How to have a support-small-business-only day on Southport

Southport Corridor is an adorable nook in Lakeview that sits just west of Wrigleyville. Known for its walkability and the use of old buildings as mixed-use restaurants, retail and living spaces, this place is a haven for families looking to have a day out.

One of the main complaints of this area from many residents in the city is that with highly-appreciating property values has come an outplacement of local shops and restaurants in favor of national chains. I met someone who lived nearby who whenever they went out would play the game called, “What local shop or restaurant closed today?” And while sometimes it’s nice to be able to rush into The Gap (because somehow your toddler has outgrown all of his pants in two weeks), supporting local businesses is a vastly important piece of the economic puzzle, too.

This is why I’m here to help you. Though this is becoming an increasingly difficult task with the ever-increasing proliferation of J.Crew and SoulCycle-esque shops that continue to make Southport feel more like an outdoor mall, you can have a small business-only day that is not only enjoyable but gives you that locals-only-yes-I-bring-my-Small-Business-Saturday-tote-with-me-to-shop-why-do-you-ask smugness that you so crave in the city.


There are a multitude of family-friendly, non-chain options on Southport, many of which offer a kids-eat-free deal from 4-6 p.m. (Crosby’s Kitchen and Tuco and Blondie are two such options). Here are a few that are especially crowd-pleasing to the younger crowds.

Bodega Sur

An offshoot of the date night favorite Argentinian steakhouse Tango Sur three doors down, Bodega Sur is more casual yet still offers some of the delicious items found at Tango Sur. Their brunch is almost indescribably delicious, and they also offer an impeccably curated wine shop that specializes in South American wines right in the restaurant with wines starting at anyone’s budget.

3755 N Southport Ave.

Cafe Tola

My family has recently discovered the beauty of empanadas. They’re hand-held, cheese-filled (typically) portable pockets of deliciousness. My 2-year-old adores them almost as much as I do, and Cafe Tola is like a beacon of doughy deliciousness at the corner of Southport and Addison. There isn’t much seating so takeaway is a must.

3612 N Southport Ave.

Coalfire Pizza

I know, I had you at “pizza.” Coalfire offers thin-crust coal-fired pizza that is delectable and comes out super quick. The servers are always willing to offer suggestions and guide your selections. Add to that a large rotating tap list and you’ll be happy for days after.

3707 N Southport Ave.


Explore and Much More

If the weather doesn’t agree with an outdoor play date (ahem, Chicago, ahem) head on over to Explore and Much More for two floors worth of indoor fun. On weekdays, your little ones can also enjoy a music class or arts and crafts included in the price of admission.

3827 N Southport Ave

Margaret Donahue Park

Known around town to parents as “The Cubs Park” because of the giant Cubs logo emblazoned on the astroturf lawn, this new(ish) park has structures for all age groups, a splash pad in the summer, and plenty of room to have picnics as well.

1230 West School Street

Southport Lanes

As someone who can repeatedly vie for the title of “World’s Worst Bowler” the fact that I would recommend bowling means this place is something special. From the old-school feel and the incredible bar menu to the fact that the pins are placed by hand, a trip to Southport Lanes could potentially make you insufferable after because all you’ll want to do is tell people about it.


Two Hearted Queen

Yes, there is a Julius Meinl and a Starbucks available on Southport but I urge you to resist! The folks at Two Hearted Queen are located just two blocks East at Racine and Roscoe and serve up the most delicious brews and beverages known to man.

1201 West Roscoe Street


Admittedly, shopping locally on Southport is getting harder and harder these days, but don’t despair, there are still some local gems available!

Uncle Dan’s Outfitters

Neither snow nor rain nor sleet nor sun nor anything will stop you from getting what you need to face the outdoors at Uncle Dan’s. The salespeople are always willing to help you and you’ll be hard-pressed to find a better selection of apparel and accessories for any outdoor adventures for any age group.

3551 N Southport Ave.

The Red Balloon

If you’re up for a bit of a splurge, head straight over to The Red Balloon for some of the cutest kids’ clothing, books and toys around.

3651 N Southport Ave.

She One Boutique

Nestled between Lululemon and Anthropologie is this adorable shop offering a great selection of on-trend clothes (at reasonable price points to boot!). The shop owner is always willing to help you find anything you want and help you with anything you need.

3544 N Southport Ave.

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