Travel: A mini-break to Chicago

Have you ever needed to just get out of the city for a few days to take a break and have a mini-adventure? I am sure I’m not alone when I say; I crave this more often throughout the year. 

As careers keep us busy during the week, if we don’t take a break at some point (aside from weekends), we became, in my opinion, mundane. So this is exactly the reason I hopped on a plane mid-week to spend a few days in another city.

A window seat on board Air Canada

With non-stop flights between Vancouver and Chicago, it makes it super easy to plan this getaway. Fly coach or opt for the Premium Economy upgrade with a touch more legroom. And the flight times make for planning dinner and drinks upon arrival completely do-able. You’ll feel as refreshed arriving as you did leaving, as the flight is just 3.5 hours long.

Upon arriving in Chicago you have 3 great options for getting into the city: 1. You can hire a taxi; 2. You can register and get the Uber app and take Uber – both these options are approx. 30-60 minutes depending on traffic. Or 3. You can take the Rapid Transit Train (blue line), which is approximately 45 minutes to downtown.

Now that I have a couple trips to Chicago under my belt, there are a couple very comfortable hotels I would recommend: The Public Chicago and The James Hotel.

After much research into hotels, I found these two looked exactly like their pictures on-line and the staff were amazing. They also both boasted great reviews via Trip Advisor and offered competitive prices as well.

The Pump Room Restaurant

The Public is a little further from the centre but it’s in a quiet neighbourhood and close to Lincoln Park (for warmer weather visits). It’s close to restaurants and also has a lounge, restaurant and café on site. But it’s still very easy to get to the centre by foot or by Rapid Transit (red line). Their restaurant The Pump Room, was created by Jean-Georges Vongerichten (a well-known Chef), offering a great menu and separate bar with a decent wine list. The Library Coffee bar just off the lobby has everything you need for a light or bigger breakfast whether you are sitting down or on the go. The rooms are modern with a touch of older nuances; the beds are comfortable and nice amenities.

The James feels more like you are centrally located as it’s just off Michigan Ave. and many restaurants and shops are right out the front door. The hotel was also recognized by Travel + Leisure’s ‘World’s Best Awards’. The restaurant on site is called Primehouse offering breakfast, lunch and dinner. I enjoyed breakfast there one morning and to my delight – they offered loose-leaf green teas (as a green tea lover this can be hard to find), fresh pressed juices and a simple menu with not too much and not too little. Their bar also offers happy hour and a social space to chat with fellow travellers. The rooms are comfortable and modern with sitting areas and chic mini-bars with locally sourced snacks.

There is much to do and explore in Chicago. It’s well known for it’s live music scene, great restaurants and shopping galore along and near the ‘Magnificent Mile’. There are also many tours by water, like an Architectural boat cruise, and lots of attractions to visit from Lincoln Park Zoo to Millennium Park. And for the sports enthusiasts who like baseball – get tickets to see the Chicago Cubs; if you prefer hoops – go courtside at the Chicago Bulls game; or see a Chicago Blackhawks hockey game.

And if you prefer exploring on foot like I do, you’ll be able to mingle with the locals by getting lost and discovering off the beaten path shops. Mid-Western folks are known for their hospitality, so get out there an meet them, as they are not just nice people, they are friendly too.

In no particular order, I’ve put together a list of some of my favourite places to visit while in Chicago:

homemade skillet cornbread at Big Jones

Big Jones – Featuring southern heirloom cooking in the cool neighbourhood of Andersonville, just 20 minutes north on the Rapid Transit red line. This quaint restaurant makes absolutely delicious soul food – something this western Canadian foodie has not enjoyed that often. They offer a nice wine list including Northern Michigan wineries and some creative cocktails. Drop by for lunch or dinner, and go hungry.


Eataly – Offers everything under one roof. It’s a place to shop for wine, cheese, groceries, pasta, meat, or have a coffee. Stop by for happy hour in the afternoon at the Wine bar where you’ll find a fantastic selection of Italian wines by the glass and bottle, or dine in for breakfast, lunch or dinner at their restaurants. One of my favourite finds in the city.

Happy Hour at Eataly

Soho House – Although this is a members club in the Fulton Market District. There is a public area in the entrance for non-members to enjoy. And if you know a member, or have a membership (worldwide houses to choose from), be sure to enjoy the delicious menu, a cocktail or glass of wine at the Club Bar. Great atmosphere indoors or out (rooftop terrace for sunny days).

Purple Pig – If you’re craving Mediterranean/Spanish food, this busy spot offers up lots of tapas, along with a really good wine list and great vibe. It attracts locals and travellers alike, because it’s delicious and the Chef Jimmy Bannos Jr. was the winner of a James Beard, Rising Star Chef 2014 award.

Untitled Supper Club – A very cool evening spot for dinner and dancing with private booths and tables, a nightclub, Whiskey Bar and Champagne Lounge. The menu had a good selection of food along with cool cocktails and a decent wine menu. It’s a night out with friends’ kind of place with live music throughout the week.

The view from the John Hancock Building

John Hancock Tower (Lounge) – Make sure you visit the John Hancock Tower, not the regular viewing deck, but instead go straight to the Signature Lounge and enjoy a drink with a complimentary view from the 96th floor. Not for the faint of heart but worth it!


RM Champagne Salon – Enter from a cobblestone alley; this is the perfect place to enjoy sparkling wine and champagne among other offerings on the menu. It’s got a speakeasy feel with the bustle of a French bistro. A hidden secret that’s worth discovering.

At the end of my stay, I had called Uber for a ride back to the airport (my favourite way to get around). The driver accidentally over shot the entrance to the hotel and parked across the street. Without a blink of an eye the bellman at the James Hotel picked up my bag and safely walked across the street with me in tow. I found myself surprised at his instant reaction. And as he loaded my bag into the trunk of the Uber car, I thanked him and the next thing I knew I had my arms wrapped around the bellman, hugging him good-bye. I think he was as shocked as I was!

I returned home from this mini-break to Chicago feeling refreshed and happy, as I know anyone would after experiencing such heart-felt hospitality. The city is easy to navigate, the locals leave a lasting impression and no matter what your budget or interest, there is something for everyone.

This article was written for ourCoup . What does ourCoup do? They promote and encourage young female entrepreneurs to reach their very own coups, but also to highlight women that have already attained their coups and inspire others.

~ Donita

Donita Dyer

Co-Founder (Vancouver, BC Canada)

As bubbly and complex as vintage blanc de blancs Champagne. Donita has worked in Sales & Marketing within the Travel & Tourism Industry for years, and in the Wine Industry since 2013, as well as being an entrepreneur. She’s studied French Wine through the French Wine Guild and has earned her WSET (Wine & Spirits Education Trust) Advanced Level 3 Certificate. She also received a scholarship from Les Dames d’Escoffier towards the ‘Master of Champagne’ course. When Donita’s not working, she’s writing on her wine and food blog called: Wine & Food Concierge; she teaches a Wine 101 class; she coordinates social wine events and shares her love for rosé wine on a Facebook page called: The Pink Tank. She also loves to travel, cook, explore any culinary scene and is an Actor and Hand Model.

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