A Joyous Journey Down Milwaukee Avenue!


I recently drove down Chicago’s famous Milwaukee Avenue, all the way from Lawrence Avenue down to North Avenue.  Since Milwaukee runs at an angle, there are dramatic urban spaces formed every time there is a major cross street, with several spots along the length of Milwaukee Avenue having a “Six Corners” layout where three major streets all come together.

 These six-corner intersections become a hub for the best restaurants and theaters and cafes, which in turn brings up the value of the real estate nearby.  People are drawn to these areas, and the City has joined in as well, scheduling several street festivals this summer along the length of Milwaukee Avenue.

Here are just a few of the attractions one can see along the way!

We’ll start with the Gale Street Inn, a block North of Lawrence Avenue, holding a prominent place in the Jefferson Park neighborhood.  It was transplanted from the heart of the Loop, going from serving business lunches in the late Seventies to serving up some of the best ribs in town in Jefferson Park today!


Then you head Southeast down Milwaukee towards the famous Six Corners intersection where Cicero, Irving Park, and Milwaukee come together.  But not so fast!  Just before you get to Six Corners you'll find Chicago’s largest costume shop, Fantasy Costumes, which has occupied a full city block for over 45 years, serving as Chicago’s Halloween headquarters.  A little farther down you’ll see the beautifully restored Portage Theater, showing classic movies in an elegant setting.  Don't miss the Monster Film Festival or Svengoolie will be knocking on your door!!


Here's a newer development at the Six Corners intersection and a picture of the Sears building that has been there for years!


The next Milwaukee hub is Logan Square, where Kedzie, Logan Boulevard, and Milwaukee come together.  Just before you get there you’ll see the landmark Logan Theater, then the Logan Square restaurant and business district.  Here you’ll find some of the best Cuban cuisine in town!

The intersection of Armitage, Western, and Milwaukee is notable for the Congress Theater but also it’s the location of the Chocolate Lover’s Jewel of Chicago, namely Margies Candies!  Besides being one of the last places in town where you can get home made ice cream and amazing hand made chocolate sodas, it’s also where the Beatles went for dessert after their two Comiskey Park concerts in September of 1964!

Finally, we reach the part of Milwaukee Avenue where the restaurants are so good I’m going to stop my tour right here!  Yes, the corner of North, Damen, and Milwaukee, also known as Wicker Park, has one of the best concentrations of all types of cuisine in all of Chicago.  In the picture above the famous Flatiron building is the middle building, where the artists who triggered the renaissance of the whole Wicker park area once lived.

Well, I hope you enjoyed our little tour.  As you can tell, you’ll never run out of fun places to visit along the famous boulevards of Chicago!



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  • I love your post. I have been in love with Milwaukee Ave for years. I love hanging there and finding a new restaurant to enjoy. It is always a unique experience and great hangout spot on lazy weekends. Great Post!

  • Good to see this information video.

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