You’ve been hitting up the bars for a bit and have a solid buzz going. You’re thinking about calling it a night, but ready for one last stop and there’s got to be food. Pulling up Yelp, there’s not a lot options other than super greasy, but you’re looking for something a bit more upscale. Then you see it: Southport & Irving (SIP) has a late night brunch menu with drinks and live jazz.

Previously on The Chicago Traveler Visit to SIP

The last time the Chicago Traveler was at SIP for dinner a couple of months ago, we had a blast. The cocktail lounge and restaurant has an old school, speakeasy-type atmosphere with modern takes on classic cocktails and adventurous American food made with fresh, local ingredients. They also have rotating jazz acts play in the bar multiple nights a week. Altogether this restaurant is definitely a gem in the Southport Corridor.

This time around, we were charged with the difficult task of sampling the restaurant’s new late night brunch menu. There was a lot standing in the way from rescheduling due to pregnancy and then potentially having to fend off swarms of drunken Blackhawks fans partying it up after the morning’s rally and parade. Fortunately, the CTA was running fine and the only band of Hawks fans I encountered complimented my shoes.

Brunch Cocktails

While you’re still free to order from SIP’s huge cocktail list, they do have a special selection of cocktails intended for (early) morning consumption. To start, I went with the Green Michelada, which from the menu description sounded pretty nuts (watermelon wheat ale, red bell pepper and coriander tequila, wasabi, tomatillo, and roasted poblano).

The best way to describe the Michelada is like a really spicy Bloody Mary minus the thickness and flavor of the tomato juice. It’s not a heavy drink and the watermelon flavor provides a bit of lightness, but overall this a kick-in-the-pants kind of cocktail designed to wake you up.

I was looking for something a bit less intense and more refreshing, so I went with the Shakedown based on a recommendation from my server (who was excellent and very attentive). Pretty much the opposite of the Green Michelada– the Shakedown mixes dry gin, lavender syrup, a bitter orange juniper extract, and cava. Drinking the Shakedown makes you think you’re walking through a field of spring flowers. It’s not grossly sweet like a lot of fruity summer cocktails, instead charting some new ground by emphasizing floral flavors.

It’s Brunch Time

Looking at their late night brunch menu, SIP offers a balance of lunch and breakfast items while also understanding that at midnight a lot of people are just looking for a juicy cheeseburger.

Shrimp and Crawfish Cocktail

For an appetizer, I went with the laughing bird shrimp and crawfish cocktail. The presentation here was pretty eye-catching with the “cocktail” served to look like it could have been a Bloody Mary with chips on the side reinforced with Clamato and tequila inside the glass. Also inside were lots of small shrimps and crawfish with plenty of fresh vegetables. Other than the glass, I’d think of this as more a complex seafood salsa.

My server described the chips’ seasoning as tasting like “Cool Ranch Doritos” and that’s a pretty accurate description albeit a little more refined and the chips were better. The corn style chips were hot and crispy while still having a bit of softness to them.

Chicken and Waffles

I loved SIP’s spin on the brunch staple. The waffles are gluten free (a corn and oat mix) that still managed to be light and fluffy with a bit of a crunch; helping to soften them up was a honey cream sauce. On the chicken end, there were two gigantic thighs fried in buttermilk with a crunchy, dark exterior and tender dark meat on the inside. To make life even more decadent, there was a “game changing” molasses syrup. Eggs and gravy are available on the side, but be warned this is a huge plate of food on its own.

Bottom Line

Served from 10:00 p.m. to 1:00 a.m. Thursday through Saturday, SIP provides a compelling alternative to the typical late night food night options. The portions are big, the price is right, and there’s live music and unique cocktails. I’ve had two solid experiences at Southport & Irving now and hopefully I’ll be able to make it back for their regular brunch sometime soon.

Southport & Irving ( SIP )
4000 N Southport Ave, Chicago, IL 60613
(773) 857-2890


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