Italian
Bar La Grassa
The North Loop happy hour by which all others get measured. Half-price bruschetta board, five-dollar wines by the glass, a bar room that fills exactly at 4pm for a reason. The soft egg and lobster bruschetta has earned a place on a thousand best-bites lists.
Gavin Kaysen, upscale
Spoon and Stable
Gavin Kaysen's flagship turns into the best deal in the metro from 4 to 5:30. Dollar oysters, half-priced burger, half-priced wines and beers. Fine-dining service at bar-tab prices for ninety minutes a day.
Seafood, lobster rolls
Smack Shack
The North Loop lobster shack runs one of the better-priced happy hours in the neighborhood: six-dollar taps, wines, and rails, plus a serious bar-snack menu that goes from oyster shooters to chowda fries to a half-dozen oysters for eighteen. Order the Shack Mule and the chowda fries and you have spent twelve dollars well.
Cocktail bar, bar snacks
Borough / Parlour Bar
Two rooms at one address: Borough upstairs for the full dining room, Parlour in the basement for the bar. Happy hour runs Monday through Friday from four to six with two dollars off drafts, house cocktails, and wine by the glass, plus ten dollars off any bottle of wine. The mushroom arancini and bar nuts are the move.
Bar, pizza
The Loop Bar + Restaurant
A long 4-to-7 window and three dollars off any pizza, which is the whole reason to come. The rest of the deal is two dollars off taps, rails, wine, and signature cocktails. On Monday nights the kitchen stays open for industry workers at 25 percent off everything until 2am.
Gastropub, in-house brewery
The Freehouse
A daily happy hour from two to six is rare enough to be the main selling point. The Freehouse backs it up with in-house brewed taps at six dollars, a Brown Sugar Old Fashioned for nine, and a patio that catches the late afternoon sun. Bring the dog. They have a dedicated dog menu.
Spanish, wine bar
Barcelona Wine Bar
Monday night is the secret: half-price bottles of wine from four in the afternoon until midnight, which is one of the best deals in the North Loop on the best night of the week for it. The Monday-through-Thursday afternoon window adds tapas specials to the picture. Pull the menu PDF when you visit to see what is on.
Cocktails and bar snacks at Butcher & the Boar
Char Bar
Daily happy hour at the small bar inside the Butcher & the Boar building. Four to six, every day, including weekends. Reasonable cocktails, snacks built for the program, and a room that knows exactly what it is.
Burger bar
Red Cow
The North Loop Red Cow runs Tuesday through Friday from two to 5:30: seven-dollar taps, seven-dollar wine, eight-dollar cocktails. The bar snack menu tops out at ten dollars. The eighteen-dollar Adult Happy Meal comes with a cheeseburger, small fry, and a classic cocktail, which is exactly as good an idea as it sounds.