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@Reynolds Wolf. One Tank of Gas. Start trip in Cleveland, Oh. See the lakefront, Indians, Browns and Cavaliers. Check out Rock N Roll Hall of fame. Head west on I-90 towards Chicago. Stop by Cedar Point, world's best roller coaster park. In Indiana hit up the College Football Hall of Fame. Stop by Notre Dame to see campus and touchdown Jesus. Onto Chicago! Bull, Bears, and Cubs plus Sox. See Wrigleyfield, Sears Tower, Michigan Avenue for shopping grab a Chicago hotdog at Weiner Circle n Lincoln Park neighborhood. Toms to see. Trip is about 325 miles from Cleveland to Chicago. About 6 hours trip from Cleveland to Chicago.
Your trip to Washington looks great. However, the tank of gas aspect is midleading, unless you plan to relocate to Washington and not go home. Otherwise, you have to pay for gas to get home, and unless you want to drive another 350 miles the same day, you'll need at least one hotel room, dinner for the night, and breakfast the next morning.
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