Dry van · October 2026
Winner, SD to Chicago, IL
$2,564
53' dry van, all-in · most quotes $2,282 to $2,846
- Per mile
- $3.47
- Distance
- 740 mi
- Transit
- 2 days
- vs last month
- +5.8%
Linehaul $1,884Fuel $680
Get a firm price on this lane
$2,564 is what the market is paying. Add your date and we price your load.
Winner to Chicago price history
- 3 months
- +14.1%
- 1 year
- +25.3%
- 5 years
- +33.0%
More lanes from Winner
| To | Estimate | Per mile |
|---|---|---|
| New York, NY | $6,440 | $4.08 |
| Los Angeles, CA | $4,334 | $3.09 |
| Houston, TX | $3,793 | $3.31 |
| Phoenix, AZ | $3,956 | $3.55 |
| Philadelphia, PA | $5,943 | $3.90 |
| San Antonio, TX | $3,771 | $3.31 |
| San Diego, CA | $4,329 | $3.09 |
| Dallas, TX | $3,087 | $3.49 |
More lanes into Chicago
| From | Estimate | Per mile |
|---|---|---|
| New York, NY | $2,447 | $2.89 |
| Los Angeles, CA | $6,880 | $3.33 |
| Houston, TX | $2,845 | $2.57 |
| Phoenix, AZ | $3,343 | $1.96 |
| Philadelphia, PA | $2,055 | $2.61 |
| San Antonio, TX | $3,117 | $2.52 |
| San Diego, CA | $6,794 | $3.34 |
| Dallas, TX | $2,503 | $2.66 |
Winner to Chicago questions
How much does a dry van from Winner, SD to Chicago, IL cost?
About $2,564 all-in for a full 53' dry van in October 2026, which is $3.47 a mile over 740 mi. Most quotes land between $2,282 and $2,846.
How long does Winner to Chicago take by truck?
About 2 days of transit for a solo driver over roughly 740 mi.
How much of the price is fuel?
About $680 of the $2,564 is fuel. The other $1,884 is linehaul.
Is Chicago, IL to Winner, SD cheaper?
The return trip is about $2,858, so Winner to Chicago is 10% cheaper.
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.