Lane · BOX · Oct 2026

Winchester, VA to Chicago, IL box truck rate

$1,218box truck

+3.1% from last month

Per mile: $1.94
Distance: 628 mi
Typical range: $1,035–$1,401
Transit: 2 days

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

Winchester to Chicago price history

3 months: +7.8%
1 year: +17.6%
5 years: +25.2%

Cost breakdown

Linehaul: $782
Fuel: $436
All-in estimate: $1,218

Return trip

Chicago → Winchester$2,074

This direction runs 41% below the return trip. Leaving VA prices below the national average and arriving in IL prices below it.

Winchester to Chicago by truck type

Estimated cost from Winchester, VA to Chicago, IL by truck type
Truck type	Estimate	Per mile	Typical range
53' dry van	$1,879	$2.99	$1,672 – $2,085
53' refrigerated	$2,241	$3.57	$1,950 – $2,532
48' flatbed	$2,309	$3.68	$1,986 – $2,632
Step deck	$2,524	$4.02	$2,120 – $2,928
Power only	$1,637	$2.61	$1,424 – $1,849
Hotshot	$1,234	$1.97	$1,024 – $1,444
26' box truck	$1,218	$1.94	$1,035 – $1,401
Sprinter van	$751	$1.20	$631 – $872

Live market check

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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

26' box truck lanes from Winchester, VA
To	Miles	Estimate	Per mile	Typical range	Transit
New York, NY	291 mi	$1,015	$3.49	$863 – $1,168	1 d
Los Angeles, CA	2,645 mi	$4,113	$1.55	$3,496 – $4,730	6 d
Houston, TX	1,383 mi	$2,393	$1.73	$2,034 – $2,752	3 d
Phoenix, AZ	2,259 mi	$3,930	$1.74	$3,341 – $4,520	5 d
Philadelphia, PA	203 mi	$806	$3.97	$685 – $927	1 d
San Antonio, TX	1,577 mi	$2,679	$1.70	$2,277 – $3,081	4 d
San Diego, CA	2,601 mi	$4,050	$1.56	$3,443 – $4,658	6 d
Dallas, TX	1,329 mi	$2,314	$1.74	$1,967 – $2,661	3 d

More lanes into Chicago

26' box truck lanes into Chicago, IL
From	Miles	Estimate	Per mile	Typical range	Transit
New York, NY	847 mi	$1,592	$1.88	$1,353 – $1,831	2 d
Los Angeles, CA	2,063 mi	$4,510	$2.19	$3,834 – $5,187	5 d
Houston, TX	1,106 mi	$1,857	$1.68	$1,578 – $2,135	3 d
Phoenix, AZ	1,705 mi	$2,189	$1.28	$1,861 – $2,517	4 d
Philadelphia, PA	787 mi	$1,336	$1.70	$1,136 – $1,536	2 d
San Antonio, TX	1,236 mi	$2,036	$1.65	$1,730 – $2,341	3 d
San Diego, CA	2,034 mi	$4,454	$2.19	$3,786 – $5,122	5 d
Dallas, TX	942 mi	$1,630	$1.73	$1,386 – $1,875	2 d

About this lane

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

A 26' box truck from Winchester, VA to Chicago, IL is estimated at $1,218 all-in in October 2026, or $1.94 a mile over about 628 mi. Quotes typically land between $1,035 and $1,401.

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

About 628 mi by road, estimated from the straight-line distance. A solo driver covers it in roughly 2 days of transit.

How much of the price is fuel?

About $436 of the $1,218 estimate is fuel at the current national diesel price; the remaining $782 is linehaul.

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

The reverse direction is estimated at $2,074, which makes Winchester, VA to Chicago, IL 41% cheaper. 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 →