Dry van · October 2026
Chicago, IL to Winter Haven, FL
$5,931
53' dry van, all-in · most quotes $5,278 to $6,583
- Per mile
- $4.98
- Distance
- 1,192 mi
- Transit
- 3 days
- vs last month
- +5.7%
Linehaul $4,835Fuel $1,096
Get a firm price on this lane
$5,931 is what the market is paying. Add your date and we price your load.
Chicago to Winter Haven price history
- 3 months
- +14.2%
- 1 year
- +25.1%
- 5 years
- +33.2%
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 Winter Haven
| From | Estimate | Per mile |
|---|---|---|
| New York, NY | $4,783 | $4.15 |
| Los Angeles, CA | $12,938 | $4.99 |
| Houston, TX | $3,963 | $4.03 |
| Phoenix, AZ | $6,315 | $2.92 |
| Philadelphia, PA | $4,003 | $3.73 |
| San Antonio, TX | $4,670 | $3.88 |
| San Diego, CA | $12,543 | $5.00 |
| Dallas, TX | $4,411 | $3.92 |
Chicago to Winter Haven questions
How much does a dry van from Chicago, IL to Winter Haven, FL cost?
About $5,931 all-in for a full 53' dry van in October 2026, which is $4.98 a mile over 1,192 mi. Most quotes land between $5,278 and $6,583.
How long does Chicago to Winter Haven take by truck?
About 3 days of transit for a solo driver over roughly 1,192 mi.
How much of the price is fuel?
About $1,096 of the $5,931 is fuel. The other $4,835 is linehaul.
Is Winter Haven, FL to Chicago, IL cheaper?
The return trip is about $2,440, so Chicago to Winter Haven is 143% 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.