Where to do everything in Chicago, from the concierge of a five-star hotel

It’s Concierge Confidential, a series in which we uncover a city’s best-kept secrets from people who specialize in the field: long-time concierges at the city’s top hotels.

At the elegant The Peninsula Chicago, the concierge desk is always buzzing 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 welcomed a true local expert. He and fellow concierges Morgan Schneider and Justin Digiamberdine have teamed up to give InsideHook their insider’s look at everything the Windy City has to offer, from their favorite locals-only restaurant to Chicago’s top politician steakhouse. To learn more, read on.

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

Where do the singles meet?
Rush Street, located a few blocks from the hotel, is a great place to find a high concentration of singles, business people, and things to do. Tavern on Rush and Gibson’s Steakhouse are a few places to stop for a bite to eat and enjoy delicious cocktails. Enjoy an after dinner walk in the small park that sits between the restaurants.

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

A late night place where I can have a little trouble (but not too much trouble)?
The Darling, located in the up-and-coming West Loop neighborhood, is a quirky and one-of-a-kind venue for a cocktail experience. Designed to look like an old mansion, this lounge is a great place to sink into one of their leather armchairs and enjoy an organized cocktail.

The best cheap restaurants in town?
Portillo’s, an iconic Chicago fast food joint, is famous for its Italian beef sandwiches and chocolate shakes. Be sure to add some giardiniera to your Italian beef sub to enjoy this local delicacy like a true Chicagoan.

What is the underutilized part of your hotel?
The library, lounge area adjacent to The Lobby restaurant. It’s a lovely place to sit, take in the ambience of the hotel’s fifth floor, and gaze out of 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 frostings your heart could desire. There are several places in Chicago, and we recommend trying their “Cupcake of the Week” or one of their amazing breakfast pastries.

The best place for a sunset cocktail?
Located on the sixth floor terrace of our hotel, the Z Bar is a one-of-a-kind cocktail experience. Guests are treated to a bird’s eye view of Michigan Avenue from the terrace and can enjoy mouth-watering snacks and small plates such as Wagyu Beef Sliders and the Disco Fever cocktail.

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

Where to go in the region for a day spent outdoors?
The Chicago Architectural Foundation hosts an incredible river cruise aboard the First Lady of Chicago ship, which embarks from the Chicago Riverwalk, a 10-12 minute walk from the hotel. Tour guides are members of the Architectural Foundation and share the stories of over 50 buildings along the river.

Where’s a good place to take 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 features installations by artists such as Yayoi Kusama and Barbra Kruger.

The best area to take a four-hour walk if I want to get to know a more “authentic” side of the city?
Lincoln Park is a very walkable neighborhood full of beautiful family homes, shops and restaurants. Armitage Avenue is a great stretch that includes a mix of restaurants and local shops, perfect for an afternoon of shopping and strolling.

What is the easiest way to get around town, in terms of transportation?
Walking or using the Chicago elevated train known as the L. Uber/Curb/Lyft are also easy choices.

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

What’s a cool architectural site that isn’t overrun with tourists?
The Rookery Building is Chicago’s oldest skyscraper. This 1888 Romanesque structure features a lobby designed by Frank Lloyd Wright.

What’s the best thing you can only get in your city?
Anyone visiting Chicago should have the honor of trying a Chicago-style hot dog. While most associate the city with deep-dish pizza, locals elevate the hot dog as Chicago’s true signature food, or perhaps related to an Italian beef sandwich. The Chicago-style dog includes a pickle spear, mustard, sport peppers, celery salt, served on a poppyseed bun.

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

Explore the 606 Trail, which resembles New York’s Highline. This retired stretch of elevated rail line is now a walking and running trail that spans several neighborhoods in northwest Chicago.

What can I say or do to make the locals like me?
Ask the locals about any of our local heroes, other than Al Capone or Michael Jordan. There’s more to Chicago than the Chicago Bulls basketball team of the 1990s or the Valentine’s Day Massacre. Think Chance the Rapper, former President Barack Obama, Oprah or Richard Wright.

What do tourists tend to do that really annoys locals?
Stop in the middle of the sidewalk! If you must stop to look at your phone or check directions, please pull over to the side of the traffic lane to avoid disturbing locals.

What is the object or activity on which tourists tend to get ripped off? Any tips to avoid this?
Taxis, unfortunately. Many visitors are unaware that taxi drivers are required by law to accept credit card payments and have a working meter. We always recommend using Uber, Lyft or Curb for a discounted fare.

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

The best place to eat a meal or drink a beer outside when the weather is nice?
The Dawson, located on Halsted Street, is a charming neo-American restaurant with extensive indoor/outdoor dining space. Weather permitting, especially during the summer months, enjoy a burger and beer on their cozy patio and soak up the sunshine that Chicagoans patiently wait all year to enjoy.

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

Are there any potential issues I should be concerned about or watch out for when it comes to public transportation (rush hours, delays, petty crimes, etc.)?
The red line will be very busy during Chicago Cubs or Chicago White Sox games, especially when they are in the evening. We recommend planning alternate transportation times to accommodate CTA delays and crowds in Wrigleyville.

What is the thing that everyone forgets to pack? Or the one thing everyone should remember to pack when visiting?
A few light layers to throw on, even in June, and especially if you’re attending an event or game at Wrigley Field or Soldier Field. Chicago’s weather is constantly changing, so it’s a good idea to be prepared for a variety of weather conditions when packing.

Finally, what is the best book to read about the region before coming?
Stud Turkel’s “Street America Division”.

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