Best Happy Hour Restaurants in Woodlawn
2 hand-picked restaurants, critic-reviewed and ranked
Last Updated: February 2026
Our Top Pick
Truth Be Told
A Woodlawn pub that delivers British comfort staples with a polished bar vibe.
Notable Picks
8
A British-leaning pub where the most reliable orders stay in the comfort-and-classics lane rather than trying to force a big, scattered meal. Treat it as a composed brunch or casual dinner spot—one hearty main, one shareable, and you’re set.
Must-Try Dishes:
Fish and Chips, Shepherds Pie, Deviled Eggs
What Makes it Special: A Woodlawn pub that delivers British comfort staples with a polished bar vibe.
Worthy Picks
7.8
A South Side bar-and-grill built for later hours, with burgers that make the most sense when you’re prioritizing utility and staying power. Go for one of the named burger builds and keep sides simple so the kitchen rhythm stays predictable during the late push.
Must-Try Dishes:
Privilege Cheddar Burger, Bacon Jalapeno Burger, The Grill Thrill
What Makes it Special: A true open-late bar-and-grill with dedicated burger builds.