I know it’s been a while since you’ve hit the restaurant scene now that you’ve got those two little boys romping around everywhere. A few years ago, you hit up all the new joints in your “trendy restaurant central” neighborhood not long after they opened. You even put together a guide for tourists to spend a weekend in Chicago like a local. Now, I’m not sure you even know the new spots exist, let alone have an opinion on their menu or vibe.
I understand you now spend your Friday and Saturday evenings climbing through piles of dirty laundry waiting to be washed, picking up scattered toys that have collected in various parts of the apartment throughout the week, and, if things really get crazy, watching an episode of New Girl or Modern Family with M. Gee. Sounds neat?
You work with a lot of youngin’s, my peers really, so I thought I’d offer up a bit of a restaurant scene newsfeed to keep you in the loop. You may not actually be cool, but at least you’ll look cool when they’re talking about the latest and greatest places to grab a bite.
In the spirit of Valentine’s Day, let me share with you a host of my favorite spots to grab a romantic bite to eat in the heart of the city (pun intended, get it? Heart?).
- Dinner En Blanc ~ This annual, invite only dinner will totally woo you. I haven’t been yet, but my friends have told me about it, and it sounds so cool. After registering for the event (if you make the cut), you dress in elegant all white and arrive at a location that’s a mystery to everyone until the day of the dinner. You bring your own table and chairs, and it’s the chicest picnic in town. Check out more about it on their website. They actually hold the event in various cities all over the world. If I were you (and I am), I’d add it to my 33 in 3 list pronto (done and done).
- Signature Room ~ A bit cliche, but the views from the top of the Hancock Tower are stunning. If possible, request a table by the window overlooking Lake Michigan. You’ll be glad you played the squeaky wheel a bit to get the “best seat in the house” oil. Just before we moved to Chicago, we visited for a weekend to find an apartment (knowing the job transfer was in the works). It happened to be the weekend of our first anniversary, and the staff kindly served us a fancy dessert plate with “Happy Anniversary” written in chocolate sauce, which I readily ate. But you probably remember that.
- La Madia ~ This local wine and artisan pizza gem may not be your traditional dark and sensual romantic restaurant. But the food is great, you can get plenty of wine, and they have a small wine room that you might be able to request if you play your cards right. After five years living down the street from that place, you still haven’t asked to sit in there? You really are boring these days!
- RPM Steak ~ Defining a steakhouse as romantic might be in the eye of the beholder. I always love a good steak dinner, though, and this is one of the best, so it’s on my list of top date night dinners for me. I saw on your calendar that you’re headed there soon as part of your (our?) Twelve Dates of Christmas, and I/you can’t wait. This is starting to get confusing, all this taking to my future self.
- Sapori Trattoria ~ Something about Italian always seems to speak romance. This little Italian restaurant in a northern neighborhood of the city has a great little menu and good food. It’s a bit off the beaten path for a traditional tourist, but I think finding local gems makes a vacation so much sweeter.
- Geja’s Cafe ~ Chocolate anyone? At this fondue restaurant, be sure to save space for dessert. After all, isn’t the chocolate fondue really the reason you go out to a restaurant like this? Given your chocoholic addition, I certainly know it’s your ulterior motive. They also have many dark, private booths and tables, so you’ll definitely feel the romantic vibe.
- Osteria Via Stato ~ Another Italian restaurant, this one resides smack dab in the middle of the tourist area. Surprisingly, given it’s location, it attracts more local clientele than one might initially imagine. This is a total favorite of ours that we’ve been to WAY too often. (Hint: There’s another very busy Italian restaurant right across the street from Osteria Via Stato. Don’t be distracted. This one is better, I promise.)
- Zed451 ~ Just call it the best darn brunch you ever did have. It’s a little expensive. It’s worth every penny. Arrive hungry!
- MK ~ Slightly out of the way but still very much in the downtown area, this classic yet quiet spot offers something for everyone.
- Piccolo Sogno ~ Back to life, back to Italian. (Just a little Soul II Soul shout out.) While impressive in the winter, this wonderful restaurant will blow your socks off during the summer. They have an enormous private and quiet patio behind the restaurant that takes you right out of the middle of the city while only being a mile or two from the Willis Tower. Good food. Great outdoor vibe. Perfect summer dinner date.
- Mindy’s Hot Chocolate ~ The food is good. The dessert? Amazing! It probably goes without being said that you shouldn’t leave without ordering a hot chocolate. You’ll need to grab a cab or jump on the Blue Line to get to this restaurant, presuming you’re coming from “tourist central” where I lived and I believe you still currently reside.
- Sunda & Mercadito ~ These two restaurants aren’t exactly ‘romantic’ but they’re awesome for a swanky date, so I wanted to add them. They also are Asian and Mexican restaurants, respectively, which helps round out the diversity of the selections I’ve included. Remember when you/me and M used to go Mercadito about once a month, it seemed, with whichever friends were visiting us for the weekend? We lived in the heart of a big city and all our friends wanted to hang out with us! Ah. The glory days. My how things have changed.
In good conscience, I can’t reference Soul II Soul and not leave you with a taste of this awesome old school song, so enjoy!
Now you’re mildly up to speed on some great romantic and swanky restaurants around town. Talk about it with your team at work. They might just wonder if you’re cool?! I’ve got no info on clubs, lounges, after-hours bars, or anything that’s busy after about midnight. Even at the ripe old age of 22 when I graduated college, those were never in my repertoire.