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The Best Piano Bars in Chicago

The Best Piano Bars in Chicago

In my opinion, it is close to impossible to have a bad time at a piano bar. I mean…think about: singing, piano music, usually dancing, cocktails. Fortunately, some of the best piano bars can be found scattered throughout Chicago. Check out this list of the Best Piano Bars in Chicago.

And…if piano bars aren’t your style, but you still need some Chicago watering hole recommendations, check out these posts to help guide you:

  • The Best Bars in River North, Chicago

Table of Contents

  • Redhead Piano Bar
  • The Zebra Lounge
  • Howl at the Moon
  • Grapes and Grains

Redhead Piano Bar

When someone says “Chicago” and “piano bar” in the same sentence, most locals immediately think of the Redhead Piano Bar. It is located in a basement space a couple blocks off of Michigan Avenue and brings in fans of all ages ready to sing-along the night away.

Get there early to grab a seat directly in front of the piano, check out their smoking space (complete with a humidor if you’d like to buy a cigar on the spot), or just boogie in any (likely very limited) free space you can find!

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The Zebra Lounge

For over 85 years a small, hidden gem called The Zebra Lounge has been busting out amazing piano tunes. At this bar, you’ll find live music seven nights a week. Expect a wide range of piano music played and requested: anywhere from Elton John to Sir Mix-a-Lot to the Hamilton musical songs. As mentioned, The Zebra Lounge is a more intimate space than others on this list and does not accept reservations, so show up early to ensure your seat!

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Howl at the Moon

Yes, Howl at the Moon is a national chain…but is it also a national treasure? Since Howl is right in a prime downtown location, you may want to check out the Best Bars in River North before ending the night dancing here. The crowd here is all ages and since there are plenty of chances to enter and win Happy Hour Party deals (check out the website and apply!), the venue can get crowded starting early.

However, keep in mind this is the least “traditional” piano bar on the list. The performers also play guitar, tambourine, drums, etc. and often rotate what instruments they are playing; it is truly a big production!

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A post shared by Howl at the Moon Chicago (@howlchicago)

Grapes and Grains

While Grapes and Grains is one of the newer piano bars in Chicago, it definitely does not lack character and a fun atmosphere. Expect to hear live music Thursday, Friday, and Saturday starting around 8pm. Bonus points if you enjoy whiskey fan as this bar prides itself on an extensive whiskey selection.

If the music really provides you with an out-of-body-experience, top it off with their ~Saber Experience.~ For instance, for a pretty penny you are led to a private room and given instructions on how to saber your own bottle of champagne. Talk about a night out! Pianos and sabers and champagne – oh, my!

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A post shared by Grapes & Grains | Chicago (@ggwestloop)

Ready to tickle the ivories?! Let me know if you have any other favorite piano bars in the city.

In the meantime, check out some of my other Chicago content:

  • 10 Best Restaurants in River North, Chicago
  • 10 Best Restaurants in Lincoln Park, Chicago
  • The Best Donuts in Chicago, IL

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About Sara

About Sara

I’m an American who quit my job in Chicago to seek out an Italian adventure. I currently live and work in Milan, Italy.

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About Me

About Me

Sara in Italia, Italophile

Ciao! I'm Sara. An American who quit her job in the US and moved to Milan to seek out my journey of La Dolce Vita. Follow along for Italy guides, tips, and general rants about the pros and cons of moving to Italy.

sara.in.italia

📍American living in Milan
Sharing Italy travel tips, guides, and more! ✨
Follow along as I try to figure out my life abroad 🇮🇹

Italy and classic car lovers unite!! The @coppamil Italy and classic car lovers unite!! The @coppamilanosanremo is an official experience you won’t want to miss. 

What started in 1906 as a speed rally from Milan to Sanremo, today has shifted into a precision rally. Attend as either a driver/co-driver or a guest (like me!) and you’ll have a blast. The teams drive through Lombardy, Piedmont, and wrap up in Liguria. 

So, if you love the idea of vintage cars winding through scenic Italian landscapes, you may want to look into joining next year’s rally (or at least seeing it it may pass through your town). 
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#lifeinitaly #livinginitaly #coppamilanosanremo #classiccars #expatinitaly 
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How to apply for the permesso di soggiorno in Ital How to apply for the permesso di soggiorno in Italy!!

Moving to Italy sounds great (and it is!) but before you can truly enjoy your new life abroad, you have to take care of some housekeeping. The first up, and one of the most important tasks, is filing for your Permesso di soggiorno (residency permit) so you can be cleared to legally live in Italy. 

The process is a pain. Depending on which city you live in likely determines how long processing this will take. For example, I’ve heard horror stories about the wait times in Florence. But Milan, despite being a large city, seems to process these fairly efficient. 

It’s your first introduction to Italian bureaucracy and the most important thing is completing this WITHIN 8 DAYS OF YOUR ARRIVAL IN ITALY!

📌Save this guide for your future move to Italy so you don’t miss a single step. 

—— 

Ciao! My name is Sara, I’m an American living abroad in Milan, Italy. I share Italy travel tips, content, and advice. Follow along to see more about my life in Italy. 🇮🇹 
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#movetoitaly #livinginitaly #lifeinitaly #movingtoitaly #americaninitaly 

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I had a new “first” as an American living in Italy I had a new “first” as an American living in Italy this week (and it was a bit of a culture shock for me) - the condo assembly. 😅

I truly wish I could have had a secret camera in the room. As an American, my understanding is most condo associations elect of a board of directors to make most day-to-day decisions. Of course if there is a bigger decision, the condos vote (usuall 1 vote for household). Well, that process is very different in Italy! 

Here, the amount of votes are determined by condo size. And everyone, I mean EVERYONE, seems to have a (loud) opinion on every topic. My imagination of a calm meeting amongst neighbors was quickly replaced by reality. 

Anyways, I love living in Italy but these experiences make me laugh at how one thing can differ so much one place to another. 

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Ciao! My name is Sara and I’m an American living in Milan, Italy. I love sharing snippets of life in Italy, Italy travel guides, and Italy travel tips. Follow for more! 🥳
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#lifeinitaly #livinginitaly #americaninitaly #italycultureshock #americanabroad 

American in Italy, Italian culture shock, American abroad, moving to Italy, buying property in Italy
Hidden costs of owning a car in Italy. 🚙🙃 I was s Hidden costs of owning a car in Italy. 🚙🙃

I was soooo thrilled after getting my license in Italy! Then, I was humbled veryyy quick by all of the beauracracy and costs that come along with it. 

My biggest shock was perhaps the Area C payments (despite being a resident within Area C) and only receiving a discount for a limited number of entries a year. 🫠 Why…

Do any of these shock you? Or are there any other costs I have still overlooked (keep in mind as a foreigner it’s hard to know sometimes what to pay - like this bollo!). 

Save this post if are in the market for buying a car in italy and all of the costs attached to buying a car in iraly. 😵‍💫
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#americanabroad #livinginitaly #lifeinitaly #movetoitaly #americaninitaly 

Moving to Italy, costs of living in Italy, life in Italy, American abroad, moving abroad, buying a car in Italy, hidden costs Italy, culture shocks Italy, American in Italy
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