Gale Street Inn Chicago

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.

june 10, 2026

06/02/2026

🎶 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!

06/01/2026

🌺🍍 Escape to the islands—without leaving Chicago. 🍍🌺

Join us on June 10th for The Great Gale Luau at Gale Street Inn!

We're bringing tropical flavors, island-inspired cocktails, live entertainment, and plenty of aloha spirit to Jefferson Park for one unforgettable summer night.

🌴 Polynesian Inspired Food Specials
🍹 Tiki Cocktails
🎶 Live Entertainment
🌺 Island Vibes All Night

Gather your friends, dust off your Hawaiian shirts, and get ready for a midweek getaway you'll be talking about all summer.

Book your reservation today: https://buff.ly/GK3fTjG

A classic Chicago restaurant and tavern offering hearty American fare, timeless neighborhood hospitality, and supper club vibes, serving Chicago since 1963

05/31/2026

🌺🌴 The Great Gale Luau is coming to Gale Street Inn! 🌴🌺

We’re bringing the island vibes to Jefferson Park on June 10, 2026 for a tropical night of live music, island-inspired food, and a little aloha spirit.

Enjoy live music from Joel Paterson on lap steel guitar, plus a Hawaiian specialty menu, Polynesian-inspired delights, Gale Street favorites, and handcrafted tiki cocktails.

Tables will fill up quickly, so make your reservation today:
https://galestreetinn.com

📍 Gale Street Inn
🌺 June 10, 2026

Come hungry, come thirsty, and join us for a little island escape, Gale Street style. 🍹

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! 🤤

05/28/2026

Therapy is expensive. Happy Hour is under $10. 🍷 🍺 🥘

Join us Mon/Wed/Thurs from 4-5pm and 8-9pm, or Fri/Sat from 3-5pm and 9-10pm!

GaleStreetInn.com

05/26/2026

🎶 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

05/25/2026

We are closed today as we take time to honor and remember the brave men and women who made the ultimate sacrifice for our country. 🇺🇸

We’re grateful for their service, courage, and dedication.

Wishing everyone a safe and meaningful Memorial Day with family and friends. We’ll see when we open our doors again Wednesday, May 27th.

05/23/2026

PRIME RIB IS ON THE MENU!!!!!

05/21/2026

The only thing better than Happy Hour… is Happy Hours.

Join us early to kick off your night (M, W, Th 4-5pm/F-Sa 3-5pm), or come back late to keep it going (M, W, Th 8-9pm/F-Sa 9-10pm).
Either way:
🍺 Beer
🍷 Wine
🍽️ Food specials
All $10 or less

Your wallet is just as happy as you are.

05/19/2026

🎶 Live Music All Weekend at Gale Street Inn 🎶

Good food. Great cocktails. Incredible music.
This weekend’s lineup at Gale Street Inn brings four nights of jazz, swing, and smooth sounds to the neighborhood.

This Weekend’s Lineup:
🎤 Thursday: Petra van Nuis Duo
🎹 Friday: Frank Kurtz Trio
🎶 Saturday: Michael Whalen Trio
🎷 Sunday: Tom Vaitsas Trio

Whether you’re planning date night, dinner with friends, or just looking for the perfect place to unwind, the soundtrack is covered.

🍽️ Dinner. Drinks. Live Music.
🎵 Your weekend plans start here.

05/14/2026

Can’t make Happy Hour? Try the other one. 😉

We’ve got you covered with early AND late night Happy Hours at Gale Street Inn.
Cold beer, great wine, and crave-worthy bites—all $10 or less.

Basically, your schedule just got a lot more flexible. Cheers!

05/12/2026

🎶 Live Music All Weekend at Gale Street Inn 🎶

The food’s hot, the cocktails are cold, and the music lineup is stacked this weekend at Gale Street Inn.

This Weekend’s Lineup:
🎹 Thursday: Michael Whalen Trio
🎸 Friday: Andy Brown Trio
💃 Saturday: Swing 33
🎷 Sunday: Kevin Fort Trio

From smooth jazz and classic guitar to the dance-worthy energy of Swing 33 on Saturday night, every evening brings its own vibe. Come for dinner, stay for the music, and make a weekend of it.

🍽️ Dinner. Drinks. Live Music.
🎶 The perfect soundtrack to your weekend starts at Gale Street Inn.

Reservations recommended: GaleStreetInn.com

05/12/2026

This Memorial Day, Gale Street Inn will be CLOSED as we take time to honor and remember the brave men and women who made the ultimate sacrifice for our country. 🇺🇸

We’re grateful for their service, courage, and dedication. Wishing everyone a safe and meaningful Memorial Day with family and friends.

05/08/2026

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

05/07/2026

Early crowd 🤝 Night owls

No matter when you clock out (or head out), Gale Street Inn has a Happy Hour with your name on it. Twice the time. Same great deal. Beer, wine, and bites $10 or less.

Because one Happy Hour just didn’t feel like enough.

05/05/2026

🎺🎶 Live Music Week at Gale Street Inn With a Cinco de Mayo Kickoff! 🎶🎺

We’re turning up the volume this week at Gale Street Inn—starting with a Cinco de Mayo celebration you don’t want to miss and rolling straight into a full weekend of incredible live music.

This Week’s Lineup:
🇲🇽🔥 Tuesday (Cinco de Mayo): Grammy-nominated Zacbe Pichardo Trio
🎹 Thursday: Frank Kurtz Trio
🎷 Friday: Greg Gear Quartet
🎺 Saturday: Paulo Villabona Quartet
🎶 Sunday: Kevin Fort Trio

Kick things off Tuesday with the Zacbe Pichardo Trio—a high-energy, can’t-miss performance perfect for celebrating Cinco de Mayo the Gale Street way. Then keep the rhythm going all weekend long with a lineup that brings serious jazz talent to the stage.

🍽️ Dinner. Drinks. Live Music.
🎶 One week. Five incredible shows.

Reservations recommended.

05/04/2026

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. 🇲🇽

05/04/2026

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

04/28/2026

🎶 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

04/24/2026

Nobody agrees on what to eat? Perfect. Gale Street Inn delivery = no negotiations, just wins.

Dinner solved in one order. You’re welcome.

Order now: https://buff.ly/5KJWnaQ

04/23/2026

Two chances at happiness. Same great excuse.

Gale Street Inn now has not one, but TWO Happy Hours—early and late night.

Beer, wine, and food specials $10 or less because we believe happiness shouldn’t come with a hefty price tag.

Stop by after work… or swing back later like you planned it all along.

04/23/2026

Our team of chef's, alchemists, magicians, culinary physicists and Mexican grandma are working around the clock to bring authentic Mexican culinary delights for Gale Street Inn's inaugural celebration of Cinco de Mayo! Here's a sneak peak at our famous ribs served A La Mexicana. A Mexican showdown between 2 mother sauces: mole & salsa verde all on one plate. Make your reservations today!!!

04/22/2026

🌺 Mom is the best. Show her how amazing she is! 🌺

Join us at Gale Street Inn for our Mother’s Day Buffet—brunch from 10–2 and dinner from 3–9. From morning favorites to evening classics (yes, the ribs are ready), we’re serving up everything she loves… no cooking required.

Brunch: $45
Dinner: $60
Kids 5-11: Brunch $20 / Dinner $25
Kids 4 & under: Free

Offerings include
Brunch:

Chilaquiles
Bananas Foster French Toast
Baked Omelete
Chicken & Waffles
Salmon
Eggs
Breakfast potatoes & Hash
Sausage
Bacon
Ribs
Rib Benedict
Shrimp & Grits
Glazed Ham Carving Station.
Ceasar Salad

Dinner
Stuffed mushrooms
Shrimp Cocktail
Ribs
Salmon
Wings
Au gratin
Mac & Cheese
Brussels
Broccolini
jambalaya
Pasta Primavera
Roasted Chicken
French Fries
Baked potato station
Prime Rib Carving Station +$15

And much more!

Bring the family, raise a glass, and celebrate Mom the Gale Street way.

Reservations recommended: GaleStreetInn.com

04/20/2026

For one night only… 🌮🔥 Gale Street Inn goes south of the border.

We’re turning up the flavor this Cinco de Mayo with authentic dishes inspired by our heritage—bold, vibrant, and made to celebrate. Think sizzling plates, rich spices, and a menu that doesn’t come around often.

Come hungry. Come thirsty. And don’t miss the one-night-only fiesta. 🇲🇽🍹

Reservations recommended: GaleStreetInn.com