The City of Cleveland has 3 professional sports teams and has not won a Championship since 1964 making them the city that has gone the longest without winning a Championship.
The Chicago Cubs of Major League Baseball are in the midst of a 102 year World Series Championship drought. (1908 was their last W.S. Title) The Cubs haven't even appeared in a World Series game since 1945. This is by far the longest individual drought in all of sports.
Sacramento
Kansas City Royals
Boston i think
if your're talking about any city in Illinois, than yes, the Chicago bulls have one several.
Germany's Schwebebahn at Wuppertal, which is suspended from an overhead rail, is the world's longest running monorail, operating since 1901
Boston is the most recent city to have championship teams in all four major sports.
I believe it is Boston Red Sox won 2 world series Celtics won 1 championship Patriots won 3 superbowls The New England Revolution(soccer) have appeared in 4 championships but lost
Berlin City Chess Championship was created in 1904.
Paris City Chess Championship was created in 1925.
That would be the Chicago Cubs who have played in Chicago since 1876.
The Chiefs have not made a championship appearance since they won Super Bowl IV in January 1970.
The City of Pittsburgh has won 14 championship trophies in all.Steelers (NFL) - 6Pirates (MLB) - 5Penguins (NHL) - 3