These icons () show footnotes as tooltips... for some browsers.
29.84 miles , Eisenhower Expressway. Starts at I-90/94 (Dan Ryan Expwy) in downtown Chicago; west to where I-88 meets I-294; then northwest to I-90 again in Rolling Meadows. IL 53 continues north as a freeway to Lake Cook Road in Long Grove.
The Eisenhower Expressway portion (east of I-294) was the first major route of the 1940 Comprehensive Superhighway System of Chicago. Construction began in late 1949, and the first section opened to traffic on December 15, 1955. The rest opened on August 10, 1956. On January 10, 1964, the road was renamed from the Congress Street Expressway to the Eisenhower Expressway.
The outer freeway (west of I-294) was done in the early 1970s. However, I-290 was marked as part of I-90 until about 1979. 
"Hillside Strangler" woes
Jason Remy writes that I-290 needs a lane or five at the I-294/I-88 "Hillside Strangler" interchange: eastbound travelers get cozy with their neighbors as seven lanes squeeze into two.
"Consider the onramps coming onto the eastbound lanes of I-290 from the West. IL-38 is a short expressway (unmarked as such on many maps, trust me, it exists) that runs from IL-83 till this interchange. At the end of this short spur, the left hand lane becomes a 2 lane ramp, the right hand lane once again roosevelt road, with access to I-294 S (there is no northbound access here, from any direction, for at least 3 miles, with no signs directing you how to get there... Go figure. There is also no westbound access to I-290).
"This 2 lane ramp drops one lane (-1 lane for the interchange) and 250 yards later picks up a lane from I-294 Northbound. This lane drops shortly before joining the remnant of I-88 (-2 lanes for the interchange) After merging with I-88, this lane too leaves, and 100 yards later, one of I-88's lanes inexplicably leaves as well (-4 lanes for the interchange) leaving a 2 1/2 car wide shoulder on the right, a 1 car wide shoulder on the left and a single travel lane. This last lane is dumped unceromoniously onto the LEFT lane of I-290 with no acceleration zone (-5 lanes for the interchange).
"Did I mention that I-290 East is 2 lanes here? Also, this interchange is only about 1 mile long, meaning that some how, SEVEN lanes of traffic must reduce itself to TWO lanes in less than 1 mile? " 
Daniel Hobson adds that IDOT is addressing the problem. Construction started in March 2000 to add a collector-distributor road on I-290 at the US 12/20/45 and Wolf Road interchanges. This would help distribute the seven lanes of traffic funneling onto I-290. The project should finish in 2002 or 2003. 
Put a lid on it
By around 2007, I-290 could be widening from 6 to 8 lanes between I-88 and Cicero. The community of Oak Park, fearing a wider Eisenhower Expressway would divide the town even more, is considering asking for a cap over the highway when it is widened. Atop the highway tunnel would be "green space, parks, commuter parking, enhanced transit, [etc.]". A similar plan was studied in 1987 but no funding or project came out of it. 
In suburban Detroit, the town of Oak Park (no relation) got a cap when I-696 was expanded a while ago.  Likewise "cut and cover" techniques have been proposed for the Interstate 710 extension in South Pasadena.
Plans for an expressway serving Worcester predate the Interstate highway system, including a 6.5-mile urban highway in 1951. The original planned alignment for I-290 would join with I-90 twice: once in Auburn (as it does today) and once near I-90/495. 
I-290 opened in segments from 1958 through 1970; by that time, its eastern end had been relocated to I-495 in Marlborough. 
In the late 1960s, the state had also planned to extend I-290 further toward Boston. Bob Coe writes that the state had a _secret_ plan for this. Here's the quote:
"Absolutely, but [the plans] were an extremely well guarded secret. Those of us who live in towns on its path knew perfectly well that I-290 was intended to continue at least to 128, but the State always denied it. (An acquaintance of mine once claimed to have seen at least one version of the planned alignment in a file at the office of the Sudbury Planning Board.) The fight continued through the 1970s, with the neighboring towns trying to get the Legislature to kill the plan and the State claiming there was no plan to kill. Eventually the State gave up; DEC's Hudson plant was built in the path of the extension; and DEC agreed to pay for the 2-lane extension (on the proposed I-290 alignment) from I-495 to the new plant. As part of the deal, the State promised to abandon the extension plan whose existence they had always denied." 
Dan Moraseski ("SPUI") adds that I-290 extension plans are available at the State Transportation Library; the highway would have either gone to MA 128 at US 20 or to MA 2 south of Concord. 
See also: Worcester Expressway (Steve Anderson)
I-290 New York
Its original name was the pedestrian Power Line Expressway, since I-290 parallels high tension lines for most of its length. Elmer G. H. Youngmann, one of the project engineers, died during the road's construction in the early 60s, and the road was named in his memory. 
The preliminary designation for this highway, as the interstate system was being laid out, was I-190. (Today's I-190 was called I-90N at the time.) This was in effect for only one week in August 1958, as AASHO directed a number change to 290, with an even starting digit more appropriate for a bypass route. 
I-290 (cancelled) Ohio
The Cleveland Heights freeway, proposed in the 1960s; would start at present-day I-490 and continue east to I-271, reuniting with I-90 to the north. This one seemed to die because it was planned to go through too affluent an area. 
Steve Hill provides this information from the 1968 official Cuyahoga county map:
"Clark Freeway (I-290):
Matt Walcoff adds that the proposed route would have gone through a park, which was prohibited for federal funding -- not helping its cause.
In an article about the 70-year-old Lorain-Carnegie (aka Hope Memorial) Bridge, the Cleveland Plain Dealer recounted a 1976 incident in which county engineer Albert Porter wanted to remove the bridge's art deco ornaments so the bridge could be widened.
"Those columns are monstrosities and should be torn down and forgotten. There is nothing particularly historic about any one of them. We're not running a May Show here," Porter is quoted as saying.
"This is the same man who wanted to run an interstate through the Shaker Lakes," the article notes.