It’s no secret that Chicago has been a significant destination for me this past year, and I’ve been getting a lot of questions about it lately. In addition to seeking travel recommendations from those of you who know I moved here last fall (after many failed attempts to get to London), there have also been a lot of you wondering why I haven’t been there in a while now.
I’ll address both of those questions in this post, but let’s start with the travel recommendations first.
I put a Chicago Travel Guide together a couple years ago prior to ever living in the Windy City. While I still stand by all those recommendations, I felt it was only necessary to do a “deeper dive” into the places that are my absolute favorites now that I know the city significantly better. So no matter what you’re looking to do while visiting Chicago, I’m confident this post pretty much has you covered in terms of any recommendations you might be looking for:
I first came to Ambassador Hotel for a drink at their swanky bar (now Booth One) and I fell in love with the posh, minimalist ambiance of the entire property. So when the time came to plan a little staycation when my friend Sarah came to visit, Ambassador immediately came to mind. I absolutely loved so many things about staying here. For starters, their Gold Coast location is just blocks from Lake Michigan (which means incredible views) and is a short walk to The Magnificent Mile. Rooms are priced very competitively, especially for how nice of a hotel it is. And most of all, I loved having Booth One (pictured below) as our home base bar- it's one of the most beautiful places to grab a drink in my opinion!
Call me basic, but The Hampton Social is a brunch-goer’s dream. This nautical hotspot evokes everything there is to love about East Coast summers. In addition to the swoon-worthy decor, they have fantastic coastal fare, delicious and eclectic menu items (try the Fried Chicken and Doughnuts!) and refreshing cocktails to leave you utterly delighted. This place is popular, so making a booking in advance is recommended.
There’s no better way to start your day than with breakfast, and there’s no better way to start your breakfast than with a beverage! Beatrix has an extensive list of beverages, everything from Bulletproof coffee to matcha to fresh juices to cocktails and even an extensive wine list (they obviously are open for other meals besides breakfast- although no shame in ordering any drink any time of day!) Beatrix has multiple locations in the city (clearly a favorite among Chicagoans) and is a top-notch American eatery. The menu is thoughtfully curated, the ambiance is enjoyable and I’ve always left wanting to come back straight away. Again- a popular spot so a booking in advance is suggested.
Cindy's has been a long-time favorite of mine in Chicago, and for good reason. This public rooftop (part of Chicago Athletic Hotel) offers stunning views of Lake Michigan, Millennium Park and the Chicago Art Institute. It has floor to ceiling windows (and actually... the ceiling is glass too) so the place is bright and cheery and flooding with natural light. Aside from the spectacular ambiance, the food is out of this world (but be warned, portion sizes are intended for sharing- so come hungry!)
I fell in love with everything about Maison Marcel, a quaint French boulangerie + patisserie in Chicago’s Lake View neighborhood. It’s European bohemian interior boasts white-washed exposed brick, beautifully detailed wicker chairs and freshly cut baby’ breath on every table. They have a pretty extensive menu (although I always seemed to opt for an almond croissant and cappuccino) and even a juice bar. There is wi-fi and plenty of seating, so regardless of if you’re popping in to meet a friend for coffee, having lunch or needing a remote office for the day, Maison Marcel is sure to please.
SOME OF MY OTHER FAVORITE COFFEE SHOPS?
Inside of Restoration Hardware in Gold Coast is 3 Arts Cafe, which offers an all-day menu with breakfast, lunch and dinner options. But regardless of whether you actually sit and dine in the restaurant, you are welcome to sit on the couches in the surrounding rooms of the cafe, use the free wi-fi and even order a coffee, juice or pastry from the coffee bar. You simply won’t find a more beautiful atmosphere to work in Chicago (in my opinion).
I have a soft spot in my heart for jazz music and so naturally I was on a mission to find the best spot to hear it live in Chicago. My Aunt and Uncle pointed me to The Green Mill, a swinging cocktail lounge famous for being Al Capone’s favorite bar during the heyday of Prohibition. Now over 100 years old, it’s one of the most prestigious jazz clubs in the world and my favorite spot to drink martinis and listen to a variety of jazz (every thing from traditional to swing to big band). The good music typically doesn’t start until late (we went around midnight) and they stay open until 4am if you’re looking for some after hours entertainment once the bars close.
Pretty much every spot on W. Randolph (AKA Restaurant Row) is a winner in my book, but I fell in love with Maude’s Liquor bar: an intimate French speakeasy meets bistro serving some of the best handcrafted cocktails in the city. Their menu offers an array of French classics (including food) as well as an extensively curated French wine list. Whether you stay for dinner or just pop in for a drink, you won’t want to miss this blend of sultry ambiance and sensational cocktails.
Eataly is obviously not exclusive to Chicago, but it's here nonetheless and thus it makes the cut on my favorites list! This "amusement park of Italian delicacies" is in the heart of downtown and quickly became a regular spot for me to pop in for lunch. They offer an array of cafes, counters and restaurants (essentially dozens of dining options in one place!) Whether you want to do your own grocery shopping to take home and cook a proper Italian meal, or sit down anytime of day to let someone else prepare it for you, Eataly has you covered. I recommend it for lunch because you'll likely be walking around the downtown area at some point if you're visiting, so it's an easy place to pop in and choose from a variety of delicious options.
Also located on Restaurant Row, Girl & the Goat opened with the goal of serving bold flavors with global influence in a fun and lively setting. They also boast the title of James Beard Award for Best Chef: Great Lakes, along with awards from Eater including: Restaurant of the year, Chef of the year, Shaker of the year... the list goes on. Whether you go for a full meal or simply drinks and appetizers, do yourself a favor and just make sure you get there when you visit Chicago-- it's hands down one of my favorite meals I've ever had!
My friend Sarah Kate took me to Leña Brava when I first moved to Chicago and I am still talking about these plantains months later. They're wood-oven roasted with butter, thick cream, and homemade fresh cheese but they taste better than just about anything else I can think of right now (I even swiped right on a Bumble guy who was a chef here and my opening line was shamelessly "Can you make those plantains?") It's worth visiting this Restaurant Row gem simply for this menu item (although fear not: nothing else you try will disappoint!)
The food at Oyster Bah blew. me. away. This casual New England seafood spot specializes in cold water Oysters, but they serve way more than just that. Some of my absolute favorite thing we tried were the macaroni and cheese and the coconut cake, but I mean it when I say that everything we had was delicious. The atmosphere is cozy and nautical, the staff is wonderful and on a more important note, the drinks are boozy and delicious!
Both my well-traveled family and my friend Domenico (who is from Napoli) have taken me to Spacca Napoli, so that alone should tell you something! In all seriousness, this Ravenswood pizzeria serves classic Neapolitan pies that will bring tears to your eyes it all tastes so good. It may not be deep dish (see the bottom of my list for my favorite Chicago-style pies!) but I'd argue you'll be far from disappointed to experience Spacca Napoli.
If you haven't picked up by the "Goat" title, this sister restaurant of Girl & the Goat (along with Little Goat) is another hit- this time in the Chinese category. Duck Duck Goat offers globally inspired cooking sauces and spice mixes with dishes from Dim Sum to noodles to fried rice and more. My friend Rachel and I split the Dan Dan Noodles with peanut and pork and the Duck Fried Rice on a cold, snowy night and left with full, happy tummies. Per usual, it's a good idea to make a booking in advance to avoid waiting for a table.
This European-inspired indoor food market offers a variety of grab and go kiosks with every global food imaginable (although they definitely heavy up in the French category). The decor makes you feel like you've just transformed to Paris and it's so fun to browse around all the different stalls to see what global cuisine is available.
Sometimes a chain restaurant ain't a bad thing, and that's certainly the case with Le Pain Quotidien, an international chain of organic bakery-restaurants originating in Belgium. There are several locations in Chicago and I often found myself cozied up by a window with a cup of coffee to do some work. It's a great spot to meet a friend for a healthy breakfast or lunch if you're looking for a cozy ambiance.
No surprise here, I'm sure! The Cubs are a Chicago staple and you simply must try to get to a game if you can. Wrigley is so much fun year round (not just for baseball, they also have everything from concerts to Christmas markets here!) Even if you can't make it to a game, be sure to explore the area to see the stadium and imagine what all the excitement must be like on a game day.
Fun Fact: The "W" flag you'll often see flying originated before the era of smartphones when people were taking the train home and wanted to know the result of the Cubs game. If they won, a W flag would be flying over Wrigley.
I've had the privilege of seeing this INCREDIBLE show twice now, once in London and for the first time here in Chicago. It truly is worth all the hype it's received and (in my opinion) is even better than the buzz you've heard. While you can enter the daily lottery for your chance to win $10 tickets, I'd advise against that tactic if you really want to see the show (it took me 3+ months of entering every single day before I finally won). It's one of the few cities (along with New York, LA and London) where you can see this Tony award winning sensation and it's sure to be the highlight of your trip if you do!
Paris has the Eiffel Tower. London has Big Ben. Chicago has "The Bean." Millennium Park was originally intended to celebrate the third millennium and is a collection of state-of-the-art architecture, and "Cloud Gate" (aka The Bean) is the crown jewel. You're sure to find tourists crowded around this art installation taking their photo in the reflection, but for whatever reason this attraction has a soft spot in my heart. Even if touristy bits aren't your thing, it's worth walking around this park (you can avoid Cloud Gate if you really must) to see all the architectural variety and well manicured landscaping.
While this is certainly more enjoyable in the warmer months, strolling along the Chicago river is one of my favorite things to do in the city. This pedestrian walkway along the waterfront gives you a front row to some of the best architecture in the city and offers plenty of restaurants and bars to stop along the way for a drink.
The Art Institute of Chicago is one of the oldest and largest art collections in the United States. It's home to some of the best-known works in America including: Edward Hopper's Nighthawks and Grant Wood's American Gothic. Even if you're not a huge art buff, there are so many fascinating and recognizable pieces in here that anyone can enjoy. I hadn't been since I was a kid and on my most recent trip this winter I was blown away by how impressive it was. If you have the time, I can't recommend it enough (and be sure to have lunch at Terzo Piano while you're there for beautiful views and delicious food!
OTHER FAVORITES TO NOTE:
I'm confident there's other favorites that I'm failing to mention, but there's still another half of this blog post that I need to write! So moving onto the "real talk" about why I haven't been back since I came home to Nashville for Christmas. For starters, I took a two week trip to London and Eastern/Central Europe for New Year's, so that carried me into the middle of January. But for the past couple weeks? I've been staying put in Nashville instead of heading back to Chicago. Why, you ask? Pour yourself a glass of wine and settle in for a minute.
It’s really difficult for me to properly articulate all of this, because the past few months have been nothing short of an emotional rollercoaster. I’d love to deliver a nice and tidy summary of everything that’s been going on in my brain, but truth be told there’s nothing too simple about it. In an effort to keep things as succinct as possible, I’ll start with this: while I was falling more and more in love with Chicago everyday, there was also voice deep inside me continuing to grow louder and louder, telling me it wasn’t time to give up on London just yet.
As I started building this new life in Chicago: making friends, dating different guys, discovering new neighborhoods that I could easily call home, it was so easy to imagine the kind of life I could see myself living if I stayed— and it was a really, really great one. I knew this said life could bring me a lot of joy and challenge me in new and exciting ways I was currently craving. But the longer I sat with that picture, I could also begin to see myself beyond the short term giddiness: being settled into a new life that was great, but not quite the one I felt peace about. Deep down, I knew moving forward with Chicago meant I'd be settling on what was easier to achieve or prolonging the work I needed to do if I ever wanted to get to London. Because at the end of the day, building a great life in Chicago will still require my time and energy, and the more of that I put forth here, the less of it I have to dedicate to getting there.
I honestly kind of wish that voice in my gut wasn’t so loud. I love Chicago so much and it was a really emotional departure to say the least. I’ve been mourning the absence of the big city energy it gave me, as well as countless other details about it I really grew to love. And if all the doors to London slam in my face and my immigration lawyer tells me I’ll absolutely never be able to live there, I will scurry back to Chicago faster than you can blink. But as long as I know there’s hope for London (even if that “hope” currently has me feeling like I’m standing at the base of Everest) I feel a burning conviction to pursue it whole-heartedly with everything that I have in me. So until something changes, be it the circumstances that are keeping me from getting a visa, or the desire itself somehow disappears, I’m all in.
I could go into a lot more detail, but the truth is none of it would lead to anything conclusive about what comes next. There’s just a lot of uncertainty ahead. For now, I’m back in Nashville where I can easily coast, which gives me more energy to put my head down and work tenaciously (which I’ve already been doing the past few weeks). I’m more committed than ever to work on not only making the harder, more disciplined choices that will get me closer to my goals (even if they take significantly longer than I’d like them to).
I’m also more committed than ever to hold on tightly to the greatest takeaway I learned during my time in Chicago: to enjoy the journey.
If I eventually do get to London I can honestly say I'll be so thankful that it didn’t happen on my original timeline. Because if it had? Chicago wouldn’t have been a chapter in my story. This past season has enriched my life in more ways than I can count, and I almost missed it because I was so stubborn and set in my ways, wishing things were different.
We often think that happiness will arrive when we finally get what we want and our circumstances change. But at the risk of sounding like a terrible cliché, it’s often the circumstances we’re cursing that God is using to change us. And if our fists are clenched and our knuckles are white because we're so set on finally "arriving" we're going to miss out on countless opportunities to see goodness along the way.
The truth is, I don’t actually know if this immigration strategy will even work or if I’ll ever successfully move to London like I’ve hoped to for so long now. I don’t know if I’ll end up right back in Chicago. In fact, I could end up living a totally different life than I imagine altogether, somewhere that’s not even on my radar. But I know with certainty that living authentically and honoring my dream right now is transforming me in the process, and that alone is reason enough to stay on course. Because "where I'm headed" is actually much less about my geographic position and more about learning to surrender to the (often painful) process of becoming.
So that’s the latest in my world. To be completely honest, it’s somewhat painful for my pride to pour out my personal details of endless uncertainty. I love sharing the fun stuff like booking a one way ticket to Europe, but this? Not so much. In fact, I debated sharing any of this at all. But it’s important to me to share my whole story, not just the pretty side of things. I hope that it serves as a reminder that our dreams aren’t merely condensed to the 2 hour timelines we watch play out in a film. Real life transformation that we hope for usually takes months and years of hard work— but I truly believe it’s worth fighting for. So fight for it I will.