Where to Meet Singles, Grab a Coffee and Get a Sunset Cocktail in Chicago, From a Five-Star Hotel’s Concierge

Ruben Caraballo and team open their little black books for some primo destinations

June 21, 2022 7:01 am
Z Bar exterior at the Peninsula Hotel
Z Bar exterior at the Peninsula Hotel
Peninsula Hotel

This is Concierge Confidential, a series in which we learn about a city’s best-kept secrets from people who specialize in exactly that: long-serving concierges from the best hotels in town.

At the posh The Peninsula Chicago hotel, the concierge desk is always abuzz with new ideas and old favorites. With longtime Chicago concierge Ruben Caraballo joining The Peninsula Chicago as chief concierge in June 2022, the award-winning five-star hotel has welcomed a true local expert. He and fellow concierges Morgan Schneider and Justin Digiamberdine put their heads together to give InsideHook their insider’s look at all best that the Windy City has to offer, from their favorite locals-only restaurant to Chicago politicians’ top steakhouse. For more, read on. 

InsideHook: Where can I get a cup of coffee near the hotel and go for a good walk?
Ruben Caraballo:
Café L’Appetito, where you can grab a coffee at this local favorite and head towards the Chicago Lakefront Trail to enjoy a leisurely walk along the lakefront and take in the city sights.

Where do singles hang out?
Rush Street, located just a few short blocks from the hotel, is a great area to find a high concentration of singles, business people and things to do. Tavern on Rush and Gibson’s Steakhouse are a few spots to stop by for a bite and delicious cocktails. Enjoy an after-dinner stroll in the parklet which sits in between the restaurants. 

How about a restaurant where only locals go?
Lula Cafe is the type of neighborhood spot Chicagoans love to frequent. One of the pioneering restaurants in Logan Square, this American diner is a great place to see the city through a local’s eye. 

Late-night spot where I can get into a bit of trouble (but not too much trouble)?
The Darling, located in the up-and-coming West Loop neighborhood, is a quirky, one-of-a-kind place for a cocktail experience. Designed to feel like an old mansion, this lounge is a great place to sink into one of their leather chairs and enjoy a curated cocktail. 

Best cheap eats in town?
Portillo’s, an iconic Chicago fast-food spot, is famous for its Italian beef sandwiches and chocolate-cake shakes. Be sure to add giardiniera to your Italian beef sub to enjoy this local delicacy like a true Chicagoan. 

What’s an underutilized part of your hotel?
The library, seating area adjacent to The Lobby restaurant. It is a beautiful spot to sit, take in the ambiance of the fifth floor of the hotel and look out the floor-to-ceiling windows onto bustling Michigan Avenue. 

Where can I go for the best dessert?
Sweet Mandy B’s is Chicago’s premier cupcake destination, offering all the flavors and frosting your heart could desire. There are multiple locations throughout Chicago, and we recommend trying their “Cupcake of the Week” or one of their amazing breakfast pastries. 

Best place for a sunset cocktail?
Located on the sixth-floor terrace of our hotel, Z Bar is a cocktail experience like none other. Guests are treated to a bird’s eye view of Michigan Avenue from the terrace and can enjoy tantalizing snacks and small plates such as Wagyu Beef Sliders and the Disco Fever cocktail.

Where to go if I want to see politicians making deals?
Gibson’s is the crossroads of business and politics in Chicago. As one of the most iconic of Chicago’s steakhouses and conveniently located nearby the hotel, it is a place where important people meet, and deals are made. 

Where should I go in the area for a day spent outside?
The Chicago Architectural Foundation puts on an amazing river cruise aboard Chicago’s First Lady ship, which boards from the Chicago Riverwalk, a short 10-12 minute walk from the hotel. The tour guides are members of the Architectural Foundation and share stories of more than 50 buildings along the river.

Where’s a good spot to snap an Instagram-worthy photo?
A great spot for Instagram-worthy photos is Chicago’s WNDR Museum located in the West Loop neighborhood. This multi-sensory, contemporary art exhibition boasts installations by artists such as Yayoi Kusama and Barbra Kruger. 

Best neighborhood to take a four-hour stroll if I want to get acquainted with a more “authentic” side of the city?
Lincoln Park is a very walkable neighborhood, boasting beautiful family homes, boutiques and restaurants. Armitage Avenue is a great stretch which includes a mix of local restaurants and shops, perfect for an afternoon of shopping and strolling. 

What’s the easiest way to get around town, in terms of transportation?
Walking, or use Chicago’s Elevated Rail known as The L. Uber/Curb/Lyft are also easy choices.

What’s a lesser-known cultural institution worth visiting?
The Driehaus Museum, located a few blocks north of the hotel, is an exciting example of a Gilded Age mansion in the heart of the Gold Coast. Open to the public for private tours Friday through Sunday, this under-the-radar destination was voted one of the top five attractions in Illinois.  

What’s a cool architectural site that’s not mobbed with tourists?
Rookery Building is Chicago’s oldest high-rise — this 1888 Romanesque structure boasts a lobby designed by Frank Lloyd Wright. 

What’s the best thing you can only get in your city?
Everyone who visits Chicago should have the honor of trying a Chicago-style hot dog. While most associate the city with deep-dish pizza, locals raise up the hot dog as the true iconic food of Chicago, or perhaps tied with an Italian beef sandwich. The Chicago-style dog features a pickle spear, mustard, sport peppers, celery salt, served on a poppyseed bun. 

What’s the best thing you can only do in your city?

Exploring the 606 Trail, which is similar to New York City’s Highline. This stretch of retired elevated rail line is now a walking and running trail that spans multiple neighborhoods in Northwest Chicago. 

What’s something I can say or do to endear myself to locals?
Ask locals about any of our hometown heroes — other than Al Capone or Michael Jordan. There is more to Chicago than the 1990s Chicago Bulls basketball team or the Valentine’s Day massacre. Think Chance the Rapper, former president Barack Obama, Oprah or Richard Wright.

What’s something that tourists tend to do that really annoys locals?
Stopping in the middle of the sidewalk! If you need to stop to look at your phone or look over directions, please step to the side of the path of traffic to avoid upsetting the locals. 

What’s an item or activity that tourists tend to get ripped off on? Any tips on how to avoid that?
Taxis, unfortunately.  Many visitors are not aware that by law taxi drivers must accept payment by credit card and have a working meter. We always recommend using Uber, Lyft or Curb for a discounted rate.  

I’m looking for a low-key brunch. Where to?
A great low-key brunch spot nearby the hotel is the Original Pancake House, located next to LUXBAR on Bellevue Place. Open every day from 7 a.m. to 3 p.m. (and 4 p.m. Saturdays and Sundays), this local favorite is a wonderful spot to grab a morning meal. 

Best place to eat a meal or have a beer outside when the weather’s better?
The Dawson, located on Halsted Street, is a lovely New American restaurant featuring an expansive indoor/outdoor eating space. If weather permits, especially during the summer months, enjoy a burger and a beer on their cozy patio and soak up the sunshine we Chicagoans patiently wait all year to enjoy. 

What’s a unique service that your hotel offers that I won’t find elsewhere?
Camp Peninsula and Peter Bear — Camp Peninsula is a one-of-a-kind experience for our younger guests. Upon arrival they are given an interactive scavenger hunt which takes them throughout the hotel and highlights features of the hotel. Once the family arrives to their suite, they are greeted by a green Peninsula tent that is set up and ready for an in-room sleepover. In addition to the exciting sleeping arrangements, a complimentary breakfast is available through the lobby restaurant or in-room dining. Upon request, our life-size Peter Bear mascot can stop by to meet the children and take a photo. 

Any potential issues I should be worried about or pay attention to when it comes to public transportation (busy times, delays, petty crime, etc.)?
The Red Line will be very busy during Chicago Cubs or Chicago White Sox games, especially when these occur in the evening. We recommend planning alternative transportation time to account for CTA delays and crowds in Wrigleyville. 

What’s the one thing everyone forgets to pack? Or the one thing everyone should remember to pack when visiting?
A few light layers to put on, even during June, and especially if you’re attending an event or game at Wrigley Field or Soldier Field. Chicago’s weather is ever-changing, so it is smart when packing to prepare for a variety of weather conditions. 

Finally, what’s the best book to read about the area before I come?
Stud Turkel’s “Division Street America.”

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