Best Restaurants with a Happy Hour in Headingley

Price

$$
$$$
$$$$

Cuisine

AmericanItalianSteakhouseSeafoodMexicanBritish

Regions

Winnipeg

Neighborhoods

Birchwood/Silver HeightsExchange DistrictPembina StripPolo ParkSouth PortageSouthwest Winnipeg

Top Rated

CharmingFancyGood for business mealsGood for groupsGood for special occasionsGreat for brunch

Dining Options

All dining options

Delivery only

Takeout only

Seating Options

BarCounterStandardHigh TopOutdoor

Accessibility

Gender-neutral restroomWheelchair access

19 restaurants available nearby

A photo of The Keg Steakhouse + Bar - St. James restaurant

1. The Keg Steakhouse + Bar - St. James

4.6

Exceptional(3261)

$$$$Price: Expensive

• Steakhouse • Birchwood/Silver Heights

Booked 42 times today

The Keg Steakhouse and Bar serves the finest cuts of succulent steak, aged for tenderness and grilled to perfection. Prime rib is a Keg specialty, slow roasted, hand carved and perfectly seasoned with special Keg spices. The restaurant also serves delicious seafood, memorable appetizers, crisp salads and decadent desserts. A casual ambiance and friendly, very knowledgeable staff are proud and reliable trademarks of The Keg Steakhouse and Bar. You will find a truly comfortable and satisfying dining atmosphere accompanied by a fun and up-scale bar setting where guests can enjoy an excellent wine list, signature Keg martinis, and fresh squeezed juice cocktails.

2. Underdogs

4.4

Awesome(133)

$$$$Price: Moderate

• American • Birchwood/Silver Heights

Booked 11 times today

Underdogs is a new local restaurant with creative comfort FOOD and a tasty BOOZE selection. We’re your home to enjoy the game or RALLY with your friends!

A photo of The Keg Steakhouse + Bar - Southside restaurant

3. The Keg Steakhouse + Bar - Southside

4.7

Exceptional(4352)

$$$$Price: Expensive

• Steakhouse • Southwest Winnipeg

Booked 67 times today

A photo of The Keg Steakhouse + Bar - Garry Street restaurant

4. The Keg Steakhouse + Bar - Garry Street

4.7

Exceptional(3346)

$$$$Price: Expensive

• Steakhouse • South Portage

Booked 48 times today

The Keg Steakhouse & Bar serves the finest cuts of succulent steak, aged for tenderness and grilled to perfection. Prime rib is a Keg specialty, slow roasted, hand carved and perfectly seasoned with special Keg spices. The restaurant also serves delicious seafood, memorable appetizers, crisp salads and decadent desserts. A casual ambiance and friendly, very knowledgeable staff are proud and reliable trademarks of The Keg Steakhouse & Bar. You will find a truly comfortable and satisfying dining atmosphere accompanied by a fun and up-scale bar setting where guests can enjoy an excellent wine list, signature Keg martinis, and fresh squeezed juice cocktails.

A photo of Earls Kitchen + Bar - 300 Main Street restaurant

5. Earls Kitchen + Bar - 300 Main Street

4.5

Awesome(810)

$$$$Price: Expensive

• American • Winnipeg

Booked 31 times today

Welcome to Earls 300 Main, the vibrant heartbeat of downtown Winnipeg. Located near Canada Life Centre and Shaw Park, our restaurant is the perfect gathering place for sports enthusiasts seeking delicious food before or after the game. Host your corporate lunches and dinners with ease and enjoy the abundance of fresh plants and greenery as it creates a refreshing and inviting atmosphere for all to enjoy. As an added convenience, we also provide free heated underground parking accessible via Fort Street. Indulge in our daily features, unwind during Happy Hour, and keep the night going with late-night Happy Hour. Join us and experience the vibrant culinary and cultural scene of downtown Winnipeg. Your table is ready. We can't wait to see you!Receive free parking validation weeknights from 4:00 PM to close, weekends + holidays all day. Please note if you arrive before 4:00 PM you will not qualify for free parking validation.

A photo of Hy's Steakhouse - Winnipeg restaurant

6. Hy's Steakhouse - Winnipeg

4.8

Exceptional(2230)

$$$$Price: Very Expensive

• Steakhouse • Exchange District

Booked 15 times today

Hy’s Steakhouse & Cocktail Bar is a local favourite and Canada's Premium Steakhouse since 1955, located at the famous corner of Portage and Main. Join us in the lively cocktail lounge or a quiet corner of the restaurant for Hy’s contemporary steakhouse menu featuring our signature Canada Prime beef and hand crafted cocktails. Professional, unpretentious service is sure to make your experience memorable. In the warmer months, a spectacular new patio is perfect for al fresco dining. Hy's has one of the city's best Happy Hours daily from 3 PM -6 PM with live music in the lounge. Valet parking - Hy's guests can valet park at the Fairmont for a special rate of $16+ tax daily after 3pm. Self Park at the Richardson Parkade and bring your ticket for validation. Payment methods include: Visa/Mastercard/Discover/Cash/ApplePay/Debit/Hy's & Gotham Gift Cards *** We are unable to accept Pre-Paid Credit Cards***

A photo of CHOP Steakhouse & Bar - Winnipeg restaurant

7. CHOP Steakhouse & Bar - Winnipeg

4.5

Awesome(2087)

$$$$Price: Expensive

• Steakhouse • St. James

Booked 26 times today

Chop was created for people who love sharing, connecting and everything steak. We are proud to offer a menu that shares our commitment to sustainable beef sourcing, serving high-quality cuts of 100% Canadian beef. It isn’t just the meat that’s special – it’s also how we cook it. Our Montague broiler cooks at up to 1800 °F, giving a beautiful crust and flavour to every steak! We slow roast our prime rib in a humidity-controlled oven, keeping it mouth-watering and tender. And we put this level of care into each of our hand-crafted drinks, and from-scratch dishes, including plant-based and seafood options, with something for everyone to enjoy. All of this quality comes with friendly hospitality in warm and energetic rooms. Open for lunch, happy hour, dinner and late-night!

A photo of James Avenue Pumphouse restaurant

8. James Avenue Pumphouse

4.7

Exceptional(823)

$$$$Price: Moderate

• International • Winnipeg

Booked 18 times today

Welcome to James Avenue PumphouseAwarded Best New Restaurant 2021 by Ciao! Magazine!Come visit us and experience a diverse menu offering from our very own Executive Chef, Mark Merano.Complimenting the historical setting and relaxed ambiance is a menu that draws both on Manitoba culinary traditions and globally inspired comfort food. Pair it with our smart cocktail list, and your night is complete!

9. JOEY Kenaston

4.7

Exceptional(110)

$$$$Price: Expensive

• American • Southwest Winnipeg

Booked 23 times today

JOEY Restaurants marries iconic hospitality with a handcrafted, locally and globally-inspired menu from award-winning chefs, to bring an unparalleled guest experience. Instead of just one chef, JOEY has a whole team of celebrated Executive Chefs bringing you an experience you can't get anywhere else. JOEY Kenaston's inviting space features sleek modern materials and a patio for upscale yet casual dining, sipping or socializing.

A photo of Cibo Waterfront Cafe restaurant

10. Cibo Waterfront Cafe

4.7

Exceptional(2116)

$$$$Price: Expensive

• Italian • Exchange District

Booked 28 times today

Take your tastebuds on a trip to the Mediterranean at Cibo Waterfront!Inspired by our historic waterfront location, Cibo pairs a quality all-day menu with craft cocktails and upscale wines. Menu highlights from our scratch kitchen include hand stretched pizzas, several unique takes on bruschetta, and an eclectic compilation of modern and classic Mediterranean cuisine. Our chic, brick building lights up in the day time sunshine or provides a warm atmosphere in the evening, with unique and stunning views of Winnipeg’s iconic Red River and Esplanade Riel. A comfortable ambiance to celebrate life.

See what locals rave about

From verified diners like you

A
Abigail
Winnipeg / Manitoba •1 review
5.0
Dined today
No straws when I went which affected my choice of drink cause I really wanted the frozen margarita, but food is always great so are the drinks.
More info
Earls Kitchen + Bar - 300 Main StreetPrice: Expensive• American• Winnipeg
•
4.5
K
Kristin
Toronto / Ontario •3 reviews
5.0
Dined 1 day ago
Service was excellent. We had a booth in a corner which was lovely , not too noisy. Food was excellent.
More info
The Keg Steakhouse + Bar - SouthsidePrice: Expensive• Steakhouse• Southwest Winnipeg
•
4.7
M
Micheline
Winnipeg / Manitoba •1 review
5.0
Dined 1 day ago
The food was great and the service was too. The restaurant and washrooms were clean and well maintained.
More info
The Keg Steakhouse + Bar - Garry StreetPrice: Expensive• Steakhouse• South Portage
•
4.7
N
Nissa
Winnipeg / Manitoba •1 review
5.0
Dined 3 days ago
It was my first time going, I took my 2 kids (ages 2 and 6) and my partner. The service we received was outstanding, the food was incredible. I definitely recommend going. Absolutely wonder and lovely evening, especially thanks to our server for being as amazing as he was. Everyone who served us and helped in a big or small way made the evening just that much better. All your hard work shows ladies and gents keep it up.
More info
The Keg Steakhouse + Bar - St. JamesPrice: Expensive• Steakhouse• Birchwood/Silver Heights
•
4.6
A
Andrea
Winnipeg / Manitoba •1 review
5.0
Dined on Feb 10, 2025
The wings and burger were so delicious . The menu is varied.
More info
UnderdogsPrice: Moderate• American• Birchwood/Silver Heights
•
4.4

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Winnipeg / Manitoba
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