Top Bars In Chicago’s Old Town

Old Town Ale House is easily the best bar for people watching. With its laid-back, divey ambiance this bar is full of regulars. Ale House has a prime location across from The Second City, and it’s also regularly open until 5am. Eccentric art adorns the walls and some of the people featured in these paintings are the local regulars that come so frequently, they’re featured in the bar. Although it’s cash only, the funky vibe is worth seeing, especially if you’re there late enough, the Chicago tamale man will be selling homemade delicious tamales.

Woodie’s Flat is an extremely lively, two-story spot with a collegial vibe and a creative menu with hefty nachos and wood-smoked burgers. Woodie’s is notorious for hosting the post game beers for those participating in team sports over on North Avenue Beach. The burgers are highly recommended because of the variety ranging from the savory favorites: ‘Mac Attack’, ‘Smoke House’, and the ‘Windy City’. This is generally a favorite because of the great music and the wide open windows on the second floor!

This upscale bar is full of pub food and a massive beer list that’s served in a cavernous space with a mezzanine. Old Town Pour House is an ideal spot to watch a game with a large group of friends, as there are plenty of screens in all directions. It’s highly recommended to try the beer sampler, the mac and cheese, and the fried pickles. Although there are only specific nights of the week to make a reservation, it’s a good idea because of the prime location on Wells St., which leads many passing by to wander in. This is a great bar for sports games and football season.

The VIG is a trendy, hip, warehouse-style spot with gastropub food, craft beer, and unique cocktails. In addition, there are multiple TVs and sports-themed art, meaning this is a place for everyone. The VIG recently opened in 2015, and it has been packed from open to close. The food deserves five stars because of the variety. Favorites include the mozzarella stuffed meatball, the turkey burger, and the brunch specialty: the skillet cinnamon roll. The decor is fun and chic, and they even take reservations.

Known as a trendy, lively sports bar, Benchmark is exceptional because of its retractable roof in the summer months. Even better, Benchmark offers daily food and drink specials. There is a wide variety of food available (ranging from ahi tuna tostadas, salads, skillet cookies, etc) and also gives the customer an option to do take-out. With an ever changing menu, the chef makes an effort to please the customers with new additions. Benchmark will make your Mondays a thousand times better with their $5 burgers and $6 22oz pours!

Long-running hangout for Iowa State and Second City fans, Corcoran’s is known for its rotating food and drink daily specials. You can always get a deal here and Corcoran’s even watches out for the Second City students because they give discounts to the Second City Training Center students that bring their IDs! The food favorite are the wings (because of their exceptional size and crispy exterior) and the brownie with Jameson ice cream. Finally, this bar is open until 2am every week night.

This tavern is known for their barbecue ribs and their oversized vodka-lemonades. It’s important to note that the 32oz or 44oz vodka lemonades are half priced on Thursdays, and come in multiple flavors like sweet tea vodka or honey whiskey. They also serve $5 mimosas and $5 Skyy bloody mary’s on Sundays. The Fireplace Inn was recently renovated and now has an upgraded, spacious interior. Their happy hours run from 5pm to 7pm every weekday with impeccable deals like $2 sliders and $3 beers! Overall, a great place to hang out whether you’re 21 or 81.

The go-to Notre Dame bar in Old Town, Declan’s Irish Pub is the best spot to snag a beer or fried pickles! With a dark interior, this lives up to the pub feel, and even has a tin ceiling. The customers rave about their fried pickles because the chef makes them with a bread crumb recipe instead of the usual beer battered recipe. To go with the Irish theme, it’s a fantastic spot to grab a Guinness and any beer on draft. On Wednesdays, Declan’s has one of the most entertaining trivia nights in Old Town, and you don’t have to be an experienced trivia guru to participate.