You didn't specify a time, so I'm going to assume you mean "during or before European contact," and not "In 1995." While the examples I'm going to mention aren't specifically midwestern, it should give you an idea of the situation, working our way backwards through time.

In the late 1800s, the old men among the Lenape living in the Six Nations of Grand River recounted that in pre-colonial times, "the Lenape had a string of white wampum beads, which stretched from the Atlantic to the Pacific, and on this white road their envoys traveled from one great ocean to the other, safe from attack." That particular piece of information is usually attributed to Albert Seqaqknind Anthony, with whom Daniel Brinton collaborated on a Lenape-English dictionary, but Brinton's writing seems to indicate that it came from multiple sources or was at least confirmed by multiple sources as a well known tradition. However, it's one of those traditions in the "good old days" genre, which is prone to overly optimistic exaggeration. Historically, white wampum belts and strings had been used in the east as symbols for peace and tokens to secure safe passage. Likewise, the Lenape were famous peace-makers and arbitrators during the colonial era. But wampum was not universally respected, and by the time one reached the Mississippi the calumet was the preferred method of advertising peaceful intention (not to say white wampum and a calumet are mutually exclusive; there is overlap and cross-cultural understanding that the two are, roughly speaking, equivalent in intent). But were Lenape really able to travel from one coast to the other in pre-colonial days? We'll get back to that question in a moment.

First, we turn our attention to the south. In the 1720s, the French historian du Pratz was working among the Natchez in modern Mississippi. While speaking with a Natchez priest, du Pratz learned of their conflicts with "the ancients of the land," a catch-all term for the people who inhabited the American Southwest and Mexico. To the Natchez, the territory of the ancients began across the southern plains and continued to the shores of the ocean on the other side, showing an awareness of the Pacific. As for the Atlantic, the Natchez were in more regular contact with people living on that coast, and knew individual nations by name as far away as New England. Around this same time and for similar reasons, du Pratz also met Moncacht-Apé, a Tunica man living among the Natchez. Moncacht-Apé personally traveled from one coast to sometime in the late 1600s. Leaving his homeland in the lower Mississippi, he first traveled northeast to New England. Later, he made a second journey to the northwest, eventually reaching the mouth of the Columbia River before journeying north along the Pacific coast for a time. You can read about his journeys in a previous post I made. Moncacht-Apé's journey lends additional credence to the idea that some Lenape travelers could also have made similar cross-continental trips.

Now we jump way back to the days of the Hopewell, between 2000 and 1600 years ago. Ohio archaeologist (and local guest AMA contributor here) Brad Lepper has explicitly equated the Lenape's wampum road with the extensive trade network spanning the Hopewell interaction sphere and beyond. While the Ohio Hopewell tend to get top billing and a lot of focus has been placed on their regular acquisition of obsidian from Yellowstone, there are artifacts dating to this period that traveled even further. Obsidian from Oregon and California made its way eastward all the way to New York and New Jersey (source). Whether people of this era were personally traveling back and forth is debatable, but people like Moncacht-Apé and the tradition of the Lenape's wampum road certainly makes it possible that such journeys happened occasionally.