Lane · VAN · Oct 2026

Chicago, IL to Winter Park, FL freight rate

$5,791dry van

+5.5% from last month

Per mile: $5.00
Distance: 1,158 mi
Typical range: $5,154–$6,428
Transit: 3 days

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Dry van · estimated all-in cost per load · monthly

Chicago to Winter Park price history

3 months: +13.9%
1 year: +25.0%
5 years: +33.0%

Cost breakdown

Linehaul: $4,726
Fuel: $1,065
All-in estimate: $5,791

Return trip

Winter Park → Chicago$2,383

This direction runs 143% above the return trip. Leaving IL prices above the national average and arriving in FL prices above it.

Chicago to Winter Park by truck type

Estimated cost from Chicago, IL to Winter Park, FL by truck type
Truck type	Estimate	Per mile	Typical range
53' dry van	$5,791	$5.00	$5,154 – $6,428
53' refrigerated	$6,902	$5.96	$6,005 – $7,799
48' flatbed	$7,012	$6.05	$6,030 – $7,993
Step deck	$7,643	$6.60	$6,420 – $8,866
Power only	$5,108	$4.41	$4,444 – $5,771
Hotshot	$3,854	$3.33	$3,199 – $4,510
26' box truck	$3,780	$3.26	$3,213 – $4,347
Sprinter van	$2,317	$2.00	$1,946 – $2,687

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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.

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More lanes from Chicago

53' dry van lanes from Chicago, IL
To	Miles	Estimate	Per mile	Typical range	Transit
New York, NY	847 mi	$4,023	$4.75	$3,580 – $4,465	2 d
Los Angeles, CA	2,063 mi	$6,306	$3.06	$5,612 – $6,999	4 d
Houston, TX	1,106 mi	$3,830	$3.46	$3,409 – $4,251	3 d
Phoenix, AZ	1,705 mi	$5,882	$3.45	$5,235 – $6,529	4 d
Philadelphia, PA	787 mi	$3,619	$4.60	$3,221 – $4,017	2 d
San Antonio, TX	1,236 mi	$4,196	$3.39	$3,734 – $4,657	3 d
San Diego, CA	2,034 mi	$6,227	$3.06	$5,542 – $6,912	4 d
Dallas, TX	942 mi	$3,369	$3.58	$2,998 – $3,739	2 d

More lanes into Winter Park

53' dry van lanes into Winter Park, FL
From	Miles	Estimate	Per mile	Typical range	Transit
New York, NY	1,101 mi	$4,607	$4.18	$4,100 – $5,114	3 d
Los Angeles, CA	2,605 mi	$12,988	$4.99	$11,559 – $14,417	6 d
Houston, TX	1,004 mi	$4,027	$4.01	$3,584 – $4,470	2 d
Phoenix, AZ	2,176 mi	$6,344	$2.92	$5,646 – $7,042	5 d
Philadelphia, PA	1,020 mi	$3,847	$3.77	$3,423 – $4,270	2 d
San Antonio, TX	1,226 mi	$4,737	$3.86	$4,216 – $5,258	3 d
San Diego, CA	2,520 mi	$12,602	$5.00	$11,216 – $13,988	5 d
Dallas, TX	1,133 mi	$4,440	$3.92	$3,952 – $4,928	3 d

About this lane

How much does it cost to ship a truckload from Chicago, IL to Winter Park, FL?

A 53' dry van from Chicago, IL to Winter Park, FL is estimated at $5,791 all-in in October 2026, or $5.00 a mile over about 1,158 mi. Quotes typically land between $5,154 and $6,428.

How far is Chicago, IL from Winter Park, FL by truck?

About 1,158 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 $1,065 of the $5,791 estimate is fuel at the current national diesel price; the remaining $4,726 is linehaul.

Is it cheaper to ship from Winter Park, FL to Chicago, IL?

The reverse direction is estimated at $2,383, which makes Chicago, IL to Winter Park, 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