Lane · VAN · Oct 2026

Winchester, VA to Chicago, IL freight rate

$1,879dry van

+5.7% from last month

Per mile: $2.99
Distance: 628 mi
Typical range: $1,672–$2,085
Transit: 2 days

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

Winchester to Chicago price history

3 months: +14.2%
1 year: +25.1%
5 years: +32.9%

Cost breakdown

Linehaul: $1,302
Fuel: $577
All-in estimate: $1,879

Return trip

Chicago → Winchester$3,198

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

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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, VA
To	Miles	Estimate	Per mile	Typical range	Transit
New York, NY	291 mi	$1,583	$5.44	$1,409 – $1,758	1 d
Los Angeles, CA	2,645 mi	$6,265	$2.37	$5,576 – $6,954	6 d
Houston, TX	1,383 mi	$3,661	$2.65	$3,258 – $4,063	3 d
Phoenix, AZ	2,259 mi	$5,992	$2.65	$5,333 – $6,651	5 d
Philadelphia, PA	203 mi	$1,264	$6.23	$1,125 – $1,403	1 d
San Antonio, TX	1,577 mi	$4,094	$2.60	$3,644 – $4,545	4 d
San Diego, CA	2,601 mi	$6,170	$2.37	$5,491 – $6,849	6 d
Dallas, TX	1,329 mi	$3,540	$2.66	$3,151 – $3,929	3 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, VA to Chicago, IL?

A 53' dry van from Winchester, VA to Chicago, IL is estimated at $1,879 all-in in October 2026, or $2.99 a mile over about 628 mi. Quotes typically land between $1,672 and $2,085.

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 $577 of the $1,879 estimate is fuel at the current national diesel price; the remaining $1,302 is linehaul.

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

The reverse direction is estimated at $3,198, which makes Winchester, VA to Chicago, IL 41% 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