Date night in Streeterville, Chicago the Weekend of Oct 9–12, 2026

Stumblday's hand-checked ranking of the best date night in Streeterville, Chicago, Downtown, the Loop & West Loop the weekend of Oct 9–12, 2026: 1 pick.

1 picks · checked Sep 21

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All Free Art Music Markets Outdoors Food Date night

Lookingglass Theatre, The Joan and Paul Theatre, Streeterville, Downtown, the Loop & West LoopChris Rycroft · CC BY 2.0 · Wikimedia Commons

Saturday, October 10, 2026 · 2 PM audio-described performanceTicketed via Lookingglass The…

Kowalski

Johnny Galecki stars in this limited engagement about Williams meeting Brando.

One Day Only

Submitted byStumblday Editors

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#1Saturday, October 10, 2026 · 2 PM audio-described performance · One Day Only

Lookingglass Theatre, The Joan and Paul Theatre, Streeterville, Downtown, the Loop & West LoopChris Rycroft · CC BY 2.0 · Wikimedia Commons

Ticketed via Lookingglass The…One Day Only

Kowalski

Johnny Galecki stars in this limited engagement about Williams meeting Brando.

Add to calendar

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Date night in Streeterville, Chicago the Weekend of Oct 9–12, 2026

1 pick

Kowalski

Kowalski

Planning ahead for Oct 9–12, 2026?

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