Create an itinerary for two different types of guests. Those that want to take in the typical touristy parts of Chicago along or those that want an off the beaten path.
For our ‘classic’ guest seeking typical touristy; Big Bus hop on hop off sits steps from our hotel entrance and is a super easy way to get a feel for the main parts of Chicago meaning Millennium Park, Museum Campus, Navy Pier etc., Architecture Boat tours with First Lady, Chicago from the Lake, or Wendalla offer tremendous boat tours with unparalleled views and smart lectures that peel back the layers of time. Breakfast at Tempo on State Street, or Meili Café. Chicago classics; enjoy Art Institute, and if with family the Field Museum, Shedd Aquarium.
Fun fact – in summer months Shoreline Sightseeing runs a boat taxi between Museum Campus and Navy Pier, so, it’s a great way to combine both sensibilities with a short but photo – worthy boat/taxi between them. For lunch you go lowbrow Chicago, Portillo’s, Mr. Beef, or my personal kryptonite, Mr. J’s Dawgs and Burgers for hot dogs etc. Obviously deep-dish pizza with Lou Malnati’s, Pizano’s, or even Uno’s which I know drives some people nuts, but the reality is this particular Uno’s sits in the original building and uses the original recipe.
For a refined expression of the above Beatrix River North, Kanella’s Breakfast Club, or even Land and Lake offer delightful takes on breakfast with farm to table focus. Touring Chicago in a Mercedes S550 or Cadillac Escalade with private tour guide? Check. Private behind the scenes tour of Art Institute by a working artist/professor? Absolutely! Touring Chicago’s lake by sail or power boat with captain are a one of a kind to enjoy our waterways with those you love most; and no one else. Beautiful side point, with motor – power boat an additional luxury is possible in terms of where guests of The Langham can access their chartered vessel; we sit very close to a dock located along our Chicago Riverwalk. Gibson’s Italia, Bar and Steakhouse on Rush for iconic status, Steak 48 – yes, it’s out of Arizona but you won’t notice once your inside and experience their service and Americana. Volare & Monteverde offer classic and delightful takes on Italian. Green Door Tavern on Orleans for old drink haunts and Andys Jazz, Winter’s, Jazz Showcase for incredible Jazz, Buddy Guy’s Legend’s or Blue Chicago truly authentic blues!
Stretching off the grid is always a super way to capture a bit more of Chicago’s soul! When heading North highlights include Wrightwood 659 for a super art gallery experience in a building designed by architect Tadao Ando. Got to see a few shows at newly opened Salt Shed last year and I’m very bullish on them. They have a monster lineup this year with Iggy Pop, The Roots and more; in a space that’s ultra-industrial and one of a kind. Not far from there is a small but delightful and vegetarian friendly Chef driven venue called 1308 Chicago, just wonderful and to the point.
Heading south I had liberating experiences at Bronzeville Winery. Their seared watermelon steak is a revelation, stay for the wine and cocktails. Beyond this in Bronzeville the bar in Sophy hotel is downhome magic with underrated art works adorning the lobby. Chef Erick Williams Virtue brings award winning southern cuisine. Silver Room for funky – carefully curated accessories. Joe and Rika Manuseuto Library with its science fiction design, Gallery Guichard showcasing global flair with its wonderful African/African American art collection, and South Side Community Art Center – this venue is historic and directly taps into the soul and history of the neighborhood in a way few places can; must see!