehaul.

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

The reverse direction is estimated at $1,391, which makes Chicago, IL to Winchester, KY 35% more expensive. 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