I absolutely love visiting Chicago. It is a world-class city with great people, shopping, culture, baseball (none for us this trip) and fabulous food. I have visited many times, first due to working for a company headquartered in Chicago (from their L.A. office), then for a variety of reasons — an All-Star game at the ballpark formerly known as Comiskey; another baseball trip for Wrigley; a trade show; a conference, etc. It doesn’t take much prodding for me to visit.
This year’s road trip stopped first in Cleveland and Detroit, so the proximity to Chicago was an easy decision as the place of choice to celebrate our 35th wedding anniversary (previous posts and links in bold). Below are two different views from our hotel — of Michigan Avenue and Lake Michigan.
So what was on the itinerary for the 3-night stay? Pretty much everything listed above, plus a first: a boat tour on the Chicago River to view the city’s stunning, historic and iconic architecture. Chicago is known for having some of the most interesting buildings, and many of the great talents in the field have contributed and continue contributing to this day. Among those greats are the names Frank Lloyd Wright, Mies van der Rohe, and Skidmore, Owings, Merrill. (Click here for more about the buildings.) And the weather gods cooperated by providing a perfect day in Chicago; timing is everything as they say. Neither cold nor hot nor humid nor windy. If only there were more of these days. Some of the photos from the tour:
Above — 333 West Wacker Street; below – Willis Tower (110 stories)
Above – Marina City complex; below – Wrigley building
Eating and shopping were next up on the agenda, even if the latter was mostly of the window type. As for the eating, a great deal of advance research was done in order to savor each meal (three lunches and two dinners).
RL Chicago was first up. Ralph Lauren has a penchant for doing everything “just so,” and that includes his namesake restaurants (NY and Chicago). While it may be considered a “scene” by some, we found the service very hospitable and welcoming and the food is delicious. Finding Pigs in a Blanket on an “upscale” menu might be surprising, but they were perfection which is not surprising in hindsight. The other dishes we tried followed suit. And, yes, it was fun taking in the scene.
A tried-and-true spot is Shaw’s Crab House, part of the epic group of restaurants from Lettuce Entertain You. It is amazing that they can do so many different cuisines so well. But they do, and we’ve tried enough of their restaurants to know that is the case.
Searching for Chicago’s “best” pizza might result in a debate over thin crust (my preference) vs. a classic deep dish, and many other types in between. I read about a place called Spacca Napoli and decided that was the winner for us. 
For our anniversary dinner, a Chicago stalwart was selected — Le Colonial — recently relocated from Rush Street to fashionable Oak Street (think upper Madison Avenue and all those glorious boutiques). I loved the food in Vietnam and thought this would be ideal. And it was. Just a word about the dessert — it is up there in the annals of dessert perfection. A chewy and crispy base of oatmeal and coconut and chocolate with a perfect scoop of vanilla gelato on top. I’d make a trip back just for that (hence the top billing below).
A last lunch was squeezed in en route to O’Hare and recommended by an LA friend who is often in Chicago. Gibson’s Italia combines the best of their reputation for steak with surprisingly delicious Italian food. Both were excellent and a terrific way to bid the city goodbye (but hopefully not for long). And that view of the river from the restaurant is just beautiful! Separately, did you ever see two happier people around food? I think not.
If the fondest visual is saved for last, then this shot of Michigan Avenue taken from our room qualifies. I could just stare and stare ..
