by Caitlin Dennis | September 14th , 2025

All images are from Conan Gray’s - The Wishbone Pajama Show Tour in Tinley Park, IL on 9/14/25.

Photo by Caitlin Dennis | @cait.dennis.photography

Conan Gray brought his Wishbone Pajama Show to Chicago-land this past week after he released his latest album ‘Wishbone’ back in August. This is Conan’s largest tour to date, playing large amphitheaters across the US. You may know him from his most popular songs ‘Heather’, ‘Memories’, and ‘The Cut That Always Bleeds.’ He has been recently going viral on the internet for his VMA performance and the insane high note he hits in ‘Vodka Cranberry’.

I caught Conan’s last two tours, and the showmanship gets better every time. This tour’s aesthetic, as mentioned in the name, was pajamas. So many fans were dressed in their best pajama sets and outfits, from silk blue pj sets, to full sailor costumes. Which without context may not make alot of sense, Conan has set up a nautical sort of visual aesthetic around this album, which was executed really well in my opinion. From the merch to the stage set, the blues, whites, greys, and reds created a wonderful visual story.

Fans began to pile in to catch the opener, Hemlocke Springs. You may think you haven’t heard of her, but I bet if you listen to music or are on tiktok you’ve heard clips of her song ‘Girlfriend’. She has opened for Doja Cat, Muna, Ashniko, and Chappel Roan, so you’ve probably seen her if you are in those music spaces. From the second the band stepped on stage you could feel the excitement from the trio. Naomi (lead singer) was all dolled up in a pink, purple, and black edgy baby doll-esque dress with super fun blue and pink hair. She instantly grabbed the crowd's attention with her synth-bedroom pop sounds. And then to my surprise, the woman can SCREAM. Full on professional screams that brought an edgy rock sound into the music that caught everyone’s attention. She really had control of the stage the whole set, dancing around full of energy, even having a waltz dance break with her drummer! Screams from the audience solidified the great set as they sadly took leave of the stage as the set came to an end. Definitely an artist to watch in that music scene, I’m eager to see where she goes next!

The energy began to buzz again as it approached Conan’s set. The lights went out and screams rattled the entire amphitheater. The set that graced the set included a mail box, a small wooden windmill, and tall wild grass, with a projector screen of a vast blue sky behind the platform the band played on. Conan made his entrance to the stage riding a bicycle, and I may be impartial but I always love a good non-walking onto the stage entrance, and the bike was fitting! He wore an all white sailor outfit with blue and red details, which was just adorable. I don't think there is any other word for it. His energy was up the entire show, never faltering which is impressive.

Several set changes throughout the show kept everyone on their toes. A moving bed, large clouds, even a small wooden boat came on to the stage as he performed inside the boat! He had several outfits as well, changing from the sailor costume, to pajamas, to a beautiful ruffled white with navy blue accented wrap blouse and pants, to a final sparkling navy blue captain's suit with a gorgeous wishbone adorning the back of the jacket. He had great banter with the audience as well, one of my favorite quotes from the evening is the following “Was my boob out?”. He is quite the funny guy, never taking anything too seriously, in the best way. You gotta have fun on stage.

Another fun moment with the audience he does is the breaking of a wish bone. He brought a young fan up to the front of the pit (it was her birthday also it was darling) and leaned down to the barricade to break a prop wishbone with her. If she got the bigger side, she got to choose their next song, if he got the bigger side, he chose. Alas, he did end up with the bigger side, but as a birthday present let her pick a song anyways. He did also hit that high note during ‘Vodka Cranberry’ and hearing it live was exciting. Overall wonderful show, and there was just enough going on on-stage with the set and theatrics that wasn't overbearing, but kept you entertained the entire show, even when he wasn't singing! Who knows, maybe the next time he tours it will be arenas. Just gotta keep watch and see what he does next!