With the rapid economic development, China has sufficient foreign exchange reserves. Together with the appreciation in Chinese currency and other conditions, more and more Chinese enterprises invest overseas especially in the USA. Based on the statistics of the National Bureau of Statistics of the People’s Republic of China, in 2012 and 2013, among the top 3 countries in which Chinese enterprises have invested, the USA ranked the second with US$ 4047.85 million and the third with US$ 3873.43 million respectively. Chinese enterprises’ FDI in the USA has been mutually beneficial to both China and the USA. However, Chinese enterprises’ FDI in the USA has encountered a variety of obstacles from the USA including American government’s interfering with FDI by political methods, difficulty to enter into some industries, and America’s protectionism. On the other hand, those Chinese enterprises also have some problems in their outward FDI in the USA such as unstable development trend of FDI, enterprises of small size with the privately-owned enterprises as the main body, and unfamiliarity with the related policies and laws. What countermeasures should Chinese enterprises adopt to deal with the obstacles or problems? This paper aims at analyzing the obstacles from the USA and the problems existing in those Chinese enterprises’ FDI in the USA by means of SWOT method and puts forward some corresponding countermeasures for the Chinese enterprises to conduct their outward FDI in the USA more effectively. The conclusions can be used for reference by companies which plan to invest in the USA or other foreign countries.