top of page
Theresa Downs

Chicago - Wine By Appointment Arrives in the Windy City

Refreshed: May 22, 2024


The first week of May 2019, Wine By Appointment traveled to Chicago for a very special family occasion. While there, we took in the sites, food, culture, and, of course, wine!

Hotels

Silversmith Hotel

Our first stop, literally, was the Silversmith Hotel. The Silversmith Hotel located at 10 South Wabash Avenue, Chicago occupies the Silversmith Building built in 1896, part of Jewelers Row. Impressively elegant, and literally steps from major must-see Chicago sites, it was a perfect place to spend a few days getting reacquainted with Chicago. (If contemplating a stay, ask for a room towards the back as the hotel is right next to the “L” trains unless you are a heavy sleeper!)



Restaurants & Bar

Bellemore Restaurant

Our first night in Chicago we celebrated with dinner at the eclectic Bellemore Restaurant, located near downtown at 564 W. Randolph Street, Chicago. Part of the Boka Restaurant Group empire, the restaurant showcases Chef Jimmy Papdopoulous’ take on American cuisine. A lavish and plush interior with whimsical touches will delight diners as will the menu with its interesting take on American classics. (The Potato Fry bread is a definite “must try” item). The restaurant has since closed, and it was a great experience. A new restaurant has opened there.


Dining room of the former Bellemore Restaurant in Chicago>
Bellemore Restaurant Chicago, IL
Bar area of the former Bellemore Restaurant in Chicago>
Bellemore Restaurant Chicago, Illinois

Berghoff Restaurant

After a busy morning of touring, we stopped for lunch at The Berghoff Restaurant, 17 W Adams Street, Chicago, Illinois. What a fun place!! Steeped in rich history, The Berghoff Restaurant has been serving Chicagoans in a fine German tradition (at least beer) since 1898. Beautiful dark wainscotting and intricate stained glass windows give diners a glimpse of European splendor while munching on, what has to be, the largest pretzels ever. Try their “Sausage Trio” plate (Bratwurst, knockwurst and smoked Thuringer) for a true delight and pair it with a dry, crisp apple cider. Don’t forget the Bravarian Pretzel!

The Milk Room

One of the highlights of our trip was our visit to the Milk Room located in the Chicago Athletic Association 12 S Michigan Avenue, Chicago, IL. A tiny (accommodates eight people only) bar that is literally a closet is a must stop for anyone who appreciates a good cocktail. The Milk Room was once a speakeasy, and one can image hearing patrons of yesteryear whispering in their ear (at least after one of the delicious concoctions the incredibly knowledgeable staff whips up). We sampled rare rum and whiskey libations , Fiji rum is now my new favorite, made by the skillful hands of Raoul. It’s a bit pricey but well worth it down to the beautiful ice cubes.

The Milk Room specializes in prohibition era mixed drink recipes and custom ingredients
Milk Room Chicago Athletic Association Chicago, IL
Two bespoke mixed drinks on the counter in the Milk Room speakeasy
Milk Room Chicago Athletic Association Chicago, IL

The Cherry Circle Room

Our next stop was for dinner in The Cherry Circle Room, also located in the Chicago Athletic Association 12 S Michigan Avenue, Chicago, IL. This is a simply gorgeous restaurant harkening back to more genteel days. Cherry wood walls and the velvet and leather seating will delight even the most ardent anti-traditionalist. The walls are graced by the most amazing tapestries. Check out this link for the full story behind them; they are definitely worth seeing by themselves; www.chicagoathletichotel.com/michigan-avenue-hotel-blog/story-behind-caas-embroidered-banners

Again, as we normally do when offered, we chose the pre-fix dinner menu. It’s a great way to see what the kitchen can do and we weren’t disappointed. And, since we were in Chicago, we had to include some local beef in the mix. Definitely a memorable evening and well worth repeating.


Wollensky’s Grill

We spent an incredibly pleasant Saturday afternoon watching the Chicago River traffic while munching our way through luscious burgers at Wollensky’s Grill located at 318 N State Street (Downstairs Riverfront at Marina City) Chicago, IL. If you like meat and, particularly burgers, this is your go-to place. Coupled with a tantalizing drink menu and the fascinating Chicago River, you can easily while away the hours relaxing with your favorite beverage. Definitely include in your itinerary just for the river access alone.


Egg Harbor Cafe

If you love eggs, make sure to stop at the Egg Harbor Restaurant located at 477 Sourth 3rd Street Geneva, IL. Sunny with cheerful staff, they have an amazing delicious array of egg dishes and omelets which makes choosing difficult (the pancakes looked scrumptious too). Topped off with the best coffee in the area, it can’t be beat. And, as a bonus, you get to tour the charming town of Geneva on your way to the restaurant.


Places to See/Things To Do

Art Institute of Chicago

A real treat was our visit to the Art Institute of America located at 111 S Michigan Avenue Chicago, IL. One of the oldest and largest museums in the United States, it opened its doors in 1879 to crowds that have not diminished over the centuries. Known for its breadth of art ranging from Japanese artifacts to empires of long-ago, the museum is known for its collection of some of the finest art works of Western culture. We found the Contemporary art exhibits and Impressionist galleries particularly intriguing but it is almost a given that everyone will find something of interest to explore there. Plan on spending a couple of hours, at least, to do the museum and yourself justice.


Millenium Park

Either before or after visiting the Art Institute of America, have a wander through Millenium Park, Chicago’s outside art museum. Located a short distance from the Art Institute of Chicago, the park is bounded by Michigan Avenue, Randolph Street, Columbus Drive and East Monroe Drive, Whether you splash around at Crown Fountain, snap photos at The Bean, or commune with the tulips, you’ll be forming lifetime memories of Chicago.


River Cruise – Chicago Architecture Foundation Center – Chicago’s First Lady

In addition to having a burger and a beer, everyone visiting Chicago must do a river cruise. There are a number of different venues available, we went on the Chicago’s Frist Lady, which I highly recommend, and it is a spectacular way to take in the beauty and architecture of Chicago. This is one event that words don’t do justice. The river docents of the Chicago’s First Lady are remarkably knowledgeable and guests spend a captivating 90 minutes seeing the old and imagining the new of Chicago. You will not regret taking this tour and you’ll be talking about it for months after.


We highly recommend paying a visit to the Chicago Architecture Center either before or after your boat tour. Fascinating facts about Chicago and the worlds’ structures are artfully displayed to capture even the most easily bored patron’s imagination. The gift shop is definitely worth paying a visit too.


Galena Cellars Vineyard & Winery

It wouldn’t be a trip without wine tasting! Lucky for us, we spied Galena Cellars Vineyard & Winery tasting room in the very quaint downtown Geneva, located at 515 S. Main Street Geneva, IL. With homey, attentive staff, we were guided through the local wines, some varieties of which we hadn’t tasted before. A number of universities and Mid-west states have been working to find grapes that will thrive in the cold winters there and it seems they have succeeded. A number of wines stood out: the Traminette (think Gewurztraminer) and it is actually a cross between the Gewurztraminer group and Seyval Blanc grape and the Chambourcin, which was referred to as “Illinois Cabernet”, which was actually quite tasty with cherry notes. A definite stop for those who want to expand their wine taste buds.


This brings to a close our wonderful trip to Chicago. We went to Chicago specifically, as I mentioned before, for a very special family gathering. I would be remiss and a bad aunt if I didn’t at least acknowledge the occasion. My beautiful, talented and amazing eldest niece was married in a wonderful ceremony in a gorgeous venue while her very proud family looked on. Here’s to the bride and groom, may they have many, many years of joy and happiness.


Till next time.

bottom of page