[10] Joslins expanded its storefront in 1987 by 43,000 square feet by taking over vacant space in the mall's lower wing.

The presence of several discount retailer anchors like Kmart and Sears likely discouraged higher-end chains from moving to the mall.

[12][13] In 1990, Dillard's announced its intent to build its first Colorado Springs location in the Chapel Hills Mall but scrapped those plans to create a new store at The Citadel instead.

[14] JCPenney moved into the vacated space a year later with a store that attempted to cater to wealthier customers with high-end décor and a limited amount of hardline goods.

[17] By the end of the decade, the mall had also added a regulation-size ice arena, a two-story Borders Books, a Ruby Tuesday, a children's play area, a climbing wall, and new nationwide retailers.

[18] In 2000, Old Navy opened its first Colorado Springs location at the mall by renovating eight storefronts' worth of space with a total square footage of 20,037.

[30] Toby Keith's I Love This Bar & Grill announced in 2014 its intent to build a restaurant on the first floor of the former Borders location but later scrapped the plans.

In 2017, Garrison Investment received foreclosure notices on the mall totaling $37 million, the largest default in El Paso County history.

[38] In response to the COVID-19 pandemic and related local health mandates, the Chapel Hills Mall temporarily closed for approximately a month in April 2020.

[39][40] The former Sears building and parking lots were razed in 2021 to make way for a 300-unit “suburban-style” apartment complex that developers are constructing adjacent to the mall, which were completed in 2023.

[41] In 2024, plans were announced to renovate the former Burlington store into a new indoor pickleball complex and to build an interactive aquarium in the mall.