Studies show that Deep Neural Network (DNN)-based image classification models are vulnerable to maliciously constructed adversarial examples. However, little effort has been made to investigate how DNN-based image retrieval models are affected by such attacks. In this paper, we introduce Unsupervised Adversarial Attacks with Generative Adversarial Networks (UAA-GAN) to attack deep feature-based image retrieval systems. UAA-GAN is an unsupervised learning model that requires only a small amount of unlabeled data for training. Once trained, it produces query-specific perturbations for query images to form adversarial queries. The core idea is to ensure that the attached perturbation is barely perceptible to human yet effective in pushing the query away from its original position in the deep feature space. UAA-GAN works with various application scenarios that are based on deep features, including image retrieval, person Re-ID and face search. Empirical results show that UAA-GAN cripples retrieval performance without significant visual changes in the query images. UAA-GAN generated adversarial examples are less distinguishable because they tend to incorporate subtle perturbations in textured or salient areas of the images, such as key body parts of human, dominant structural patterns/textures or edges, rather than in visually insignificant areas (e.g., background and sky). Such tendency indicates that the model indeed learned how to toy with both image retrieval systems and human eyes.