Chicago was a breath of fresh air. With the chilling winds, christmas lights abound, fantastic shopping, and the most delectable cuisine, it was the perfect way to kick off our Christmas season.

It is unlike any other “big city” experience I have had before. Prior to visiting, many people told me that I would love Chicago – and they were right. Of course, the natural thing to do when you venture a new city is compare it to others that you have visited. People, the rumors are true. It might just be the cleanest US city I have ever traveled to. Somehow, the streets feel spacious while they still manage to maintain that “big city” feel.



We stayed for 4 nights and split our time in two different hotels. One of our hotels was the Wyndham Grand Chicago Riverfront. Upon check-in, the manager generously upgraded us to a 1,200 sq. ft. suite with living areas and views of the Chicago River. If you’re looking for clean, affordable, 4-star accommodations, this is a fantastic hotel. The location is perfect. It seemed as though we were within walking distance of everything, including Millennium Park. On one morning, we got up before the sun to beat all of the tourists to Cloud Gate.



An early morning like that called for some quality caffeine. With Chicago being the birthplace of Intelligentsia Coffee Roasters, we had to pay a visit. All I need to start my day is a good cappuccino and an almond croissant.


Our second hotel was the picture perfect Waldorf Astoria Chicago, one of the top 10 hotels in the United States (U.S. News & Review). This hotel is just about as luxurious as they come. Because of my Hilton status, we were upgraded to a corner suite with a fireplace, soak tub and a balcony with views of the city. The accommodations were elegant, spacious and festive. The Christmas decor helped add to the ambiance. The hotel has an incredible spa, a complimentary town car service, and is situated in the prestigious Gold Coast neighborhood with some of the best shopping in the country. 


Of course, any trip to Chicago wouldn’t be complete without heading to catch a production in the theatre district. So, months before our trip, Cameron waited in a queue for almost 6 hours on Ticketmaster in an attempt to score us Hamilton tickets. Hamilton is the winner of 11 Tony awards and the Pulitzer Prize and is taking the nation by storm.

After countless website crashes and just when we were about to throw in the towel, two balcony seats popped up for a Friday showing. The Hamilton hype is real; we were thoroughly entertained. Right now the only two places you can see Hamilton are in New York and Chicago. And if you are lucky enough (or are willing to pay second hand ticket prices), I highly recommend going and seeing it. 


After Hamilton, we decided to grab some of Chicago’s best deep dish pizza. We went to Lou Malnati’s, which is considered to be the oldest family name in Chicago Pizza. The family has been serving up deep dish pizzas since the 1940’s. Every Pizza is handmade from scratch and is held together with their perfect flaky, buttery crust. We ordered their famous Malnati Chicago Classic that is topped with Lou's exclusive sausage blend, some extra cheese and vine-ripened tomato sauce on buttercrust. It was every bit as good as we expected Chicago deep dish to be. 


Chicago’s food scene is as diverse as it is delicious. It’s so much more than just deep dish pizza. It couldn’t be any easier finding a restaurant that meets your craving at the price point you’re comfortable with. One of the standouts we visited was The Purple Pig. A previously Michelin-rated dining experience, The Purple Pig has been featured on Food Network, and a variety of other high-profile media outlets. Here, it is all about the cheese, wine & swine. The food is Mediterranean inspired and explodes with flavor. Of the items we ordered, we had three favorites. (1) Pig’s ear with crispy kale, pickled cherry peppers & fried egg, (2) Milk braised pork shoulder with mashed potatoes, and (3) Lamb ribs with Harissa, troves marmalade, Israeli couscous & orange. The menu is so fresh, it changes twice, daily.


We couldn’t be in Chicago and not get a hot dog! So, after talking to many locals, we landed at Portillo’s which is known for their authentic Chicago Dogs and Italian Beefs. If you’re ever there, make sure to order their famous chocolate cake shake. They blend an entire piece of their homemade chocolate cake into a milkshake. It’s incredible. 


Chicago is known for being a passionate sports town and is home to the 2016 World Series Champion, Chicago Cubs. After 108 long years of waiting, the city was ready for that win. You can’t walk five steps in the city of Chicago without seeing a Cubs logo somewhere. On one of our afternoons in the city, we took a Chicago Transit train to Wrigleyville. It was clear that we were not the only ones making this pilgrimage. Although the stadium is under heavy renovations, people from all over were flocking to the gates of the stadium just to take their photo in front of that Wrigley sign.


If you’ve never been to Chicago and you’ve been thinking about going, pull the trigger. You won’t be disappointed. We’re already looking forward to planning another trip to the Windy City. On our next visit, we’re making it a priority to hit the jazz clubs, a cubs game, and of course, try more pizza.

With love,

TravelCameron Tyler