Ask ChicagoNow: What is the best street in Chicago?

Ask ChicagoNow: What is the best street in Chicago?

ChicagoNow is a group of bloggers from all sorts of different backgrounds. One thing that helps tie them all together? Chicago.

With so much collective experience with the city, we’ve decided to put that knowledge to use by posing some of the oldest and most popular questions about Chicago to the group.

What is the best street in Chicago?

“Hawthorne Place between Lake Shore Drive and Broadway for its homes. West Randolph Street for its atmosphere and great restaurants.” — Carole Kuhrt Brewer, Show Me Chicago

“Clark street in Andersonville”. — Jayson J Crady, Confessions of a Coffeholic!

“No contest: Lake Shore Drive. There is a whole song about it!” — Kim Z. Dale, Listing Beyond Forty

“Devon!” — Julie VonderHeide Hammerle, Hammervision

“100th Street, where I grew up. It’s like many other Chicago streets. I lived across the street from school, surrounded with great friends. Walk down the hill to Fox’s Pizza with the family. Walking distance to CTA, work, parks. Neighbors stopped by to say hello, admire our dad’s antique cars and his welding ‘artwork’ in the backyard.” — H. Van Howe, Pizza For Breakfast

“I’m a big fan of Milwaukee. It just goes through a whole lot of stuff. It has been gentrified like crazy, and lost some of the quirk it had at one time or another, but it’s still a pretty cool place to be depending on where you are. From Richard’s at the very foot of it, the only ‘smoking’ bar in Chicago (I think?) to all the weird, cool polish places further northwest, to wherever it ends, Alaska?” — Brian Kremen, ConFIdences

“Wabash Avenue downtown, in and out of the Loop, is best because it has a mix of jewelry stores, department stores, and boutiques, but it still works at other jobs, from medical offices to apartments. Beside all that, it’s time Wabash gets some attention between the glitter of Michigan Avenue and the busy-ness of State Street.” — Margaret Laing, Margaret Serious

“Love Wacker and LSD, but there is a little gem way up north called Eastlake Terrace. It is a sweet little street just south of Evanston and east of Sheridan right on the lake. Hidden and lovely.” — Mary Tyler Mom

“I was gonna say Milwaukee but instead I nominate The boulevards”. — Michael Messinger, Mysteries of Life

“I truly enjoyed Rush Street as a teen! Rubus Game Room, Mrs. Field’s Cookies, and shopping for the latest album at the record store (can’t remember the name) were the highlights of my weekend!” — Sabrina Nixon, Purple Reigns: How to Live a Full Life with Lupus

“As a suburbanite who loves the city – but still don’t know it as well as someone who is there more than me – I LOVE LSD – When it’s not rush hour, to me there’s nothing like a sunny day driving down that drive. I like Michigan Ave, too.” — Colleen Boland Sall, Raising Teens Right

“I have several favorite streets for different reasons: there are Lake Shore Drive and Sheridan for beauty, Elston for drivability (except for the part between Western and Logan), Lawrence for diversity, and Pulaski simply because of Andrew Bird’s song.” — Angela Soriano, less than perfect

“Lincoln Avenue, from where it begins at the northern end of Wells all the way to Lincoln Square. It could be the most eclectically Chicago street in town. Wonderful vintage townhouses, theaters (including the historic Biograph where Dillinger went to the movies, set up by the Woman in Red, and was gunned down by federal agents in the alley just south of the theater), lots of nightlife, restaurants (from diners to more upscale boites), bars (from dives to the very nice) and historic Chicago retailers such as Dinkel’s Bakery and Paulina Market. The beautiful Avery Brundage “flatiron” building near School Street. The L crosses over Lincoln, what? 4 times at least — near Armitage, Roscoe, Addison and north of Wilson at the Western stop. The newly restored Davis Theater near Wilson. The Old Town School of Folk Music. Lots of fun shops, resale shops, gift stores. An improv theater near Berteau. And Lincoln Square with one of the last old school German restaurants, a French bakery, a German deli (the one that replaced Meyer’s — they have the Meyer neon sign mounted on a wall), the Book Cellar where you can shop for books while sipping a glass of wine, a gourmet kitchen store, a shop with unique olive oils, vinegars, wines and spirits out of casks, a fun toy store (there’s another great toy store north of School Street), and Merz old-timey apothecary shop. What am I missing. Lincoln Avenue has just about everything!” — Floyd Sullivan, Waiting4Cubs

“The best street in Chicago is Wacker Drive. It’s a beauty, running west from Lake Michigan following the Chicago River as it curves along the south branch. Walk past the historic movable bridges and bridgehouses, Merchandise Mart, Wrigley Building and Marina Towers with the Aqua building and Willis Tower peeking through. Architectural tour boats, water taxis and kayaks, along with the new Riverfront green spaces below, make me swell with pride and say, ‘Yes, this is my Chicago.'” — Very Terry

“Alta Vista Terrace is just steps from Wrigley but it feels like stepping back in time – and it’s an architectural marvel. Each house on one side of the street is essentially the mirror image of the house diagonally opposite it on the other end of the block. Samuel Gross built it over 100 years ago after being inspired by the Mayfair neighborhood of London, but it still feels uniquely Chicago to me.” — Shannan Ball Younger, Between Us Parents

“Wells Street for Old Town things or Taylor Street for the food!” — Jayme Ryan Zobel, Life: One Post at a Time

If you have a question about Chicago that you want answered, email it to Think you have the answer to the above question? Let us know in the comments below.

Lead image via Alyssa Pointer/Chicago Tribune

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