Spending a weekend in the Windy City

My wife (The Boss as you may know her), our son and I headed off to Chicago to see what it would be like spending a weekend in the Windy City.

Now my son and I had run up to Chicago two summers ago for a day trip just to check out the city for a little bit and of course to eat. This time the three of us were flying up early on Saturday and coming back to Florida Sunday evening. Plenty of time to get in some more exploring.

We left from Orlando International Airport and even though we did pop into one of the lounges, it’s almost required to get a Cuban sandwich from Zazza Cuban Cafe when we’re there.

Now I typically don’t book our flights, that’s something we’ve left up to our son since he was in middle school because he enjoys finding deals. For this trip we flew Spirit up and Frontier back and yes I cringe every time we’re booked on one of the discount airlines because they do seem to get delayed more than most others.

We arrived in downtown Chicago by 9:30 a.m. and knew that our room at the historic Palmer House wouldn’t be ready, so we left our single suitcase with the bellman crew and went off to get in the first round of exploring.

This is the view from one end of the lobby of this hotel that was built in 1873 (which makes it the oldest continually operating hotel in the United States.). The hotel has hosted presidents, kings and all sorts of other dignitaries and celebrities over the years. Read more about the history of the hotel here.

Another view of the lobby and the pictures do not do it justice. BTW, the brownie (as in the yummy chocolate treat many of us enjoy) was created here in 1893 because Bertha Palmer asked a pastry chef in the Palmer House kitchen for a dessert suitable for ladies attending the Chicago World’s Columbian Exposition!

I actually didn’t know this until we were back home and no I did not eat a brownie at the hotel. Next time for sure!

We wanted to head out for a bit and then go grab lunch, so it was off to see some of Chicago!

When my son and I had come up to Chicago previously, “The Bean” (It’s actually called Cloud Gate) was covered up because of some construction, so this was our first time actually seeing it.

There were flowers blooming everywhere downtown. Lots of tulips which made The Boss happy since they’re her favorite.

The Nutella Cafe is one of the places my son wanted to visit on our first trip, but the line was way too long. We toughed it out this time and I am going to go ahead and say that I don’t think I had ever had the stuff until this trip. I didn’t even want to try anything, but I’ll never say no to eating something new.

And now I’m a Nutella fan. Especially when it’s on a toasted baguette.

Yep, tulips everywhere!

My son and I visited Adams Street Brewery, which is attached to The Berghoff Restaurant. The restaurant has been open for over 125 years and they specialize in German cuisine. We enjoyed it so much on our first trip that we wanted The Boss to try it out. What’s even better is that they were literally around the corner from our hotel!

Since we were about to go visit a couple other local breweries, we split a “flight” and some of the food on the menu.

We went with a brat on a pretzel bun, cedar plank salmon (to compare it to mine at home), German potato salad and spatzle. Everything was delicious and we decided to go check into our room to get ready for continuing the brewery tour and our visit to Wrigley Field to see the Cubs play the Phillies.

The inside of Adams Street Brewery.

The room at Palmer House was nothing special, but we were staying here for the history.

We’re all about trying out different forms of public transportation wherever we are and it’s easy to get around Chicago

Our next brewery was Goose Island Beer Co. and again, a flight was split.

Gotta love those Goose Island beer taps!

There’s actually several breweries in this part of Chicago, just west of the Fulton Market District and we only had time to visit one more before the game. So we popped into Great Central Brewing Company to split a couple pints.

Due to the time, we popped in an Uber for the ride up to Wrigley and it’s always fun to see different parts of whatever city you’re visiting while driving around.

Wrigley Field opened in 1914, making it the second oldest ballpark in the Majors (Fenway Park in Boston is two years older.) and this was our first visit. The coolest part to me is that it’s in the middle of a neighborhood. I love that. No having to run out to the edge of town to see a game. It’s right freaking there.

Of course a beer and a Chicago dog were going to be consumed! The bad news for this crew from Florida is that the afternoon high that day was 49 and the wind coming off Lake Michigan made it feel colder. I had purchased our tickets a couple months prior and the thought process was that we shouldn’t be in the sun because of the heat. That’s a Floridians way of thinking and we all wished that we were sitting in the sun for the game.

What an amazing experience though! Even for this Braves fan.

Across the street from Wrigley is a Do-Rite Donuts location and yes I grabbed my first Chicago doughnuts on this trip. Mmmm

We ran (okay, we didn’t run, we took the train) back to the hotel to drop off the doughnuts and to get ready for our last bit of exploring for the night which would include dinner, more doughnuts and looking for a couple of “hidden” bars.

Dinner that night was one of the Lou Malnati’s Pizzeria locations on the north side of the Chicago River in downtown. To be completely honest, my son and I ate at a different location on our first trip and we were not all that impressed. I figured that we needed to give it another try since it’s such a well known place for both Chicago deep dish pies and the thin crust version.

Here’s the Chicago thin crust pie we tried.

And here’s the deep dish pie we tried.

I’m still going with this isn’t my preferred place to get pizza in Chicago, but plenty of people are fans.

Three Dots and a Dash was on our list of bars to attempt to find and it did take a little looking before we discovered it as it’s in sort of an alley.

Yep, that’s a lot of skulls to look at on the way down the stairs into the bar.

They make some super creative drinks at this place and it was packed even though we were there early in the evening.

There’s actually a “secret” bar inside the bar at Three Dots and a Dash, but it’s mostly by reservation only and we couldn’t get into it that night.

I believe the Green Door Tavern is the oldest pub in Chicago and while that’s typically interesting enough to get me to stop by for a visit, there’s another reason we walked in.

Down the stairs at the back of the pub and behind this bookshelf (that you can’t open from the outside) is the speakeasy known as The Drifter. This place offers over 100 rotating drinks on their menu and each one is described on custom made tarot cards. It was going to be a loooong wait, so we called it a night and headed back to our hotel which has a couple of very nice bars to hang out at.

But first some made to order fried chicken from JJ Fish and Chicken which was right around the corner from our hotel.

As I stated, Palmer House has a pair of very nice bars. One in the massive lobby and this one off to the side which was much less noisy. After enjoying a drink at each, we called it a day and got up to our room to prepare for one more day of exploring.

The first thing I did the next morning was to walk down seven blocks to visit Tilly Bagel. Now I would visit a local bagel store anyway, but this one was extra special because the owner grew up in Titusville, FL before moving to Chicago. They had just opened their second location the day before and she was at the other spot when I stopped in. Oh, and the Chicago seasoned bagel (think of it as all the flavors from a Chicago Dog, but on a bagel) was amazing.

There wasn’t really a doubt that I was going to stop by one of the Stan’s Donuts locations and I sure checked that box.

Chicago has a beautiful downtown and it’s easy to get around. This is the view looking south from the north side of the Chicago River.

I’m not a coffee drinker at all, but The Boss and our son weren’t going to be deterred from stopping by the Starbucks Reserve Roastery and to be honest, I don’t mind going to these either. There are locations in NYC and Seattle as well, but the one in Chicago is five stories high! Oh, and yes they offer much more than coffee, plus their menu is a bit more involved than your typical Starbucks.

An espresso flight, for adults since they include alcohol.

This is a bourbon barrel aged cold brew and even though I am not a coffee drinker, I’d have one of these every day if they were offered at a regular Starbucks.

I had always wanted to go into an Eataly and we decided to walk through the one here since we had to go by it anyway. I will say it’s quite nice inside and there were plenty of people picking up items in the different sections of the market.

We grabbed a couple of slices of margherita pie on the way out and both The Boss and our son are much bigger fans of this style of pizza than either Chicago style.

We happened to catch an obnoxious green subway back to the hotel to pick up our bags as we needed to get out to the airport for the flight home.

Right around the corner from our hotel was Pizano’s Pizza & Pasta and it turns out that a member of the Malnati family, Donna Malnati, opened this place in 1991 and THIS is the deep dish pie I’d been looking for! BTW, three slices of this pizza came back to Florida with me.

Then it was off for the lengthy train ride out to O’Hare for that flight back home.

In the lounge at O’Hare, I discovered that M&M’s and Jameson Irish Whiskey when combined in my mouth, tastes just like the Irish whiskey fudge I make at Christmas.