Skip to content

Sara in Italia

Italy Travel Guides and Itineraries

  • Visiting Italy
    • Abruzzo
    • Campania
    • Emilia-Romagna
    • Lazio
    • Liguria
    • Lombardy
    • Piedmont
    • Sardinia
    • Trentino-Alto Adige
    • Tuscany
    • Veneto
  • Moving to Italy
  • About Me
  • Visiting Italy
    • Abruzzo
    • Campania
    • Emilia-Romagna
    • Lazio
    • Liguria
    • Lombardy
    • Piedmont
    • Sardinia
    • Trentino-Alto Adige
    • Tuscany
    • Veneto
  • Moving to Italy
  • About Me
Destinations

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
    • Share this:

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!

View this post on Instagram

A post shared by Redhead Piano Bar (@redheadpianobar)

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!

View this post on Instagram

A post shared by Zak Shapiro (@zakonthekeys)

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!

View this post on Instagram

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!

View this post on Instagram

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

Share this:

  • Share on X (Opens in new window) X
  • Share on Facebook (Opens in new window) Facebook
  • Share on Reddit (Opens in new window) Reddit
  • Share on Pinterest (Opens in new window) Pinterest
ChicagoDestinationsItineraries & GuidesTravelUSA
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.

Related Posts

How to Visit Cala Dragunara in Alghero, Sardinia
How to Visit Cala Dragunara in Alghero, Sardinia
Best Things to do in Sorrento, Italy
Best Things to do in Sorrento, Italy
How to Spend One Day in Trani, Puglia
How to Spend One Day in Trani, Puglia
How to Spend a Weekend in Pescocostanzo, Abruzzo: Italy’s Hidden Mountain Gem
How to Spend a Weekend in Pescocostanzo, Abruzzo: Italy’s Hidden Mountain Gem

Post navigation

The Best Donuts in Chicago, IL
The Best Bars in West Loop, Chicago
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 🇮🇹

I’ve been a bit MIA the last couple weeks as my li I’ve been a bit MIA the last couple weeks as my life has forever changed for the better. We welcomed our baby girl! 🩷In due time I’ll be eager to share some insights on pregnancy, birth, and babies in Italy vs the U.S. In the meantime, I’m going to continue to soak up these early days as a new family of three. It’s a happiness I can’t even describe. 💖...#livinginitaly #americaninitaly #lifeinitaly #expatinitaly #babyinitaly
Every time I think I can have a fully confident ni Every time I think I can have a fully confident night out speaking Italian I am quickly humbled. The hard part is when I miss a key sentence or word and continue interpreting the following portion of the conversation COMPLETELY wrong. 🤣If you’re learning Italian (or any language) can you relate?..Ciao! My name is Sara, an American living in Italy. Follow along as I share all about my life abroad in Milan. 🇮🇹..#learningitalian #livinginitaly #americaninitaly #learnitalian #expatinitaly language learning, learn Italian fail, life in Italy, American abroad, expat in Italy, American in Italy, living in Italy, moving to Italy, move to Italy, Italian language
Did you know that it is not common to take your hu Did you know that it is not common to take your husband’s last name when you get married in Italy?I have started the process of investigating what is required and 😵‍💫😵‍💫😵‍💫😵‍💫😵‍💫I’ve asked on forums and have done some research and WOW it’s not for the faint of heart. For any Italians who may not realize: in the US it is a fairly straightforward process if you opt to change your surname after marriage. Meanwhile, I’m discovering in Italy that it is very difficult!!I can already anticipate the comments that will tell me to adapt to the culture or that people will think we’re siblings (the forums blessed me with plenty of those comments already 🙃) but honestly I still want to do it! I’m just trying to understand what I may be getting myself into. Anyways, let’s see what I decide to do - but thought I’d share as this was a very unexpected Italy culture shock for me. Italy constantly confuses me on where it stands on traditional vs vs modern vs progressive vs everything else lol. ..Ciao! I’m Sara, an American living in Milan, Italy. Follow along on my life in Italy as I share about my journey to move abroad as well as my favorite Italy travel tips. 🇮🇹..#livinginitaly #americaninitaly #cultureshock #italianculture #usavsitaly Life in Italy, getting married in Italy, changing last name Italy, Italian culture shock, Italian cultural difference, living in Italy, Italian surname, American in Italy, expat in Italy, moving to Italy
🇮🇹 How I Moved to Italy series! 🇮🇹 In this episod 🇮🇹 How I Moved to Italy series! 🇮🇹In this episode I dive into how I was able to transition my Italian study visa into a work visa. (Hint: it took nearly 6 months). During this time I could work 20 hours a week, which provided a nice ease back into corporate. I hope these videos show that moving to Italy is not necessarily “easy” or a walk in the park. Online social media platforms tend to be a highlight reel and my entire journey as an American in Italy has been anything but simple.That being said, I wanted this life and understood and accepted the various sacrifices I’d have to make along the way. Where there is a will, there’s a way. But prepare yourself accordingly. So yes, even though I had signed an Italian full-time work contract, I had to wait for the paperwork to go through and get approved. At least I was finally making some money again after a year off 😅..Ciao! I’m Sara, an American living in Italy. Follow along as I share snippets of my life abroad: the good and the bad. I also use this platform to highlight Italy travel tips and some of my favorite hidden gems. ✨..#movingtoitaly #permessodisoggiorno #workinginitaly #movetoitaly #italyvisa how to find a job in Italy, how to move to Italy, converting Italian visa, study to work visa Italy, working in Italy, Italian work visa, living in Italy, American in Italy, expat in Italy, American abroad, Italy culture shock
Follow on Instagram

Recent Posts

  • How to Visit Cala Dragunara in Alghero, Sardinia
  • Best Things to do in Sorrento, Italy
  • How to Spend One Day in Trani, Puglia
  • How to Spend a Weekend in Pescocostanzo, Abruzzo: Italy’s Hidden Mountain Gem

Popular Posts

Italy ➤ July 26, 2024

Must-Eat Foods in Milan, Italy: A Foodie Guide

Milan, Italy is not well-known for being a “foodie” city. However, I tend to find it can be underrated destination. I mean, they have everything! During your trip to Milan, I encourage you to try...

Read More
Italy ➤ June 2, 2024

My Favorite Hidden Gems in Milan, Italy

Milan gets a lot of hate when it comes to Italian cities. And I’ll be 100% transparent; I am a former Milan hater. My hate was solely based off visiting the city on a gloomy...

Read More
Italy ➤ May 30, 2024

The Best Brunch Spots in Milan, Italy

As an American, the weekend can truly mean one thing for a food lover: brunch. Yes, that perfect mid-day meal with friends to recap the week together. I was nervous that Italy wouldn’t have the...

Read More

Italy Posts

Everywhere Else

Expats in Italy Guides

You may have the world, if I may have Italy

Giuseppe Verdi
  • Blog
  • About Me
  • Contact Me
Copyright © 2026 | All Rights Reserved | Designed by Little Theme Shop