Following the numbered releases (volumes 1 and 2) and both the Ibiza... releases, the albums were themed to seasons, starting with The Winter Collection 2003 (actually released in late 2002, as the sort of style Chillout Annual 2003). The Summer 2003 edition reached #10 in the UK Compilations Chart. A third Ibiza... edition, Ibiza Sunsets, was released shortly afterwards. This series, despite sales success, was suspended in favour of other Ministry of Sound albums in 2003. Its final album The Very Best of the Chillout Sessions was released in late 2003, but did not sell well and until 2011 was the worst-selling album in the series.

Chillout Sessions XX is the twentieth installment of the Chillout Sessions series of compilations, released by Ministry of Sound and was released in April 2018. Chillout Sessions 8 is the eighth installment in the Chillout Sessions series, released by Ministry of Sound.

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Chillout Sessions is a series of compilations released by Ministry of Sound that focus on songs from the chillout genre. Songs on Chillout Sessions compilations vary in style from lounge to electronica and are released by many different artists. Chillout Sessions XII is the twelfth installment of the Chillout Sessions series of compilations, released by Ministry of Sound. The cover art for the album used on the slipcase depicts the Ministry of Sound logo uprising out of water. Chillout Sessions XV is the fifteenth installment of the Chillout Sessions series of compilations, released by Ministry of Sound. The Chillout genre of compilations started in the UK and since 2003 Ministry of Sound has released them under different tropes such as "Chilled", "After Hours", "The Morning After..." which has shown MOS to have seemingly ended its branding of the genre as Chillout Sessions.Since 2018, Ministry of Sound exclusively moved their Playlists to Apple Music. Many of their well known compilation brands such as Anthems, Fitness, I Love and Chilled have moved to a Playlist format, which accounts for the limited releases of non-streamable Chilled Compilation albums. A notable example is the Chilled House Session series that ran from 2009 to its final release in 2019 (Chilled House Session 9) and is now an exclusive Playlist on Apple Music. In 2007, Ministry of Sound launched a new series, Anthems, beginning with Anthems 1991–2008. It sold very well and it generated a spin-off album, Chilled 1991–2008. This was followed by a second volume in 2009, a third (suited to acoustic chill-out music) in 2010 and a fourth ( Chilled Afterhours, similar to the label's Late Night Sessions albums) in 2011. 2011 was also the year that Ministry of Sound launched its large-scale campaign 20:20, to celebrate 20 years of The Ministry of Sound as a club. One of the associated releases was the box set XX Twenty Years, each disc made up of a different dance genre; the final disc in the box set was Chillout Sessions. Around the same time, Anthems Collection was released, with five discs, each from a different genre, the final one being Anthems Chilled. Chillout Sessions XVII is the seventeenth installment of the Chillout Sessions series of compilations, released by Ministry of Sound.

Ministry of Sound started the series again in January 2006, with an album titled simply The Chillout Sessions (titled to reflect the fact that it was a reboot for the series). This album had good sales but there were no subsequent releases.Chillout Sessions XIV is the fourteenth instalment of the Chillout Sessions series of compilations, released by Ministry of Sound. Chillout Sessions 7 is the seventh installment of the Chillout Sessions series of compilations, released by Ministry of Sound. Chillout Sessions 4 is the fourth installment in the series. It was the first to remove "The" from the title, leaving the series title simply 'Chillout Sessions'.

A similar series started in Australia, where the series changed its name from The Chillout Session to The Chillout Sessions and then simply to Chillout Sessions and continued until 2016 with XIX until the record label rebranded to TMRW following the acquisition of MoS by Sony in the UK. Some Chillout Sessions albums have become known and distinguishable for the symbol of a turntable (with the Ministry of Sound logo on it) frozen in ice, or in one case ( The Summer Collection 2003) the turntable itself is made of ice. In the UK this motif is used on the covers of volumes 1, 2, The Winter Collection (2003), The Summer Collection 2003, and The Very Best of album. In Australia, the image is used for volumes 1–6 except on volume 3. The idea of the turntable with the Ministry of Sound logo on had been used on the covers of the Ministry of Sound Clubbers Guide in prior years (and in The Annual IV), the idea of such turntable on the covers was last used on Clubbers Guide albums in early 2001 when The Chillout Session began using the idea. Chillout Sessions XI is the eleventh installment of the Chillout Sessions series of compilations, released by Ministry of Sound. It is the first of the Chillout Sessions to use Roman Numerals in the title, instead of standard numbers. The Chillout Session 2 is the second installment in the series and was released on 3 July 2001 in the United Kingdom and Australia. It reached #2 in the UK compilation album chart. Fifth in the series, Chillout Sessions 5 is a two-disc compilation of songs by various artists that was released in 2004. Its front cover uses the same image that the UK release The Very Best of the Chillout Session does. The image is also similar to that used on the front cover of Chillout Classics.The front cover uses the same image that the UK release The Chillout Session 2003: Winter Collection does. The Chillout Sessions 3 is the third installment in the series and was released on 30 September 2002. It was the first album to be released in Australia only, and the first to use the name 'Sessions' in the title instead of simply 'Session' Chillout Sessions 10 is the tenth installment of the Chillout Sessions series of compilations, released by Ministry of Sound. Chillout Sessions XIII is the thirteenth installment of the Chillout Sessions series of compilations, released by Ministry of Sound.