Fly into the City of Chicago as I did early one Fall morning, and you’ll be struck by the gleam of the sun bouncing off scores of skyscrapers nestled on the shores of Lake Michigan. The city lives up to its reputation for architectural stunners;  it’s not every town that boasts glass ceilings by Tiffany & Co. in its Cultural Center (itself a former library), a major department store and office buildings.

Nor do many cities have built-in icebreakers-cum-tourist-draws such as the massive Bean (aka Cloud Gate) sculpture by Anish Kapoor, seen above by night with the city’s architecture as a backdrop.

You may have seen images before of the Chicago River, and I can tell you that its lovely green is not limited to Saint Patrick’s Day celebrations.  There are a series of canals through the city, constructed beginning in the late 1800s as early public health and economic rivers. Taking a tour of the city by river, you also get an ideal perspective on the city’s skyscrapers.

Chicagoans may have to deal with wind and winter cold, but they have warm hearts. I was repeatedly struck by locals’ friendly approach; the highly hospitable and efficient Will outside the InterContinental Chicago Magnificent Mile, and that same hotel’s exemplary Chef Concierge, Kathy McClanathan.

Trying a deep dish pizza despite a heads up that locals don’t down them, other travellers and I couldn’t have asked for better service than we had from Dawn (seen here) at Gino’s East Village. The same is true of Jessica at Merz Apothecary, the great team at The Purple Pig, Concierge Hailey Fasse at the Fairmont Chicago, and many more. Antonio at Palmer House is justifiably proud of his hotel, and I found myself happily receiving more than one history lesson from people throughout the city.

Where to Stay?

I began with  InterContinental’s Chicago Magnificent Mile which, apart from providing visual treats and insights on the city’s storied past, has some very good people on staff. Arriving in town shortly after the sun, and slightly bleary eyed after the combination of two flights and then a cab ride that lasted longer (I kid you not) than the second leg of my flight, I felt genuinely welcomed by Will, who hustled my luggage in from the cold before I could blink. Claudio, with a giant wall of live (and lively) Magnificent Mile images behind him, took care of early registration and offered to text me as soon as a room was available. Not realising he’d have a room in the Historic Tower ready before 9:00 a.m., I checked my luggage and did a brief spin through the hotel before checking with the concierge on tour options.

I decided to start with the pool, situated on the 14th floor  – and what a beauty. I later learned that the junior Olympic sized pool, with its elevated seating areas originally intended for race spectators (and now used for at least one wedding reception during my stay), is also known as the Johnny Weismuller Pool, given the athlete and actor’s use of this site for training purposes.

Seeing the sun shining outside, I decided to pop down and ask the Concierge for sightseeing advice. That’s when I met Chef Concierge Kathy McClanathan, who is a member of Les Clefs d’Or (Keys of Gold) USA. She gave helpful directions to this first time visitor  and, over the course of a couple of subsequent encounters, it came as little surprise to learn that McClanathan also serves as President of CHCA, the Chicago Hotel Concierge Association.

A wealth of knowledge, McClanathan is justifiably proud of her hotel and her city, and does them both proud. I’ve found that concierges can significantly impact a visitor’s experience in a new city, and have appreciated most I’ve met, but McClanathan truly shines. Over the course of two or three highly enjoyable conversations with this professional, I learned a good deal about the heart of Chicago.

Part of Chicago’s Michigan-Wacker Historic District, the hotel is listed on its country’s National Register of Historic Places and underwent a massive and highly respectful renovation not long ago. This hotel hosted one of the original docking stations (for a dirigible/blimp), and now boasts modern amenities alongside its sense of history.

You can borrow an i-Pod from the concierge for an audio walking tour of the hotel, and return to a room outfitted with all the outlets you’ll need to keep your tech tools charged. With large windows overlooking the Chicago Tribune tower and the Wrigley Building, it almost didn’t matter that my room was spacious and inviting.

At the Fairmont Chicago Millennium Park, I was housed in a generously sized room with great amenities, but this was not a typical Fairmont experience. We live a short drive away from the Fairmont Hotel Vancouver, and have visited the chain’s Empress Hotel in Victoria.  Having also been a guest at this brand’s Banff Springs in the Rockies, the Chateau Laurier in Ottawa, and the Royal York in Toronto, I arrived at the Chicago Millennium Park anticipating a hotel of substantial character.

All other Fairmonts I’d visited to this point were proud reflections of the history of their respective areas, and I admittedly have a bias toward older hotels, even  with their imperfections.  Our meeting spaces at the Fairmont in Chicago were lovely and the food service was of high quality. The hotel boasts a recent $60M renovation that – while likely appreciated by many – gave this guest little sense of the city’s history. If you stay here, though, you’ll be well positioned for a quick walk to Millennium Park, the Art Institute of Chicago and the shopping and sights of South Loop – so, it’s really a matter of what’s most important to you in your choice of hotels.

Palmer House

The Hilton chain has a gem in the Palmer House,  above and below. I’ve not yet stayed at this hotel, but it’s tempting me.

It emanates romance, luxury and – as you’ll see if you stop by its lobby – style. The original Palmer House served as a wedding gift from businessman Potter Palmer to his bride Bertha Honore, but burned in the Great Chicago Fire within two weeks after its 1871 grand opening. The Palmer House you see today rose relatively quickly from the ashes of that fire, and this East Monroe establishment – not far from the establishment owned by Potter’s friend Marshall Fields – reopened in November 1873.

More to follow on Chicago … check back soon for more of Chicago’s gems, architectural and otherwise!