NXT TakeOver: Chicago II was the 20th NXT TakeOver and the second and final TakeOver: Chicago professional wrestling livestreaming event produced by WWE. It was held exclusively for wrestlers from the promotion's NXT brand division. The event aired exclusively on the WWE Network and took place on June 16, 2018, at the Allstate Arena in the Chicago suburb of Rosemont, Illinois as part of that year's Money in the Bank weekend.

Five matches were contested at the event. In the main event, Tommaso Ciampa defeated Johnny Gargano in a Chicago Street Fight. On the undercard, Aleister Black defeated Lars Sullivan to retain the NXT Championship and Ricochet defeated Velveteen Dream.