ChicagoAfter Five

Romantic Events in Chicago

9 events in Chicago

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High-End Mixology Experience at Sojourn
Sat, Jun 6
Every Friday & Saturday
2:30 PM

High-End Mixology Experience at Sojourn

Sojourn Cocktail LoungeLincoln Square

Boutique craft cocktails, gourmet smash burgers, and charcuterie at Sojourn. Sophisticated, intimate, romantic. Weekend afternoons and evenings.

Summer Fireworks Aboard the Tall Ship Windy
Sat, Jun 6
Every Saturday
8:45 PM

Summer Fireworks Aboard the Tall Ship Windy

Navy PierNavy Pier

Sail aboard a tall ship watching Navy Pier fireworks. Romantic, sophisticated, majestic. Full craft cocktail bar. Every Saturday 8:45PM through August

Swinging Sounds Late Night Jam Sessions at The Green Mill
Sat, Jun 6
Every Friday & Saturday
9:00 PM

Swinging Sounds Late Night Jam Sessions at The Green Mill

The Green MillUptown

Live jazz jam sessions at the historic Green Mill. Prohibition-era vibes, classic martinis, premium spirits. Soulful, dimly-lit. Open until late.

First Sunday Historical Walking Tour at Pullman
Sun, Jun 7
Monthly
1:00 PM

First Sunday Historical Walking Tour at Pullman

Pullman National Historical ParkPullman

Guided walking tour of Pullman National Historical Park. Labor movement history, the Pullman Strike, and the company town. Intellectual, reflective. 1

The Unlikely Candidates
Sun, Jun 7
8:00 PM
Starting soon

The Unlikely Candidates

Cobra LoungeUkrainian Village

Texas alt-rock band The Unlikely Candidates bring infectious hooks and arena-ready energy to Cobra Lounge's intimate stage.

Nunsense
Tuesday
1:30 PM

Nunsense

Drury Lane TheatreOakbrook Terrace

Nunsense opens at Drury Lane Theatre in Oakbrook Terrace on June 9.

The Poetry Brothel Chicago: Life is a Cabaret
Thursday
8:00 PM

The Poetry Brothel Chicago: Life is a Cabaret

Chicago Theater WorksLakeview

Immersive poetry and burlesque cabaret experience at Chicago Theater Works.

$45–$8521+
Giordano Dance Chicago: Ignite the Soul
Mon, Jul 6
7:30 PM

Giordano Dance Chicago: Ignite the Soul

Harris TheaterMillennium Park

Modern jazz dance performance by Giordano Dance Chicago at the Harris Theater. Kinetic, soulful, and inspiring.

& Juliet: The Musical
Wed, Jul 22
7:00 PM

& Juliet: The Musical

The Auditorium TheatreLoop

& Juliet flips Shakespeare's tragedy into a fever dream of pure pop euphoria—imagine Juliet center stage, taking control of her own story while Max Martin's greatest hits soundtrack every defiant moment. You'll spend two hours in the Loop's architectural masterpiece, The Auditorium Theatre, watching a cast that moves like they're powered by pure adrenaline, as decades of pop bangers (we're talking Britney, The Weeknd, Ariana Grande) propel a narrative that's equal parts romance and rebellion.