Lane · BOX · Oct 2026

Chicago, IL to Middletown, NY box truck rate

$2,524box truck

+3.0% from last month

Per mile: $3.12
Distance: 808 mi
Typical range: $2,145–$2,902
Transit: 2 days

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

Chicago to Middletown price history

3 months: +7.6%
1 year: +17.3%
5 years: +24.8%

Cost breakdown

Linehaul: $1,963
Fuel: $561
All-in estimate: $2,524

Return trip

Middletown → Chicago$1,535

This direction runs 64% above the return trip. Leaving IL prices above the national average and arriving in NY prices above it.

Chicago to Middletown by truck type

Estimated cost from Chicago, IL to Middletown, NY by truck type
Truck type	Estimate	Per mile	Typical range
53' dry van	$3,880	$4.80	$3,453 – $4,307
53' refrigerated	$4,627	$5.73	$4,025 – $5,228
48' flatbed	$4,737	$5.86	$4,074 – $5,400
Step deck	$5,172	$6.40	$4,344 – $5,999
Power only	$3,399	$4.21	$2,957 – $3,841
Hotshot	$2,564	$3.17	$2,128 – $3,000
26' box truck	$2,524	$3.12	$2,145 – $2,902
Sprinter van	$1,552	$1.92	$1,304 – $1,800

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 Middletown

26' box truck lanes into Middletown, NY
From	Miles	Estimate	Per mile	Typical range	Transit
New York, NY	70 mi	$619	$8.84	$526 – $711	1 d
Los Angeles, CA	2,868 mi	$8,294	$2.89	$7,050 – $9,539	6 d
Houston, TX	1,676 mi	$3,601	$2.15	$3,061 – $4,141	4 d
Phoenix, AZ	2,498 mi	$4,199	$1.68	$3,569 – $4,829	6 d
Philadelphia, PA	125 mi	$647	$5.17	$550 – $744	1 d
San Antonio, TX	1,865 mi	$3,956	$2.12	$3,363 – $4,550	4 d
San Diego, CA	2,834 mi	$8,204	$2.89	$6,973 – $9,434	6 d
Dallas, TX	1,608 mi	$3,473	$2.16	$2,952 – $3,994	4 d

About this lane

How much does it cost to ship a truckload from Chicago, IL to Middletown, NY?

A 26' box truck from Chicago, IL to Middletown, NY is estimated at $2,524 all-in in October 2026, or $3.12 a mile over about 808 mi. Quotes typically land between $2,145 and $2,902.

How far is Chicago, IL from Middletown, NY by truck?

About 808 mi by road, estimated from the straight-line distance. A solo driver covers it in roughly 2 days of transit.

How much of the price is fuel?

About $561 of the $2,524 estimate is fuel at the current national diesel price; the remaining $1,963 is linehaul.

Is it cheaper to ship from Middletown, NY to Chicago, IL?

The reverse direction is estimated at $1,535, which makes Chicago, IL to Middletown, NY 64% 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 →