Barhopping Milwaukee Ave (Bucktown to Logan Square)
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 • ago
Free
eat
eat
The Robey, Chicago, a Member of Design Hotels
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.
Details
drink
drink
Gracie O' Malley's- Wicker Park
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.
Details
eat
eat
Small Cheval- Wicker Park
Stop optional if you are't hungry they do have a few beers, and milkshakes. But the burgers are good, and inexpensive.
Details
drink
drink
Noisette
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.
Details
drink
drink
Snakes & Lattes Chicago
Play games, get your drink on, get your second wind with an espresso shot. They also have trivia nights.
Details
drink
drink
Beautiful Rind
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.
Details
drink
drink
Easy Does It
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.
Details
drink
drink
The Pink Squirrel
Old School drinks, boozy shakes, and a small bowling lanes. While you're there get the booze ferris wheel.
Details
drink
drink
The Welcome Back Lounge
Kitschy and cute. And the food is tasty too. Fun drinks.
Details
drink
drink
The Native
Cash only dive bar, big patio in the back. Also they have Malort cocktail you should try, if you like Malort that is.
Details
drink
drink
Estereo
One of my favorite bars when its warm out. Open garage style windows, a DJ, discoball in the bathroom, frozen drinks. Good times.
Details
eat
eat
BiXi Beer
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.
Details
eat
eat
Andros Taverna
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.
Details
drink
drink
Websters Wine Bar Chicago
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.
Details

Photo Ops Along The Way

do
do
Quincy Jones Mural
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.
Details
do
do
Robin Williams Mural
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.
Details
do
do
Greetings From Chicago Mural
Cute mural designed to mimic a post card is very cute. Multiple murals in this area.
Details

Barhopping Milwaukee Ave (Bucktown to Logan Square)
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 • ago
Free
eat
eat
The Robey, Chicago, a Member of Design Hotels
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.
Details
drink
drink
Gracie O' Malley's- Wicker Park
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.
Details
eat
eat
Small Cheval- Wicker Park
Stop optional if you are't hungry they do have a few beers, and milkshakes. But the burgers are good, and inexpensive.
Details
drink
drink
Noisette
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.
Details
drink
drink
Snakes & Lattes Chicago
Play games, get your drink on, get your second wind with an espresso shot. They also have trivia nights.
Details
drink
drink
Beautiful Rind
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.
Details
drink
drink
Easy Does It
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.
Details
drink
drink
The Pink Squirrel
Old School drinks, boozy shakes, and a small bowling lanes. While you're there get the booze ferris wheel.
Details
drink
drink
The Welcome Back Lounge
Kitschy and cute. And the food is tasty too. Fun drinks.
Details
drink
drink
The Native
Cash only dive bar, big patio in the back. Also they have Malort cocktail you should try, if you like Malort that is.
Details
drink
drink
Estereo
One of my favorite bars when its warm out. Open garage style windows, a DJ, discoball in the bathroom, frozen drinks. Good times.
Details
eat
eat
BiXi Beer
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.
Details
eat
eat
Andros Taverna
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.
Details
drink
drink
Websters Wine Bar Chicago
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.
Details

Photo Ops Along The Way

do
do
Quincy Jones Mural
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.
Details
do
do
Robin Williams Mural
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.
Details
do
do
Greetings From Chicago Mural
Cute mural designed to mimic a post card is very cute. Multiple murals in this area.
Details