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New Yorkers 1st Choice
Best of River North

Cool nightlife spots

You are looking for nightlife that feels genuinely cool, not just a place that happens to be open late.

Based on 690 Opinions
+687
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Updated April 2026
01
The 101 Bar, Grill & Rooftop image 1
The 101 Bar, Grill & Rooftop image 2
The 101 Bar, Grill & Rooftop image 3
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Mediterranean restaurant

Mediterranean restaurant with a rooftop bar offering spectacular city views and multiple seating options including fire pits and private couches. Live music creates a lively atmosphere that balances well with conversation. Cocktails and food receive strong praise, contributing to an overall vibrant and welcoming vibe.

Outdoor lounge tables by the firepit create a relaxed vibe for groups and dogs. Friendly hosts add to the welcoming atmosphere that invites easy socializing.

Rooftop offers a cool space with relaxing upbeat music and cool decor. The atmosphere stays consistently cool and inviting throughout the day.

People are saying

"The rooftop views of the city are beautiful."

"RJ, the bartender, made our nightlife unforgettable with his amazing cocktails."

"The rooftop views are beautiful, especially at sunset."

Good to know

1

Happy hour is available 7 days a week from 5-7pm.

2

Reservations are typically required, but walk-ins may be accommodated if available.

3

The happy hour offers a great selection of drinks and appetizers at unbeatable prices.

02
Blue Chicago image 1
Live music bar

Small, vintage blues bar with an intimate, no-frills setup focused on live music. Atmosphere feels authentic and cozy, with close proximity to local talent performing on a narrow stage at the back. Venue stays lively until late, attracting an enthusiastic crowd and offering cash-only service with room to dance.

An intimate spot with a down and dirty blues vibe offers an authentic experience. The club has a hallowed atmosphere that captures the true spirit of blues nightlife.

Classic jazz and blues music create a cool atmosphere with old school Chicago style vibes. Live bands and singers keep the energy authentic and lively.

People are saying

"The live music here is phenomenal and top-notch."

"The live blues music here is amazing, truly the real deal."

"I found the atmosphere really cool during the blues concert."

Good to know

1

Blue Chicago is a cash-only bar, so bring cash for drinks.

2

There is a $15 cover charge to enter Blue Chicago.

3

Live performances start at 9pm, with doors opening at 8pm.

03
Arbella image 1
Cocktail bar

Large space divides into distinct atmospheres with comfortable booths and a lively club room. Music features a DJ-driven sound system playing chill, high-energy tunes that shape a fun, unpretentious vibe. Patrons include stylish young crowds, but the atmosphere welcomes all ages for drinks and conversation.

A club vibe kicks in from Thursday to Saturday around 10 PM with lounge electronic music setting the tone. The club room's chaos stays separate from the quieter restaurant area, keeping the space balanced.

A super cool vibe fills the space with great music and stylish decor. The bars offer a nice, cool ambiance perfect for cocktails.

People are saying

"The cocktails here are delicious and creatively made."

"It's got a really cool vibe with stylish decor and great music."

"The cocktails here are adventurous and perfectly mixed."

Good to know

1

Reservations are recommended to secure a table, especially on weekends.

2

Happy hour runs from 5 to 7 PM Monday to Saturday with limited menu options.

3

Arbella turns into a club starting around 10 PM from Thursday to Saturday.

04
Shamrock Club image 1

Old-school bar extends deep inside with a pool table, jukebox, and popcorn machine adding to the casual vibe. Loud, fun crowd creates a welcoming, neighborhood atmosphere where people relax and socialize. Outdoor patio offers a perfect spot for warm days, enhancing the laid-back energy.

A traditional sports and dive bar vibe dominates with a divey atmosphere and free popcorn at the bar. Service happens all at the bar, making it a straightforward spot to unwind after work or celebrate events like St Patrick's Day.

Atmosphere feels relaxing with a cool vibe. Staff stay responsive and add to the laid-back mood.

People are saying

"The food here is great, especially with a cold pint."

"It's a great little dive bar with fairly priced drinks."

"It's a chill spot to unwind with a friendly, welcoming vibe."

Good to know

1

Happy hour runs from 4-7pm on weekdays with half-price appetizers.

2

Expect the bar to get crowded around 6-7 PM.

3

Pitchers are available for $13, making it a budget-friendly option.

05
Charlie Martin's image 1

Cozy space with Hollywood regency decor and mood lighting creates a speakeasy vibe. Bartenders craft exceptional cocktails, including standout Old Fashioneds and martinis. Atmosphere suits jazzy date nights and sophisticated dining with white tablecloths.

An intimate supper club with a 1950s vibe offers a unique nightlife experience. The atmosphere blends old fashioned supper club charm with Hollywood nights energy.

Ambiance and interior design feel like traveling through time. The bar stands out as super cool, though the vibe could improve with better music and clientele.

People are saying

"The seafood, especially the oysters, was super fresh and amazing."

"The food here is outstanding, especially the steak frites."

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

Good to know

1

Reservations are recommended, especially during busy weekend nights.

2

The restaurant closes early at 11 pm, so plan your visit accordingly.

3

They often run out of popular menu items by 8 pm on weekends.

06
Howl at the Moon Chicago image 1

Rocking piano bar with live music and high energy atmosphere. Crowded seating near the stage creates an intimate vibe while the buzzing sound level keeps the energy lively. Specialty drinks come with sweet, cutesy presentations and the food offers elevated bar fare.

Live music drives the energy with exceptional talent performing classics like Bohemian Rhapsody and recent hits such as Pink Pony Club. A piano duel adds a unique twist to the positive vibe throughout the club.

Piano bar vibes set a cool tone with good music and a great atmosphere. Emo night adds a unique edge to the overall cool experience.

People are saying

"You'll have so much fun; the crowd is always energized."

"The atmosphere here is really cool, especially during emo night."

"The live music nightlife here is fantastic, with talented musicians playing classics and hits."

Good to know

1

There is a $12 cover charge to enter the venue.

2

Happy hour offers the first two drinks for $2 each.

3

Dueling piano nights are popular and feature audience requests.

07
UMMO image 1
Italian restaurant

Italian restaurant offers a modern jazz inspired design with upstairs loft featuring live music and pool table. Atmosphere shifts from quiet and intimate dining to a lively late-night hangout with DJs and bands. Decor includes quirky records and stylish interiors creating a warm, upbeat vibe.

Upstairs offers a vintage lounge vibe with billiards, old records, and a full bar. The loft feels more open with a relaxed lounge atmosphere and live music.

People are saying

"You honestly canโ€™t go wrong with the outrageously good pasta here."

"The atmosphere here is cool, with a classy, moody jazz vibe."

"Emiliano's passion and artistry make the nightlife here second to none."

Good to know

1

Reservations are recommended, especially for larger groups, to ensure seating.

2

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

3

The loft space converts into a club after 10pm with a DJ and dancing.

08
Broken Shaker at Freehand Chicago image 1

Cozy, dark basement setting blends 70s funk and tiki bar vibes with a hidden, tucked-away layout. Live jazz and DJ sets create an energetic yet civilized atmosphere where people chat and relax. Seating offers ample lounging space near bars that face both street and interior areas.

A chill lounge vibe sets the mood with a well balanced cocktail menu and club-level music volume. The bar feels cute and the servers bring a fun, friendly energy.

Ambiance stands out with a really cool vibe. The spot feels like a cool little place to hang out.

People are saying

"The cocktails here are inventive and delightfully complex."

"The cocktails here are strong, creative, and perfectly balanced."

"The drinks here are great."

Good to know

1

Happy hour offers $4 off cocktails, but check for specific times.

2

The bar closes an hour earlier than usual on some nights.

3

Parking can be challenging in front of the bar.

09
Redhead Piano Bar image 1

Piano bar offers live piano music with a phenomenal, engaging pianist in a small, crowded space that encourages standing and dancing. An outdoor cigar lounge provides additional seating with couches and ashtrays. The atmosphere is lively and packed, creating an intense but vibrant vibe.

A speak-easy style cigar lounge offers a cozy, calm atmosphere with attentive service. The outside deck and live music at the piano bar add to the relaxed nightlife vibe.

Outdoor cigar-smoking area hides behind a secret path, giving an exclusive vibe. Redhead Piano Bar hosts live music and draws cool people from around the world.

People are saying

"This piano bar is the perfect spot to end your night."

"It's a cool place with live piano music and a lively crowd."

"The nightlife here has great music and a welcoming vibe."

Good to know

1

Expect large crowds on weekends, especially after 10 PM.

2

Reservations are recommended for special events or large groups.

3

Happy hour offers discounted drinks from 4 PM to 7 PM on weekdays.

10
Moe's Cantina - River North image 1
Mexican restaurant

Massive Mexican restaurant with ample seating and a unique design that shifts into a nightclub on weekends. Lively atmosphere with energetic music, including reggaeton and clear TV audio for games. Outdoor seating and artistic decor add to the vibrant vibe.

Vibrant nightlife centers on a great dance club atmosphere with efficient bartenders enhancing the experience. Security staff provide helpful directions, supporting a smooth night out.

A cool atmosphere fills the space with a nice vibe and a crowd of cool people.

People are saying

"The staff here makes the Mexican food experience so friendly and attentive."

"Miguel was the highlight of my night, super nice and professional."

"I found the atmosphere and people here to be really cool."

Good to know

1

Expect a $20 cover charge for entry during club hours.

2

Reservations are recommended, especially for larger groups.

3

All guests must arrive together to avoid additional cover charges.

11
Freehand Chicago image 1

Retro art deco style hotel combines chic lobby with a lively bar scene featuring a spacious bar and fast internet. Rooms offer comfortable beds and clean amenities, while the lounge area provides a relaxed vibe contrasting the nightclub energy downstairs.

Beautiful lounge area offers a relaxed, laid-back vibe. Cozy and spacious bar and lounge serve drinks like gin and tonic with excellent music.

Shared space, bar, and lounge have a cool vibe. The hotel feels charming and avoids a corporate atmosphere.

People are saying

"The bar staff here is amazing and super fun."

"The rooms felt cool and stylish with a modern design."

"The location is perfect for nightlife, letting you walk anywhere easily."

Good to know

1

Expect a mandatory resort fee of $15โ€“40 per night not included in the initial price.

2

Breakfast is included in the morning for all guests.

3

Security on the floors is lacking, making the area feel unsafe after dark.

12
DISCO image 1
Night club

Five-level club combines multiple dance floors with an upscale restaurant and lounge. Energetic vibe thrives on nostalgic 80's and 90's music and a light-up disco floor that enhances the atmosphere. Crowds are diverse and lively, creating a unique and engaging night out.

Multiple levels include an upscale restaurant, a disco area, and an upscale house music section. The atmosphere differs from typical nightclubs, featuring 80's music rather than disco tunes.

One dance floor features a fully lit floor that creates a really cool atmosphere. The overall vibe leans into an 80's/90's theme that stands out.

People are saying

"The nightclub atmosphere and lights were amazing."

"The nightlife here has an amazing atmosphere with great music."

"The dance floor's lit-up vibe is pretty cool."

Good to know

1

Entry to DISCO is free before 11 pm.

2

Drink prices are high, with shots at $12 and beers at $8.

3

Expect long lines for the single bathroom located two floors down.

13
Celeste image 1
Night club

Four floors offer distinct vibes, from a local bar feel to a jungle-themed rooftop with LED light dance floors. Music varies by level, featuring passionate DJs and diverse scenes for dancing or relaxing. The venue maintains a clean, upscale style with a lively, fun atmosphere throughout.

Four levels offer distinct vibes, from a local bar feel to a full nightclub. The rooftop serves as a cozy dancing lounge, and the spot combines an amazing restaurant with lively nightlife.

Four stories offer different vibes from moody to art deco. Live DJs spin cool music while calm, cool doormen keep the mood steady.

People are saying

"You can hear great DJs and dance all night at this nightclub."

"The nightlife here has a cozy vibe with different atmospheres on each floor."

"The vibes here are pretty cool and differ floor to floor."

Good to know

1

Entry is free before 11pm on Saturday night.

2

A $20 cover charge applies for men, while women enter for free.

3

Disco starts at 9:00 p.m. on weekends.

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