Timothy O’Toole’s is Streeterville’s go-to for game day. Highlights include creative mocktails and gluten-free options, alongside crowd favorites like the butter-glazed pretzel and saucy wings in flavors ranging from BBQ and buffalo to garlic parmesan and honey sriracha. Feeling bold? Try the Holy Water cocktail, a mix of 12 liquors and three juices. For something heartier, the shepherd’s pie blends Guinness beef stew, vegetables, Irish soda bread, and a parmesan potato crust.

An Irish pub with a chic twist, Kerryman pairs moody lighting and multiple floors with comfortable booths ideal for lunch or dinner with friends. Order the corned beef sandwich with truffle fries, or opt for shepherd’s pie. Friday nights call for the $15 fish and chips special. Behind the bar, you’ll find old-fashioneds, Irish coffee, and perfectly poured Guinness. Weekend brunch features authentic dishes from Chef Damien, plus Bloody Marys and mimosas.

Lizzie McNeill’s blends Chicago staples with Irish favorites. The patio is a prime summer perch for a pint in the sunshine. The menu ranges from bangers and mash and lamb stew to nachos and Chicago dogs. Explore the Irish whiskey list or order a classic Guinness and enjoy the laid-back waterfront setting. P.S. The patio is dog-friendly, so bring your pooch for lunch!

A River North mainstay for more than 30 years, Brehon Pub delivers classic neighborhood bar vibes, complete with pool tables, darts, and friendly service. Pair a Guinness with fish and chips, a pub burger, or one of the indulgent mac and cheese variations, including buffalo chicken, chili mac, spinach artichoke, or the classic topped with garlic breadcrumbs.

Steady crowds, lively bartenders, and a jukebox turned up loud make O’Callaghan’s feel like an instant favorite. Order a draft Guinness, challenge friends to a round of pool, and dig into comfort-forward plates like shepherd’s pie, a wagyu Guinness burger, or Italian beef egg rolls. It’s just as fitting for a casual meet-up as it is for a solo stop at the bar.

Daily specials and happy hour deals keep the Emerald Loop Club buzzing. Look for discounts on domestic buckets, cider buckets, and classic cocktails, then grab a high-top or patio seat. The menu features Irish staples such as corned beef, sausage rolls, and an all-day Irish breakfast. Weekend brunch adds corned beef hash, steak and eggs, and plenty of mimosas.

In Chicago’s South Loop, Kitty O’Shea’s pairs classic Irish hospitality with thoughtful, farm-driven fare and perfectly poured pints. Kick off the weekend with a hearty Irish brunch and a cup of Sparrow Coffee, or stop in any day for burgers, whiskey flights, and staples like fish and chips. Steps from Soldier Field and near Grant Park, it’s an easy gathering spot before or after exploring the neighborhood’s museums, green space, and arts scene.

Steps from Guaranteed Rate Field, Cork & Kerry is a favorite before and after White Sox games. In summer, the brick-walled beer garden fills with live music and cold drafts. Choose from the rotating tap list and snack on corned beef egg rolls, oversized burgers, or wings while soaking up the post-game crowd.

This old-school Lakeview favorite draws a loyal following, especially among Ohio sports fans, and is known for one of the city’s best Guinness pours. Try a Dublin Sour made with Irish whiskey, then order a tavern pizza or giant pretzel for the table. When the weather cooperates, grab a seat outside or settle in indoors to watch the game.

If you’re a soccer fan, AJ Hudson’s is a must. The beer flows, the comfort food satisfies, and the match is always on. Stop by for Monday trivia or Wednesday karaoke, or simply come hungry. The fish and chips rival the city’s best, and the bacon French onion grilled cheese delivers serious indulgence.

D4 strikes the perfect balance between upbeat and snug, with a vibrant patio for warm days and a fireplace-lit interior when Chicago turns chilly. Start with cheese curds before diving into shepherd’s pie, fish and chips, or a stacked Reuben. A whiskey flight featuring Irish, Scottish, and Kentucky pours offers a tasting tour in one sitting. Visiting for brunch? The full Irish breakfast arrives loaded with sausage, eggs, rashers, black and white pudding, potatoes, and beans.