Summer in Chicago Bucket List

summer in chicago


While I've written about my love for Chicago many times over the years, it wasn't until a few weeks ago that I could truly say I've had the privilege of experiencing this city in it's prime. Simply put, summer in Chicago is other-worldly. With idyllic temperatures in the seventies and a buzzing energy that's been fought for all winter long, this city comes alive in the summer in a way you won't see any other time of year. I've spent the last couple of months polling trusted locals and food enthusiasts so I could try just about every recommended rooftop, patio or outdoor experience in the Windy City that I could first-hand. After working hard (or hardly working?) it's my pleasure to bring you this curated "bucket list" of favorites that you simply can't miss when you visit Chicago this time of year. 


Experiencing the ideal seasonality of Chicago wasn't the only way I saw this city with fresh eyes over the past several weeks. One of the most memorable moments of my summer was easily with Chicago Helicopter Experience. Departing from their downtown heliport just minutes from the “Loop", this tour took us over the most popular sights including Willis Tower, the Hancock building, Soldier Field, Navy Pier, Buckingham Fountain, Lake Shore Drive and the Magnificent Mile. The ride was incredibly smooth, and I was pleasantly surprised by how large and unobstructed the viewing windows were (also loved the Bose noise-cancelling headphones to make for a much more enjoyable flight). Even after flying into Chicago by plane dozens of times now, nothing compares to soaring so closely to the skyline like this (especially at sunset!) and taking in the spectacular aerial views of the city. It was one of the coolest things I've done in a long time (and not just in Chicago!) Learn more about booking with Chicago Helicopter Tours here

chicago helicopter experience

shore club chicago
shore club chicago

I spent several afternoons over the course of the summer parked at Shore Club: an elevated venue at North Avenue Beach inspired by Mediterranean cuisine and beautiful beaches around the world. Alcohol is strictly prohibited at the beach, with the exception of here and Castaways their neighboring beachside burger joint, so if you're craving a cocktail to go along with your beach views-- this is the place to find it.  Shore Club's restaurant features floor to ceiling glass windows in a temperature controlled space, along with an outdoor patio if you prefer to be outside. For guests seeking more of a semi-private VIP experience, you can also reserve a Cabana, Daybed or Sun Bed in The Oasis at Shore Club. I tried them all and can personally attest that there is no bad experience here, regardless of where you decide to spend your time! My only advice? Don't leave without trying their frozen cocktail flight or a large format specialty cocktail served in a copper pineapple-- both are novelties everyone will enjoy!

shore club chicago


Every Wednesday evening in the summer, Chicago's Shedd Aquarium hosts  "Jazzin' at the Shedd": a paradise for people like me who thoroughly enjoy live jazz music, sweeping city views and a glass of wine (especially all at once!) Tickets are $25 and offer full aquarium access in addition to performances by some of Chicago's top jazz musicians - all paired with cocktails, the city skyline and Navy Pier fireworks for the cherry on top!

Chicago is known around the world for its architecture, and it would be a cardinal sin to visit this city (especially in the summer!) without doing the Chicago Architecture Foundation river cruise. There are actually a handful of companies offering these tours, but the Chicago Architecture Foundation is by far the most credible and educational. Order a beverage (available for sale on board) and sit on the upstairs deck while you expand your knowledge of some of Chicago's most iconic Art Deco, Gothic, Modern and Post-Modern buildings. Tours last 1.5 hours and tickets should be booked in advance here


kayak chicago

Back to the river we go! Another amazing way to get on the water and take in the architectural offerings of the city is with Kayak Chicago. They offer a variety of group tours, but we opted to take the kayaks out and explore on our own. You can also rent kayaks (or stand-up paddle boards!) with them on Lake Michigan, but I personally think it's a more unique opportunity to see the city from a different perspective by opting for the river. Rentals are $30 per hour for a single kayak ($80 for the day) and $40 per hour for a double kayak ($120 for the day). Whether you go for a tour or an on-your-own approach, kayaking the river starts just at the northern point of Goose Island, which equates to roughly 7 miles (and ~2 hours) round-trip to go to the heart of downtown and back. 

I developed a serious addiction to biking during my time in Chicago. The city's bike-sharing program, Divvy, makes it so easy (and cheap!) to take a bike to/from wherever you want to go. While I'd suggest taking this form of transportation as often as you can, be sure you do so along Chicago's Lakefront Trail. Almost daily, I'd start at Belmont Harbor and would ride until I hit North Ave. Beach (then would usually commute to wherever I was going in the city through Old Town). This particular stretch (while not very long!) is full of beautiful views, both of the lake and the city skyline. The pathways are easy to navigate, even if it's been a minute since you've been on two wheels...



Is there anything more all-American than going to a Cubs game?! I'll admit, I'm usually more of a sport enthusiast for the sake of experience and camaraderie than I am the actual sport itself,  but I find Cubs games to be such a great time. You can either buy standard tickets at Wrigley (only one of the most iconic ballparks of all time) or you can also purchase tickets from neighboring venues like Wrigley Rooftops, which also overlook the stadium. I love going to night games (if it's a warm day, you're less likely to be sweating if you don't have to factor the sun!) Wherever you sit and whenever you go, be sure to indulge in a Chicago dog + a few beers... and sing "Go, Cubs, Go" as loud as you can!

In the heart of Wicker Park, easily one of my favorite Chicago neighborhoods, is The Robey: a beautiful Art Deco building-turned-hotel on the corner of North Ave and Milwaukee. But before I send you upstairs to their rooftop (which we’ll get to in a minute) allow me to dote on Café Robey, their street level eatery. We came for dinner and fell in love with so many items from their menu (don’t leave without trying the tartar, the pork entree and most importantly, the gnocchi!) The cocktails were made wonderfully and the smart staff rounded it all out to make for the perfect meal before heading to…


The Up Room is The Robey's 13th floor lounge boasting twinkling skyline views of Chicago. They maintain a (seemingly) lower capacity that doesn't feel over-crowded which I loved, however this means there's often a line to get in. If you're dining at Café Robey, you can request to be put on the list while you eat so that you can go straight up whenever you finish your meal. Either way, you don't want to miss this elevated (in more ways than one) space. 

If you're a visitor to Chicago, chances are you'll find yourself on the Magnificent Mile at some point during your trip. While the city is exploding with culinary delights, I've found this area to be particularly touristy and not usually my favorite place to come for food + drink. Luckily, when my friend Sarah came to town I found Upstairs at the Gwen - a standout among rooftop terraces in the area. They focus on the art of craft cocktails paired with shareable small plate fare, all while offering cityscape views from among the Art-Deco-infused architecture. In addition to being impressed by the food + drink (don't leave without trying the smoked cauliflower!), I had befriended all of the staff by the end of our meal-- they were all such lovely people!  Even if I didn't have a tourist in town, I'd easily go back to Upstairs at the Gwen anytime.  

upstairs at the gwen


I came to Tied House a few times over the course of my Chicago summer and it never disappointed. The bar is set in a sleek and airy space that’s idyllic for cocktails on a nice day (as is their 3-season patio). Should you stay for dinner, their James Beard Award-Winning chef has an array of dishes worth trying (and don’t overlook the bread & smears). Cocktails and dinner menu items are both rotated seasonally, but the smart staff is fantastic about helping you navigate any questions you may have during your decision making. 

The rooftop at LondonHouse Chicago offers some of the best views in all of the city. But be warned- I'm not the only one with this popular opinion. Should you decide you want to see these views for yourself, I'd recommend arriving around 4 to avoid a long wait. The sun can be ruthless this time of day, so simply leave your ID with the hostess to take a paper umbrella out on loan and create your own shade. In all honesty, cocktails are a bit over-priced and there's usually a crowd so I often don't stay longer than one drink. But even with those drawbacks, the views are still absolutely worth paying this spot a visit-- especially on a perfect summer day. 


parsons Chicken and Fish Chicago

Parson’s Chicken & Fish is a low-key eatery in Logan Square with a patio that’s a favorite among locals in Chicago. While chicken and fish may get all the name-sake glory, Parson’s is also widely known for inventing their famous Negroni slushy (you simply can’t leave without trying one- they’re delicious!) 



parson's chicken and fish

TO MY NASHVILLE FRIENDS: Keep your eyes peeled, because this gem is making it’s way to the Wedgewood-Houston area this fall!

I’m a sucker for novelty, so I jumped at the chance to try the boozy snow cone cocktails from Noyane- an upscale Japanese restaurant perched atop the Conrad. Served in takeout boxes (complete with chopsticks) these are such a fun summer treat to enjoy on a nice day, along with the sweeping city views. To be honest, you probably won’t want more than one (they’re a bit on the sweet side for my taste) but nevertheless, worth indulging in for the sake of experience!

noyane snowcone cocktails

Aba is the hot new rooftop patio in Chicago’s historic Fulton Market District. This Mediterranean restaurant is Chef CJ Jacobson’s second restaurant and  incorporates a light style of cooking with a large emphasis on raw and cooked protein. Whether you’re inside or outside, the ambiance is stunning (although book far in advance or be willing to wait a while — they’re still in their honeymoon phase of new popularity!

aba chicago

lost lake tiki

Recently named the #1 cocktail bar in America, I couldn’t leave Chicago without going to Lost Lake for one of their beautiful (and delicious) elixirs. This unassuming facade in Logan Square wouldn’t speak to you if you were simply passing by on the street, but from the moment you walk into this topical oasis, you’ll be drinking the Kool-Aid (or as I would recommend, a “Heaven is a Place”). 

There are dozens of others I could include on this list (see more of my Chicago favorites here) but these were the ones I felt couldn't be looked over. Chicago will always be one of my favorite cities and I'm so glad I could experience it in all it's summer-time glory over these last couple of months! 

But for now? I have lots to do as I prepare to leave for Europe in a few days. Thanks as always for stopping by and be sure to come back soon--I have a lot of upcoming adventures to share!



belmont harbor chicago
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Hidden Travel Gems to Consider (Instead of the Overly-Popular-on-Instagram Destinations)

hidden travel gems to consider

I recently listened to an influencer podcast that was highlighting how Instagram has made a handful of travel destinations overly-popular in recent years. Our feeds have become infiltrated with the same photos of Positano, Tulum, Palm Springs and countless other destinations. 

Don't get me wrong... I love a lot of these places. Some of them you absolutely should see and there is a reason they've become so popular! But it got me thinking... are these the only places a lot of people are planning travel to? The ones that are "Insta-famous"? 

If that's the case, consider this my humble attempt to put drop in the bucket and point us toward a better way forward... one that involves a greater curiosity for the world and a sense of discovery (beyond your Instagram explore page). If you too have found yourself lusting over these type of destinations, here are some other wonderful places I'd argue you should consider that aren't overly-infiltrated with tourists or "grammers" seeking out the same exact shot.





In a sparkling sea of deep cobalt blue just off the northwest coast of Africa, you'll find Madeira: a rugged island with mountains soaring straight out of the water. If you don't already know its country of origin, based on its geographic positioning you'd likely guess Morocco. But this tiny island is Portuguese through and through. Known for its famous namesake wine and warm, subtropic climate, Madeira is a little slice of heaven that you won't want to miss. 

Similar to Positano, Madeira offers a stunning, rugged, dramatic coastline...


Perhaps you were looking forward to drinking copious amounts of Italian wine?  Fear not-- Madeira is known for their very own fortified wine that's made directly on the island. In fact, Maderia actually has a long winemaking history, dating back to the Age of Exploration when it was a port of call for ships heading to the New World (or East Indies). 


Rich in culture and exploding with color, Madeira has more to offer in terms of natural beauty than most destinations I've visited. For further reading, check out my Madeira Travel Guide.  

madeira portugal
madeira portugal
madeira portugal





hvar croatia

Known for beautiful beaches and ancient ruins, Tulum has been attracting travelers by the thousands. Yet there's a tiny Dalmatian Island in the Adriatic sea that offers all of these as well. Hvar, Croatia may already be a popular summer destination among Europeans, yet I'd argue that American tourists will find this resort-town to be a breath of fresh air with a unique spin. Hvar is a 13th century town (that also claims to be the sunniest spot in all of Europe). The architecture is historic and beautiful, and there are countless boat excursions available to hop around all the neighboring islands for those who want to soak up the scenery of the sparkling sea. Read my Hvar Travel Guide to learn more about this breathtaking hidden gem. 

hvar croatia
hvar croatia






I'm a big fan of Palm Springs, but I'd also argue it's not the only town outside of LA that deserves a spot on your travel list. Set in the Topatopa Mountain Valley, Ojai is brimming with beauty + charm. Similar to Palm Springs, it's a perfect retreat from the hustle + bustle of southern California where you can enjoy scenic landscape, delicious food + wine and the perfect touch of character. To read more, check out my Ojai Travel Guide







Before I dive into my reasons you should consider Granada, let me be clear that Morocco is somewhere I haven't traveled to and somewhere I very much want to see. With that said, I still chose to include this comparison because it's no secret that Morocco has become a very popular Instagram destination. Again, none of the above reasons should deter you from visiting a popular destination... my point is simply that you have options- and you shouldn't overlook the ones that aren't as "Insta-famous."

Nestled in the foothills of the Sierra Nevada mountains in Spain's Andalusia region, you'll find Granada- one of the most interesting cities I've ever visited. You can practically throw a stone to Morocco, so naturally there is tons of Moorish influence peppered all throughout the city (my favorite bits? the architecture + the cuisine). Head to my Granada Travel Guide to get the full scoop on this beautiful Spanish city.

granada spain
granada spain
granada spain


There are countless other destinations I could include in this list, but for the sake of brevity I'll end here. My hope is that this serves as a friendly reminder that while tools like Instagram are an incredible way to introduce us to places we'd like to visit, they shouldn't be our only source of inspiration. The world is wide and full of wonders. Stay curious and always be open to the idea of venturing somewhere that maybe isn't the most popular path... I've discovered some of my favorite destinations this way. 

Still looking for more inspiration to decide where your next trip should be? Head to the travel guide section of my site and start dreaming!


Thanks as always for stopping by!




Travel Day Uniform Essentials

travel uniform

Travel days: they too often start at an ungodly hour in the morning and drag you through a variety of temperamental climates and circumstances. So how does one dress in a way that’s functional, comfortable and still somewhat presentable throughout all of these variables? I’d like to think I’ve kind of mastered this art by now, so here are a few things you need to know. 

But before I share, let me point out that a lot of these items are currently marked down significantly thanks to the Nordstrom Anniversary Sale. If you’re not a current cardholder who gets early access to these particular items, you can check back in after July 19th for full access.



comfortable flats

Whether you’re traveling by plane, train, ferry, car, broomstick or any other vehicle, comfortable flats are a must. With that said, this doesn’t mean gym shoes are your only choice here. This can also be in the form of a loafer, a sandal, a ballet flat or a slide depending on the outfit you choose, but there are several reasons why I suggest against any kind of heel. In addition to heels being more cumbersome when it comes to metal detectors or any kind of security screening, they’re also generally uncomfortable (I don’t care if you are Carrie Bradshaw, don’t tell me you honestly think heels are an ideal footwear choice to schlep around a suitcase in). 



Sit. Stand. Stairs. Sprint to gate. Sit again. Stand again. Schelp your luggage… you get the picture. Travel days certainly aren’t the time to be wearing a mini-skirt or pants that are even remotely uncomfortable. I always love to wear leggings with some sort of detail that dresses it up a bit. Sure, you may have a zipper at the ankle or some sort of leather component, but you’re essentially wearing glorified yoga pants that are comfortable enough to sleep in. If leggings aren’t your thing, I love a boyfriend jean which wears a bit more loose and comfy than your skinnies. And if you really just want to be cozy AF, go for a jogger like these



basic layer t shirts

When your plane feels like a sub-zero Icelandic tundra but minutes later your cab to the city feels like a furnace occupied by Lucifer himself, light layers are the name of the game when it comes to maintaining a comfortable temperature… but where do you start at the base of all of that? I almost wear a basic tee that can be worn under a cardigan, scarf, light-jacket or on it’s own. If you’re feeling cheeky, go for a graphic tee like this, but a safe bet for me is always a classic stripe, which pairs well with just about any later you throw over it. 



blanket scarves

Per my commentary above, a scarf or wrap is a great additional layer to throw on when someone gets a bit too carried away with the AC. I love these because you can wrap it around your neck or your entire body if you want to wear it, but they also come in handy for a blanket you can snuggle up in on a plane. Pay attention to the material and weight of the fabric depending on the time of year you’re traveling (wool is a bit aggressive in the summer, but a light-weight cashmere will pretty much always be your best friend). 

blanket scarf

Surprise! More ways to layer. Cozy cardigans are a must in my opinion (I seem to always go for long ones that feel like a robe and can double as a blanket if needed.) Even if it’s 100 degrees outside and you’re convinced there is no way you’ll need a sweater… bring one. They’re light enough to not weigh down your bag if you don’t need it but will be a game changer if you do. 



Sometimes interchangeable with a cardigan or oversized wrap/scarf, a light jacket or sweatshirt can also make a great final addition to top off your layering. This time of year we don’t need a parka, but having some sort of thicker shell from a denim or utility jacket can provide not only an additional layer for warmth if needed, but also double as a shield if you get caught in unexpected rain.  




Acting as another base layer, I’m a huge fan of t-shirt dresses. Not only are they cool and breezy for warm summer travel days, they also mean you don’t have to wear pants, which I’m always a big fan of. I’d definitely advise bringing a couple layers if you opt for this base, as my legs almost always get cold on a plane when I go for this look. 


Looking for some other essentials for your upcoming travel day? Be sure to check out my blog reviewing my favorite travel bags or check out the “Shop Travel Gear” section of my site for some of my “can’t live without” items. 


Thanks as always for stopping by... I’m excited to share a lot more travel essentials with you in the near future with all of my upcoming adventures!




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