9. Chicago Express
In Chicago Express, players take on the role of railroad executives just as four major railroads are pushing west, all trying to be the first to make it to Chicago. Gameplay is relatively simple with each player taking one of three actions on their turn, but the ramifications of those actions can run deep. On your turn, you can lay one to three trains on the board, develop a section of land (thus raising money for your company), or you can auction of more shares of a company.
The game ends when three companies run out of trains, three companies run out of stock, when houses run out or when Detroit is worth eight points. Ultimately you have to make the most money in the short timeframe of a game and make sure you don't overpay for your shares. However you need to pay enough to make sure your company has some capital to spend to build railroads. The player with the most profit at the end, wins.