The fair place to meet is Denver, CO — the city closest to the midpoint of Chicago and Portland. From the farther side that’s about 20 hr 34 min of driving.
Recommended midpoint
Denver, CO
From Chicago
19 hr 15 min
918 mi to Denver
From Portland
20 hr 34 min
981 mi to Denver
Chicago has the shorter trip; the split is off by about 1 hr 19 min. The alternatives below can even it out. Chicago and Portland are about 1,755 miles apart.
Chicago and Portland are about 1,755 miles apart by road. Split the difference and you arrive near Denver, the city closest to the halfway point between them. That puts roughly 19 hr 15 min of driving on the Chicago side and 20 hr 34 min on the Portland side — the fairest single meeting point among the cities near the middle.
Over this distance most people will fly rather than drive the whole way. Denver still makes a fair, central place for Chicago and Portland to converge, splitting the travel instead of asking one side to cross the country.
If Denver doesn't have what you're after, Salt Lake City and Omaha are also close to the midpoint and worth a look — each keeps the drive reasonably balanced between Chicago and Portland.
Denver is the capital and most populous city of the U.S. state of Colorado. Officially a consolidated city and county, it is located in the South Platte River valley on the western edge of the High Plains, and is just east of the Front Range of the Rocky… Read more →
Chicago is the most populous city in the U.S. state of Illinois and in the Midwestern United States. Located on the western shore of Lake Michigan, it is the third-most populous city in the United States, with a population of 2.74 million at the 2020 census. Read more →
Portland is the most populous city in the U.S. state of Oregon. Located in the Pacific Northwest at the confluence of the Willamette and Columbia rivers, it is the 28th-most populous city in the United States, sixth-most populous on the West Coast, and… Read more →
City descriptions adapted from Wikipedia (CC BY-SA); photos via Wikimedia Commons, credited above.
Estimates use straight-line distance and typical road speeds; real drive times vary with route and traffic.