Chicago Trip – A&C Live Show, Shopping, Eataly, and more!

A few weekends ago I traveled to Chicago with my friends Annabelle and Meagan for the live show of their podcast Adderall & Compliments. I have been helping the girls in any way I can for the past few months after I saw what an incredible impact they have had on their community of listeners (referred to as “kittens”) all over the world. Annabelle and Meagan have shared on the podcast about their mental health ups and downs and the response has been incredible. Kittens at every show come up to the girls with tears in their eyes saying they have changed their lives and they are forever grateful. They feel so much less alone and like someone finally understands them and what they’re going through and that is just priceless. People have said they were contemplating suicide and the podcast got them through their low point and now they have finally reached out and gotten help- it’s amazing. I think the work they are doing is SO important so I am doing whatever I can to support them in their mission- hence why I have been traveling with them for their live shows!

I seriously wish I could go back to Chicago right now because I love that city so much. If you’ve never been to Chicago it’s beautiful, clean, fun, filled with amazing shopping and food and there are lots of hot and nice Midwestern men. The first time I went to Chicago was about 7 years ago for a professional conference and I seriously fell in LOVE. That being said, I actually haven’t been to some of the biggest landmarks so if you want a locals guide to Chicago I highly recommend this post by Gisele Chic.

Thursday night we flew to Chicago and we stayed at the W Hotel Lakeshore and had a really awesome room that overlooked Lake Michigan. I was so confused the first time I visited Chicago and saw water lol, but now I know that bright blue water is beautiful Lake Michigan!

Friday we ventured to Drybar (the River North location) to get blowouts.

Jailyn slayed my blowout and clipped in and styled my Girl Get Glamorous clip-in hair extensions (use my code HOLLYWOOD for a discount) as well so I could be my most fabulous self. I always get the Southern Comfort style and usually tell them to go nuts with the teasing because I love HUGE volume.

Southern Comfort style blowout fro Drybar with my Girl Get Glamorous Hair Extensions clipped in

I wore my Halloween fave skull shirt which I get SO many compliments on. The skull shirt is a knock-off of the Alexander McQueen print and is super cheap on Amazon. I seriously get SO.MANY. compliments on this shirt. My lip color is my all-time fave Rimmel Eastend Snob.

Drybar is not sponsoring this post, I just wish they were.

Post-blowout we headed over to Yolk for a super casual and delicious brunch. There’s a few locations around Chicago and I definitely would recommend it.

Yolk restaurant in Chicago


Breakfast at Yolk in Chicago

From there the girls went back to the hotel room to work and I wandered down to Michigan Street where all the amazing shopping is. They have Nordstrom, F21, TJ Maxx/Marshalls, Zara, H&M, Express, all of the huge chains are on Michigan St. After picking up some beauty items at Marshalls and some super cute office accessories at F21 I headed back to the hotel and stopped in at Dollop Coffee & Tea on the way because there were some QTs up in there and I needed a pm caffeine fix.

Dinner at Current in the W Hotel in Chicago

That night Fancy Nancy and RJ (Annabelle’s parents) flew in and we just had a casual dinner at the restaurant at the W called Current.

Annabelle’s makeup for the Chicago live show.

The day of the show Annabelle’s stylist from Drybar Mary Rios (@stylist.mrios) came to our hotel to refresh our blowouts and she was AMAZING. I HIGHLY recommend her if you need a stylist for a special occasion in Chicago. Annabelle had Jose Deleon (@jdeleonmakeup) come to the hotel to do her makeup for the show and I did my own and Meagan’s.

Meagan and Annabelle post-live show in Chicago. Someone asked what lipstick they’re wearing and the answer is none lol it had rubbed off already.

For Meagan’s makeup I used my current favorite foundation for day OR night- the It Cosmetics CC Cream in the shade Light. It has SPF 50 but no flashback in fact it looks amazing in photos. For concealer I used another longtime favorite- the Maybelline Fit Me Concealer in Fair to cover a blemish. I applied both of these with a Sigma F80 Flat Top Kabuki Brush and it made her skin FLAWLESS! I set the foundation with a small amount of MAC Studio Fix Powder Plus Foundation in the t-zone to help take down any shine. For her brows I used the Billion Dollar Brows Universal Brow Pencil which I somehow lost halfway through doing them and never found again! This brow pencil is awesome though! Be sure to use Annabelle’s code TUXEDO for a discount. For eyeliner I used the Stila ‘Stay All Day’ Waterproof Eyeliner in Black along her lash line. For blush I used my all time fave Milani Baked Blush in Luminoso which is the perfect peach on everyone. BTW Meagan wears the same Girl Get Glamorous clip-in hair extensions in the same color as me (Beach Day- don’t forget to use HOLLYWOOD for a discount ;).

Close-up of Annabelle’s makeup for the Chicago live show.


Meagan, Ally, Sydney, and Annabelle

We had the show at Chicago Theater Works and only had 30 minutes to set up so we were SCRAMBLING. Then my friends/real life human angels Anna and Mark came to save the day and run the merch table. I had them working so hard I managed to not get a single photo of us together! The show went amazing and Nancy, RJ, Annabelle, and Meagan were all hilarious. I told RJ he was only getting 10 minutes for this show and I’m pretty sure we will never have a conversation about anything else ever again because he is never going to let me forget it lol.

Kittens Ally and Sydney and myself at the show!

All of the kittens waited for photos (some waiting up to 2 hours!) and they were all so unbelievably sweet! I took the photos with my “magic” camera- the Sony A5100. We call it the magic camera because it has a beauty filter on it that smoothes the skin and automatically color corrects. I also love this camera because it’s not as big and bulky as a DSLR so it’s much easier to travel with.

Annabelle, me in my Asa kaftan, and Meagan after the Chicago Adderall and Compliments live show.


Meagan and Annabelle after the live show in Chicago

And of course I had to bring it with the wardrobe so after the great responses to my kaftan from the Boston show, I decided to get my very own Asa Kaftan. Mine sold out on Nordstrom’s website, but here’s the shorter version. The kaftans definitely run big I can be an M/L and I ordered a medium and it’s huge.

A card a kitten named Sydney made for me! So sweet!

A kitten named Sydney even brought me a card and took a photo with me everyone was seriously SO sweet.

Bruschette Trio at Il Pesce at Eataly, Chicago

After the show we went to the Italian mega complex that is Eataly. Eataly is a giant Italian maker place with several restaurants, a bar, an Italian grocery store, food stands (gelato, cannolis, pastries, espresso bar, etc.). It seemed only fitting since Annabelle was the princess of Italy (according to a rumor from high school).

Fiori di Spinaci e Funghi at Il Pesce- had to take a photo before I devoured the rest!

We had dinner at Il Pesce which is a sit-down Italian restaurant and it was good (but not great).

Chocolate Chip cannolis from Eataly

After dinner I got a chocolate chip cannoli at the cannoli bar downstairs and an espresso.

Meagan being candidly and effortlessly hot


Fancy Nancy and Annabelle

 That night we went to Stephanie Miller’s Sexy Liberal Resistance Tour to see John Fugelsang at the Athenaeum Theatre and we met some kittens that had traveled from out of town at the show.

Annabelle, John Fugelsang, and Annabelle’s mom Fancy Nancy DeSisto. Yes, that is all Annabelle’s hair.


Nancy showing off her SLUT bag.


Fancy Nancy and Stephanie Miller


Nancy with Frangela

After that Meagan somehow managed to go out to the bars all night, but Annabelle and I were dead already so we got French fries and gummy bears from room service like adults and passed out.

I had to share this because Meagan took it and excitedly told me I was going to love it because it is the best photo of me ever. To be fair I think I would love it if it weren’t blurry as hell.

The next morning we had a super casual and low key brunch at Hash House a Go-Go with Annabelle’s parents and the kittens where we basically just laughed at RJ for 2 hours.

My portobello burger at Hash House a Go-Go. They have enormous portions here.


Brunch at Hash House a Go Go

Then after brunch Nancy casually did this move and we said peace out Chicago!

Fancy Nancy is a woman of many talents


We were basically dead at the end of this trip, but it was a blast!!

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Author: Lindsay

Lindsay is the creator of Blushing in Hollywood a beauty, dating, travel and lifestyle blog based in Los Angeles, California.

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