When fashion-forward pixie Hannah Soboroff, the Business Development Director of one of our beloved shopping sites, TheRealReal.com, told us she was headed to Chicago we decided we needed to know every single move she made.  Here, she shares her postcard from ‘Chi-Town’—complete with excursions around the city and her absolute favorite new discovery: deep dish pizza!

Just back from:

Chicago! This was my second time there. We went for a friend’s wedding.  It was a quick trip—just 2 nights and 3 days (we went early Friday morning and came back Sunday afternoon).

How did you get there:

I flew American Airlines non-stop from Los Angeles.  It was a 6am flight and I slept all 4 hours—making it the easiest flight ever.

Who did you go with:

My fiancé, Eran.

Place where you stayed:

We stayed at the Four Seasons Hotel, which is where the wedding was held. The hotel was in a great location for exploring and shopping (we were able to do a lot of walking too), and our room had an incredible view of the city.

Places you ate:

We had breakfast at Little Goat Diner, which has a very cool vibe and is a delicious spot for brunch. There was a bit of a wait, so we passed the time in their photo booth (so fun!). I highly recommend the ‘Bull’s Eye French Toast’ (it’s a sweet onion brioche, with a runny egg in the middle, topped with crispy chicken & BBQ maple syrup). We also got the farm oatmeal which was topped with honey, yogurt, apples & oat crumble.  For lunch we went to Athenian Room, which is a little Greek restaurant in Lincoln Park. My sister-in-law is from Chicago, and this was, and still is, one of her favorite spots. It’s casual, affordable and super delicious. We had gyros, greek salads, kabobs and crispy french fries. Of course, about an hour before the wedding I realized I hadn’t gotten ‘deep dish’ yet, and one thing was for certain—I wasn’t leaving chicago without trying it! I called in a small pie of plain cheese deep dish pizza from Lou Malnati’s and my fiancé ran out to get it while I was getting ready…sooooooo good. We also grabbed snacks during our stay at Garrett Popcorn (this place is famous in Chicago!). We got a bag of the ‘Garrett Mix’ which is a combo of sweet & salty popcorn.

Local delicacy you feasted on:

DEEP DISH PIZZA! Shockingly delicious.

Cocktails you sipped:

Lots of wine.

Books you read:

I bought Bon Appetit and Martha Stewart Living at the airport to read on the plane.

Music you listened to:

John Legend for the plane, and Rihanna Radio on Pandora while I was getting ready.

My daily uniform there was:

Jeans, t-shirt, a coat and booties.

Brand of luggage you traveled with:

I’ve had the same black, Prada, rolling-duffle bag since college…and its the best! It’s a carry-on size (I never check bags), and it’s been all over the world with me—and it somehow fits everything. I also used my Mansur Gavriel small, tote bag as my other carry-on.

Did you over-pack or under-pack:

I under packed. I actually really wish I had brought a hat (it was cold!!).  I also didn’t really need my black, Eres, one-piece bathing suit. The hotel had an indoor pool, but sadly I never got around to taking a dip.

Items you packed in your suitcase:

For the daytime I brought J.Crew high-waisted jeans—I recently ordered them online (they are the Vintage Crop Jean) and they’re super comfy and flattering.  I also packed 2 James Perse, white T-shirts—these are my go-to t-shirts—the neckline and overall fit is perfect! I brought a cozy, grey Isabel Marant sweater, and an oversized, knit, Michael Kors sweater, which is one of my favorite purchases from The RealReal. I also had a poncho that I love to wear while traveling—it’s from Mohawk General Store and it’s made by A Piece Apart…it’s like wearing a giant blanket. My coat was by Band of Outsiders—it’s black and oversized and fabulous.  I also packed black Barbara Bui booties—I got them as a birthday present about 4 years ago, and they are still my favorites.  For sunglasses I packed a pair of Celine sunnies (The Joe, round, in horn), and a pair of Equipment shades. Plus, I threw in a black, Eres, one-piece swimsuit.

For the evening I brought a bright, pink, floral Oscar de la Renta dress for the rehearsal dinner—this was another epic score from The RealReal. I paired it with a pair of Christian Dior pointed pumps, and used a black Chanel clutch (which I got in Paris while on a girls trip with my mom & one of my sisters). For the wedding, I wore a Michael Kors dress, which I matched with a pair of Narciso Rodriguez pointed pumps, and used the same black Chanel clutch as my evening bag.

Beauty-essentials you packed:

I use all of J’ai Lone’s skincare products. I start with cleaning my face with the antioxidant pads, then use the balancing scrub, followed by her oxygen cream. I also brought Darphin Jasmine face oil to keep my skin hydrated at night. For my makeup I packed Nars laguna bronzer + orgasm blush, liquid eyeliner, and Dior mascara. I don’t like lipstick on me, so I brought Hydrating Tinted Lip Balm by Benefit in Posiebalm, which is like a poppy-pink color. I also packed my Shu Uemura eyelash curler.

My perfume is Ambre Blends pure essence roll-on oils. I love mixing the Ambre and Solace scents together. I also use their Solace Natural Deodorant—it’s the best. I’m not a shampoo/conditioner snob, so I just used what was at the hotel. My hairbrush is a Tangle Teezer. My hairdresser, Shin, turned me onto this brush—it’s funny looking but it detangles without pulling all of your hair out.  I also packed a travel-size Marvis toothpaste in the Jasmin/Mint flavor. Plus I always make sure to travel with things like band-aids, Q-tips, Advil, floss and hair ties.

Favorite place to shop and find local treasures:

I didnt have much time to shop, but I stopped by Blake (212 W. Chicago Avenue), which was a great Goop recommendation. They had an amazing and unique collection of designers, and had everything from clothing to shoes to accessories, etc.

 A typical day included:

We ventured out for breakfast, walked along the lake and made our way to the Lincoln Park Zoo. I hadn’t been to a zoo in years, and I’m so glad we went! The best part: it’s free! After the zoo we walked to the Athenian room for lunch, walked around Lincoln Park, and then headed back to the hotel to relax before the wedding.

Best part of the trip:

Ordering in deep dish pizza and eating it in my bathrobe and hotel-slippers!

First time visitors must:

I know it’s super touristy but check out “The Bean” at Millennium Park. The (giant) bean reflects the city’s skyline, and it’s pretty amazing.

The #1 tip you’d give a friend that’s going:

4 words…Get. Deep. Dish. Pizza.

I loved it here because:

This city has the best grub! Seriously delicious!