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Escape to Chicago: Where to Stay, Dine, and Shop

I had the great pleasure of once again joining Choose Chicago on a press trip to experience the vibrant city of Chicago. Chicago was recently voted the Best Big City in America and as usual, Chicago was a dream, and I can't wait to return. (To read more about all the fun things to do in Chicago if you're planning a trip to the Windy City for your next holiday escape, you can read my article in Canadian Geographic Travel). 

Here are a few highlights that'll help you plan your next Chicago trip with ease--how to get there, where to stay, where to dine, and what to do: 

Porter Airlines

Travelling during the pandemic can be challenging, but my flight with Porter Airlines made the experience smooth, comfortable, and safe. I had all the necessary documents with me (proof of vaccination and rapid test for entry to the USA) and Porter took care of the rest--I was met with excellent service checking in, and in-flight (we loved our flight attendant so much!) along with tasty snacks and drinks--a huge bonus on every Porter flight. Flying with Porter to Chicago is an excellent option, because you avoid flying into O'Hare, which can be much busier, especially during peak holiday travel. I love that Porter now flies to even more US destinations--I try to book Porter for all my flights, because I know I'll be satisfied with my entire experience. The Porter lounge in Toronto is awesome, and makes travelling that much more special. (Thank you so much, Porter!) 

Langham Chicago 

If you've ever stayed at a Langham property before, you know you'll be met with the most exceptional service from the moment you arrive. I've stayed at Langham NYC a couple of times, and I was so excited to check in to the Langham Chicago, knowing it would be a wonderful experience. Langham Chicago exceeded all expectations, and was simply perfection. The hotel is located in the heart of the city's downtown core, with stunning views of the Chicago River and Lake Michigan. It's minutes away from the famous Chicago sign and Magnificent Mile, making it easy for you to walk everywhere without needing transportation. (Tip: Magnolia Bakery is nearby, as well--just across the street from the Chicago sign). 

Our room wasn't ready when we arrived because we got to the hotel early, so we were invited to enjoy the Langham Club Lounge, on the 12th floor. (We had access to the Lounge during our entire stay). If I didn't have a packed itinerary, I would have spent my entire trip here--the views were breathtaking, with plenty of work stations, a writer's corner, comfortable seating, complimentary food and beverages throughout the day, including wine and appetizers in the evening, and a delicious breakfast buffet every morning. We were sent a personal text message when our room was ready. 

Of course, our room was stunning--spacious, elegant, and modern, with a huge marble bathroom, an oversized tub, and wonderful amenities. The views? Amazing. The floor to ceiling windows overlooked the water and downtown buildings, which was especially beautiful at night because of all the dazzling lights. 

The hotel's restaurant, Travelle, is a great spot to visit for dinner or late night drinks. (My server even created a special margarita for me, which was so good!). You can also enjoy a classic Langham afternoon tea at the Pavillion, located on the lobby floor. If you have time, make sure to visit the beautiful swimming pool, fitness centre, and Chaun spa. (A massage after hours of walking the city is a great way to unwind). 

The attention to detail, elegant design, location, and excellent service made our stay truly perfect. I can't wait to check in to Langham Chicago again.


Whether it's your first of fifth time visiting Chicago, it's never complete without having some deep-dish pizza--the food Chicago is famous for. Giordano's is one of the best places to go to for classic Chicago-style deep-dish pizza. Just remember, deep-dish pizza takes some time to prepare, so order some appetizers while you're waiting to dig in to your delicious slice!


Mexican food is my favourite, so I was excited to see Tzuco's was on my itinerary. Tzuco's is an authentic Mexican restaurant featuring a delicious menu created by Michelin-starred chef Carlos Gaytan. The homemade guacamole, fish tacos, and avocado flatbread--along with the traditional margaritas--made this one perfect meal. The restaurant's floor to ceiling windows provided great views of the city, and the interior design included clear glass boxes, framed with indigenous wood containing preserved artifacts from Gaytan's homeland. From the food to the decor, it was a very authentic and delicious experience. Add this restaurant to your list of 'must' places to dine at when you're in Chicago.

Athena Restaurant

Chicago is known for deep-dish pizza, baseball, architecture, and diverse neighborhoods. Exploring the many different neighborhoods in Chicago is a great way to get a taste--literally and figuratively--of different cultures. Foodies know that Chicago's West Loop is one of the best dining districts in America, and this includes Greektown. Opa! Visiting Greektown in Chicago can make you feel like you're visiting Greece, with all the classic restaurants, stores, museum, and Greek signage. If you're looking for traditional Greek food, book a table at Athena--it's a busy, upbeat, and spacious restaurant with an extensive menu featuring classic Greek food--large plates made perfect for sharing and enjoying (think roasted lamb, gyro with fresh pita bread, tzatziki, Greek salad, and saganaki). I felt like I was back in Athens on a summer day! 


I hope you're not scared of heights, but even if you are--you have to check out Skydeck to get over your fear! Skydeck is at the top of the famous Willis Tower--we're talking 442 metres high--so be prepared to see some incredible views of Chicago. My advice is to book your visit to Skydeck first thing in the morning, to avoid the crowds. (You can treat yourself for waking up early by visiting Garrett Popcorn afterwards!) This was my second time experiencing Skydeck, and this time, I was able to enjoy the new immersive experience (like an interactive museum) showcasing things the Windy City is famous for. After this, you'll head up 103 floors to take in the spectacular views from the observation deck. You can even step out onto The Ledge--there are four glass viewing boxes you can choose from, and it's quite the experience to step out onto the glass floors and look down. 

Magnificent Mile

One of the best things about Chicago is the shopping. It's a city made for spending countless hours of 'shopping 'til you drop' and I love it. Magnificent Mile is one of the most famous shopping areas in the world, and it's where you can find many great department stores, high-end luxury boutiques, stunning architecture, and restaurants, all on one street. Check out Water Tower, too--an eight level shopping centre. (Yes, eight floors!). Here you'll find American Girl, Macy's, Victoria's Secret, and so many more of your favourite stores. 

From shopping to dining, Chicago is one of my favourite cities. It's got everything I love: the busy, bustling streets, incredible shopping, gorgeous architecture, countless dining options, luxury hotels, friendly people, history, culture, outdoor activities, museums, art galleries, theatre, and more. Chicago has often been compared to NYC 'only cleaner', and this is very much true. It's a great city to visit with friends, family, or as a couple. There is so much to do, and I can't wait to go back to explore even more--there is still so much I need to experience in Chicago. 

A very special thank you to Choose Chicago and Fathom Co. for inviting me on this press trip and taking care of everything. It was magical, and I can't wait to return. Thank you!