Lane · BOX · Oct 2026

Chicago, IL to Winter Park, FL box truck rate

$3,780box truck

+2.8% from last month

Per mile: $3.26
Distance: 1,158 mi
Typical range: $3,213–$4,347
Transit: 3 days

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Box truck · estimated all-in cost per load · monthly

Chicago to Winter Park price history

3 months: +7.6%
1 year: +17.3%
5 years: +24.4%

Cost breakdown

Linehaul: $2,976
Fuel: $804
All-in estimate: $3,780

Return trip

Winter Park → Chicago$1,555

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

Live market check

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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

26' box truck lanes from Chicago, IL
To	Miles	Estimate	Per mile	Typical range	Transit
New York, NY	847 mi	$2,618	$3.09	$2,225 – $3,010	2 d
Los Angeles, CA	2,063 mi	$4,134	$2.00	$3,514 – $4,754	5 d
Houston, TX	1,106 mi	$2,499	$2.26	$2,124 – $2,874	3 d
Phoenix, AZ	1,705 mi	$3,852	$2.26	$3,274 – $4,429	4 d
Philadelphia, PA	787 mi	$2,353	$2.99	$2,000 – $2,706	2 d
San Antonio, TX	1,236 mi	$2,740	$2.22	$2,329 – $3,152	3 d
San Diego, CA	2,034 mi	$4,082	$2.01	$3,470 – $4,694	5 d
Dallas, TX	942 mi	$2,195	$2.33	$1,865 – $2,524	2 d

More lanes into Winter Park

26' box truck lanes into Winter Park, FL
From	Miles	Estimate	Per mile	Typical range	Transit
New York, NY	1,101 mi	$3,006	$2.73	$2,555 – $3,457	3 d
Los Angeles, CA	2,605 mi	$8,526	$3.27	$7,247 – $9,804	6 d
Houston, TX	1,004 mi	$2,625	$2.61	$2,232 – $3,019	3 d
Phoenix, AZ	2,176 mi	$4,160	$1.91	$3,536 – $4,785	5 d
Philadelphia, PA	1,020 mi	$2,508	$2.46	$2,132 – $2,884	3 d
San Antonio, TX	1,226 mi	$3,094	$2.52	$2,630 – $3,558	3 d
San Diego, CA	2,520 mi	$8,271	$3.28	$7,030 – $9,512	6 d
Dallas, TX	1,133 mi	$2,898	$2.56	$2,463 – $3,332	3 d

About this lane

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

A 26' box truck from Chicago, IL to Winter Park, FL is estimated at $3,780 all-in in October 2026, or $3.26 a mile over about 1,158 mi. Quotes typically land between $3,213 and $4,347.

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 $804 of the $3,780 estimate is fuel at the current national diesel price; the remaining $2,976 is linehaul.

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

The reverse direction is estimated at $1,555, which makes Chicago, IL to Winter Park, 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 →