In　this　study,　a　new　bridged　bis(β-cyclodextrin)　(CD)　functionalized　urea-formaldehyde　monolithic　column　was　prepared　by　＇one-pot＇method　within　30　minutes.　The　structures　of　bridged-CD　and　the　obtained　monolithic　column　were　characterized　by　scanning　electron　microscopy,　nuclear　magnetic　resonance　spectroscopy,　infrared　spectroscopy　and　energy　dispersive　spectroscopy.　The　chromatographic　performance　of　native-CD-monolith,　N,N′-methylenebisacrylamide　(MBA)-bridged-CD-monolith　and　N,N′-(1,2-dihydroxyethylene)　bisacrylamide　(DAA)-bridged-CD-monolith　was　systematically　evaluated　by　separating　five　analytes.　As　a　result,　all　tested　analytes　were　separated　on　an　MBA-bridged-CD-monolith　and　DAA-bridged-CD-monolith　with　high　resolutions　(1.21-6.80),　which　showed　that　the　bridged-CD-monolith　exhibited　a　better　chromatographic　performance　with　enantioselectivity　due　to　providing　mixed-modes　such　as　hydrophilicity,　hydrogen　bonding,　ionic　dipole　and　synergy　compared　with　those　of　the　native-CD-monolith.　In　addition,　the　enantioselectivity　of　the　bridged-CD-monolith　was　related　to　the　polarity　of　a　functional　linker.　As　a　new　chiral　separation　material,　the　bridged-CD　functionalized　urea-formaldehyde　monolithic　column　may　be　widely　applied　in　the　analysis　of　chiral　compounds　due　to　its　rapid　preparation　and　higher　enantioseparation　performance.　©　2021　The　Royal　Society　of　Chemistry.