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Loved by locals

Cocktails with parking in Milwaukee

A cocktail bar where you can arrive by car without the stress of hunting for a legal space.

Based on 616 Opinions
+613
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Updated May 2026
01
O'Lydia's Bar and Grill image 1
O'Lydia's Bar and Grill image 2
O'Lydia's Bar and Grill image 3
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Irish pub with spacious indoor and outdoor seating and a friendly, welcoming atmosphere that encourages conversation. Donation-based shuttles run to major events, adding convenience. Nearby train tracks cause occasional loud noise, but the well-lit enclosed patio offers a pleasant, secluded space.

Convenient parking exists across the street with a large free parking lot nearby. Free street and lot parking in the neighborhood makes it easier to find spots than on the other side of the river.

Classic cocktails feature prominently with an emphasis on old fashioned drinks. The cocktail prices hover around $8 to $10, paired with a nice beer selection.

People are saying

"The pub food here is fantastic and reasonably priced."

"I found parking available right across the street."

"I enjoyed the excellent cocktails and nice beer selection."

Good to know

1

Happy hour runs all day on Sundays with special drink prices.

2

Saturday Steak Night features discounted steak options and drink specials.

3

Daily food and drink specials are available throughout the week.

02
Oscar's Pub & Grill image 1

Bar and grill with a 1920s look and charming, lively interior in a restored building. Atmosphere offers relaxed, local charm with family-friendly vibes and plenty of TVs showing sports. Known for exceptional burgers and a notable craft beer and cocktail selection including standout Bloody Marys and spicy Palomas.

A dedicated parking lot sits right outside with plenty of space. Street parking also surrounds the area, making it easy to find a spot.

Offers 40 beers on tap alongside specialty cocktails. Cocktails are tasty and fun with a good variety to choose from.

People are saying

"I thought their burgers were the best I'd ever had."

"There's plenty of parking available, with a lot right next door."

"I found some of the best burgers in the city here."

Good to know

1

Taco Tuesday offers $1 tacos, Al Pastor or Carne Asada, with cilantro and onions.

2

Mystery pints of beer are available for $3.

3

An 18% gratuity is automatically added to bills for large parties.

03
Five O'Clock Steakhouse image 1

Classic old school supper club with authentic vintage decor and live jazz music creates a lively yet intimate atmosphere. Free valet parking and a skilled bartender crafting standout cocktails add to the experience. Tables are small and seating is close, enhancing a bustling, packed vibe.

Easy valet parking is available with no charge. The service operates smoothly despite the slightly sketchy neighborhood.

Cocktails stand out with fantastic craftsmanship and a next level flavor profile. Service complements the drinks, making the experience smooth and enjoyable.

People are saying

"I thought the steaks here were the best Iโ€™ve ever had."

"It's like stepping back in time to a supper club."

"The valet parking here is free and convenient."

Good to know

1

Reservations are recommended on weekends due to high popularity.

2

Valet parking is available for guests.

3

Live music occurs at the bar on Friday nights.

04
Saint Kate - The Arts Hotel image 1

Hotel combines art galleries with live music and a stylish bar, creating an uplifting atmosphere. Comfortable rooms include unique touches like a turntable with albums. Views overlook historic architecture, enhancing the romantic and elegant vibe.

A self-park parking structure sits right next door, letting you park and enter without stepping outside. Walking is easy here, so parking is not always needed.

The bar serves great cocktails with top-notch service. Complimentary drinks and desserts sometimes accompany sincere apologies from the friendly staff.

People are saying

"The Hotel staff were so welcoming and attentive."

"Parking was available and super convenient."

"The cocktails here are top-notch and served with great service."

Good to know

1

The hotel has a parking garage available for $31 with in/out access.

2

The hotel frequently hosts live events at the bar, ideal for networking.

3

Brunch is served on weekends, but reservations are recommended.

05
Drury Plaza Hotel Milwaukee Downtown image 1

Hotel offers spacious rooms with amazing city views and complimentary food and drinks that encourage mingling. Atmosphere varies from quiet and comfortable in rooms away from main roads to noisy near downtown streets. Facilities include a pool and gym, though the pool often feels crowded and loud.

Attached parking garage offers unlimited come and go for $25 per day. Parking sits right next door with secure access via skywalk and fits larger vehicles like a half-ton pickup.

Complimentary cocktails come with snacks during a daily 5:30 Kickback that feels like dinner. The free happy hour offers three cocktails or beers alongside popcorn, meatballs, and vegetables.

People are saying

"The complimentary breakfast was amazing, like homemade meals."

"I found the parking convenient and attached."

"The complimentary evening cocktails and food were top notch."

Good to know

1

Happy hour runs from 5:30 to 7:00 PM with three complimentary drinks and a buffet.

2

Parking costs $25 per day with unlimited in-and-out privileges.

3

The hotel offers free breakfast and dinner for guests.

06
Harry's Bar and Grill image 1

Spacious bar and grill with outdoor patio and Halloween decorations creates a lively setting. Atmosphere shifts from relaxed dining during off-peak hours to loud and dark inside. Long bar design and close seating shape the social experience.

A small parking lot sits near the entrance with additional street parking available. Parking spots fill up but there is generally plenty of parking close by.

Habanero cocktails stand out with bold spice. Drinks use premium liquor and include options like a creamy cherry lime cocktail and brunch cocktails that are decent.

People are saying

"The burgers here are juicy, thick, and cooked perfectly."

"I found plenty of parking available right at the place."

"I found the habanero cocktails to be awesome."

Good to know

1

Reservations are advisable as it can get busy, especially on weekends.

2

Happy hour runs from 3-6 pm with $6 or less menu items.

3

Thursday features $4 tacos and $6 margaritas during happy hour.

07
The Pfister Hotel image 1

Historic hotel with elegant architecture and integrated art creates a warm, nostalgic atmosphere. Luxury amenities include a rooftop pool with waterfront views and a sophisticated lobby bar. Energy varies from quiet elegance to lively with music echoing through hallways.

Cocktails come from a lounge and Blu restaurant on the 23rd floor. The lounge offers a beautiful setting to relax. Drinks here are consistently fantastic.

People are saying

"This hotel is beautiful and located in a prime area."

"The parking available here is surprisingly convenient."

"I loved their fantastic cocktails at the top floor bar."

Good to know

1

The hotel hosts weddings, conventions, and parties every day.

2

Expect a lively atmosphere with live music on weekends.

3

Reservations are recommended for special events like brunch.

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Milwaukee, Wisconsin

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