Chicago Trip 2019

My view arriving in the windy city

Today’s blog is going to recap my latest travel. On Boxing Day 2018, Porter Airlines offered a great promotion – 30% off select flights. One of the offerings that caught my attention was the city of Chicago.  If you know me, I love to pull the trigger on a great deal.  So last weekend I flew out to the windy city and here’s a recap of what I did.

Arriving in the Chi

I arrived at Chicago Midway Airport around 11am local time. The first thing I thought upon my arrival was how I would get into the city. Luckily, I checked my Lyft app and there was a promotion offer for 50% off six rides!  I couldn’t believe it, what perfect timing.  My 40-minute Lyft ride into downtown Chicago was only $6 USD!

Once I checked into my hotel at the Hampton Inn Chicago Downtown/Magnificent Mile, I picked up my online shopping mail that I sent to my address. This is a great way to save money if you don’t want to get hit with pricey Canadian shipping and duties fees. Always mail it to an American address if you can, it’s cheaper in the long run.

Cloud Gate aka The Bean
Cloud Gate aka The Bean

The Bean / Buckingham Fountain

After settling in at my hotel, one of the first destinations that I wanted to check out was one of the city’s top tourist attractions – The Bean. It is a stainless-steel structure that debuted in 2006 and its actual named is called Cloud Gate. But “The Bean” has a nice ring to it as well lol.

When I arrived there, there were hundreds of people taking selfies and group pics. It turns out that it is also a cool visual to take your wedding day photos there too. I saw some great bride and groom shots take place. This was nothing short of genius and definitely a memory to remember.

Buckingham Fountain
Buckingham Fountain

Up next was the iconic – Buckingham Fountain, the centre piece of Grant Park. I really enjoyed taking in this spot. This historic fountain has been a mainstay for over 90+ years. I was able to capture some beautiful shots. Truthfully, I only know about this water fountain because it was used in the intro for the TV show Married…With Children 😂.

Giordano’s vs. Lou Malnati’s 🍕

It’s no secret that Chicago is a deep-dish pizza town.  This was one of the main reasons why I flew down here, was to try out the local foods.  As I was researching restaurant spots I wanted to check out, Giordano’s was constantly getting praised in top ten lists.  I decided this would be my first stop on the food train agenda and placed an order online.

The usual cook time for a deep-dish pizza is 40 minutes.  I had more than enough time to get there as my hotel was just a four minute walk from the closest location.  Part of my planning and researching for trips is to always ensure most places are within walking distance from where I am staying at.

When I got there, I was immediately impressed by the look and feel of the restaurant.  There was a modern feel to it, brightly lit with lots of TV screens for patrons to support their local sports teams.  It was a very clean looking venue with friendly, attentive staff.


Their take-out entrance was impressive as well. They had a large looking menu board display, offering a variety of takeout options.  I’ve been to some dingy looking takeout places in my lifetime, just hideous looking. However, Giordano’s understands first impressions and this ranks as one of the best out there.

I guess I wasn’t paying attention, but I made the mistake of placing my order at a different Giordano’s location.  They have over 40 franchises in the whole city. Instead of waiting, I ended up taking a basic pepperoni and cheese that was ready to be served.  At this point in the afternoon, my hangry stage levels could not wait any longer.

Honestly, I didn’t think their pizza was that good.  I think it had more to do with that first bite – if it doesn’t hook you in right away, nothing else will.  It might have been a different story if I ordered the right pizza though!

Lou Manalti's Pizzeria
Lou Malnati’s Pizzeria bested Giordano’s in my opinion.

The next night I tried Lou Malnati’s. They too were a franchise pizzeria with multiple locations around town. Their restaurant was jam packed busy and that made me more intrigued.  Located on Rush street, this is one of the cities best streets for downtown restaurant options.

This time I actually ordered what I wanted. My toppings of choice were mushrooms, green peppers, mild sausage and pepperoni.  I can confirm from the first bite that heaven was in my mouth lol. I give them the edge over Giordano’s.  Check them out if you’re ever in Chicago!

Gibsons famous logo
Gibsons famous logo

Gibsons Steakhouse

Anywhere I travel to, I always Google what the top steakhouse restaurant is in the city.  That top mention belonged to Gibson Bar and Steakhouse.  The iconic chophouse recently celebrated their 30th anniversary this past month and I made it my top choice to dine at.

There are three locations in the greater Chicago area, with their main location on Rush street is where I placed my reservation. The first thing you notice as you approach the front entrance of the restaurant is their large logo in neon LED signage.

Secondly upon checking into Gibsons, you are in awe with all of the picture frames scattered throughout the venue of high-profile celebrities, athletes and politicians who have dined here over the years.  On your left-hand side is a mini gift shop with branded products available.  Across the hall is their bar area, with a live pianist playing classical tunes as you mingle with your guests.

Once you get into the dining room area, you are met with exceptional wait staff attending to your needs.  They provide great recommendations and really go out of your way to impress you.  Each server presents a table with raw meats on a cutting board displaying their steak options and providing additional insight as well. It is small examples like this that really separates a great restaurant from an average one.

I selected the W.R. Chicago Cut bone-in rib eye steak.  If you’re wondering, the W.R. initial is short for the late Chicago Tribune food critic William Rice, who christened the Chicago Cut steak name.  In return, he was blessed back and immortalized on the menu for doing so.

Rib eye in general is one of my favourite steak cuts and I like to have mines prepared medium well. I paired the entrée with my two favourite go to side dishes: sautéed mushrooms and cream of spinach.  I also included a bowl of their lobster bisque soup as well.

Gibson dinner was on point
Gibson dinner was on point

The biggest difference that really separates a steak from others is the seasoning.  I’m here to tell you that their signature seasoning salt is one of the best I have ever tried in my life.  It just puts their steak over the top, it really enhances the taste experience by 10x. It was so good I had to take a buy a few bottles at their gift shop.

I couldn’t leave without trying out one of their praised dessert offerings. The Macadamia Turtle Pie is the one that everybody talks about online, which is a towering, three-pound dessert spectacle.  It is visually astonishing, standing at one feet tall!  Vanilla ice cream, toasted macadamia nuts draped in chocolate and caramel sauce says it all.

It is truly a heavyweight battle if you are trying to tackle this solo.  I did as best as I could, but was humbled in defeat.  Putting it into size perspective, it is a dessert that could easily be cleared by three people.  For an ice cream lover like myself, it is unique and nothing I’ve ever seen before.  I highly recommend you check it out if you ever touch down at Gibsons.

An epic dessert.
An epic dessert.

Overall, the dinner was phenomenal.  It was a good pace in between dishes, not too much wait time is always key.  The vibe inside adds that classic feel to the steakhouse, which really sets the tone for everything else.  You can tick off all the boxes when it comes to great ambiance, great food and great service.

Next time I visit Chicago, I will be sure to stop by again.  It’s funny how when you’re younger, you want to try out the best nightclubs in town to have a good time.  Now a days, my idea of a good time is having a meal at a venue I’ve never ate before and having it exceed all expectations lol.

Wrigley Field
Wrigley Field is the second oldest ballpark in all of MLB.

Take me out to the ball game

No trip to the Chi would be complete without stopping by Clark street to visit the historic home of the Chicago Cubs.  Organizing this trip with a visit to one of Major League Baseball’s most iconic ballparks, Wrigley Field is an essential.  I have always wanted to visit this landmark.

Being able to stop here really fulfilled my inner baseball childhood.  I chose not to see a ball game but instead, woke up early on the Saturday morning to attend a 1.5 hour ballpark tour.  I was able to get a knowledgeable history lesson, that culminated with the Cubs finally winning their first World Series in 108 years.  This milestone finally happened in 2016 as all Chicagoan’s rejoiced!

Our tour guide was very friendly, entertaining and covered a lot of ground.  He took us all over the ballpark, providing commentary and great context. A highlight for me was being able to take a picture along the on deck circle in front of the Cubs dugout with Wrigley in the backdrop.

As the tour concluded, outside waiting were these poor looking elder locals acting like Cubs staff members.  They offered to take your picture while asking for a small donation for their efforts.  You quickly realize that every photo was extremely off angle.  Taking photos isn’t rocket science.  But that’s what you get when you have crackheads trying to make a quick buck lol.

Mia Franceca
Mia Francesca restaurant

I was also able to have a fantastic lunch at this restaurant called Mia Francesca.  The Italian trattoria was just a nine-minute walk on Clark street and has been a fixture in the Wrigleyville community for over two plus decades now.  I came across their name from a YouTube vlogger, who says the popular restaurant serves 600 orders per day.

When I got there the whole entire staff there make you feel at home.  They made me a custom order and it was one of the best pasta dishes I have ever tried.  I asked for a pasta dish with salmon mixed in a rosée sauce and they delivered big time.  It was a delicious serving and large portion as well.  Very affordable price point too.  If you’re ever in town and feel like authentic Italian cuisine, definitely check out Mia Francesca!

Chicago souvenir shop
Not bad for a souvenir shop name.

Time to call it a weekend

On the way back home, I tried to catch an early flight. The flight check-in attendant however would not accommodate me. She wouldn’t budge when I know she could have made a better effort customer service wise.  That literally left a sour taste in my mouth.  I now had to wait for my original flight time, which meant waiting for two hours doing nothing.  On top of that, that flight ended up with delays too.  Just my luck lol.

Arriving back at Billy Bishop airport proved much better, as my Uber driver was just a super kick ass of a person.  He was an engaging host and made really great conversation for the shared riders.  He went out of his way when most drivers are generally mutes.  I really admired that level of commitment and he helped improve the mood coming back home.

Until next time Chicago
Until next time Chicago

Closing Thoughts

That sums up my Chicago weekend trip.  It was my first time visiting the windy city since I was in the ninth grade.  I remember that Christmas break visit being too brief.  To be honest, there’s not much to do around there.  Don’t get me wrong, they have their signature food options, but some wore thin after.

Their Chicago Dog aka hot dog was overloaded with all the works, I just simply like ketchup on mines.  Their Garrett signature popcorn mix is tiresome after a few bites.  Stan’s Donuts was over hyped and wasn’t worth lining up for either.

At the end of the day good or bad, I always enjoy exploring other destinations and taking in a bit of what their city has to offer.  This includes sight seeing, shopping and food hopping around town.  It’s always great to do all of this without breaking the bank either.  Travel time wise, I like that the flight is roughly only an hour and a half.

My thoughts on the windy city is that it is a lot reminiscent like my birthplace of Toronto.  It has its own identity and has its own unique offerings in the same regard.  Next time, I’d like to explore outside of the downtown core and see what their pocket communities look like.  That’s where the real gems are. Peqod’s anyone? 🍕

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