Immune checkpoint blockade (ICB) that enhances the anti-tumour immune response is a treatment option for multiple cancer types. However as a stand-alone therapy, objective response rates only occur in a minority of patients. Chemotherapy is widely used in combination with ICB. Although a variety of isolated immunostimulatory effects have been reported for several classes of chemotherapeutics, it is unclear which chemotherapeutics provide the most benefit when combined with ICB. Here, we investigated 10 chemotherapies from the main canonical classes dosed at the clinically relevant maximum tolerated dose in combination with ICB (anti-CTLA-4/anti-PD-L1) in two murine mesothelioma cancer models from two different genetic backgrounds. We identified chemotherapies that produced additive, neutral or antagonistic effects when combined with ICB. Vinorelbine displayed an antagonistic interaction with ICB, while 5-Fluorouracil (5-FU) or cisplatin were additive when combined with ICB. Using flow cytometry and bulk RNAseq, we characterised the tumour immune milieu to understand mechanisms of additive chemo-immunotherapy combinations. Both 5-FU and cisplatin in combination with ICB resulted in a profound expansion of tumour draining lymph nodes. Both chemo-immunotherapies markedly increased CD8+ and CD4+ T cell activation and depleted CD4+Foxp3+ regulatory T cells in tumours. 5-FU treated tumours were enriched for immune-related genes, and addition of ICB to 5-FU increased the expression of proinflammatory genes TNF