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New Yorkers 1st Choice
Local picks in Near South Side

Bar date spots

Made for those who prefer to get to know someone in a setting where the drinks are the primary focus.

Based on 628 Opinions
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Updated April 2026
01
Buttercup image 1
Buttercup image 2
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Small, intimate space shifts from cozy daytime cafe to swanky speakeasy bar with soft lighting and curated 1940s/50s decor. Atmosphere stays chill and welcoming, ideal for quiet dates or after-work drinks. Music complements the vibe, creating a relaxed yet stylish setting.

Cozy daytime cafe turns into an excellent cocktail bar at night with a friendly, attentive bartender who knows the menu well. The drink selection includes fun options for both alcoholic and non-alcoholic tastes.

Soft lighting creates a cozy atmosphere ideal for date nights. The spot offers custom cocktails like make-your-own grattachecca and classic old fashioneds, perfect for evening drinks.

People are saying

"The cafe's specialty coffees are unique and fantastic."

"The truffle pizzetta here has an incredibly rich flavor."

"This bar has an unreal selection of amaro bottles."

Good to know

1

Happy hour runs from 4-7pm with a great menu of drinks and appetizers.

2

Buttercup transforms into a cocktail bar after 4pm.

3

Street parking is available nearby for easy access.

02
The Staley image 1
Sports bar

Large sports bar with huge projector screens and plenty of TVs creates a strong focus on watching games. Atmosphere feels like a dark basement man cave with a mix of upscale gastropub décor. Free arcade games and a mini game room add casual entertainment beyond sports viewing.

A large and classy neighborhood bar offers a welcoming atmosphere without any dive bar vibes. Bartenders are friendly, fast, and knowledgeable, providing solid drink recommendations.

Offers a relaxed spot for date nights with a casual vibe. Works well for quick hangouts or family outings too.

People are saying

"The food here is unique, delicious, and top-notch."

"The staff here is super friendly during live sports."

"The service here for date spots is amazing, with staff like Colin and Ulysses."

Good to know

1

Reservations are not accepted on game days; plan accordingly.

2

A 20% service charge is automatically added to bills on game days.

3

Happy hour features discounted drinks and appetizers from 4-7pm on weekdays.

03
MIKAMI IZAKAYA & RAMEN image 1
Japanese restaurant

Japanese restaurant combines industrial-chic design with elegant touches for an upscale look and vibrant, casual vibe. Atmosphere stays quiet and spacious, fitting for romantic dates or relaxed chats. Full bar offers Japanese beer on tap and notable cocktails alongside rare ramen varieties.

The bar offers an impressive whiskey and scotch selection alongside a variety of sake. Service at the bar stays flawless and attentive, even when busy, making it easy to enjoy drinks paired with food.

Offers a romantic atmosphere suited for special occasions like anniversaries and birthdays. Serves unique dishes that make celebrations feel different and memorable.

People are saying

"The Japanese food, especially the ramen, is flavorful and comforting."

"The ramen here is rich, tasty, and loaded with seafood."

"I loved pairing the delicious starters with a beer at the bar."

Good to know

1

Lunch specials are available for $21.95, including a side, main dish, and drink.

2

Happy hour features discounted cocktails and appetizers, making it a great time to visit.

3

The restaurant offers a variety of Japanese dishes beyond ramen, like gyudon.

04
Brûlée image 1
Restaurant

Warm, modern space with thoughtful decor and a spacious bar and waiting area creates a welcoming atmosphere. Music ranges from R&B at moderate volume to occasionally loud, influencing the energy. Tables are closely arranged, balancing elegance with a busy, lively vibe.

A beautiful full bar stands out in a spacious, elegant area that feels comfortable and simple. Staff at the bar and throughout are friendly and welcoming.

Reservations happen smoothly with quick seating. The atmosphere feels intimate and comfortable, fitting for couples and close friends celebrating special moments.

People are saying

"The food here is so flavorful and fresh."

"The drinks here are immaculate and the food is almost too good to be true."

"The food here is delicious and flavorful for Date Spots."

Good to know

1

Reservations are recommended for large groups or after 10 PM on weekends.

2

Expect a wait for tables, especially during peak brunch hours.

3

Brûlée enforces a strict 90-minute table limit for diners.

05
Casa Tulum image 1
Mexican restaurant

Mexican restaurant with beautiful decor and an energetic vibe featuring a live DJ and upbeat music. Two bars with TVs add to the lively atmosphere, complemented by a fire show and flaming desserts. The place draws a crowd enjoying great margaritas and flavorful dishes in a clean, vibrant setting.

Two bars offer ample seating even on weekdays. Staff like Rafael and Bar Manager Nia provide efficient, welcoming service that enhances the experience.

Fun date night vibes come with attentive service from Guillermo and an environment that impresses. Food quality stands out, making it a solid choice for couples and special outings.

People are saying

"The food here is amazing, fresh, and perfectly seasoned."

"The service here for Date Spots is attentive and above and beyond."

"Nia at the bar was amazing and made great suggestions."

Good to know

1

Happy hour starts at 3 PM.

2

Ask for the $10 margaritas special on Mondays and Tuesdays.

3

Street parking is easy to find and free on Sundays.

06
Reggies Chicago image 1
Bar & grill

Multilevel bar and grill with live bands and a rooftop deck featuring a basketball hoop creates a punk rock vibe. Atmosphere is lively and energetic, often very loud with dark, moody lighting. Seating includes comfy balcony spots and ample bars throughout the venue.

A dive bar with a unique atmosphere featuring cool graffiti and an off the beaten path vibe. The bar offers great food and a fun spot for live music in a small setting.

Wedding after parties happen here, making it a spot for special celebrations. Burgers stand out with juicy, flavorful meat and great barbecue sauce.

People are saying

"The bar food, especially the pulled pork, is some of the best I've had."

"It's a live music hub with gritty charm and energetic vibes."

"The food here is fantastic, with fresh ingredients and creative burgers."

Good to know

1

Parking can be challenging; consider using public transport or rideshares.

2

The venue hosts live music events almost every weekend.

3

Food service ends at 10pm, so plan accordingly.

07
Signature Steak image 1
Restaurant

Upscale sports bar with modern black-and-white decor and large screen TVs creates a lively, sometimes loud atmosphere. Dim, private lounge offers a contrasting intimate vibe with great music. Signature cocktails and well-crafted drinks stand out amid close seating and energetic crowds.

Bar offers a moody ambiance with a great R&B playlist and big screens showing sports all night. Unique dill sauce stands out for dipping fries and topping the chicken sandwich.

Upscale sports bar vibe blends moody ambiance with big screens showing games all night. Dark seating and a great R&B playlist create a mix of date night and game day energy.

People are saying

"The food and drinks here are thoughtful, indulgent, and expertly executed."

"The cocktails here are delicious and perfectly balanced."

"The food here is so flavorful, I'm driving three hours back for dinner."

Good to know

1

Reservations are recommended, especially during peak hours.

2

Happy hour offers discounted drinks and appetizers from 4-6pm on weekdays.

3

Expect small portion sizes relative to the price.

08
Southern Chicago image 1

Elegant space features beautiful décor and a warm, comfortable atmosphere with great music enhancing the vibe. Guests enjoy thoughtfully crafted cocktails and high-quality Southern-inspired dishes in a setting that feels both inviting and refined.

Amazing bar offerings fill a beautiful space with a great aesthetic. Service is warm and friendly, especially from Richard at the bar.

Options for pescatarians and meat eaters both exist, making it easy to find something for everyone. The atmosphere suits special occasions like birthdays, with food that impresses across the board.

People are saying

"The food here is amazing, fresh, and thoughtfully prepared."

"The food and drinks at this Bar were outstanding."

"The fried chicken here is the star, perfectly crisp and flavorful."

Good to know

1

Happy hour offers great prices on food and drinks.

2

Reservations are recommended for dinner, especially on weekends.

3

Valet parking is available for guests.

09
Williams Inn Pizza & Sports Bar image 1

Big-screen TVs cover every wall, creating a sports-focused environment with rustic charm. Loud music from a live DJ energizes the space, encouraging singing and dancing. Seating is ample, designed for casual family dinners and lively game nights.

A very large bar creates an intimate, neighborhood feel with a warm, inviting ambiance. Staff provide excellent service even when busy, making it a lively spot for sports and socializing.

Social atmosphere suits date nights and casual hangouts. Drinks include a Hennessy margarita similar to a sidecar. The spot works well for hotel guests and happy hour.

People are saying

"This deep dish pizza is amazing and straight out of the oven."

"The bar staff treated me like a regular with a smile."

"It's a great place for a laidback, beautiful date night."

Good to know

1

Happy hour runs from 4-7pm on weekdays with great drink specials.

2

Parking is difficult; consider using a ride share or park a block away.

3

A DJ performs on Friday nights, creating a lively atmosphere.

10
VU Rooftop image 1
Restaurant

Rooftop restaurant offers spectacular city views and a lively atmosphere with live jazz music and fire pits for warmth. Seating includes a cozy lounge area ideal for relaxing with friends. The venue combines indoor and outdoor spaces, creating a vibrant setting for group gatherings.

A full bar offers quick, knowledgeable bartenders and a wide selection of drinks. The space includes a large dance floor, an indoor restaurant, and an outdoor area with breathtaking views that create a lively atmosphere.

Vu burger and margaritas create a tasty combo for date nights. The rooftop offers a romantic vibe suitable for anniversaries, birthdays, or casual outings.

People are saying

"The food here is great, and the staff are so friendly."

"The bar has incredible views and a chic ambiance."

"The service here is always prompt, friendly, and inviting."

Good to know

1

Reservations are recommended, especially on weekends due to high demand.

2

A 20% automatic gratuity is added to all bills, regardless of party size.

3

Security checks are similar to TSA procedures before entry.

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Near South Side, Chicago

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