Explore The West Loop: 10 Cool and Chill Places

Favorite Spots to Chill in The West Loop

The West Loop has become kindof my second home and I get that there are some of the best restaurants there – I read Emily Belden’s “Hot Mess” (and also interviewed her on a West Loop Entrepreneur panel) and partnered with some Randolph Street restaurants. I get it – I love the shimmer and sparkle of the west loop. But sometimes, I want to be low key and just grab a good drink and be silly with my girls.

So, since I get asked this question – the question of where to go and what to do in the west loop – as a community and marketing manager for luxury coworking space, Co-Optim, I want to share with you those cool and chill places where you can unwind and get those much needed laughs with friends in the west loop.

Parlor Pizza

I’m not biased – even though Parlor Pizza regramed my cheese pull video. It seriously is always happening at Parlor Pizza- maybe because it’s right next to SoHo house or just off the ever-busy Randolph Street. I love the rooftop during the summer. If you do go, don’t order the pizza, order the pizza bread. It’s so good that me and my friend ordered it and had it delivered to a bar while watching a basketball game. It is life changing and the salads are pretty good.

Also, my friend and fellow blogger, Sany, did an insane video on Parlor Pizza covering their dessert bar – dessert tacos never seemed so appealing.


CH Distillery and Cocktail Bar

CH Distillery has a flight of vodka – need I say more. It’s across the street from Olgilvie Transportation Center. Fair warning, it opens at 4 pm and they have a cute patio.

The cocktails can be a little bit much – don’t order the mojito. It’s not good. I heard the Rosemary’s Baby cocktail is good. Oh, and P.S. the burger looks insane. P.S.S. they have a cocktails and humor night with stand-up comedians on September 8, 2018. You can learn more and get tickets here. 

Lone Wolf

Lone Wold is right next to Au Cheval. Good beer list and artisanal hot dogs on the menu. A fellow Chicago blogger, Blair Bitove from The Blair Necessities shared “[Lone Wolf] was a nice little bar where you can actually talk to people but still have fun.”

Blind Barber

For a cool experience  – Blind Barber is a barber shop by day and an old school bar at night. It’s still on my list to go – so if you do go, tag me in your Instagram post please. One of my favorite Chicago bloggers, Tavi from Chi At A Glance wrote a Yelp review about it – sharing that it is like a speakeasy because “Unless you know about this spot you’ll never find it. Lol. You actually have to enter the barber shop and then walk through the unmarked door once inside.”

Punch Bowl Social

Punch Bowl Social is so nice and chill. Their motto is “Here’s to going out right.” When you walk in, you feel like you are at the wrong place because it looks like a laundromat, but you go up the stairs and there’s so much to explore. Punch Bowl Social is huge – like Marco Polo huge. With karaoke bars and a bowling alley and a gigantic scrabble board – you are sure to have one of the best nights of your life. Once you get bored of one activity, there’s another. It’s perfect for a windy/cold/too hot – basically every other day in Chicago. It’s seriously The Monopoly of this year – with multiple locations throughout the nation. We were lucky to get one this spring.

El Che Bar

El Che Bar was inspired by time spent eating, drinking and traveling in Argentina and you definitely get that flavorful cool and trendy vibe from the interior to the patio. I had a few drinks there with fellow Chicago food bloggers, but honestly – you go there for the food, particularly their steak because it’s an Argentinian-style steakhouse. I wouldn’t pass over the appetizers – the braised beef and horseradish aioli empanada was delicious as were the Spanish olives and their – never discounted – buttery and grilled oysters.


So, these are some of the gems in Chicago’s West Loop to chill grab a drink, and just live after a long day at work. My next question is – who are you taking with you?

Amanda Whitfield
Amanda Whitfield

Amanda Whitfield is a writer and speaker and a relationship builder. She believes that meeting people in person is important. After attending numerous fashion, startup, and creative events, she founded Windy City Cosmo is 2015 to help people make connections in the city as they build their businesses, start and end relationships and see and be seen. Over the past three years, the entrepreneurs she’s interviewed have become the most successful in Chicago and Windy City Cosmo won an award in 2017 for her work for female entrepreneurs.

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