Located in Lakeview’s Southport Corridor, Southport & Irving (SIP) is a classy yet relaxed cocktail bar and restaurant taking inspiration from the days of speakeasies and jazz clubs giving it the feeling it’s been around since the days of Capone and Machine Gun McGurn. Their cuisine, though, is quite hip and modern, injecting world flavors into American mainstays. SIP also stands out from the Southport restaurant pack by offering live jazz in their bar Thursday through Saturday.

General Atmosphere

Perfect for fans of Mad Men, SIP has a classic feel to it with its leather seats, ornate ceiling, and stained glass windows that’s livened up by the modern art aligning the exposed brick walls. The establishment is divided into two rooms with the cocktail bar in one and dining room in the other. There is also an outdoor sidewalk patio space for when the weather cooperates.

At least on a Thursday night, SIP is a lot less chaotic and much more chill than other hip, “throwback” restaurants like RL and lacking in the “pretensions” of other cocktail, speakeasy-influenced bars like Wicker Park’s Violet Hour (not to knock those places). Judging by the other diners, SIP offers enough atmospheric variety to appeal both to older and younger people. SIP can act as both a classy date and a nice place to take your parents.

Thursday, Friday, and Saturday the bar features differently-themed live jazz. Thursday night stars vocal jazz Chicago mainstay Elaine Dame while Friday’s performance is more speakeasy themed and Saturday takes inspiration from Ernest Hemingway (you can see their full jazz lineup online).


Don’t come to Southport & Irving if you’re looking to get in and get out. While it’s not painfully slow, the staff and kitchen operate on a more relaxed pace that matches the cool jazz atmosphere. This is where you come to make an evening of it. Order a couple drinks, eat your food, and then head over to the bar to hear some jazz while sipping an after dinner cocktail or glass of wine.

My waiter was excellent, offering suggestions based on personal tastes and explaining what flavors I could expect in certain entrees. The bartender was also around frequently to give drink recommendations and to see if I needed anything else.


While they do have a large wine and craft beer list, SIP definitely specializes in cocktails. They highlight different drinks to go with the different jazz nights and drinks are rotated seasonally. Upon recommendation, I tried their Spiced Old Fashioned. It was more on the bitter side, but the use of Chinese 5 Spice Bitters gives it a kick you don’t find at other bars.

Cherry Rickey at sipThe best was the Cherry Rickey, served in a tall, bubbled depression-style glass (SIP really excels thanks to all these little details). It’s on the sweeter side with a strong cherry flavor that feels fresh and lively.


Like the drinks, SIP changes their menu seasonally (it was the “Late Winter” menu while I was there). The entrees are a bit pricey, hovering close to the $30 mark, but diners on a budget could get by sharing a couple small plates and sharing an entrée. Everything I tried had rich, complex flavors and beautiful presentation:

Poached Lobster and Coffee Cured Bacon

If this sounds like the best thing, it is. This creamy appetizer centers on cheesy grits and packs in a world of flavor with mushrooms, bacon, and bits of lobster. It’s small, but the richness of the grits makes it easy to share.

Baby Kale Caesar

I can admit I’m not a big salad fan, but I can get behind this one. SIP’s Baby Kale Caesar contrasts fresh, zesty flavors with savory. The freshness is in the form of the kale and the Meyer Lemon dressing that gives the zesty lemon taste without the sourness. On the savory side, there was a small quail egg sitting on the top and this amazing, smoky bacon resting within the kale. Bacon fans are going to crazy for this.

Study of Winter Vegetables

My companion had the “study” as her entrée. Served beautifully on a long, slim plate, SIP has layered squash gnocchi, crispy Brussels sprouts, pear, and a parsnip cream that’s a nice compliment. This was described to me as “warm winter happiness” and “like sitting in front of a fire.”

Hanger Steak

On the advice of my waiter, I went with the hanger steak and wasn’t disappointed. Hanger steaks can be tough to cook without ending up horribly tough, but that wasn’t the case here (I recommend going medium rare at the most). A well spiced, slightly crunchy exterior gave way to juicy, tender beef surrounded wonderful, creamy Sunchoke mashed potatoes that still had pieces of skin left in. This is a classic dish done right.

Bottom Line

With its classy and cool ambiance, exciting food, and clever cocktails, SIP is a true Lakeview highlight. Chicago restaurant trends come and go as quickly as the weather changes, but SIP impresses me most for doing their own thing and carving out a unique space in the neighborhood.

dessert at Southport & Irving

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


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