Lane · BOX · Oct 2026

Chicago, IL to Winchester, KY box truck rate

$1,206box truck

+2.9% from last month

Per mile: $3.16
Distance: 381 mi
Typical range: $1,025–$1,387
Transit: 1 day

Request a firm quote

Box truck · estimated all-in cost per load · monthly

Chicago to Winchester price history

3 months: +7.5%
1 year: +17.5%
5 years: +24.4%

Cost breakdown

Linehaul: $941
Fuel: $265
All-in estimate: $1,206

Return trip

Winchester → Chicago$895

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

Live market check

Get live dry van quotes on this lane

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.

Request a quote for box truck →

More lanes from Chicago

26' box truck lanes from Chicago, IL
To	Miles	Estimate	Per mile	Typical range	Transit
New York, NY	847 mi	$2,618	$3.09	$2,225 – $3,010	2 d
Los Angeles, CA	2,063 mi	$4,134	$2.00	$3,514 – $4,754	5 d
Houston, TX	1,106 mi	$2,499	$2.26	$2,124 – $2,874	3 d
Phoenix, AZ	1,705 mi	$3,852	$2.26	$3,274 – $4,429	4 d
Philadelphia, PA	787 mi	$2,353	$2.99	$2,000 – $2,706	2 d
San Antonio, TX	1,236 mi	$2,740	$2.22	$2,329 – $3,152	3 d
San Diego, CA	2,034 mi	$4,082	$2.01	$3,470 – $4,694	5 d
Dallas, TX	942 mi	$2,195	$2.33	$1,865 – $2,524	2 d

More lanes into Winchester

26' box truck lanes into Winchester, KY
From	Miles	Estimate	Per mile	Typical range	Transit
New York, NY	681 mi	$1,482	$2.18	$1,260 – $1,705	2 d
Los Angeles, CA	2,267 mi	$5,395	$2.38	$4,586 – $6,204	5 d
Houston, TX	1,010 mi	$1,894	$1.88	$1,610 – $2,179	3 d
Phoenix, AZ	1,873 mi	$2,613	$1.40	$2,221 – $3,005	4 d
Philadelphia, PA	596 mi	$1,195	$2.00	$1,016 – $1,374	2 d
San Antonio, TX	1,193 mi	$2,172	$1.82	$1,846 – $2,498	3 d
San Diego, CA	2,218 mi	$5,289	$2.38	$4,496 – $6,083	5 d
Dallas, TX	936 mi	$1,782	$1.90	$1,515 – $2,050	2 d

About this lane

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

A 26' box truck from Chicago, IL to Winchester, KY is estimated at $1,206 all-in in October 2026, or $3.16 a mile over about 381 mi. Quotes typically land between $1,025 and $1,387.

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 $265 of the $1,206 estimate is fuel at the current national diesel price; the remaining $941 is linehaul.

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

The reverse direction is estimated at $895, which makes Chicago, IL to Winchester, KY 35% more expensive. Direction matters because trucks are scarcer leaving some markets than others.

Figures are estimates for a standard full load. Get a firm quote for this lane →