The Magnificent Mile is Chicago’s self proclaimed “premier commercial district.” It is Fifth Avenue mixed with Rodeo Drive. It’s as if London’s Oxford Street was an extension of high end Bond Street shopping. Throw in the world’s largest Starbucks, and you can see why shoppaholics flock from around the world for this mile stretch of luxe shopping in Chicago.
I know I’m kind of selling it here, so I digress.
Think about it this way — if you’re in New York, you’ll never get a sense of the city by staying in midtown the entire time. Yes, you should see Fifth Ave, but if you want an authentic New York shopping experience you’d head to Soho or the villages, or a classic NY sample sale. The same goes for Chicago. As soon as you get away from the Loop and River North, you’ll begin to get a feel for the distinct personalities of each neighborhood.
All of the below recommendations have three things in common: local small businesses, great restaurants to fuel up, and easy access to the ‘L’.
Southport in Lakeview
Take the Brown Line to the Southport Stop
If you are at Wrigley, you can alternatively walk west on Addison for three blocks until you reach Southport. That will bring you to the top of the shopping district and allow you to walk south until you reach the Southport Brown Line, which can easily take you to your next Chicago destination.
Typically the only reasons tourists find themselves this far from the Loop is to catch a game at Wrigley Field. Just a few blocks west of Wrigley, is Southport Avenue. If you’re in the Wrigleyville area and want to buy something that’s not blue, red, or white, head over to Southport.
Shop Local on Southport
- Alice & Wonder
- Krista K Boutique
- Batik
- The Denim Lounge for Men
- Aura Candle Bar
- Three Avenues Book Shop
Shop Brand Name on Southport
- Lululemon
- Anthropology
- Free People
- Abercrombie
- Benefit
- Bonobos
- Lush
- Gap
- Athleta
- J-Crew
- Sephora
- Blue Mercury
- Kendra Scott
- Warby Parker
Where to Eat on Southport
- GG’s Chicken Shop
- Coda Di Volpe
- Little Goat Diner
- Tuco and Blonde
- Southport Grocery & Cafe
- Corridor Brewing
- Itoko
- Crosby’s Kitchen
- Tango Sur
- Jeni’s Ice Cream
- Cafe Tola
- Steingold’s Bagels
Armitage in Lincoln Park
Take the Brown Line to the Armitage Stop
The historic brownstones of Lincoln Park sit on tree-lined streets perpendicular to Armitage Avenue. Lincoln Park draws a mixed crowd of young professionals and young families — keep an eye out for strollers, dogs, and Lululemon clad yogis heading to and from the many boutique fitness classes in the area. Armitage is the perfect street to stroll on a Saturday morning with a coffee in hand — I’d suggest making Foxtrot Market or La Colombe your first stop for coffee.
If you’re not from the area and looking for souvenirs or a hostess gift, Lincoln Park is dotted with cute local boutiques that feature Chicago apparel and gifts that locals love. The main shopping strip of Armitage is pretty condensed between Sheffield and Halstead. Head east from the Brown Line stop to start your shopping. Once you reach Halstead, you’ll hit a number of local restaurants for brunch, lunch, or dinner.
Shop Local on Armitage
Shop Brand Name on Armitage
- Lush
- Kiehl’s
- Gorjana
- Benefit Cosmetics
- Marine Layer
- Margaret Oleary
- Aesop
- Allbirds
- Warby Parker
- L’Occitane
- Bonobos
- Outdoor Voices
- UpWest
- Jenni Kayne
- Indochino
- The Tie Bar
Where to Eat near Armitage & Halstead
- Beacon Doughnuts & Herb-N-Juice
- Summer House Santa Monica
- Cafe Ba-Ba-Reeba
- Blue Door Farm Stand
- Ramen-San
- Willow Room
- Athenian Room
- Jeni’s Ice Cream
Milwaukee & Damen in Wicker Park
Take the Blue Line to Damen
Wicker Park to Lincoln Park is East Village to West Village of New York.
Milwaukee has a little more grit to it than Southport or Armitage, in the best way. Here you’ll find quirky cafes, vintage and thrift shops, even a grand old bank converted into a Walgreens — worth a stop just to see the basement vitamin vault.
Kick start your shopping at The Wormhole, a local coffee shop that gives a nod to all things 80s, complete with a full-sized DeLorean. Hey, I warned you it’d be quirky.
Shop on Milwaukee
- Myopic Used Bookstore
- Volumes Bookcafe
- Adidas Originals Flagship Store
- Store B Vintage
- Crossroads Trading
- Ragstock
- Buffalo Exchange
If vintage clothing isn’t quite your style, Bucktown still has a street for you. At the six corners intersection where Milwaukee, North, and Damen meet, take Damen north towards Bucktown for elevated, but approachable, shopping in Chicago.
Shop on Damen
- Benefit Cosmetics
- Shinola
- Lululemon
- Scotch & Soda
- Marine Layer
- Aesop
- Oak + Fort
- Journelle
- Lush Cosmetics
- Club Monaco
Eat near Milwaukee & Damen
- Piece Brewery
- Etta
- Big Star
- Dove’s Luncheonette
- Bongo Room
- Stan’s Donuts
- Brobagel
- Brü
- Goddess and the Grocer
- Mindy’s Bakery
