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New Yorkers 1st Choice
Local picks in Sheffield and DePaul

Cool spots

A spot with a distinct personality that feels authentic instead of curated for a social media feed.

Based on 592 Opinions
+589
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Updated April 2026
01
The High Crowd Cafe image 1
The High Crowd Cafe image 2
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Cafe blends chill atmosphere with cool vibes and friendly staff. Tables invite board games while enjoying caffeine and sweets. Artwork adds to the vibey environment making it a fun spot to relax and socialize.

Cool vibes fill the space with a clean and friendly atmosphere. Awesome artwork and consistently friendly staff add to the overall cool experience.

People are saying

"The lemonade here is super sweet and the staff is so friendly."

"These date spots have infused drinks that get you stoned."

"The staff here is so friendly and cool."

Good to know

1

The cafe offers a variety of baked goods, lemonades, coffees, and teas.

2

Expect prices for marijuana products to be competitive with local dispensaries.

3

The cafe frequently offers special deals to customers.

02
Delilah's image 1

Dive bar boasts huge whiskey selection and two bars with a rock'n'roll atmosphere. Punk vibe adds a dark, underground feel while pool tables upstairs create a chill hangout. Walls show unique art, crowd stays relaxed and drink-savvy.

A cool punk vibe fills the space with a dark, underground atmosphere. The place feels like a relaxing dive bar with a party area and amenities.

People are saying

"The bartenders here are amazing and so helpful."

"I found the whiskey selection to be extensive and impressive."

"The vibe here is so cool, it feels like a party."

Good to know

1

Delilah's allows you to bring your own food to the bar.

2

Dollar beer night happens on Mondays, offering great deals.

3

They offer daily drink specials, including $3 beers and shots.

03
The Red Lion Pub image 1

Pub boasts handcrafted wooden interiors and walls lined with WWI and WWII memorabilia. It offers a cozy British and Irish pub vibe with traditional ales and hearty food. Atmosphere feels cool and relaxed with a strong English touch.

Atmosphere feels very cool with a strong English vibe inside. The setting creates a distinct and relaxed mood.

People are saying

"This pub's atmosphere feels so authentic, like a place in London."

"It's a super cozy spot with a warm, inviting atmosphere."

"The atmosphere here is really cool."

Good to know

1

Reservations are required for dining, especially during peak hours.

2

Happy hour offers good deals on drinks and appetizers from 4-6pm.

3

Expect a 1 hour and 40 minute limit on table reservations.

04
Tapster Lincoln Park image 1

Self-serve taps offer a unique concept that lets you pour drinks by the ounce in a laid-back bar with a dog-friendly policy. Outdoor patio and board games create a casual, neighborhood feel with a chill college vibe.

A unique concept sets this place apart, something rarely seen elsewhere. The idea feels fresh and stands out clearly.

People are saying

"I loved pouring my own beer from the huge selection."

"The outdoor seating area out back is great."

"I thought the concept was so cool."

Good to know

1

Happy hour features rotating deals, like Chicago beers for $5 per pint.

2

Tapster Lincoln Park is dog-friendly, making it a great spot for pet owners.

3

Self-serve taps allow you to pour drinks by the ounce or full pint.

05
Pour Decisions Chicago image 1

Live jazz and loud sports create a unique mix of top-tier performances and multiple large TVs. Upstairs offers a speakeasy vibe with a pool table and private rooms. Specialty cocktails and highly praised wings keep the crowd happy in a modern bar setting.

Upstairs offers a cool and calm vibe during private parties. The spot features many TVs and a modern bar setting that feels relaxed and inviting.

People are saying

"The bar staff here really make sure you're taken care of."

"You have to try the bottomless wings; they just melt off the bone."

"It's a cool spot with a lot of TVs to watch the game."

Good to know

1

Wednesdays feature $20 all-you-can-eat wings, a popular deal.

2

Thursdays offer an $8 burger with fries and $5 domestic drafts.

3

Trivia night happens every Wednesday, adding to the midweek fun.

06
Chicago's Dog House image 1
Hot dog restaurant

Small space with Chicago-themed decor and Motown music sets a laid-back atmosphere. Cramped seating fills fast, but Mini Jenga and football on TV keep it fun. A variety of hot sauces adds an authentic, modern take on Chicago-style hot dogs.

A cool little hole in the wall with a laid-back atmosphere and unique decor inside.

People are saying

"I found the food here to be fresh and of great quality."

"I thought the American food, specifically the hot dogs, were the best I've ever had."

"I found the Chicago dog here to be the best I've ever had."

Good to know

1

Reservations are not accepted, so expect potential wait times during busy hours.

2

The restaurant has limited seating, which may lead to a wait for a table.

3

Prices are reasonable for the quality of food offered.

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Sheffield & DePaul, Chicago

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