Chicago. The Windy City. The City of Big Shoulders. The Second City. It goes by a lot of names, but one thing is certain, Chicago is an incredible city. So incredible that Frank Sinatra wrote and sang a song about it. Here at TTS, we believe it doesn’t get enough love, so we whipped together a list of spots to hit the next time you’re in Chicago, whether you’re there for Lollapalooza, to catch a Cubs game, or visit some friends.
If you’re in the market for a boutique hotel, Lincoln Hotel is the perfect fit for you. Located in the heart of Chicago’s Lincoln Park, the Lincoln Hotel is eccentric, cozy, and a must-stay. In true Midwest fashion, the staff is the kind of nice you can only find in Chicago. With its views of Lake Michigan and proximity to Downtown Chicago, it has us wanting to make a trip to Chicago immediately.
Location: 1816 N Clark St, Chicago, IL 60614
The Peninsula Hotel in Chicago is nothing short of incredible. Whether you’re in the main dining room, the spa amenities, or any of the hundreds of rooms, you’ll be sure to feel right at home… well, a classy home. Even though it was recently renovated, it still holds the charm of the years it spent on Superior and Michigan Ave.
Location: 108 E Superior St, Chicago, IL 60611
The Robey is the perfect place to stay if you’re in the mood to veer off from the touristy areas of Chicago and want to discover a whole new neighborhood. With 69 guest rooms, this simple yet effective hotel is petite, but right up our alley. P.S. Get the full experience thanks to our Staycationers.
Location: 2018 W North Ave, Chicago, IL 60647
Located inside of the newly renovated Restoration Hardware, the Three Arts Club is nothing short of breathtaking. Not only is the room beautiful, but the food is equally as delicious. Wrap your hands around a decadent Truffle Grilled Cheese, or dive into the Shaved Ribeye French Dip. This place is not only easy on the eyes, but it’s insta-worthy.
Location: 1300 N Dearborn St, Chicago, IL 60610
Sometimes you just need a refreshing margarita, a classic taco, and chips and guacamole. Thankfully, Big Star has all of those necessities waiting for you in Chicago’s Wicker Park. With a variety of Mexican Street Food (Queso Fundido, tacos, and guac… oh my!) and a cozy vibe, Big Star should be on your list. Whether you’re sitting outside or enjoying the ambiance indoors, Big Star makes it so you never want to leave… one more margarita, please!
Location: 1531 N Damen Ave, Chicago, IL 60622
Au Cheval is not your regular diner. This Chicago Restaurant takes diner food to a whole new (classier) level. The open kitchen serves up upscale “diner” food that ranges from a Double Cheeseburger to Foie Gras and Scrambled Eggs. Wash down all this scrumptious food with one of their many signature cocktails; we love the Horse’s Neck (Old Overholt Rye, Ginger Beer, Angostura). Try Au Cheval for brunch or dinner, either way, you’ll be happy you went.
Location: 800 W Randolph St, Chicago, IL 60607
Down for a cozy diner vibe? Then Little Goat is the place for you. Famous Chicago chef Stephanie Izard serves up a plentiful menu of gourmet comfort food. Stick with your basic Fat Elvis Waffles, Biscuits and Gray, and Spanish Omelette or go crazy and get the Ooey Gooey Cinnabun and the Goat Chili Cheese Fries.
Location: 820 W Randolph St, Chicago, IL 60607
Sunda is the place to be if you’re in the mood for some out-of-this-world cocktails and delicious Asian-fusion cuisine. With fresh sushi, finger-licking-good chicken and waffles (their brunch is a must-have), and many more great bites, at Sunda you can never go wrong. If you’re feeling wild, get an order of the Gambler sushi — spin the plate to see who gets the roll with a ghost pepper on it. Let the games begin.
Location: 110 W Illinois St, Chicago, IL 60654
Cindy’s Rooftop Bar
Grab your squad and head to Cindy’s Rooftop in Downtown Chicago. Situated next to Millennium Park, the views from this rooftop bar and eatery are breathtaking. Go for a date, a girls’ night out, or just a casual drink — any reason will do. Snag a charcuterie plate and wash it all down with one of their many delicious cocktails. We’ve been dreaming of the Kick in the Daisy for the past few months (Avion Reposda, Ancho Reyes, Liquor 43, Fresh Watermelon, Lime, Maldon Sea Salt).
Location: 12 S Michigan Ave, Chicago, IL 60603
Chicago is far-too breathtaking to sit inside while you drink, so this next drinking destination is the perfect place to soak in those views. If you’re in the market for a speakeasy-inspired rooftop, then Drumbar will be right up your alley. Grab a whiskey (it was named one of the best Whiskey Bars in Chicago) or one of their many inventive craft cocktails. Our favorites? The Thailand (Glasgow Blended Scotch, Sticky Rice, Mango, Coconut, Black Sesame), and the Spain (Prairie Path Vodka, Sherry, Cucumber, Cantaloupe, Almond).
Location: 201 E Delaware Pl, Chicago, IL 60611
Down for a more chill vibe? Head over to Lost Lake in Logan Square. This fun, festive, and fabulous tiki bar has you feeling like you’re at the beach. Lost Lake offers up an extensive drink menu with over 275 varieties of rum, and tropical-inspired craft cocktails. Try their signature cocktail called the Lost Lake (Aged Jamaican Rum, Passionfruit, Lime, Pineapple, Marschino, Campari), or try something unique and order up the Stranger in Paradise (Respoda Tequila, Rhum Agricole Blanc, Pineapple, Lime, Falernum, Cinnamon, Allspice, Angostura Bitters, Absinthe).
Location: 3154 W Diversey Ave, Chicago, IL 60647
Art Institute of Chicago
As you pass the famous Lions in front of The Art Institute of Chicago, you are met with some of the World’s finest art. Time and time again it has been voted the #1 art museum in the world, so it’s a must see. Our tip? Spend some quality time in the Modern Wing. With its newly built modern design and beautiful art, you’ll get lost in there for hours.
Location: 111 S Michigan Ave, Chicago, IL 60603
Where do we begin? Grant Park is not only beautiful, but it’s the host to many of Chicago’s crowning jewels: Lollapalooza, Chicago Blues Fest, Taste of Chicago — to name a few. Plus, history has been made in this park (Barack Obama’s election victory speech). Performers leave their heart on the stage (Chicago’s own Chance the Rapper headlines Lollapalooza this Saturday) and Chef’s from all over Chicago come together for the most delicious Food Fest. Grant Park is perfect when it’s throwing the next-big event, or when it’s just a plain ole’ park, so go! You’ll thank us later.
Location: 337 E Randolph St, Chicago, IL 60601
Grab your squad and head to Chicago’s famous Metro to watch the latest band crush it on stage. This stage has hosted many up-and-coming bands striving for their big break, so you’re sure to see a performance that will go down in history. Check out who’s playing, snag a ticket, grab a few drinks at the bar and enjoy the music and ambiance of Chicago’s Metro.
Location: 3730 N Clark St, Chicago, IL 60613
Written by Sydney Lehmann
Feature image via 3artsclubcafe.com