Monica Gisele Simanovsky

Weekend In The Windy City

May 3, 2023

I never lived in my hometown of Chicago as an adult, so playing tourist over the last decade has been a real treat. This most recent trip made even more fun because I got to see my high school friends as moms’ and thirty-somethings’ living in the city I grew up in from a different vantage point this time around. For the first time I didn’t have a wedding to attend or a birthday 5celebration; I just wanted a snapshot of their lives as they’ve come to be with age, kids, pups, partners and of course, a lot of great food!

The early appearance of summertime-chi weather was the unexpected and highly appreciated guest of honor on a weekend in mid-April, so much so that I couldn’t pass up a chance to relive my teenage A&F ensemble after I snagged a pair of denim cutoffs immediately upon arrival, appropriately re-branded as the mom short to replace the mom jeans I had packed for the 75 degree expected temps.

75 degrees in Los Angeles just isn’t 75 degrees in Chicago, and the humidity and sunshine reminded me just how fun this city gets when it’s warm, despite it dropping right back down to a rainy 50 degrees come Sunday.

Hence the trench coat part of my cozy plane outfit, completed with the roomiest varsity style sweatshirt from The Bar and my one and only vintage inspired carry-on that always gets a compliment or two in addition to leveling up a less glamorous travel outfit. Travel is always easier sans child and dare I suggest without my husband babbling off about what show we will joint binge together while sharing one headphone set. I am happy to report I was super productive on my morning flight with my strong coffee and a big head start on the current book club pick of the month, Pineapple Street, a read I’d suggest for any New Yorkers in Brooklyn and not exactly anyone else to be honest.

Hello Chicago!

I basked in the beautiful sunshine on the ride downtown and after checking into my hotel room I set foot into Chicago’s Gold Coast neighborhood for some goodies for the kids and spectacular city walking for me that I never really get to experience in LA.

The streets were perfectly abuzz as it was truly a Friday afternoon that must have got it’s dates messed up. People were out and about in summer dresses and shorts, sipping drinks at sidewalk tables, ready to devour every inch of warm weather for the weekend ahead.

That’s the thing about Chicago, people wait all year long for summer and when it comes they actually indulge in it, show gratitude for it, wade in its most simple of offerings like taking a dip in the pool they worked so hard to maintain all year long. They don’t take it for granted like everyone in LA who sees a pool as a piece of dining room furniture, necessary for aesthetics but not something you would actually at utilize without good reason.

So this weekend (the only one I’ve had alone since God knows how long) felt similar to me. I wanted to really enjoy the time with my friends and make the most of being away from my family and daily routine.

Which for me meant walking up without an alarm clock, running for leisure and treating my morning coffee runs like an ancient sacred ritual.

As they say, it’s the little things!

Quick note on my hotel. I always love to stay at The Ambassador, formerly known as Ambassador East, which in the last decade has had lots of changes in branding and management but overall the same elegant vibe and most charming location in my opinion nestled in Chicago’s chic Gold Coast. This time around I was disappointed in the lack of amenities (no room service, no hotel restaurant, no maid service!) and the rooms were not up to par considering that I most definitely overpaid a few months back compared to what the prices were when I checked in. Overall I still loved the lobby decor, French 75 I ordered at the bar (next to the old Pump Room) and the walkability is unbeatable if you want to be downtown but still feel a neighborhood vibe without all the bustle right in your face. I was able to get to all my favorite spots so location wise great, but just not nearly as elegant as it once was sadly.

So after my random errands I hurried back to my hotel to get ready to see the girls for an early dinner. An early dinner that turned into a long, fun night, but one I am happy to report, did not require much recovery because I wasn’t about to f*** up my precious morning and only full day over an extra tequila shot the night before.

Friday Night at Elina’s

The one thing that never disappoints in Chicago, however, is the food! Chicago is a foodie city and unlike NYC and LA, Chicagoans do care about quality over anything else. This must be what got me out of the city because you know I judge my restaurants first on decor/ambiance and food second, but I digress!

Elina’s knocked both out of the park being the most quaint and chic little Italian eatery with it’s wax dripping candalabra’s, 12 table max capacity and bread baskets made individually for each table with it’s own accompanying sides of salami and some type of purple pickle. It actually reminded me a bit of Il Mulino in NYC, another must go spot with a cozy family feel but beyond what your Italian mother can whip up in her kitchen, no offense to the mamas out there!

There signature rigatoni alla vodka is worth the hype and the angel hair scampi was a delicious second runner up for pastas. We ordered the mozzarella sandwich and my only complaint about the night is that they didn’t bring it out! I loved the chicken parm and could have skipped the caesar salad because the Italian fries were the only vegetable I got excited about. Loved that they had a full bar in addition to just wine. Unfortunately we had absolutely no room for dessert but perhaps next time!

After our early dinner we found another spot to venture out into in West Loop for some cocktails and the best conversations you can only have with people you’ve known since high school. I consider myself so very lucky to have maintained such solid friendships over time, it’s perhaps one of the things I am most proud of. I see them at best once a year and we don’t necessarily talk on the phone or text all that often but can always pick up right where we left off and it’s been such a privilege to see how they’ve evolved over the years.

We couldn’t help but keep the party going and did our best to find a bar with dancing that would let us and shall we say causal, thirty something-selves in. Thank god one of my friends had the hookup so we could bop to the beat of the sax over the DJ, something I hadn’t seen since our beach club day in St. Barts! It was so fun and I am so proud of myself to have decided to stop consuming anything but water early on to preserve my few days sans bebe!

And I am happy to report I woke up feeling fresh the next morning, without my husband, dogs or alarm clock, ready for a leisurely run along Lake Michigan to take in the lovely Chicago skyline! I never really make time to run for fun outside anymore since joining OrangeTheory and I forgot what a great way it is to see a city.

Coffee at Ralph’s

Afterwards I walked to the new Ralph’s Coffee they installed at their Michigan Ave store, right next to the RL Restaurant that’s been around way before Polo Bar in NYC and the original Ralph’s Coffee on Madison Ave, which I’m absolutely obsessed with, to get my fix. I desperately need one in Los Angeles and I know they tested the market a bit before with a cart around the holidays last year so fingers crossed!!

This location, perfectly situated on Michigan Avenue, did not disappoint with its classic green and white color combo and elegant cafe vibe that I just cannot get enough of. So much so that I scoured the internet to find a Ralph’s Coffee baseball cap because they are consistently out of stock. The Ralph’s coffee merch is unbelievably versatile for any kitchen and I’ve already set my sights on their adorable latte saucers that will go well with my green scheme for our new patio.

So I sat and sipped while listening to some of my favorite podcast hosts, completely savoring the moment to myself, after which I found a nice young lady to snap a pic before heading out to a nearby boutique I had been pinning to visit for some time now down the street.

Space 519 is the type of boutique we all miss in this digital age of curated websites and collections on the gram. It’s extremely upscale and the products aren’t so unique that you can’t find them elsewhere like the coveted Ginori 1735 egg I’m lusting after, however, the presentation most certainly stands out. It’s a lost art and something that unfortunately can’t be translated digitally, although they do have an e-commerce site you can shop here. But like most savvy high end retailers they offer an upscale lunch spot and even a quick grab and go cart to diversify the experience with the shop.

Lunch at Le Colonial

Later on I met up with the girls for a chic little lunch at one of my faves when I’m in town, Le Colonial. It’s a perfect lunch spot with a Caribbean-esque decor, despite the fact that it serves French-Vietnamese cuisine that I always find consistently delicious every time I’ve been. They have other locations across the US but unfortunately one of the original locations in Los Angeles is no longer. Outside the stunning design details that instantly transport you to a glamorous tropical escape, some of my favorites are the tuna tartar, chicken dumplings, cold veggie rolls and chicken soup. All the rice and noodle dishes are great too and I recently loved their well regarded lychee martini which I requested to be lighter on the vodka and with plenty of ice hoping to preserve myself for the rest of the day! We had a great time reminiscing about the night before and I think my outfit matched the environment and outstanding weather!

After lunch I got in some quality time with my friends and all their babies, it was mind-blowing to see these ladies I went through adolescence with become mamas and I am so excited for us to have further developed relationships with each others’ kids in the future. It’s a blessing too for Parker to get to have so many built-in friends his age and I imagine we will all get to take some fun trips together as they grow up!

Later that night I made a stop at the hotel bar view a view of the former Pump Room and sipped my usual French 75 over ice (in a wine glass) because when will I ever get to do something like that, before meeting my sister for dinner at Ralph Lauren.

Dinner at Ralph Lauren

RL restaurant is essentially your city country club but with better cocktails and more pristine details. It’s not as sceney as the Polo bar in NYC but definitely a similar vibe and a more sophisticated clientele. Of course Ralph’s Coffee wasn’t enough for me and I had to get my Polo Bar adjacent fix before heading back to lalaland, where even restaurants are encouraged to stay young. I devoured the mini lobster rolls, oysters and French fries I begrudgingly shared with Becky, while catching up and remarking on the insanely good weather. I was almost happy to sit in air conditioning as the fur cuffs on my tweed blazer felt quite out of step even in Chicago’s version of April!

Cafe at 3 Arts Club at Restoration Hardware

Alas Sunday came, as did the rain, and so I made it out for one last run through the Gold Coast before rolling off to brunch with the girls.

But not before a coffee stop nearby at the chicest one of all! The coffee bar at the 3 Arts Club at Restoration Hardware is essentially my dream kitchen come to life and I AM MANIFESTING IT! We were so close to having grey cabinets in our kitchen but ended up with basic white and I regret it. However, the brass/gold fixtures wouldn’t have gotten past my hubby so I will have to fight harder next time around!

The 3 Arts Club is a perfect place for any meal, it’s bright and airy in the atrium for lunch and so well lit at night you’ll feel transported to a perfectly hedged evening in an east coast garden for dinner. They finally take reservations so it’s much easier to bank on a mealtime now.

After one last luxurious sip of coffee I headed straight to brunch with the ladies at The Whale, where I was greeted with quite the boozy, bumping brunch scene that only Chicagoans on a rainy day can procure. Every table had a mimosa tower and well dressed inhabitants clearly enjoying the ambiance and ready to party. Fortunately my girlfriends weren’t and we enjoyed a fairly tame meal in comparison to the other patrons around us.

I was still so overwhelmed by all the other meals out that I resorted to a boring black coffee and simple fish dish but my girlfriends seemed to love the lobster and waffles entrée and bloody Mary’s they seem to be known for. The crab rolls also looked great but I was still puffy from the lobster rolls the night before!

The main showstopper, however, was the gorgeously grandmillenial restroom I couldn’t help but take a million photos of given how cute the wallpaper was and fun details like a “vintage” payphone I doubt any gen z’s ever used before!

Alas my weekend was almost over after one last stop to see my sister and get my deep dish fix at Pequod’s before jetting back home to la la land and the family. It was such a great trip away and I am so proud of myself for taking the time away to reconnect with my friends, hopefully the next time will be somewhere we can all be on vacation, hotel robes and alarm free living and all!

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