Gale Street Inn Chicago
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06/10/2026
This is your sign to stop texting and start Happy Hour-ing.
Beer, wine & food specials $10 or less at Gale Street Inn.
Twice a day because we believe in second chances.
GaleStreetInn.com
06/04/2026
🍷 An Evening of Exceptional Wine & Dining 🍷
Join us on June 11 for a one-night-only wine dinner featuring the acclaimed wines of Pine Ridge Vineyards, perfectly paired with a specially curated multi-course menu.
Designed for wine lovers and food enthusiasts alike, each course has been thoughtfully crafted to complement the unique character of every pour—creating an unforgettable culinary experience from start to finish.
✨ Limited seating available
📅 June 11
🍽 Multi-Course Dinner + Wine Pairings
Reservations are strongly encouraged: https://buff.ly/nHiq2e4
Gather your friends, raise a glass, and join us for an evening worth savoring.
Wine Dinner - Gale Street Inn june 10, 2026
🎶 Live Music All Weekend at Gale Street Inn 🎶
Looking for the perfect soundtrack to your weekend? We've got four nights of incredible live music, delicious food, and all your Gale Street favorites.
🎤 Thursday: Natalie Scharf Trio
🎹 Friday: Frank Kurtz Trio
🎷 Saturday: Lee Rothenberg Trio
🎶 Sunday: Tom Vaitsas Trio
Whether you're kicking off the weekend with friends, planning a date night, or winding down Sunday evening, there's a seat, a cocktail, and a great tune waiting for you.
🍽️ Chicago's Finest Ribs
🎵 Live Music Every Weekend
🥂 Great Food, Great Drinks, Great Company
Join us for dinner and stay for the show!
05/29/2026
The new seasonal pierogi just dropped! Stuffed with cremini, maitake & button mushrooms & ricotta; served over a braised leek& lemongrass cream sauce with our homemade leek & red onion kraut. And topped with crispy maitake! 🤤
🎶 Live Music All Weekend at Gale Street Inn 🎶
The lineup is set and the weekend is sounding good at Gale Street Inn.
This Weekend’s Artists:
🎸 Thursday: Neal Alger Trio
🎤 Friday: Rick Sherry Trio
🎶 Saturday: Andy Brown Trio
🎷 Sunday: Sam Fazio Trio
From laid-back jazz and blues to Saturday night energy, every night brings a different vibe to the room. Grab dinner, order a cocktail, and settle in for a weekend full of great music and neighborhood charm.
🍽️ Dinner. Drinks. Live Music.
🎵 The perfect way to spend a Chicago weekend.
Reservations Recommended: GaleStreetInn.com
05/23/2026
PRIME RIB IS ON THE MENU!!!!!
Thank you to everyone who joined us at Gale Street Inn for our Cinco de Mayo celebration.
From authentic Mexican favorites to Gale Street classics reimagined with south of the border flavor, this was a night filled with incredible food, live music, cocktails, and great company.
We loved bringing these special dishes to the table and can’t wait to continue the tradition into next year’s Cinco de Mayo celebration, with even more chef curated Mexican inspired creations, signature Gale Street twists, and another unforgettable night at the Inn.
Gracias for celebrating with us. See you next Cinco de Mayo. 🇺🇸🇲🇽
And look out for our next themed event, “A Luau at the Gale!” More details coming soon. 🌺
galestreetinn.com
For one night only 🇲🇽
Gale Street Inn heads south of the border.
This Cinco de Mayo, we’re bringing bold, heritage-driven flavor to the table, vibrant dishes, rich spices, and a menu you won’t see again anytime soon.
Sizzling plates, strong pours, and a night built to celebrate.
Come hungry. Come thirsty. Make it count. 🇲🇽🍹
Reservations recommended: GaleStreetInn.com
🎶 Live Music All Weekend at Gale Street Inn 🎶
Four nights. Four incredible acts. One perfect weekend at Gale Street Inn.
This Weekend’s Lineup:
🎹 Thursday: Kurt Lubbe Trio
🥁 Friday: Gerald Dowd
🌎 Saturday: Maracujaz Trio
🎤 Sunday: Abigail Riccards Trio
Start smooth, turn it up Friday, and don’t miss Saturday’s Maracujaz Trio bringing vibrant, global rhythms to the room. Then ease into Sunday with rich vocals to close out the weekend just right.
🍽️ Dinner. Drinks. Live Music.
🎶 Your weekend soundtrack is ready.
Reservations recommended: GaleStreetInn.com
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Website
Address
4914 North Milwaukee Avenue
Chicago, IL
60630
Opening Hours
| Monday | 4pm - 11pm |
| Wednesday | 4pm - 11pm |
| Thursday | 4pm - 11pm |
| Friday | 3pm - 12am |
| Saturday | 3pm - 12am |
| Sunday | 3pm - 10pm |
