Top 10 Bars In Chicago’s Old Town

© Paul Joseph/Flickr
© Paul Joseph/Flickr
Photo of Katie Mastropieri
9 February 2017

Old Town is full of live entertainment ranging from Second City to Zanie’s Comedy Club, but it’s mainly popular because of its close proximity to the Loop, North Avenue Beach and shopping in Gold Coast. Furthermore, Old Town has a phenomenal variety of bars and restaurants that feature bottomless mimosa specials, the legendary tamale man, and even shots of the infamous ‘Malort’.

Old Town Ale House

Bar, Pub Grub
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Old Town Ale House, Chicago
Old Town Ale House, Chicago | © victorgrigas/Wikicommons
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.

Wells on Wells

Bar, Pub Grub, $$$
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This neighborhood bar is known for its back patio and beer garden. Even in the colder months, there are heaters set up so that people can enjoy the outdoor seating. Wells on Wells also serves drink specials every night of the week. This is a fun place to watch the game and have beers with friends. Even better, the food menu is divine! Customers rave about their blackened chicken wraps, turkey burgers, and their cheeseburgers on the pretzel bun. Another neighborhood hot spot that’s located across from The Second City!

Old Town Social

Further from Wells Street, Old Town Social is known for their fun cocktails and fantastic food with an upscale ambiance. This American menu features favorites like tasty pretzel bites, pork belly sandwiches, and mac and cheese. The interior is considered ‘upscale’ for Old Town because of its swanky velvet furniture. It has been noted that customers love their beer flights on draft, because it’s three tastings for only $10!

Old Town Social, 455 W North Ave, Chicago, IL. USA(312) 266-2277

Woodie’s Flat

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!

Woodie’s Flat, 1535 N Wells St, Chicago, IL, USA(312) 643-0093

Old Town Pour House

Bar, Restaurant, American, $$$
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Outside of Old Town Pour House
Outside of Old Town Pour House | © Benita Gingerella
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.


Bar, Restaurant, Beer, Cocktails, American, Pub Grub, $$$
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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.


Bar, Pub Grub, $$$
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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!

Corcoran’s Grill & Pub

Bar, Pub, Restaurant, Irish, $$$
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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.

The Fireplace Inn

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 Fireplace Inn, 1448 N Wells St, Chicago, IL, USA(312) 664-5264

Declan’s Irish Pub

Bar, Pub, Irish, $$$
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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.