Weekend Getaway Tips for the Windy City

 Weekend Getaway Tips for the Windy City

Photo: Neal Kharawala

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After having to sideline traveling for a couple of months I was very excited when I was surprised with a weekend getaway to the Windy City.

A quick 3-day trip to Chicago was just what I’d been longing for. I’d heard of its great summer weather, beautiful city landscape, and of course, it’s been on my radar as a city I must eat my way through – bite by bite.

With talks of Covid cases starting to decline there, I decided to pack my carry on and venture to the Midwest. Chicago was a breath of fresh air for me. In a time of so much uncertainty, fear, and chaos, I so needed to get back to my happy place. And you all know that’s discovery.

Grab your notepad and pen and take a few notes as I walk you through the places to stay, play, dine, and unwind in Chicago.

Weekend Getaway Tips for the Windy City
Weekend Getaway Tips for the Windy City
Weekend Getaway Tips for the Windy City


With so many places to consider in the city to stay, we settled in on the River North area. Just north of the Chicago River — the River North business and residential area is now home to some of the city’s trendiest art galleries, hotels, bars, and restaurants.

Attracting locals and visitors alike, it’s come a long way from its beginning as the red light district of the city. Leave it to me to sniff out a red light district 🙂 It’s also just a few blocks away from Chicago’s Magnificent Mile. I definitely would rate this area’s walkability at 100, which is important for someone who wants to explore the city.

Our unique hotel was a highlight. Priding itself on its intersection of Art and Science, Hotel EMC2 was full of little curiosities, and it was GORGEOUS. While all of the amenities were not quite yet available to guests, we did have Cleo and Leo, the hotel robots who made sure to take care of our room service needs.

The location was central to everywhere we ventured to. Outside of the hotel, we found ourselves surrounded by restaurants and shops, neighboring boutique hotels, and rooftop bars. Anything not within steps, a quick Uber ride did the trick.

Book a discounted stay at Hotel EMC2


While indoor bars, clubs, theaters, and other places that hold large amounts of people are still shut down, I was relieved to find that Chicago had moved into Phase 3 of reopening about a week or so before our trip. This meant that rooftop bars and patios were open!

While I definitely wanted to take precautions and limit too much interaction with others, I’d always heard about the city’s skyline and how rooftop bars are a thing there, so I was happy to indulge a bit. Hours were limited and social distancing definitely was in place but I made it my business to take in the city’s drop-dead gorgeous views with a few cocktails in hand.

Some businesses, like Streeterville Social, even got a bit creative allowing local partnering restaurants to deliver to the rooftop so you could enjoy your cocktails and good eats while relaxing, enjoying the weather, and mingling – at a distance. I had a great time here, chatting with a few fellow bartenders, where I learned about how this experience has been for them and the changes they’ve had to make to sustain their careers.

Other cool rooftop experiences included delicious bites and drinks inside of the Kimpton Grey Hotel, Boleo, and the Ivy Sky Terrace, located in the Ivy Hotel, literally a few feet outside of our hotel’s doorstep.


If I plan anything when traveling it’s where I’d like to eat! Luckily upon our arrival, Chicago had just entered into Phase 4 and most restaurants were officially open for business. When I think of Chicago, I think of food, and it didn’t disappoint. From the yummy BBQ sandwich enjoyed rooftop from Carson’s Ribs to an official Chicago style hot dog from Portillo, I was in culinary heaven.

The perfectly caramelized crust of the deep dish pizza at Pequods did me in, and the mouth-watering Wagyu Tomahawk shared at Steak 48 put me in a state of bliss for that entire evening. Chicago is a goldmine for those with a vast tasting palette.

More importantly, it was cool to see how restaurants were adjusting to our new 2020 normal – QR code’s, paperless payments, pre-made cocktails, disposable cups, plates, etc. virtual waitlists and ordering your meal ahead so it’d be ready for you to enjoy upon arrival were just a few initiatives some of the restaurants we visited put into place. While everyone had different protocols, it was refreshing to see systems in place to allow businesses to move forward while being conscious of guests’ health.


Fun fact: Chicago is the 3rd largest city in the US. Staying in the River North put us right in the heartbeat of the city. Though I’m sure upon further exploration of some of the other beautiful neighborhoods the city has to offer, I may feel differently. Even so, the walks to and from our hotel were probably one of the highlights of the trip – people watching on the Riverwalk, browsing the stores on the Magnificent Mile, venturing down to the Theatre District (another area I was very fond of). We were steps away from all of these amazing landmarks.

When we weren’t walking around the city, we found ourselves taken away by all of the surrounding water. Lake Michigan is vastly beautiful. We opted to take a boat tour courtesy of Wendella Tour and Cruises, where we sailed out and captured some of the beauty of the city from afar.

Walking alongside the Riverwalk was also calming and rejuvenating. Pride month was coming to an end and being celebrated at the famous Navy Pier, where it felt good to be amongst others – sitting, relaxing, laughing, and looking out miles into the lake (I’m sure all counting our blessings). A quick pedicab to Millennium Park and we’d be right back in the center of the bustling city, and on the walking path to our next destination!

In short, Chicago is just what you need if you’re looking to take in a new city, but enjoy and appreciate it’s earthy elements. A city that is an architectural dream – with massive buildings that seem to touch the sky, surrounded by lush and green parks and miles and miles of blue waters.

Have you visited the windy city? If not, get a taste of what I experienced through the video below. If you have, did it whisk you away as it did me?

Are you coming to Chicago soon? Why not book an excursion and make sure you see and taste all that Chicago has to offer. Visit Urban Adventures Chicago

The Capricious Traveler

The Capricious Traveler


It is discovery that excites me when it comes to traveling, in all of its whimsical, unpredictable, inconstant and changeable ways. Whether it’s a 45 minute or a 10-hour flight, the unknown is always right outside your door.

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