The Windy City. Chi-Town. The Second City. City by the Lake. Whatever you call it, Chicago is pretty phenomenal.

The Windy City. Chi-Town. The Second City. City by the Lake. Whatever you call it, Chicago is pretty phenomenal.

Don’t you hate it when you have to fly to one of your favorite cities for work, but they keep you occupied indoors for most of your time there? Yeah, me too. I adore Chicago. Now, I know, it has its issues (like ALL cities, mind you), but I simply can’t get enough of Chicago. I always forget that it’s a real city…big, busy, noisy. I was reminded of the noise every night as the passing L Trains vibrated my hotel room…


As I mentioned, I was here on business which meant a limited time to get out and about; however, the Hilton Chicago is in a prime location for a little sight seeing and people watching. Located on South Michigan Avenue, you’re right across the street here from Grant and Millennium Parks and you can see Lake Michigan. (I’m a water sign and any chance to be close to any body of water gets me giddy. And what a body of water Lake Michigan is! First timers to Chicago almost always exclaim that it looks like the ocean).

So, if you’ve got more time to kill, check out all of the amazing things to do in this city. If you’re like me, busy with work, you can at least get out for a quick walk around. Lots of hotels are in historic buildings, including the Hilton Chicago. Built in 1927, the hotel has been purchased and sold and purchased again and remodeled …but, a lot of the original charm remains, including a gorgeous mural on the ceiling of the lobby.  I think it’s alway fascinating to find the histories of hotels and this glorious building went from an expensive hotel to bankruptcy during the Great Depression to Army barracks during World War II. Conrad Hilton purchased the hotel in the 1940s and I’m happily here earning Hilton points in 2017.

Hilton Chicago

Out the doors and across the street are the glorious parks of Chicago.  Easily walkable, full of art and fountains.  I lucked out.  The weather this week in Chicago was GLORIOUS!  (Those of you that live here or come here frequently know that isn’t always the case).  There’s an interesting art installation at the end of Grant Park called Agora.  Agora is a sculptural piece by Polish artist, Magdalena Abakonwicz. The installation includes 106 sets of giant legs with torsos (no arms, no head).  You can get right up into this art installation which is really incredible.

Cloud Gate

The parks also feature the wonderful piece Cloud Gate. (You all know this piece as The Bean).  Go get a selfie with your reflection and the reflection of the city skyline.  You know you want to.  I should also mention that Chicago hosts free music nights in the park. What a great way to spend a summer evening.  If you can make that work, take a bottle of wine and some snacks and enjoy!

One of my other favorite things about

Music in the Park

wandering a city, is looking at the murals and graffiti painted on buildings.  And Chicago doesn’t disappoint when it comes to “building art.”  Among the interesting things you might see on your walk:


Ok, let’s get down to the important stuff: food.  Chicago has some of the best restaurants anywhere.  I’m going to give you the run down on three places that I experienced this week.  (Chicago has the best deep dish pizza around.  It’s an institution.  I didn’t get a chance to go for pizza this week, so I’m going to avoid the whole who-has-the-best-deep-dish-pizza-in-Chicago argument.  Ask a local.  They’ll tell you all about their favorite. Really. They’re quite passionate about this topic).

I did get to dine at Siena Tavern, the brainchild of Fabio Viviani, darling of the Top Chef franchise. I don’t believe you can eat a bad thing here.  I ordered the melt-in-your-mouth gnocchi.  Coworkers ordered the brick chicken diavolo and the lasagna and we shared.  I highly recommend this tactic as it means you can try more delicious food! Siena can be a bit loud because of the open design concept, so it may not be the best place to take your honey for a quiet meal, but maybe you can go when you’re angry and don’t want to speak to him or you can go with a group of loud girlfriends instead.

Another place you want to check out (with an appetite and some friends to help you plow through mass quantities of food) is River Roast.  Situated right on the revitalized Riverwalk, River Roast features roasted entrees meant to be shared family style.  You’ve got delicious options here for every appetite (we had chicken, fish, beef, and veggies) and a glorious view of the river and surrounding architecture.  There are fireworks on the LaSalle bridge on Tuesday nights in the summer (because, you know, when you can get outside in Chicago and the weather cooperates, you do it).  You’ll get a great view if you’re seated outside.

Riverwalk Fireworks

If you’re at the Hilton Chicago, you might also want to grab a bite at Kitty O’Shea’s.  Located right in the hotel, they’ve got a mean cheeseburger and a nice patio right on Michigan Ave.

As I’m grabbing an Uber (or Lyft or cab) back to the airport, I’m reminded of a few additional thoughts. 1. Unless you are insane (or a well seasoned local) you do not want to drive in downtown Chicago.  Trust me.  (And mind your pedestrian self while crossing streets).  2. Take a chance to chat with someone that reminds you that the American dream still exists.  This week I rode with cab and Uber drivers from Brazil, Senegal, and Poland all making their way in Chicago by driving tourists like me around.  It’s refreshing to turn off the (horrible) news and talk to someone who appreciates the opportunities that can still be found here. 3. Tip your drivers and your servers well. They work hard and it’s difficult to make a living in a big city.