Lane · BOX · Oct 2026

Winter Park, FL to Chicago, IL box truck rate

$1,555box truck

+3.1% from last month

Per mile: $1.34
Distance: 1,158 mi
Typical range: $1,322–$1,789
Transit: 3 days

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

Winter Park to Chicago price history

3 months: +7.2%
1 year: +17.6%
5 years: +24.1%

Cost breakdown

Linehaul: $751
Fuel: $804
All-in estimate: $1,555

Return trip

Chicago → Winter Park$3,780

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

Winter Park to Chicago by truck type

Estimated cost from Winter Park, FL to Chicago, IL by truck type
Truck type	Estimate	Per mile	Typical range
53' dry van	$2,383	$2.06	$2,121 – $2,645
53' refrigerated	$2,840	$2.45	$2,471 – $3,209
48' flatbed	$2,885	$2.49	$2,481 – $3,289
Step deck	$3,145	$2.72	$2,641 – $3,648
Power only	$2,101	$1.81	$1,828 – $2,375
Hotshot	$1,586	$1.37	$1,316 – $1,855
26' box truck	$1,555	$1.34	$1,322 – $1,789
Sprinter van	$953	$0.82	$801 – $1,106

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 Park

26' box truck lanes from Winter Park, FL
To	Miles	Estimate	Per mile	Typical range	Transit
New York, NY	1,101 mi	$2,033	$1.85	$1,728 – $2,338	3 d
Los Angeles, CA	2,605 mi	$3,215	$1.23	$2,733 – $3,697	6 d
Houston, TX	1,004 mi	$1,454	$1.45	$1,236 – $1,672	3 d
Phoenix, AZ	2,176 mi	$3,012	$1.38	$2,560 – $3,464	5 d
Philadelphia, PA	1,020 mi	$1,817	$1.78	$1,545 – $2,090	3 d
San Antonio, TX	1,226 mi	$1,714	$1.40	$1,457 – $1,971	3 d
San Diego, CA	2,520 mi	$3,119	$1.24	$2,651 – $3,587	6 d
Dallas, TX	1,133 mi	$1,605	$1.42	$1,364 – $1,846	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 Park, FL to Chicago, IL?

A 26' box truck from Winter Park, FL to Chicago, IL is estimated at $1,555 all-in in October 2026, or $1.34 a mile over about 1,158 mi. Quotes typically land between $1,322 and $1,789.

How far is Winter Park, FL from Chicago, IL 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 $1,555 estimate is fuel at the current national diesel price; the remaining $751 is linehaul.

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

The reverse direction is estimated at $3,780, which makes Winter Park, 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 →