Lane · BOX · Oct 2026

Winter Haven, FL to Chicago, IL box truck rate

$1,593box truck

+3.0% from last month

Per mile: $1.34
Distance: 1,192 mi
Typical range: $1,354–$1,832
Transit: 3 days

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

Winter Haven to Chicago price history

3 months: +8.1%
1 year: +17.5%
5 years: +25.3%

Cost breakdown

Linehaul: $765
Fuel: $828
All-in estimate: $1,593

Return trip

Chicago → Winter Haven$3,872

This direction runs 59% below the return trip. Leaving FL prices below the national average and arriving in IL prices below it.

Winter Haven to Chicago by truck type

Estimated cost from Winter Haven, FL to Chicago, IL by truck type
Truck type	Estimate	Per mile	Typical range
53' dry van	$2,440	$2.05	$2,172 – $2,708
53' refrigerated	$2,908	$2.44	$2,530 – $3,286
48' flatbed	$2,952	$2.48	$2,539 – $3,366
Step deck	$3,218	$2.70	$2,703 – $3,733
Power only	$2,153	$1.81	$1,873 – $2,433
Hotshot	$1,625	$1.36	$1,349 – $1,901
26' box truck	$1,593	$1.34	$1,354 – $1,832
Sprinter van	$976	$0.82	$820 – $1,132

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 Winter Haven

26' box truck lanes from Winter Haven, FL
To	Miles	Estimate	Per mile	Typical range	Transit
New York, NY	1,153 mi	$2,112	$1.83	$1,795 – $2,429	3 d
Los Angeles, CA	2,594 mi	$3,203	$1.23	$2,722 – $3,683	6 d
Houston, TX	984 mi	$1,431	$1.45	$1,216 – $1,645	3 d
Phoenix, AZ	2,165 mi	$2,998	$1.38	$2,548 – $3,448	5 d
Philadelphia, PA	1,072 mi	$1,892	$1.77	$1,608 – $2,176	3 d
San Antonio, TX	1,205 mi	$1,689	$1.40	$1,436 – $1,942	3 d
San Diego, CA	2,507 mi	$3,104	$1.24	$2,639 – $3,570	6 d
Dallas, TX	1,124 mi	$1,594	$1.42	$1,355 – $1,833	3 d

More lanes into Chicago

26' box truck lanes into Chicago, IL
From	Miles	Estimate	Per mile	Typical range	Transit
New York, NY	847 mi	$1,592	$1.88	$1,353 – $1,831	2 d
Los Angeles, CA	2,063 mi	$4,510	$2.19	$3,834 – $5,187	5 d
Houston, TX	1,106 mi	$1,857	$1.68	$1,578 – $2,135	3 d
Phoenix, AZ	1,705 mi	$2,189	$1.28	$1,861 – $2,517	4 d
Philadelphia, PA	787 mi	$1,336	$1.70	$1,136 – $1,536	2 d
San Antonio, TX	1,236 mi	$2,036	$1.65	$1,730 – $2,341	3 d
San Diego, CA	2,034 mi	$4,454	$2.19	$3,786 – $5,122	5 d
Dallas, TX	942 mi	$1,630	$1.73	$1,386 – $1,875	2 d

About this lane

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

A 26' box truck from Winter Haven, FL to Chicago, IL is estimated at $1,593 all-in in October 2026, or $1.34 a mile over about 1,192 mi. Quotes typically land between $1,354 and $1,832.

How far is Winter Haven, FL from Chicago, IL 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 $1,593 estimate is fuel at the current national diesel price; the remaining $765 is linehaul.

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

The reverse direction is estimated at $3,872, which makes Winter Haven, FL to Chicago, IL 59% cheaper. 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 →