The northern section of the H. E. Bailey Turnpike carries I-44 north, serving Chickasha before ending at US-62 (exit 107) in Newcastle.

I-44 then passes west of the state fairgrounds and continues north to provide access to Bethany and Warr Acres.

It then turns more eastbound before reaching a junction with I-235, which also signifies the northern end of I-235, and US-77 also known as the Broadway Extension, which connects Downtown Oklahoma City to Edmond.

It then meets and follows a stretch of I-35, which it runs concurrently with until the Turner Turnpike interchange, where it takes an easterly turn again.

The Will Rogers Turnpike section serves many northeast Oklahoma towns, including Claremore, Vinita (where it passes under the world's former largest McDonald's), and Miami.

[citation needed] Southeast of Catoosa, I-44 was redesigned to have an interchange with the eastern expansion of the Creek Turnpike.

A 1.5-mile (2.4 km) stretch of the original roadbed remains; it, however, is unused and is not maintained by the Oklahoma Department of Transportation (ODOT) or any of the surrounding cities.

In 2012, the only bridge over the abandoned stretch, Pine Street, was removed and replaced with graded fill over the old turnpike.

In 1975, the American Association of State Highway and Transportation Officials (AASHTO) approved renumbering I-440 as I-240 to create a single numeric designation for the Oklahoma City loop.

In 1982, as part of Oklahoma's "Diamond Jubilee", I-44's western terminus was moved from the I-35/I-44 junction near Edmond, to the Texas state line via the Belle Isle Freeway (part of the recently designated I-240 connecting the former I-440 with I-35); I-240, the H. E. Bailey Turnpike; and the turnpike connector road on the eastern edge of Lawton.