Lane · BOX · Oct 2026

Chicago, IL to Winter Haven, FL box truck rate

$3,872box truck

+3.2% from last month

Per mile: $3.25
Distance: 1,192 mi
Typical range: $3,291–$4,453
Transit: 3 days

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

Chicago to Winter Haven price history

3 months: +7.6%
1 year: +17.3%
5 years: +25.0%

Cost breakdown

Linehaul: $3,044
Fuel: $828
All-in estimate: $3,872

Return trip

Winter Haven → Chicago$1,593

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 Haven by truck type

Estimated cost from Chicago, IL to Winter Haven, FL by truck type
Truck type	Estimate	Per mile	Typical range
53' dry van	$5,931	$4.98	$5,278 – $6,583
53' refrigerated	$7,068	$5.93	$6,149 – $7,987
48' flatbed	$7,176	$6.02	$6,171 – $8,181
Step deck	$7,821	$6.56	$6,570 – $9,073
Power only	$5,233	$4.39	$4,553 – $5,913
Hotshot	$3,949	$3.31	$3,278 – $4,620
26' box truck	$3,872	$3.25	$3,291 – $4,453
Sprinter van	$2,372	$1.99	$1,993 – $2,752

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 Haven

26' box truck lanes into Winter Haven, FL
From	Miles	Estimate	Per mile	Typical range	Transit
New York, NY	1,153 mi	$3,122	$2.71	$2,654 – $3,591	3 d
Los Angeles, CA	2,594 mi	$8,493	$3.27	$7,219 – $9,767	6 d
Houston, TX	984 mi	$2,583	$2.63	$2,196 – $2,971	3 d
Phoenix, AZ	2,165 mi	$4,142	$1.91	$3,520 – $4,763	5 d
Philadelphia, PA	1,072 mi	$2,611	$2.44	$2,220 – $3,003	3 d
San Antonio, TX	1,205 mi	$3,050	$2.53	$2,592 – $3,507	3 d
San Diego, CA	2,507 mi	$8,232	$3.28	$6,997 – $9,467	6 d
Dallas, TX	1,124 mi	$2,879	$2.56	$2,447 – $3,311	3 d

About this lane

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

A 26' box truck from Chicago, IL to Winter Haven, FL is estimated at $3,872 all-in in October 2026, or $3.25 a mile over about 1,192 mi. Quotes typically land between $3,291 and $4,453.

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 $828 of the $3,872 estimate is fuel at the current national diesel price; the remaining $3,044 is linehaul.

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

The reverse direction is estimated at $1,593, which makes Chicago, IL to Winter Haven, 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 →