Lane · VAN · Oct 2026
Chicago, IL to Winter Haven, FL freight rate
$5,931dry van
+5.7% from last month
- Per mile
- $4.98
- Distance
- 1,192 mi
- Typical range
- $5,278–$6,583
- Transit
- 3 days
Dry van · estimated all-in cost per load · monthly
Chicago to Winter Haven price history
- 3 months
- +14.2%
- 1 year
- +25.1%
- 5 years
- +33.2%
Cost breakdown
- Linehaul
- $4,835
- Fuel
- $1,096
- All-in estimate
- $5,931
Return trip
Winter Haven → Chicago$2,440This direction runs 143% above the return trip. Leaving IL prices above the national average and arriving in FL prices above it.
Chicago to Winter Haven by truck type
| Truck type | Relative cost | Estimate | Per mile |
|---|---|---|---|
| 53' dry van | $5,931 | $4.98 | |
| 53' refrigerated | $7,068 | $5.93 | |
| 48' flatbed | $7,176 | $6.02 | |
| Step deck | $7,821 | $6.56 | |
| Power only | $5,233 | $4.39 | |
| Hotshot | $3,949 | $3.31 | |
| 26' box truck | $3,872 | $3.25 | |
| Sprinter van | $2,372 | $1.99 |
Live market check
Get live dry van quotes on this lane
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.
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 |
About this lane
How much does it cost to ship a truckload from Chicago, IL to Winter Haven, FL?
A 53' dry van from Chicago, IL to Winter Haven, FL is estimated at $5,931 all-in in October 2026, or $4.98 a mile over about 1,192 mi. Quotes typically land between $5,278 and $6,583.
How far is Chicago, IL from Winter Haven, FL by truck?
About 1,192 mi by road, estimated from the straight-line distance. A solo driver covers it in roughly 3 days of transit.
How much of the price is fuel?
About $1,096 of the $5,931 estimate is fuel at the current national diesel price; the remaining $4,835 is linehaul.
Is it cheaper to ship from Winter Haven, FL to Chicago, IL?
The reverse direction is estimated at $2,440, which makes Chicago, IL to Winter Haven, FL 143% more expensive. 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