Games like Three Days to Chicago
Games like Three Days to Chicago include LoveChoice, Our Life: Beginnings & Always, Coffee Talk, Love Is All Around, and I Wani Hug that Gator!. We matched them by the tags players give Three Days to Chicago on Steam (LGBTQ+, Romance, Casual, Visual Novel, and Interactive Fiction): closest matches first, and among equally close ones the better-known games.

LoveChoice
Shared: Romance · Visual Novel · Dating Sim

Our Life: Beginnings & Always
Shared: Romance · LGBTQ+ · Visual Novel

Coffee Talk
Shared: Visual Novel · Dialogue Heavy · LGBTQ+

Love Is All Around
Shared: Romance · Dating Sim · Visual Novel

I Wani Hug that Gator!
Shared: Romance · Visual Novel · Story Rich

Senren * Banka
Shared: Visual Novel · Dating Sim · Casual

Until Then
Shared: Visual Novel · Interactive Fiction · Romance

Doki Doki Literature Club Plus!
Shared: Visual Novel · Romance · Dating Sim

Slay the Princess — The Pristine Cut
Shared: Visual Novel · Romance · Choices Matter

Dream Daddy: A Dad Dating Simulator
Shared: LGBTQ+ · Romance · Visual Novel

ATRI -My Dear Moments-
Shared: Visual Novel · Romance · Casual

Dispatch
Shared: Romance · Choices Matter · Story Rich

恋爱绮谭~不存在的夏天~
Shared: LGBTQ+ · Visual Novel · Casual

CLANNAD
Shared: Visual Novel · Romance · Story Rich

错过的暑假可以放第二次吗?
Shared: LGBTQ+ · Visual Novel · Casual

Love Curse: Find Your Soulmate
Shared: LGBTQ+ · Visual Novel · Romance

Florence
Shared: Casual · Romance · Interactive Fiction

Knowledge, or know Lady
Shared: Romance · Visual Novel · Dating Sim

Tricolour Lovestory
Shared: Visual Novel · Dating Sim · Casual

If My Heart Had Wings
Shared: Romance · Visual Novel · Dating Sim

The Hungry Lamb: Traveling in the Late Ming Dynasty
Shared: Visual Novel · Interactive Fiction · Dating Sim

Sweet Home
Shared: LGBTQ+ · Visual Novel · Interactive Fiction

Monster Prom 3: Monster Roadtrip
Shared: LGBTQ+ · Visual Novel · Dating Sim

My Vow to My Liege
Shared: Romance · Visual Novel · Casual