Where to Wine & Dine In Chicago

Most recognized as the “Windy City”, Chicago has been home to my younger brother since 2010. Now, on my sixth visit, I really don’t consider myself a tourist. I did most of the touristy things during my first few visits: Navy Pier, John Hancock Center, Big Red Double Decker Bus, Wrigley Field, Soldier Field, Shedd Aquarium, to name a few. I’ve even become an expert packer for the unpredictable weather.

So this November, I headed to the windy city with my hubby. He had to attend a conference for work, and I jumped at the opportunity to join him. Going to Chicago meant seeing my brother and 5-month-old niece, while also visiting some cool spots to share with you.

We stayed at the historic and centrally located Hilton Chicago on South Michigan Avenue. According to Wikipedia, it’s the third-largest hotel in Chicago by number of guest rooms and largest total meeting and event space of any Chicago hotel. I believe them! Catching the elevator sometimes took over 10 minutes, and I had to wade through a crowd every time I went to the lobby.

So enough about the hotel accommodations, let’s move on to my wine and dine highlights.

Eleven City Diner

If you are ever in Chicago, you need to eat at Eleven City Diner. With its Jewish deli standards, classic American fare, and friendly staff, this local diner is a must try for foodies. We were seated near the kitchen, giving me a full view to all the yummy dishes. I ordered the open-faced tuna melt and it was seriously the best tuna melt I’ve ever had (YOLO).

Eleven City Diner

Eleven City Diner

ELEVEN CITY DINER: Tuna melt

ELEVEN CITY DINER: Tuna melt

Pequod's Pizza

You can’t go to Chicago without getting a pizza fix. A friend of a friend recommended the award-winning, brick-walled pizza pub, Pequod's Pizza. This casual eatery is popular for its deep-dish pies with caramelized crust. While 100 times better than Giordano’s, I just prefer thin crust pizza. If you are a fan of deep-dish pizza, I recommend this cool spot. And yes, I had wine with dinner (not pictured).

Pequod's Pizza

Pequod's Pizza

Niu B

If you are in the mood for sushi, check out Niu B. Instead of wine, I had the Genmai Green Tea. Still can’t get over how cute the pot and cups were. I ordered the miso soup to start and also tried the Wild Mushroom Hot & Sour Soup, which was spicy-mazing. Our table ordered a few rolls to share. All were yum yum, but my favorite was the Mellow Yellow: fresh salmon, tempura crunch, avocado, spicy mayo, sliced mango, ginger sauce. We tried the fried rice, but it was nothing to write home about. For dessert, our table ordered three to share. My favorite was the Green Tea Creme Brulee (OMG!).

Niu B: Genmai Green Tea

Niu B: Genmai Green Tea

NIU B: Green Tea Creme Brulee

NIU B: Green Tea Creme Brulee

Whole Foods: Red Star Bar

Hope you are sitting down for this one. Did you know that some of the Whole Foods in Chicago have bars? I know. I was jelly too! I’m not sure if that’s a good thing or a bad thing. I probably wouldn’t get any shopping done (LOL).  The Red Star Bar concept showcases local beer and spirits. Here, I thought I was going to grab a tea. Instead, I sat at the bar and enjoyed a glass of Bogle Cabernet Sauvignon

The Red Star Bar

The Red Star Bar

City Winery Chicago

If you love wine, City Winery Chicago is a great spot. This impressive establishment is not only large in size, it’s also a music venue and favorite among local foodies and wine enthusiasts (and now me). It was a bit quiet during my visit, but then again, it was a Thursday afternoon (winos are at work). It really didn’t matter though, because Brendon, my server, was able to answer my every question. He was awesome!

City Winery chicago 

City Winery chicago 

For food, I got my cheese fix with the New World Cheese Tour. It came with three different cheddar cheeses, two spreads and crackers. The mustard seed cheddar and quince spread were my favorite. Two flatbreads later: the flatbread of the day, which had cherry tomatoes, bacon, pesto, provolone and asiago cheese (my mouth is salivating right now) and the Wild Mushroom flatbread, which had sautéed wild mushrooms, crispy sage and goat cheese béchamel. Both were yummy, but the flatbread of the day was my favorite.

CITY WINERY CHICAGO: New World Cheese Tour

CITY WINERY CHICAGO: New World Cheese Tour

CITY WINERY CHICAGO: flatbread of the day

CITY WINERY CHICAGO: flatbread of the day

I tried the wine on tap. If you don’t know what wine on tap is, it’s the distribution method. Wine on tap is housed in stainless steel kegs, which is known to maintain the quality of the wine better.  I ordered a glass of “Big Shoulders” 2013 Cabernet Sauvignon from North Coast, California. Brandon brought me three other wines on tap to sample: Windsor Oak Vineyard 2013 Petite Sirah from Dry Creek, Sonoma, California; 2014 Cabernet Sauvignon from Bousquet Vineyard, Argentina and the 2013 Randolph Reserve from Mendocino, California.

I enjoyed them all, but must rave about the City Winery Randolph Reserve 2013, a Bordeaux style blend of Cabernet Sauvignon 40%, Cabernet Franc 45%, and Merlot 15%. On the nose, blackberry jam, cedar resin, and floral aromas with a hint of toasted rye bread. On the palate, sour cherry, choke cherry and dark plum fruits. Special thanks to City Winery Wine Education Director, Rachel Lea Driver Speckan for taking the time to give me the 411 on this wine. She even gave me the best news! The wine will soon be bottled and available for purchase online in 2016 (someone please send me a reminder).

At City Winery, wines on tap are offered by the glass, in a carafe, or in a growler to go. Bottled wines are also available. I really hope to visit this spot again, and since I’m slowly learning more about wines, I hope to be able to do a tasting with the wine experts followed by some live music.  

The last few days of my trip consisted of family time (obsessed with my niece, a.k.a. cheeks), eating and wine. These are really a few of my favorite things. I even got invited to a “Spooning with Friends” gathering. Now I know what you’re probably thinking, but it’s not that kind of spooning (LOL), it’s a name given to a stew potluck. My brother’s neighbor invited us, and I admit that I enjoyed every stew I tasted. I even had peanut butter ramen noodles. Hello, why didn’t anyone think of this sooner? The weather was perfect for stew. I only eat soup in Miami when I’m sick.  It’s too warm for stews and soups.

Greek food from Athenian Room

One night my brother brought home Greek food from Athenian Room on 807 W Webster Ave. They don’t have a website, but OMG, their gyro platter was as authentic as it gets. And if you need some more convincing, Tina Fey is a fan. Unfortunately, I don’t have pictures. Sorry, it was just too good to stop and take a picture, because upon first bite, I was transported to Latin Quarters in Paris. Yup, still remember the gyros I had during that trip. 

Special thanks to my brother and his girlfriend for hosting the hubby and I (and filling our bellies). And for something touristy, here’s a picture of me at Cloud Gate “The Bean”, where you’ll find tourists going picture happy.

Some undisclosed pounds later, I must admit that I had my share of food and wine during this visit, but there are still so many other eateries I want to try. I really love this city. Yes, it could be because Chicago is famous for its food, but truthfully a big part of my heart lives there. To my brother and niece, this is post is for you. Love you both.

My brother and niece 

My brother and niece 

Cheers to Chicago! 

Special thanks to Nicky Valdes,  my unofficial proofreader.