Full Bellies & Full Beers: Chicago Style.

Where to eat, drink, shop, & learn. Windy city style!

Chicago will always be one of my favorite cities in the world. I’m not sure if it has to do with the fact that it was one of my first independent trips abroad with a friend when I was 21, or the many wonderful & eclectic qualities it offers as a city. So perfectly situated on bright Lake Michigan, accompanied with a boardwalk that stretches from one end of the city to another. The bars, comedy clubs, delicious restaurants, museums and shopping havens vary in there uniqueness throughout the neighbourhoods that make up Chicago.

I’ve been to Chicago 3 times now, and every time its been a vastly different experience. First in my early twenties, a bright eyed girl (unknowingly) about to catch the travel bug, then again a few years later with friends from the area I had met in Italy - and the most recent trip was with Lindsey! I was super excited to share the experiences of Chicago with her as she had never properly traveled around the area. We had a lot of ground to cover on this trip, and with it being St.Patricks Day (the ever so famous celebration in Chicago) we were bound to have a blast. Keep reading to hear our top picks for where to eat, drink, shop, and learn in Chicaaaago!

Where to eat

Brunch - Cafe Marie-Jeanne

Home cooked food, authentic & fresh ingredients, unique menu items and impeccable service. Cafe Marie-Jeanne is a must when choosing a brunch spot during your time in Chicago. Situated in between Wickpark & Bucktown, after brunch you've got to take a stroll through these neighbourhoods to take in the funky record shops, vintage clothing stores and colourful street art.

Dinner - Bar Siena

The most authentic Italian delicacies you’ll find in town, situated in the trendy West Loop area! Everything is made in house from scratch, the servers offer fantastic paring suggestions, it’s a full house every weekend and the DJ will keep you grooving all night long. Oh, and it’s full of beautiful people. Feeling flirty? Definitely head over to Bar Siena for the evening to dabble in Chicago’s watering hole.

Late Night Noms - Giordanos

Looking for some classic deep dish pizza on your Chicago adventure? Look no further than Giordanos. Cheesy, warm, fulfilling, pizza goodness! Oh and there beer list is pretty sweet as well. Trust me on this one, I go every visit!

Where to drink

Day Drinks - Sugar Factory

This bar is like a child’s playground, except it’s a drink playground for adults! Craving something sweet? Sugar Factory is where you’ll find the most delicious cocktails. They’re fruity, boozey and very very large. Admittedly, we had to share. Cause you know… Pace yourself!

Downtown Drinks - Three Dots and a Dash

This is the perfect bar if you’re in the mood for some Hawaiian vibes in a Chicago style speakeasy. Located in the River North neighbourhood, Three Dots and a Dash offers a variety of uniquely designed cocktails in a selection of tropical and authentic glassware.

Drinks With a View - Signature Room

A bit of a tourist destination, I wouldn’t recommend going for more than one. But it’s definitely worth a trip up for the views and to taste one of their signature drinks. The bartenders and high vibes definitely make the experience!

Feeling Adventurous? Cubby Bear

Head on over to the Wrigley Field neighbourhood if you’re looking to party in what feels like an authentic U.S. college town. We ended up here on St.Patricks Day and actually had the best time! There are rows of lively bars to chose from whether you’re going after a Cubs game near by, or heading out for some live music. Cubby bear was one of our faves!

Where to shop:

Top Fashion Brands - Magnificent Mile

This bustling street runs through the central business district and is a hot spot for all the top fashion brands. If you’re keen to find stores offering the latest trends and looking for name brands, you come to the Mile. Even if you just want to participate in some window shopping! It’s worth the walk, you’ll enjoy the views either way!

Unique Vintage Finds - Wicker Park & Bucktown

These neighbourhoods are key if you’re looking to do some solid thrifting while in Chicago. Both Wicker Park and Bucktown are filled with awesome coffee shops, classic record stores, vintage warehouses, local designer boutiques and even a place to score a pair of authentic cow boy boots. You’ll want a full day in these areas so that you can try the local cuisine and take your time browsing!

Where to learn:

What once was the tallest building in the world (back in 1973) - Willis Tower/Skydeck Chicago boasts some pretty stellar views of the surrounding Chicago area. Definitely worth the trip up to the top, unless you’re afraid of heights of course ;)

Feeling Artsy? - The Art Institute of Chicago

This is by far the best museum in Chicago. The art collections are extensive, you’ll get lost wandering the different exhibits and definitely walk away with a new take on art. If you’re looking to fill a few hours with knowledge, we recommend going here. Located in the downtown core, prices for admission start at $25USD.

Looking to learn more about the history of Chicago? There’s no better way to learn the city than to simply, walk the streets. The architecture is unique to the turbulent times of Chicago’s past, and varies greatly pending on the neighbourhood you’re exploring. The city also has a river running through it that leads to Lake Michigan - a few more perks that make this city one of a kind!

We can confidently say Chicago is a city you should not miss! It’s pretty accessible via a flight from anywhere in the states and is quite easy to drive to if you’re coming from other states or Canadian provinces that are a close proximately to the Mid West. For us Torontonians, it’s only about an 8 hour drive! 100% worth the road trip :)