Taylor Swift Takes Over the Windy City: A Weekend of Music & Magic

Photograph by Chaz McGregor

Taylor Swift is spending the weekend in Chicago, how will you be spending yours? Unless you have magically acquired golden tickets to The Eras Tour, it is likely that your schedule has a “Blank Space.” Let us help fill it up with some of these Taylor Swift-themed deals and events that will undoubtedly enchant your first weekend of June!

Offshore Rooftop | Drag Brunch

Navy Pier’s seminal rooftop bar, Offshore, is honoring Swiftie weekend in the best way possible: a themed drag brunch! The performance, titled “In My Swifty Era,” will present two shows on Sunday that showcase some of the top drag performers in Chicago. The stellar lineup entails Utica, a beloved contestant from RuPaul’s Drag Race Season 13, as well as Miss Toto, Mimi Marks, and Bella DeBalle. Indulge in a delectable brunch buffet while jamming to some of your favorite TS tunes. 

Moe’s Cantina | Mimosa Day Party

This Wrigleyville establishment is combining two beloved passions for this weekend: Mimosas and Taylor Swift. On Saturday, Moe’s Cantina is hosting a ticket-entry day party that includes 3 hours of bottomless bubbly flutes and $5 shot specials! Taylor tunes will ensue as well as an array of other pop bops. Gather your friends and prepare to dance like you’re 22!

Macy’s Walnut Room | Drag Brunch

One of the most well known rooms in the city just happens to be one of the best spots for a drag brunch. Macy’s Walnut Room has a knack for hosting drag queens with its beautifully spacious interior, providing optimal room for strutting and singing! Mimosas and Midnights is all you’ll be needing for this Sunday, so get your tickets today! 

Replay | Sing-A-Long

This Lincoln Park arcade bar is well versed in theme nights of all sorts. Throughout the month of May, Replay has been decked out in all things TS. They have been hosting sing-a-longs every Friday, and it just so happens that their last night coincides with some of her best albums! 1989 and Reputation will be blaring through the speakers as $5 shots beckon patrons. Represent your favorite era while connecting with other passionate Swifties!

Radio Room | Pop-Up

Head down to State St. this weekend to pregame for The Eras Tour in ‘Style’ at Radio Room’s TS Pop-Up! The establishment will be decorated in all things Taylor on Friday and Saturday, with specialty cocktails, TS music, music videos, photo ops, and more! Reserve your spot while you can as we all know how quick Swifties can be.

Venteux | Cocktails

Michigan Avenue’s iconic French brasserie, Venteux, is celebrating Taylor’s arrival by presenting “The Cocktail Tour.” This Era-inspired list of sips is sure to make a Swiftie’s eyes sparkle with the lemony ‘Lavender Haze,’ spicy ‘Bad Blood,’ and strawberry ‘Enchanted.’ These concoctions will make you feel as though you’re sipping some of the best melodies of this generation. Try them out any time during the weekend!

Simone’s | Drag Brunch

Show off your different scarlet letters at The Un-Official Eras Brunch this Sunday! Simone’s is throwing an electric drag brunch, hosted by Jasmine Phoenix & co-host Dahlia Phoenix. Every era will get a chance to shine as patrons sip bottomless mimosas and munch on brunch bites. This show is the perfect opportunity to fulfill your Era’s Tour void and lose yourself to some of the Queen’s best music.

Ina Mae Tavern | Drag Brunch

This Saturday, everyone will be spinning like a girl in a brand new dress at this Wicker Park establishment. Ina Mae Tavern is having Kitty Banks + Friends take over with a Swiftie flavored drag brunch! With Taylor-inspired cocktails and sensational dance numbers, this event is certainly a way to spend your Swiftie weekend in the Windy City. 

Written by Bridget McGann

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