Dry van · October 2026
Chicago, IL to Winchester, KY
$1,872
53' dry van, all-in · most quotes $1,667 to $2,078
- Per mile
- $4.91
- Distance
- 381 mi
- Transit
- 1 day
- vs last month
- +5.6%
Linehaul $1,522Fuel $350
Get a firm price on this lane
$1,872 is what the market is paying. Add your date and we price your load.
Chicago to Winchester price history
- 3 months
- +13.9%
- 1 year
- +25.0%
- 5 years
- +32.7%
More lanes from Chicago
| To | Estimate | Per mile |
|---|---|---|
| New York, NY | $4,023 | $4.75 |
| Los Angeles, CA | $6,306 | $3.06 |
| Houston, TX | $3,830 | $3.46 |
| Phoenix, AZ | $5,882 | $3.45 |
| Philadelphia, PA | $3,619 | $4.60 |
| San Antonio, TX | $4,196 | $3.39 |
| San Diego, CA | $6,227 | $3.06 |
| Dallas, TX | $3,369 | $3.58 |
More lanes into Winchester
| From | Estimate | Per mile |
|---|---|---|
| New York, NY | $2,284 | $3.35 |
| Los Angeles, CA | $8,225 | $3.63 |
| Houston, TX | $2,906 | $2.88 |
| Phoenix, AZ | $3,988 | $2.13 |
| Philadelphia, PA | $1,844 | $3.09 |
| San Antonio, TX | $3,326 | $2.79 |
| San Diego, CA | $8,065 | $3.64 |
| Dallas, TX | $2,736 | $2.92 |
Chicago to Winchester questions
How much does a dry van from Chicago, IL to Winchester, KY cost?
About $1,872 all-in for a full 53' dry van in October 2026, which is $4.91 a mile over 381 mi. Most quotes land between $1,667 and $2,078.
How long does Chicago to Winchester take by truck?
About 1 day of transit for a solo driver over roughly 381 mi.
How much of the price is fuel?
About $350 of the $1,872 is fuel. The other $1,522 is linehaul.
Is Winchester, KY to Chicago, IL cheaper?
The return trip is about $1,391, so Chicago to Winchester is 35% more expensive.
How do I get an exact price?
Use the quote form on this page. Add your pickup date and you get one reply with a firm price for your load.