Best of Chicago

This was my second time in Chicago, and I loved being able to experience it in a different light. The first time I went was about 4 years ago, and it was a girls’ weekend to see the Avett Brothers (who put on the most amazing, intimate show in the beautiful Chicago Theatre). This time, Bally and I ate and biked our way through the city, which I’ve discovered is the ONLY way to appreciate a place like Chicago!

I’m always here for the food, if you know me at all. Good food. I am definitely a snob when it comes to eats. It doesn’t always need to be fru fru, but it needs to all work together in terms of texture, heat, acidity, etc. — and let me tell ya, Chicago is one hell of a foodie town, which puts it near the top of my list for places to go back to. I love finding places where the atmosphere is alive and has been intentionally designed to curate a particular vibe. And I always appreciate an adventurous chef who puts together an inventive menu. We definitely ate our way through town and made the most of our quick weekend getaway! Some of our favorite spots were:

  1. Cabra – Quinoa and Tuna Salad = might go down as one of the best dishes I’ve ever had. We also loved the shrimp-y brunch-y tacu tacu and the goat empanadas, as well as the alpaca my bags cocktail. The atmosphere here is super memorable… I was quite obsessed, actually. It has a rooftop lounge with a super chill wading pool, daybeds, and outdoor bar on one end, and the remainder of the restaurant has quite an airy feel to it, with tropical plants, mixed materials, beautiful garage doors that let in tons of natural light, and some open air patio space that brunch dreams are made of. What’s even better is it doesn’t just rely on its killer atmosphere. Its menu is creative, comforting, fresh and delicious… therefore earning every bit of rave review IMHO.

2. Cindy’s Rooftop – Another spot that’s great for lunch… this space, which sits atop the beautiful Chicago Athletic Association Hotel, has almost an atrium feel, with gorgeous windows that surround it, plus a rooftop patio that overlooks the gorgeous waterfront and city line, including a great view of the Cloud Gate Sculpture (AKA the Bean). The Sundown Cocktail was amazing, as was the Seafood Roll (only offered M-F), served with the most amazing homemade salt and vinegar chips.

3. Duck Duck Goat – This place is so good we went twice in one day! We put our name in at the Little Goat for brunch, and the wait was so long that we walked over to their sister restaurant, Duck Duck Goat, for a little “snack” as Bally calls it. We got the Jiaozi — the beef short rib and bone marrow pot stickers, which were so good that we just looked at each other and could tell we were both feeling the same way: mind blownnnn. We had to scoot out of there to catch our table for the main meal, and you can read below what happened there. Long story short, we felt jipped and just had to go back to sample some more of the goodness. If you give it a go, the Coconut Culture cocktail and  Octopus, Cucumber and Peanut salad were delicious as well!!

4. RPM Steak – I love that this steakhouse has some really nice offerings for the non-steak lover, too. I like a good steak from time to time, but I’m definitely choosy when it comes to a higher quality meat. I personally look for grass-fed beef, although this time I ordered the broiled black cod and shared some of Bally’s Imperial Waygu, both of which were outstanding. The steak was cooked to perfection, and I practically needed to get wheeled outta there because I was so stuffed. We indulged on the Mr. Price’s whipped potatoes, salt roasted beets and wedge salads, and the parker house rolls, of which I easily ate about nine. I have zero interest in visiting a steakhouse that makes no attempt to extend beyond the status quo. Those kinds of places seem cliche to me, and call me a food snob, but I am all for a restaurant that really strives to provide a little swank, and also packs an impressive flavor punch with a menu that stretches beyond what everyone expects. I am definitely recommending RPM, because it made my picky ass happy, while still coming thru for my date who craves all those classic steakhouse feels. It was the perfect date night spot before heading off to see Hamilton, which is a show NOT to be missed! The talent, musical composition and energy was absolutely fantastic!

Honorable mention:

  1. Au Cheval. Bally is hard core obsessed with red meat (trust me, I’m trying hard to change that), so when he heard this place has one of the best burgers in the nation, we just had to be put on the 3 hour wait list. I just wish that that title hadn’t been put in our heads prior to going, because there were a whole lot of expectations building up there. We ordered the double cheeseburger and french fries, just like every other person in the establishment, and it was… good. I’m just glad they have a modern day reservation system that allows you to put your name in and watch your place on the list from your phone so you can go out and explore the city, which is exactly what we did. If you’re dying to just see what all the hype is about, go for it! It’s definitely a well crafted burger… but for us, it just fell a bit short of such expectations. If you’ve been before or end up giving it a try, I would love to hear if we’re the only ones left feeling this way!?
  2. Little Goat Diner. The blueberry pancakes were outstanding, and we also enjoyed the fish tostadas. I like that this restaurant has a menu that expands past the traditional diner fare. Unique dishes that demonstrate pride in the art of the culinary world gets props in my book. We just wish our server was a little more on her A-game, and were left a little underwhelmed with their popular scallion pancakes (okonomiyaki)… but I still think this spot is worth a trip if you’re craving some traditional brunch with a twist!

As you can see, we were clearly living like total gluttons. So it felt good to get out and bike around the waterfront for a full day. I’ve never experienced such a beautifully designed biking and running trail that surrounds a gorgeous waterfront and metropolitan area like the Lakefront Trail in Chicago. After we started renting bikes on our trip to Montreal, we have become totally sold on the idea, as it allows you to be more fully immersed in the energy of the city, spontaneously hop off and stop at things that fit your fancy, and justify those extra calories that you’re crushing on vacation mode. Much more so than taking Ubers everywhere, and a whole lot more economical. We rode for a good 6 hours, but coasting along the water way and soaking in all the sights around us, was honestly so invigorating! I would catch myself smiling as I rode and think what a dork I must’ve looked like, but I don’t even care… because in that moment I felt such a sense of gratitude for this life!

Along our path, we decided to stop off at the Londonhouse rooftop to take in some of the best views in town. Up there, you sit among the skyscrapers and look down upon the charming river way. We enjoyed an hour or so up there and then went down a couple floors to cozy up next to their gorgeous fireplace and enjoyed a glass of red and some fresh oysters. It was a perfect midday stop and definitely made for some very impressionable memories!


All in all, Chicago treated us so well! If you decide to book a trip, we highly recommend staying at the Hoxton Hotel. It hit the mark on all accounts, with some of its best features being proximity to all the hip and trendy restaurants and social scene, its fresh and vibrant energy, and warm and stylish finishings. The very moment we walked in, we felt immersed in its energy. From the warm fireplace and quaint little groupings of trendy seating areas, to the funky DJ spinning tunes in the lobby, all the well blended mixed materials, and the natural light flooding in. You can also go underground to their cozy Lazy Bird lounge or up to the rooftop to the aforementioned Cabra restaurant and pool before retiring to you room, which naturally fits those cool vibes carried throughout the property. Easy to say, I’m a huge fan of this fairly priced boutique hotel and its hip and energetic culture!



  • Amy
    Posted October 2, 2019 3:30 pm 0Likes

    So helpful! I can’t wait to refer back to this for our next girls trip! 😘😘

    • Kristen
      Posted January 17, 2020 6:08 pm 0Likes

      Always gotta be scoping out those menus, right?! lol

  • Katie
    Posted October 2, 2019 10:01 pm 0Likes

    This makes me want to book a trip to Chicago ASAP and go to all these restaurants!! Your pictures are pretty amazing too 😍

    • Kristen
      Posted January 17, 2020 6:07 pm 0Likes

      You’ll have to! It is such a wonderful city!!

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