Barhopping Milwaukee Ave (Bucktown to Logan Square)
Kiara Brown
A guide to kitschy, classic, and favorite bars on a 3 mile stretch directly on Milwaukee Ave. A pleasant journey with food, booze, and light exercise. Includes 10 bars, and 4 food stops.
17 Places • 1 Save • ago
Free
The Robey, Chicago, a Member of Design Hotels
@Quiera
The starting point. Directly off the Damen Blue Line CTA stop. I always recommend eating before bar hopping. The food here is delicious, they have multiple food & beverage outlets along with a rooftop pool bar.
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Gracie O' Malley's- Wicker Park
@Quiera
A few steps away headed up Milwaukee is Gracie O'Malley's Irish Pub, if you're into sports, great place to catch a glimpse of the game. They also have a small arcade game section. Drinks are inexpensive.
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Small Cheval- Wicker Park
@Quiera
Stop optional if you are't hungry they do have a few beers, and milkshakes. But the burgers are good, and inexpensive.
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Noisette
@Quiera
Technically not on Milwaukee Ave, but its the wine bar inside of the wine shop 'Red & White Wines' Grab you a white wine, maybe some bubs' and enjoy their patio and the sun. Maybe grab some oysters and tinned fish.
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Snakes & Lattes Chicago
@Quiera
Play games, get your drink on, get your second wind with an espresso shot. They also have trivia nights.
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Beautiful Rind
@Quiera
Another wine bar, has a few tables on the outside facing Milwaukee, and you can also buy cheese, tinned, fish and wine inside. Also they offer classes, and speciality dinner events.
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Easy Does It
@Quiera
I've been told by multiple people to come here. Very chic, hip, they have a single serving pet nat that comes in a bottle that looks like a high life can. You get the vibes. Not too much in terms of food. Also a no & low cocktail list.
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The Pink Squirrel
@Quiera
Old School drinks, boozy shakes, and a small bowling lanes. While you're there get the booze ferris wheel.
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The Welcome Back Lounge
@Quiera
Kitschy and cute. And the food is tasty too. Fun drinks.
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The Native
@Quiera
Cash only dive bar, big patio in the back. Also they have Malort cocktail you should try, if you like Malort that is.
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Estereo
@Quiera
One of my favorite bars when its warm out. Open garage style windows, a DJ, discoball in the bathroom, frozen drinks. Good times.
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BiXi Beer
@Quiera
Fantastic Chinese, Vietnamese, and Korean inspired food. They also brew their own beer, so stopping in for drinks only works too. The vibe downstairs is more swanky, upstairs though it is more casual.
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Andros Taverna
@Quiera
One of my favorite restaurants in the city. Brunch fire, dinner fire. Highly recommend. In case you didn't eat at the other stops along the way. You won't be disappointed.
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Websters Wine Bar Chicago
@Quiera
If you're still standing. aka, you paced yourself this is the last stop right after the park. Yes, another wine bar! Then you can get on the train, or call an uber.
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Photo Ops Along The Way

Quincy Jones Mural
@Quiera
If you've seen his documentary or if you're a fan you know that Mr. Jones is from the Southside of Chicago. There are other murals on this block as well.
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Robin Williams Mural
@Quiera
A must stop for Robin William's fans. Is a parking lot though so might be hard to get a full shot like the one pictured. There are lots of mural on this block.
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Greetings From Chicago Mural
@Quiera
Cute mural designed to mimic a post card is very cute. Multiple murals in this area.
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* * *
CURATED BY
Kiara Brown
Solo travel, bestie travel, Will travel for food. I went on my first adult vacation for my 21st birthday to New Orleans, and was hooked ever since then. Years of experience in boutique and luxury hotels, as well as Travel Operations. I offer customer itineraries, and travel planning services.
Feeling overwhelmed?
Thatch can help.
Send a request and we'll handpick a list of Thatch-verified travel creators who would love to help with your trip.
No request is too big or small...
"Research places for beach trips this winter."
"Help me plan a romantic getaway to Milan."
"Find and book kid-friendly activities in Paris."
"Curate a walking tour of historic Berlin."
"Suggest wineries worth visiting in Napa."
You can relax now :)
Person laying on a bed relaxing
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Barhopping Milwaukee Ave (Bucktown to Logan Square)
Kiara Brown
A guide to kitschy, classic, and favorite bars on a 3 mile stretch directly on Milwaukee Ave. A pleasant journey with food, booze, and light exercise. Includes 10 bars, and 4 food stops.
17 Places • 1 Save • ago
Free
The Robey, Chicago, a Member of Design Hotels
@Quiera
The starting point. Directly off the Damen Blue Line CTA stop. I always recommend eating before bar hopping. The food here is delicious, they have multiple food & beverage outlets along with a rooftop pool bar.
Add to
Details
Gracie O' Malley's- Wicker Park
@Quiera
A few steps away headed up Milwaukee is Gracie O'Malley's Irish Pub, if you're into sports, great place to catch a glimpse of the game. They also have a small arcade game section. Drinks are inexpensive.
Add to
Details
Small Cheval- Wicker Park
@Quiera
Stop optional if you are't hungry they do have a few beers, and milkshakes. But the burgers are good, and inexpensive.
Add to
Details
Noisette
@Quiera
Technically not on Milwaukee Ave, but its the wine bar inside of the wine shop 'Red & White Wines' Grab you a white wine, maybe some bubs' and enjoy their patio and the sun. Maybe grab some oysters and tinned fish.
Add to
Details
Snakes & Lattes Chicago
@Quiera
Play games, get your drink on, get your second wind with an espresso shot. They also have trivia nights.
Add to
Details
Beautiful Rind
@Quiera
Another wine bar, has a few tables on the outside facing Milwaukee, and you can also buy cheese, tinned, fish and wine inside. Also they offer classes, and speciality dinner events.
Add to
Details
Easy Does It
@Quiera
I've been told by multiple people to come here. Very chic, hip, they have a single serving pet nat that comes in a bottle that looks like a high life can. You get the vibes. Not too much in terms of food. Also a no & low cocktail list.
Add to
Details
The Pink Squirrel
@Quiera
Old School drinks, boozy shakes, and a small bowling lanes. While you're there get the booze ferris wheel.
Add to
Details
The Welcome Back Lounge
@Quiera
Kitschy and cute. And the food is tasty too. Fun drinks.
Add to
Details
The Native
@Quiera
Cash only dive bar, big patio in the back. Also they have Malort cocktail you should try, if you like Malort that is.
Add to
Details
Estereo
@Quiera
One of my favorite bars when its warm out. Open garage style windows, a DJ, discoball in the bathroom, frozen drinks. Good times.
Add to
Details
BiXi Beer
@Quiera
Fantastic Chinese, Vietnamese, and Korean inspired food. They also brew their own beer, so stopping in for drinks only works too. The vibe downstairs is more swanky, upstairs though it is more casual.
Add to
Details
Andros Taverna
@Quiera
One of my favorite restaurants in the city. Brunch fire, dinner fire. Highly recommend. In case you didn't eat at the other stops along the way. You won't be disappointed.
Add to
Details
Websters Wine Bar Chicago
@Quiera
If you're still standing. aka, you paced yourself this is the last stop right after the park. Yes, another wine bar! Then you can get on the train, or call an uber.
Add to
Details

Photo Ops Along The Way

Quincy Jones Mural
@Quiera
If you've seen his documentary or if you're a fan you know that Mr. Jones is from the Southside of Chicago. There are other murals on this block as well.
Add to
Details
Robin Williams Mural
@Quiera
A must stop for Robin William's fans. Is a parking lot though so might be hard to get a full shot like the one pictured. There are lots of mural on this block.
Add to
Details
Greetings From Chicago Mural
@Quiera
Cute mural designed to mimic a post card is very cute. Multiple murals in this area.
Add to
Details

* * *
CURATED BY
Kiara Brown
Solo travel, bestie travel, Will travel for food. I went on my first adult vacation for my 21st birthday to New Orleans, and was hooked ever since then. Years of experience in boutique and luxury hotels, as well as Travel Operations. I offer customer itineraries, and travel planning services.
Feeling overwhelmed?
Thatch can help.
Send a request and we'll handpick a list of Thatch-verified travel creators who would love to help with your trip.
No request is too big or small...
"Research places for beach trips this winter."
"Help me plan a romantic getaway to Milan."
"Find and book kid-friendly activities in Paris."
"Curate a walking tour of historic Berlin."
"Suggest wineries worth visiting in Napa."
You can relax now :)
Person laying on a bed relaxing
Powered by Thatch
The home for unique & authentic travel
Powered by Thatch: Where great trips are made.
© Kiara Brown Privacy Terms