Lane · BOX · Oct 2026

Chicago, IL to Winter Garden, FL box truck rate

$3,778box truck

+3.1% from last month

Per mile: $3.27
Distance: 1,157 mi
Typical range: $3,211–$4,344
Transit: 3 days

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

Chicago to Winter Garden price history

3 months: +7.9%
1 year: +17.6%
5 years: +24.8%

Cost breakdown

Linehaul: $2,974
Fuel: $804
All-in estimate: $3,778

Return trip

Winter Garden → Chicago$1,554

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 Garden by truck type

Estimated cost from Chicago, IL to Winter Garden, FL by truck type
Truck type	Estimate	Per mile	Typical range
53' dry van	$5,787	$5.00	$5,151 – $6,424
53' refrigerated	$6,897	$5.96	$6,001 – $7,794
48' flatbed	$7,007	$6.06	$6,026 – $7,988
Step deck	$7,638	$6.60	$6,416 – $8,860
Power only	$5,104	$4.41	$4,440 – $5,767
Hotshot	$3,852	$3.33	$3,197 – $4,506
26' box truck	$3,778	$3.27	$3,211 – $4,344
Sprinter van	$2,315	$2.00	$1,944 – $2,685

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 Garden

26' box truck lanes into Winter Garden, FL
From	Miles	Estimate	Per mile	Typical range	Transit
New York, NY	1,113 mi	$3,033	$2.72	$2,578 – $3,488	3 d
Los Angeles, CA	2,590 mi	$8,481	$3.27	$7,209 – $9,753	6 d
Houston, TX	987 mi	$2,590	$2.62	$2,201 – $2,978	3 d
Phoenix, AZ	2,161 mi	$4,135	$1.91	$3,514 – $4,755	5 d
Philadelphia, PA	1,031 mi	$2,530	$2.45	$2,150 – $2,909	3 d
San Antonio, TX	1,208 mi	$3,056	$2.53	$2,598 – $3,514	3 d
San Diego, CA	2,504 mi	$8,223	$3.28	$6,990 – $9,456	6 d
Dallas, TX	1,118 mi	$2,866	$2.56	$2,436 – $3,296	3 d

About this lane

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

A 26' box truck from Chicago, IL to Winter Garden, FL is estimated at $3,778 all-in in October 2026, or $3.27 a mile over about 1,157 mi. Quotes typically land between $3,211 and $4,344.

How far is Chicago, IL from Winter Garden, FL 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 $3,778 estimate is fuel at the current national diesel price; the remaining $2,974 is linehaul.

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

The reverse direction is estimated at $1,554, which makes Chicago, IL to Winter Garden, 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 →