I contemplated titling this post “Date Night in Chicago” but thought twice, because while what I am about to share can be romantic it can also just be a fun adventure for two friends out on the town. Either way, Chicago is full of fun and excitement any time of day, but it really comes alive at night. Once the sun sets and the evening sky rolls in, all the lights start to twinkle and you feel the magic that a big city evokes. It’s elegant, it’s romantic and it’s just calling you in, asking you to love it. With this game plan, I promise you will!
Part 1 – A stroll through the heart of the city: This magical evening in Chicago is going to start in one of the most beautiful places in all of the city, the river-walk. An area that has always been popular has become even more so with recent renovations and expansions. You can now pretty much walk along the river all the way through the city, with bars, restaurants and parks to enjoy along the way. We will start this evening around 5:30pm on Michigan Avenue and Wacker Drive, heading down the stairs to the glittering water below. Stroll West as far as your heart (and your feet) desire. Maybe stop for a glass of wine at City Winery, where you can not only people watch but also boat watch. It’s a great way to take in the architecture and the beauty of downtown Chicago. And a good way to build up your appetite for our next stop.
Part 2 – A delectable dinner: You can’t spend a spectacular night in Chicago, a foodie town if there ever was one, and not have a good meal. For both the stellar service and the impeccable (incredibly fresh) food, I recommend Ocean Prime. It’s situated right along the river (easy to access after your river-walk stroll) and will make for a meal you won’t soon forget! From the minute you walk into the restaurant you will feel like Chicago royalty. The staff are the most kind and courteous set of people I have ever encountered in a restaurant setting, attending to every need you could possibly have. (Huge shout out to our very knowledgeable and very kind server, Darren. He was the best waiter!) It’s likely due in part to their Young Leaders Program, where they take managers and up-and-coming talent from all Ocean Prime locations across the country and immerse them into extensive training, menu planning, etc. Their last summit was in Napa and the employees in tandem with the chefs came up with an incredible summer pairing menu. They have a staff that truly loves working for Ocean Prime, and you can tell it’s due in large part in their investment and development of their staff. It makes for top quality service and food! I can attest that everything on the Ocean Prime menu is AMAZING – trust me, I pretty much have tried it all. Here’s what I think you’ll love too…the Ocean Roll (probably the best sushi I have ever had), the Ahi Tuna Tartare (literally melts in your mouth), the Ocean Prime House Salad, Filet (perfectly cooked with the best flavoring), the Gouda Tater Tots and for dessert you can’t go wrong with the carrot cake or the chocolate cake. Everything is fresh, made daily in house and I kid you not, is the best you’ll have. Come with room in your belly and time to spare, as you’ll likely spend hours enjoying the wonderful experience that is dining at Ocean Prime.
Part 3 – Landmark sightseeing and arrow flinging: After that large meal you’ll eat at Ocean Prime you might want to get the blood flowing post dinner, so why not take another little stroll to a famous landmark just a couple blocks away, at State Street and Lake Street, the Chicago Theater. Seeing the neon glow at night is such a highlight for both locals and tourists alike. From there if you want to keep moving try an activity like darts or ping-pong at nearby Flight Club, Point & Feather, Ace Bounce or SPIN. Chicagoan’s love a good bar, but they love a good bar with sporting activities even more.
Part 4 – Late night drinks: I am giving you 3 options here. Maybe you’ll pick one, or maybe if you are feeling wild, you’ll pick all 3. Each has their own dynamic crowd and distinct atmosphere. Option 1 is an elegant, refined place to grab a bubbly glass of champagne or wine and be interspersed among Chicago’s elite. It’s Pop’s for Champagne. Option 2 brings you underground into a hidden tiki bar. You’ll feel transported to another world, one filled with tropical drinks (they are so good!), festive music and the feeling that you are on an island in the middle of the sea. It’s Three Dots and a Dash. The last option gives you a rowdy crowd, great piano music and a chance to sing and dance into the wee hours of the morning. A classic staple of Chicago nightlife, it’s The Redhead Piano Bar.
Every part of our itinerary is within blocks of each other – easy enough to walk or if you desire, to take a taxi or Uber. It will show you the best the city has to offer – incredible scenery, world class dining, amazing cocktails, and fun around every corner. Whether you plan you special night in spring, summer, fall or winter, you are guaranteed to have a good time!
Signed with Style,