Lane · BOX · Oct 2026

Winter Garden, FL to Chicago, IL box truck rate

$1,554box truck

+3.1% from last month

Per mile: $1.34
Distance: 1,157 mi
Typical range: $1,321–$1,787
Transit: 3 days

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

Winter Garden to Chicago price history

3 months: +7.2%
1 year: +17.5%
5 years: +24.0%

Cost breakdown

Linehaul: $750
Fuel: $804
All-in estimate: $1,554

Return trip

Chicago → Winter Garden$3,778

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

Winter Garden to Chicago by truck type

Estimated cost from Winter Garden, FL to Chicago, IL by truck type
Truck type	Estimate	Per mile	Typical range
53' dry van	$2,381	$2.06	$2,119 – $2,643
53' refrigerated	$2,838	$2.45	$2,469 – $3,207
48' flatbed	$2,883	$2.49	$2,479 – $3,286
Step deck	$3,142	$2.72	$2,640 – $3,645
Power only	$2,100	$1.81	$1,827 – $2,373
Hotshot	$1,585	$1.37	$1,315 – $1,854
26' box truck	$1,554	$1.34	$1,321 – $1,787
Sprinter van	$952	$0.82	$800 – $1,105

More lanes from Winter Garden

26' box truck lanes from Winter Garden, FL
To	Miles	Estimate	Per mile	Typical range	Transit
New York, NY	1,113 mi	$2,051	$1.84	$1,744 – $2,359	3 d
Los Angeles, CA	2,590 mi	$3,198	$1.23	$2,718 – $3,678	6 d
Houston, TX	987 mi	$1,434	$1.45	$1,219 – $1,649	3 d
Phoenix, AZ	2,161 mi	$2,993	$1.39	$2,544 – $3,442	5 d
Philadelphia, PA	1,031 mi	$1,833	$1.78	$1,558 – $2,108	3 d
San Antonio, TX	1,208 mi	$1,693	$1.40	$1,439 – $1,946	3 d
San Diego, CA	2,504 mi	$3,101	$1.24	$2,636 – $3,566	6 d
Dallas, TX	1,118 mi	$1,587	$1.42	$1,349 – $1,825	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 Garden, FL to Chicago, IL?

A 26' box truck from Winter Garden, FL to Chicago, IL is estimated at $1,554 all-in in October 2026, or $1.34 a mile over about 1,157 mi. Quotes typically land between $1,321 and $1,787.

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

About 1,157 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 $1,554 estimate is fuel at the current national diesel price; the remaining $750 is linehaul.

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

The reverse direction is estimated at $3,778, which makes Winter Garden, 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 →