September 11, 2019

Three Days in Chicago: Where We Ate & Where We Stayed

how to spend three days in chicago like this woman in a white outfitSatin Skirt: Topshop (I also own it in black. I sized up 2 sizes to accommodate bump) | Knit: Theory (few years old, but great alternative) | Sneakers: Axel Arigato (true to size) | Bag: Chanel ‘Coco’ | Sunglasses: Celine

How to Spend Three Days in Chicago

A couple of weeks ago, I took a trip to Chicago with a couple of my best girlfriends and it was just what we needed. Before children and our bigger, life responsibilities, we used to always go away together. This time around, it’s been years since we’ve actually had more than a two hour dinner, to really catch up on each others lives and bond over the course of a few days.

Aside from spending time with each other, our entire trip revolved around food – ha! We literally had a food itinerary and let me tell you, I remember Chicago being a great food city, but I forgot just how good. I really don’t think we ate one mediocre meal.

I don’t want to call this a Chicago guide as I’m certainly not an expert on the city. However, many of you expressed interest in a compiled list of where we ate and the hotels that were recommended, so I’m here to provide that info.

friends next to a shiny ballRestaurants we ate at that I’d recommend in a heartbeat:

Au Cheval:

Holy moly. One of the best burgers I’ve ever had in my entire life. Also, the wings. The General Tso chicken wings were to die for. They also have fancy, chipped ice for the fountain soda, which makes me abnormally happy. The wait is usually hours.  But if you come during “off peak” hours (basically, not lunch time or not on weekends), you could get away with waiting between 1-2 hours. I’m told is not that bad. If you’re coming on a weekend or during lunch, be prepared to really wait. The good news is that they take your name and phone number down. So, you’re able to walk around the cute neighborhood and perhaps, grab a cocktail at one of the nearby restaurants.

RPM Italian:

We went to RPM on our “lets get a little dressed up and go out for dinner” night (the navy dress outfit I’m wearing in the below photo). It’s the restaurant owned by Guliana & Bill Rancic and I didn’t really know what to expect, but a friend assured me it was one of her favorites and she was right. Everything from the bread to the pasta to the dessert was fabulous! If you’re looking for a nice dinner out, highly recommend. Also, you could totally get away with wearing jeans, but we felt like getting a little spruced up.

The Girl & The Goat:

This was probably the most recommended from all of them and I get why. Aside from being beautiful inside, the food was incredibly delicious. We ordered a bunch of everything, including the bread (a must) and each plate was better than the last. I can’t even comment on what to get because it feels like we got it all, but come hungry and expect to share a bunch of small dishes. Also, fun fact: The chef and owner of the restaurant is 2008 Top Chef winner Stephanie Izard. 

Side note: There are a few restaurants from the “Goat” chain and they all came highly recommended. We only went to Girl & The Goat, but if you’re unable to get into this one (we booked one month out), try looking into the others!


We came here for brunch and I think it was one of my favorite meals of the trip. I live for good spreads and Aba had all of that and then some. The hummus, the feta dip, the warm pita and bagels to go along with it. I am salivating just thinking about it. Again, we got a bunch of things to share and everything was DELICIOUS.

Velvet Tacos:

Being a New Yorker, I cannot say I’m a taco expert, but my entire group absolutely loved this place. Not a restaurant, but an order-at-the-counter type spot that was very conveniently located by our hotel (the Viceroy-more on that below). The tacos are far from traditional, which is part of the reason we enjoyed it so much. Crisp Tikka Chicken, Chicken and Waffles and Fish N’ Chips, to name a few. We went here on two occasions: one day for a quick snack and then for a midnight hunger run.

Restoration Hardware:

Ate an outdoor lunch here on our first day and aside from being absolutely beautiful and aesthetically pleasing in each and every way (as RH does), everything we ordered was really, really good.

how to spend three days in chicago is to go out to dinnerDress: Zara (purchased a large) | Shoes: Manolo ‘Hangsi’ 


We stayed at the Viceroy because when we booked back in June, we wanted a hotel with an outdoor pool. I believe the Viceroy was the only hotel that had one, so that was the reason we chose it. Nonetheless, we couldn’t have been happier with our choice. I’d definitely stay there again, but there were a few others, that seemed to be “hipper” that got recommended a lot more.

Obviously, I cannot comment on them personally.  But in the event you want to look into them and do your own research, they were:

The Hoxton

Soho House


The Langham

London House

Hope you found this post helpful and Chicago, thank you for treating us so well!



  • Kerrie

    Great post Helena, I love reading your posts when you’ve been away and you look so so lovely. Your navy dress is gorgeous.

    It’s great you were able to get away and have some time with your girlfriends x

  • Janine

    Chicago is definitely on my bucket list for the next time I visit the States! 🙂 This post just made me hungry now haha! Sounds like you had an amazing girls trip!
    I remember so many of these outfits from last year! I adore your fall/ winter style 🙂
    xx Janine

  • Kristina

    The first picture is amazing! And you are always lovely.:))
    Regards from Bulgaria

  • ayushya

    This is awesome post thank for share your post this is great post

  • Nipa

    I went to Chicago twice earlier this year and LOVED it. We went to the Girl And The Goat, as well as The Publican and Frontera Grill which were equally amazing. Also, loved all that shopping within a mile!! xo Nipa

  • Rach

    So glad to hear you enjoyed your time in Chicago! You definitely dined at the best spots!!

  • teri

    5th Generation native who is living in MI and FL now. Chicago is still my favorite city. I would recommend, if you want to be centrally located, stay at the Park Plaza and get a room with a lake view. You are right on Michigan Ave with a view of the Water Tower (right in front of the hotel) and you can walk anywhere worth going other than a few restaurants that are a little more “out there.”

    Love the restaurant recommendations as there are SO many and more open (and close) every day that it’s impossible to keep track. Our favorite used to be the Erie Cafe but a rude bartender pretty much ruined the place for us.

  • Robyn

    I live in Australia, so this account of your girls’ getaway was particularly interesting. I hope to visit the US in the future, so I’ll keep this information for my “travel must do” list.
    Thanks for sharing and let us all know when “bub” arrives. You look gorgeous in that navy dress.

  • kathy b

    Oh you didn’t get to the theatre! Second CITY is a MUST on your next trip. So many great comedians were “born” here. The Music box theatre always has amazing events as does the Old Town School of Folk Music. Lincoln park zoo, is FREE!!! A city zoo that is beautiful.

  • robeyou

    I think, I prefer wedding dresses or dresses. It looks even more beautiful.

  • saianudeep

    Nice post..Keep Sharing your experience

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