Lane · VAN · Oct 2026
Chicago, IL to Winter Garden, FL dry van rate
$5,787dry van
+5.5% from last month
- Per mile
- $5.00
- Distance
- 1,157 mi
- Typical range
- $5,151–$6,424
- Transit
- 3 days
Dry van · estimated all-in cost per load · monthly
Chicago to Winter Garden price history
- 3 months
- +13.9%
- 1 year
- +25.0%
- 5 years
- +33.0%
Cost breakdown
- Linehaul
- $4,723
- Fuel
- $1,064
- All-in estimate
- $5,787
Return trip
Winter Garden → Chicago$2,381This direction runs 143% above the return trip. Leaving IL prices above the national average and arriving in FL prices above it.
Chicago to Winter Garden by truck type
| Truck type | Relative cost | Estimate | Per mile |
|---|---|---|---|
| 53' dry van | $5,787 | $5.00 | |
| 53' refrigerated | $6,897 | $5.96 | |
| 48' flatbed | $7,007 | $6.06 | |
| Step deck | $7,638 | $6.60 | |
| Power only | $5,104 | $4.41 | |
| Hotshot | $3,852 | $3.33 | |
| 26' box truck | $3,778 | $3.27 | |
| Sprinter van | $2,315 | $2.00 |
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 Garden
| From | Estimate | Per mile |
|---|---|---|
| New York, NY | $4,648 | $4.18 |
| Los Angeles, CA | $12,920 | $4.99 |
| Houston, TX | $3,973 | $4.03 |
| Phoenix, AZ | $6,305 | $2.92 |
| Philadelphia, PA | $3,880 | $3.76 |
| San Antonio, TX | $4,680 | $3.87 |
| San Diego, CA | $12,529 | $5.00 |
| Dallas, TX | $4,392 | $3.93 |
About this lane
How much does it cost to ship a truckload from Chicago, IL to Winter Garden, FL?
A 53' dry van from Chicago, IL to Winter Garden, FL is estimated at $5,787 all-in in October 2026, or $5.00 a mile over about 1,157 mi. Quotes typically land between $5,151 and $6,424.
How far is Chicago, IL from Winter Garden, FL by truck?
About 1,157 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 $1,064 of the $5,787 estimate is fuel at the current national diesel price; the remaining $4,723 is linehaul.
Is it cheaper to ship from Winter Garden, FL to Chicago, IL?
The reverse direction is estimated at $2,381, which makes Chicago, IL to Winter Garden, FL 143% more expensive. Direction matters because trucks are scarcer leaving some markets than others.
Figures are estimates for a standard full load. Get a firm quote for this lane →