Dry van · October 2026
Winter Park, FL to Chicago, IL
$2,383
53' dry van, all-in · most quotes $2,121 to $2,645
- Per mile
- $2.06
- Distance
- 1,158 mi
- Transit
- 3 days
- vs last month
- +5.6%
Linehaul $1,318Fuel $1,065
Get a firm price on this lane
$2,383 is what the market is paying. Add your date and we price your load.
Winter Park to Chicago price history
- 3 months
- +14.4%
- 1 year
- +24.8%
- 5 years
- +32.9%
More lanes from Winter Park
| To | Estimate | Per mile |
|---|---|---|
| New York, NY | $3,116 | $2.83 |
| Los Angeles, CA | $4,898 | $1.88 |
| Houston, TX | $2,231 | $2.22 |
| Phoenix, AZ | $4,593 | $2.11 |
| Philadelphia, PA | $2,787 | $2.73 |
| San Antonio, TX | $2,624 | $2.14 |
| San Diego, CA | $4,752 | $1.89 |
| Dallas, TX | $2,459 | $2.17 |
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 |
Winter Park to Chicago questions
How much does a dry van from Winter Park, FL to Chicago, IL cost?
About $2,383 all-in for a full 53' dry van in October 2026, which is $2.06 a mile over 1,158 mi. Most quotes land between $2,121 and $2,645.
How long does Winter Park to Chicago take by truck?
About 3 days of transit for a solo driver over roughly 1,158 mi.
How much of the price is fuel?
About $1,065 of the $2,383 is fuel. The other $1,318 is linehaul.
Is Chicago, IL to Winter Park, FL cheaper?
The return trip is about $5,791, so Winter Park to Chicago is 59% 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.