The Seven Best Moments From Taylor Swift’s Final Night in Chicago on Her Eras Tour

While attempting to introduce The Eras Tour and herself — following songs including “Cruel Summer,” “You Need to Calm Down” and “The Man” — Swift soon realized her bedazzled mic was no longer working. “Helloo??” she mime screams into it. She then sticks her tongue out in agony while leaning back in playful despair, only to then bang her palm against it a few times for good measure. As soon as it’s replaced with a less glamorous, though functional, mic, she tells the crowd with a smile: “None of that happened.” But it wasn’t the only oops of the night, as later on Swift accidentally swallowed a bug, after which she joked, “Ooh, delicious … Is there any chance none of you saw that?”

While in her evermore era, Swift speaks of her pandemic-induced creative flurry, during which she wrote, recorded and released both evermore and its predecessor folklore. When speaking of this pair of albums, she admits that she wasn’t sure how they would translate to the stage — because at the time live music seemed a distant memory. But, she says, “one song in particular I was so excited to perform live…” She then delivers the stunning and reflective “Champagne Problems” while seated at the piano. By the end she’s holding back tears as the applause only grows louder and louder, soon morphing into a “Taylor, Taylor!” chant. Swift allows it to continue, quenched by the comfort, before saying, “I love you guys so much… you’re so generous.”

Though Speak Now (Taylor’s Version) is just about a month away from release, the album is only allotted one single song in the Eras setlist: the magical “Enchanted.” As the stage lights up magenta, Swift speak-singing, “Please don’t be in love with someone else,” can be heard offstage. Soon enough, she emerges in a puff of pink smoke wearing a bedazzled ball gown. As she delivers the pop ballad with commanding power and conviction, the stadium — and fans’ color-changing wristbands — light up in cotton candy colored hues, casting an as-of-yet unfamiliar calm across the open space.

While giving the lowdown on her rerecording project — for which Swift is rerecording her first six albums in order to gain full ownership ––she explains in simple terms the thought behind the ambitious task: “The thing about this project is that I haven’t seen it done too many times before, so there weren’t a lot of examples for me to look at and see, you know, ‘Is this a good idea commercially?’ It wasn’t about that, it was a passion project. And a passion project is something that an artist will do regardless of whether it’s successful or not, because it just matters to them personally.” And as Swift then thanked her fans for embracing each Taylor’s Version release wholeheartedly — and even only acknowledging such versions going forward — the applause of support hit a new peak in volume. Until, that is, Swift introduced the next song: the devastatingly gorgeous (and impressively long) “All Too Well (10 Minute Version, Taylor’s Version, From The Vault).”

Most of the more shocking, humorous or enjoyable moments from The Eras Tour have by now been long circulating online — including one from folklore track “The 1.” During the song, for which Swift lies down on top of the moss-covered A-frame cabin, the line, “You meet some woman on the internet and take her home” has garnered special attention for her delivery of its latter half. Rather than singing it as heard on the album, Swift chops it up and draws it out — “and take. her. home,” she sings, prompting “ow ows” and “woops” from the crowd.

For the evening’s anticipated surprise songs, Swift started with the live debut of “Hits Different” off the recently released Midnights (The Til Dawn Edition) extended album (which was previously only available on the Target exclusive version of Midnights). “I don’t know if you’ll know this one, it’s kind of new… But we’ll seee….” teased Swift with a smile. She then performed the song on acoustic guitar standing solo at the edge of the stage. To no one’s surprise, fans knew every word. After, she sauntered over to a wooden piano painted with flowers and butterflies for her second surprise song: “The Moment I Knew” from Red. 

Cross ‘em both off the list.

Prior to the intimate, stripped down surprise songs, Swift praised those in the front rows who were performing for their lives, saying, “I’m making a lot of new friends tonight.” She then shared another message of gratitude for her devoted fans: “People ask me, ‘Are you tired at the end of the show?’ I’m like, ‘No, are they tired? You guys are head banging and thrashing and screeching. It’s so valiant and beautiful. It’s a noble thing to do… I salute you.”