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.
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!
Photo c/o Shedd Aquarium
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.
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…
Photo c/o The Up Room
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.
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.
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!)
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!
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!
Photo c/o Aba
Photo c/o Lost Lake
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!
xx,
Whitney
