I don’t remember the first time I visited Chicago or even when I fell in love with the city. Born and raised in Milwaukee, just 90 minutes away by Amtrak or a similar-length car ride, Chicago has been the big city I need to keep me from moving right back to my beloved Brooklyn. It just has a special flavor, with its Midwestern charm, rivers and Lake Michigan — and, of course, big-city food.
I’ve spent countless birthdays in the city (as a Capricorn, what else is there to do but live my best life in Chicago?). Even this winter, the snow and record low temperatures couldn’t dully my getaway.
If you’re headed to Chicago, be prepared to be surprised in all the best ways. Here are just some of the hotels I stayed at, restaurants I enjoyed, and things I did while in Chicago over the last year or so — and I’ve been around. So, use this to inspire your itinerary to this midwest destination.
Where to Eat
Esmé— Experiential dining, the likes of which Esmé specializes in, has my name written all over it. While the food is certainly the main focus, your experience at Esmé is designed to be so much more than that. It’s almost likely you’re stepping into a unique art museum, where you participate and enjoy the art — which covers the wall, informs the plates, and fuses with the food — creating a narrative that you won’t forget anytime soon. If you’re a frequent Chicago visitor, the menu and the artist change quarterly, so you’ll have a completely different experience the next time you dine, if you so choose.
Frontier—I’m always appreciative of a restaurant that does vegetables just as well, or in this case, even better, than their meat offerings. At Frontier, their smoked carrot salad, which is topped with smoked goat cheese, mint, dill, Za'atar, lemon and pistachios, is magical. You’ll just have to try to appreciate it fully. Frontier offers wild game options, including a venison cheese steak, smoked and braised elk shanks and BBQ boar mac and cheese. Whole-animal dinners, which must be ordered in advance and serve a crowd, include options like alligator, antelope, goat, wild boar and free-range American pigs.
El Che Steakhouse— At the heart of El Che is a wood-burning oven on which everything on the menu is cooked. You’ll find a nice selection of top-grade steaks, including the well-loved ribeye, New York strip and filet, as well as a 48-ounce porterhouse and an American Wagyu flank steak. The sides are imaginative; think beef fat fries offered alongside mushroom polenta and Japanese purple potato. The Argentinian-inspired steakhouse stands out in all the right ways amongst the bustling Chicago steakhouse scene, with top-notch customer service and flavors that are perfectly balanced and perfect for a summer evening.
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Brasero—Another concept by Chef John Manion of El Che, you won’t want to miss Brasero while visiting Chicago. The whole red snapper was super flavorful and flaky, the steak was perfectly cooked, and the cocktails were really great, too. Pro tip: If you’re usually a steakhouse girly, head to Brasero and order the wagyu picanha, cooked over house-made charcoal. It’s truly a fantastic cut of meat that can be harder to find, and the rest of the menu will let you enjoy a little variety while still getting your steak fix. Brasero is fantastic. I can’t wait to dine again.
Shaw’s Crab House — For a truly “old school” or “proper” seafood restaurant, complete with white tablecloths and all the classics — from oysters to a grand seafood tower, and, of course, seasonal crab, lobster, and fresh fish — you’ll want to dine at Shaw’s Crab House. And they have sushi, too, along with more traditional, steakhouse-evocative side dishes, like lobster mac and cheese, sauteed spinach and crispy brussel sprouts. Definitely worthy of a special occasion dinner and dress to impress.
Demera Ethiopian Restaurant— First of all, don’t skip the Sambusas! They’re simply divine and a worthy start to a delicious meal. There are five fillings to try: lentil, spinach, beef, chicken, potato and carrot, but we do not regret getting the combination plate featuring one of each.
For our main dish, we shared a combination plate with stews and vegetables, including all my favorites, like doro wat, a Berber spiced chicken served with an egg, quosta, stewed spinach with garlic and onion, and yemisir wat, red lentils cooked in the same Berber sauce as doro wat.
If you typically avoid vegetarian cuisine when eating out, Demera is a great place to try it again. The vegetable dishes are just as good, and sometimes better, than the meat counterparts.
Heritage Restaurant and Caviar Bar—For the caviar connoisseur and newbie, Heritage Restaurant and Caviar Bar is a must when in Chicago. The low-key restaurant has a come-as-you-are dress code, and its staff is incredibly knowledgeable. They’ll guide you through the menu, make suggestions and ensure that your experience is exactly what you’re hoping for. While caviar is certainly the main attraction, the food itself is a must-try, too, as it is both imaginative and quite tasty.
Juno—Whenever I’m in Chicago for my birthday, you can bet that Juno is on my itinerary. Located in Lincoln Park, Juno has wonderfully fresh sushi with a selection of both traditional and inventive bites. I’m partial to the individual cold-smoked bites of yellowtail and salmon. Presented covered by a cloche, you’ll first indulge in the smoke as the dish is revealed before enjoying the two spoonfuls of goodness. But the signature nigiri, dressed to drive the unique flavors of each variety of fish home, is a close second.
Juno now offers omakase, a set tasting menu of 20 bites, including appetizers, nigiri, sashimi, warm plates and dessert. I find it to be a surprisingly more budget-friendly approach to dining at Juno if you’d like to try a little bit of a lot of different things. Personally, it’s not my preference as the restaurant simply excels in raw preparations, and I intend to fully indulge when splurging on dinner.
Juno is expensive, but you’ll leave dreaming of every single bite and planning your next visit. Be sure to buy a bottle of their soy sauce on your way out to uplift your meal the next time you order takeout.
Lawrence Fish Market — Not ready to splurge for Juno, but want a wonderful, yet budget, alternative? That would be the Lawrence Fish Market — spectacular in its own way and perfect for feeding a crowd or satisfying your munchies. The cash-only establishment usually serves its sushi to-go, although there is a small dine-in area, and you can order your platter via phone so it’s ready to go when you arrive. Offering both the classics available at most sushi spots, as well as more luxurious options like o-toro, Japanese uni, sweet shrimp and octopus, there is not a single thing that’s not fresh and delicious.
Where to Stay
The Viceroy—There really isn’t anything that you won’t love at the Viceroy. Views as far as the eye can see, fantastic customer service and the best couples shower I’ve seen in at least the last year, hands down! Located in the Gold Coast and just moments from the Magnificent Mile, the Viceroy boasts an 18th-floor rooftop pool with city views. There’s free WiFi throughout the building. The Viceroy is definitely a luxury splurge, but if you’re in town for a little romance or celebrating a special occasion, it would certainly add to your experience in the Windy City.
The Fairmont—The views from our room at the Fairmont were fantastic. The hotel is located relatively centrally, just over a block from the Chicago River on one side and Millennium Park on the other. Customer service was top-notch and the bed was comfortable. I’m not sure if there was construction or something else going on, but we were woken up really early due to noise, so if you’re easily woken, consider bringing earplugs to ensure a restful sleep.
The Gray—The shower was fantastic! I also really liked the room layout and the modern rooms in contrast to the ornate lobby and elevator areas. Located minutes from Union Station, it was a convenient location given we arrived by train, but it seemed a bit far from everything we were doing that weekend. The Gray hosts a free evening social hour between 5 and 6 p.m. and also offers complimentary coffee and tea in the morning. For dog owners, this hotel is particularly attractive, given pets are allowed at no additional charge.
Things to Do
Newport Theater — If you love a good show before dinner or are a connoisseur of burlesque, you absolutely must check out the Newport Theater. From the outside, Newport Theater might not look like much, but walk through the door and up a flight of stairs to a lovely theater with a bar and more comfortable seating than you’ve probably come to expect. With multiple shows on Fridays, Saturdays and Sundays, as well as some weekday offerings, there’s a performance for everyone’s taste and availability. I’ve been to quite a few shows at this point and recommend Newport Theater to just about anyone who will listen to me, so you’re in for a treat.
Shedd Aquarium—Perfect for a cold, hot or rainy day, the Shedd Aquarium offers hours of fun, all protected from the elements. The aquarium offers multiple encounters available for visitors at an additional fee, including the Beluga, Sea Otter and Sea Lion “meet & greets.” For a different spin on a romantic night out, check out Shedd’s Jazz and House Party nights for the 21-plus crowd.
Shot of Art — Have you gazed longingly at dozens of videos of fabulous fluid or spin art? Well, now you don’t need to get paint all over your home to make it happen! Make Shot of Art a stop on your Chicago itinerary. The painting studio allows you to select a project — or make it a date and choose a few different projects — and a style of art (fluid, spinning, etc) along with a canvas to create your dream abstract art. An artist will walk you through every step of the process, ensuring that you leave confident that the art you create is everything you were hoping for. It takes a few days to dry, so be prepared to pay for shipping, which you can only do by phone after the painting is dry.
Aroma Workshop—I’m a sucker for workshops of all kinds, so the perfume-making experience at Aroma was right up my alley. It’s a fun experience that leaves you with a lovely gift to yourself that reminds you of your trip to the Windy City. For a perfect date night experience, make perfume for each other instead of for yourself. Choose between a variety of scents blended to create your own unique fragrance.
Color Factory—The Color Factory is an oddly satisfying experiential “art museum” of sorts. You move from room to room, with new colorful exhibits and experiences in each. The 90-minute experience is self-guided and perfect for adults and kids alike. We especially enjoyed the photography stations, where a timed camera allows for in-action shots around the Color Factory, which you can claim and download online for no additional charge. Hot Tip: Place your phone above the camera to simultaneously record video if that’s your jam.
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