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In this paper, a novel transition design using vertical ldquocoaxial transitionrdquo for coplanar waveguide (CPW-to-CPW) flip-chip interconnect is proposed and presented for the first time. The signal continuity is greatly improved since the coaxial-type transition provides more return current paths compared to the conventional transition in the flip-chip structure. The proposed coaxial transition structure shows a real coaxial property from the 3-D electromagnetic wave simulation results. The design rules for the coaxial transition are presented in detail with the key parameters of the coaxial transition structure discussed. For demonstration, the back-to-back flip-chip interconnect structures with the vertical coaxial transitions have been successfully fabricated and characterized. The demonstrated interconnect structure using the coaxial transition exhibits the return loss below 25 dB and the insertion loss within 0.4 dB from dc to 40 GHz. Furthermore, the measurement and simulation results show good agreement. The novel coaxial transition demonstrates excellent interconnect performance for flip-chip interconnects and shows great potential for flip-chip packaging applications at millimeter waves.