Over the weekend, I ventured to Chicago for a quick 48 hour trip. Although the Cardinals lost on Saturday (sigh), I still greatly enjoyed my time in the windy city. I was able to try several amazing restaurants and bars during the trip. I’ve broken down my favorites below. Cheers!
The Hampton Social
If you have not been to Hampton Social, I guarantee you have seen photos from there on Instagram. Hampton Social has only been open for two years, but it has quickly become one of the most popular spots in Chicago. Bloggers, visitors, and locals alike flock here to take pictures of their famous “Rose All Day” sign and enjoy delicious small plates. The restaurant serves as a breezy destination with large open windows, beach themed drinks, and nautical touches. I was happy to discover that not only was the restaurant beautiful like all the pictures I had seen on Instagram, but the food was equally as wonderful.
Must try menu items:
Tuna Tartare – Ahi tuna, orange-chili glaze, soy reduction, watermelon and avocado.
The Royal Treatment – absolute ely, velvet falernum, cinnamon syrup, rely martin 1738 tiki and ango bitters served in a copper pineapple.
The Hampton Social
353 W Hubbard Street
Chicago, IL 60654
The Sugar Factory
The Sugar Factory has been one of the most popular restaurants in several areas of the country. Its delicious candy and fun-filled restaurant makes it a must-go destination. When you walk into The Sugar Factory, you are greeted by a wall of candy, pictures of celebrities dining there, and even a step & repeat. The first thing I noticed about the menu was the size – IT IS HUGE (38 pages to be exact). Like many of the portions at The Sugar Factory, the menu is over-the-top. While it would be impossible to sample it all, I did enjoy the few items our table was able to sample.
Side note – there is a $100 dessert that includes 24 scoops of ice cream! When it is ordered, loud music blasts through the restaurant, the servers gather and the dessert comes out with sparklers on top of it! No wonder this restaurant was so crowded, it’s celebration station!
Must try menu items:
Goat Cheese Flatbread – served with a yummy side of marinara.
Raspberry Watermelon Mojito – fruit juices, silver rum, watermelon candies and fresh mint leaves. (This is served “goblet style” and has over seven shots. Make sure you share it with a crowd!)
The Sugar Factory
55 E Grand Ave
Chicago, IL 60611
Cindy’s Rooftop Bar
Cindy’s Rooftop Bar & Restaurant has one of the most beautiful views of Chicago. The balcony looks over Millennium Park, the Chicago Art Institute, and the lake front. Although I did not get to dine at Cindy’s (next time), I did get to soak in the loveliness of the ambiance and enjoy a few signature cocktails. The outside patio is filled with comfy lounges and two charming fire pits, while the inside is filled with long wooden tables, a big bar, floor to ceiling windows, and super tall ceilings.
Must try cocktail:
Evelina – Nardini grappa, tiki thai syrup, lemon, peychaud’s bitters and pea flower
Cindy’s Rooftop Bar
12 S Michigan Ave
Chicago, IL 60603
Three Dots and a Dash
Three Dots and a Dash is a tropical tiki bar hidden below the streets of River North. This secret hideaway serves craft cocktails that will knock your socks off. Three Dots and a Dash is a little hard to find because it is quite literally located underground. When you pull up to the address, make sure to look in the alley. There you will see blue lights above one single door. Once you enter through this door, you will go down two flights of stairs and through the last door you will find a modern tropical paradise. While you won’t find any food at this hidden paradise, you will find a wonderful cocktail list. The menu is peppered with exotic combinations that feature flowers from Hawaii, rums and seasonal fresh fruit.
Must try cocktail:
Tropical Itch – Kentucky Burbon, Navy Strength Jamacian Rum, Demerara Rum, Passionfruit, Lemon and Falerum
Three Dots and a Dash
435 N Clark St
Chicago, IL 6065
Beatrix
Beatrix was the perfect destination after a night out on the town in Chicago. This neighborhood restaurant and coffeehouse is warm and inviting. The vibe is fresh, modern American with a menu filled with yummy options.
Must try menu items:
Power Greens Fresh-Squeezed Juice – kale, romaine, celery, pineapple and mint
Light & Fluffy Lemon Pancakes – served with blackberries and lemon syrup
Beatrix
519 N Clark St
Chicago, IL 6065
Portillo’s
During this trip, I was accompanied by several local Chicagoans who were horrified when I admitted to never having tried Portillio’s. So of course, on my way out of town, I had to stop by here to see what the buzz was all about. Portillo’s is the perfect family spot. It feels like a 1950’s diner on steroids. Portillo’s serves up specialty hotdogs, burgers, and salads. I got one of their famous cake shakes for the ride home and I have to tell you… it was the BEST milkshake I have ever had! It’s official. I love Portillo’s.
Must try menu item:
Char-Grilled Maxwell Street Style Polish (their original menu item) – Grilled in the traditional way, it was done on Historical Maxwell street and prepared with mustard and grilled onions.
Chocolate Cake Shake – There is literally chocolate cake at the bottom of this milkshake (enough said). Don’t forget the spoon to scoop out the bottom!
Mangiamo! (Let’s Eat)
-Rose