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New Yorkers 1st Choice
Local picks in River North

Cool spots with outdoor space

You want an outdoor environment that maintains a distinct sense of style.

Based on 739 Opinions
+736
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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.

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

Outdoor seating offers a warm, cozy atmosphere with fireplaces on the patio. This setup enhances the dining experience by creating a comfortable and inviting space.

People are saying

"The rooftop views of the city are beautiful."

"The outdoor space offers beautiful city and skyline views."

"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
Chicago Chop House image 1

Restored brownstone with early 1900s decor and photos of local celebrities creates a traditional steakhouse atmosphere. Live piano music plays softly, adding to the luxurious and old-fashioned vibe. Comfortable seating and personalized touches enhance a refined dining experience.

A very cool spot with an old school steakhouse vibe. Walls feature historic pictures and memorabilia that add to the atmosphere.

Tables on the patio come with personally printed menus to keep. Staff treat guests with attentive, experienced care outdoors. Seating at 4:30 enhances the outdoor dining experience.

People are saying

"I found the steak to be tender and flavorful."

"The staff here are so friendly and attentive."

"You can sit outside and enjoy the cooler weather."

Good to know

1

During the 40th anniversary, all food ordered was 40% off.

2

Valentine’s Day celebrations offer special menu items.

3

Reservations are recommended, especially during holidays.

03
Lizzano Focacceria & Spritzeria image 1

Italian restaurant offers traditional focaccia sandwiches with fresh ingredients and large portions. Atmosphere feels authentic and quaint, with lively music and bright, cute decor featuring Aperol and Campari bottles. Outdoor patio seating adds to the welcoming vibe.

Atmosphere feels really cool for a quicker service spot. Music selection adds to the nice vibe.

Plenty of outside seating exists on the patio. Tables allow for sitting outdoors comfortably.

People are saying

"I found the sandwiches to be delicious and amazing."

"The focaccia really makes the paninis extra good."

"I found plenty of outdoor space seating available."

Good to know

1

Happy hour is available from Wednesday to Friday between 4pm and 6pm.

2

During happy hour, spirits and wine are $9, and Italian boards are 50% off.

3

The restaurant offers a variety of vegetarian options on the menu.

04
Ema image 1
Mediterranean restaurant

Mediterranean restaurant offers warm, modern interior with two bar areas and outdoor seating including a patio and rooftop. Atmosphere stays lively but not noisy, creating an inviting and relaxed vibe. Extensive gluten-free menu and accommodating options stand out for dietary needs.

A very cool atmosphere with soft music sets a hip vibe throughout the space.

Great patio offers outdoor seating that many prefer over indoors. The space feels well appointed and creates a nice vibe for dining outside.

People are saying

"The food here is amazing, truly incredible."

"The outdoor seating here is really comfortable and cute."

"I found the food here to be delicious and amazing."

Good to know

1

Ema offers an extensive gluten-free menu with many options.

2

Reservations are recommended as the restaurant tends to fill up quickly.

3

Happy hour features generous portions but a limited list of spreads.

05
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.

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.

A hidden outdoor cigar lounge sits behind a secret pathway, creating an exclusive vibe. The outside deck offers the only seating and blends well with live music and drinks inside.

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."

"It's a cozy outdoor cigar lounge with a calm atmosphere."

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.

06
Dave’s Hot Chicken image 1
Chicken restaurant

Outdoor and indoor spaces feature colorful artwork and a vibrant, lively atmosphere with loud 1980s rock music. Staff engage actively, often dancing, creating a welcoming and energetic vibe. Seating includes a spacious patio and walk-up counter service.

Artwork in the space stands out with sick designs and the decor adds a cool vibe throughout. The place stays super clean and keeps a consistently cool atmosphere.

Outdoor seating offers an incredible atmosphere with a colorful vibe and impressive decorations. A spacious patio complements the clean and inviting environment.

People are saying

"The food here is amazing, delicious, and full of flavor."

"The chicken here is so juicy, flavorful, and perfectly cooked."

"The place felt super cool and clean."

Good to know

1

Dave’s Hot Chicken is halal, making it a great option for those who need it.

2

Parking next to the restaurant is limited, fitting maybe 7 or 8 cars.

3

The restaurant is very clean, including the bathrooms.

07
The Boss Bar image 1

Bar combines sports bar and dive bar elements with a single pool table and a semi double story design. Atmosphere stays laid back with lively traffic and a cool DJ playing music patrons pick. Outdoor patio offers a local vibe distinct from upscale spots.

Local vibe blends sports bar and dive bar styles. Semi double story design adds a unique touch inside. The DJ and wall pictures bring a super cool atmosphere.

A small patio sits out front for cocktails and beers. The outdoor area offers a relaxed vibe but lacks ADA compliance at the entrance. Security sometimes directs people to stay on the patio.

People are saying

"The bar has a really great atmosphere and a cool vibe."

"The staff here are super nice, even when they're slammed."

"I enjoyed the nice outdoor area for a cocktail."

Good to know

1

Bring your ID to enter The Boss Bar.

2

The bar is open late, making it a good option for late-night travelers.

3

The entrance is not ADA compliant.

08
Su Casa Mexican Restaurant image 1
Mexican restaurant

Colorful decor and a mural telling cultural stories create an authentic Mexican atmosphere with a cozy yet open layout. Outdoor seating is abundant, and a bar with televisions adds a lively touch. Complimentary group photos and occasional live Mariachi music contribute to a festive vibe.

Cool vibe comes from the chill atmosphere and characteristic building. The decor adds to the picture-worthy setting that invites hanging out for hours.

Outdoor seating offers a cute and inviting patio with plenty of space. Both indoor and outdoor options are available for dining.

People are saying

"This Mexican food is so delicious and authentic."

"The atmosphere here is really cool and chill."

"The outdoor seating here is really enjoyable."

Good to know

1

Happy hour runs from 3 to 6pm, valid only at the counter.

2

Couples special available on Valentine's Day.

3

A parking garage is on the same block, with SpotHero reservations.

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River North, Chicago

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