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New Yorkers 1st Choice
Local picks in River North

Upscale cocktail spots

An upscale evening defined by refined cocktails.

Based on 702 Opinions
+699
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Updated May 2026
01
Sophia Steak Chicago image 1
Sophia Steak Chicago image 2
Sophia Steak Chicago image 3
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Upscale steakhouse offers intimate indoor seating and a welcoming outdoor patio with plants and shade. Atmosphere feels warm and inviting with stylish decor including Deco lamps and a flowered canopy. Cocktails and wine pairings complement perfectly cooked steaks in a comfortable setting.

Cocktails here offer a mix of light, floral flavors and balanced, flavorful classics. The lounge staff are welcoming and the weekend brunch features bottomless cocktails alongside specialty drinks.

Elegant and relaxing atmosphere sets an upscale vibe throughout. Sides and starters feature bold flavors with elegant presentation.

People are saying

"The steak here is melt-in-your-mouth tender and perfectly seasoned."

"The cocktails here are amazing and the staff makes you feel so welcome."

"The steaks here are perfectly aged and seared to juicy tenderness."

Good to know

1

Happy hour runs from 4:30 PM to 5:30 PM, including weekends.

2

Reservations are recommended for special occasions like birthdays.

3

Half off bottles of wine are available on Monday nights.

02
VELA image 1
Mexican restaurant

Space channels sophisticated Mexican vibes with warm, vibrant design inspired by Mexico City. Music shifts from chill to loud with a live DJ mixing house, reggaeton, and hip hop, creating a lively atmosphere. Guests enjoy upscale casual energy with comfortable seating and standout cocktails.

Cocktails feature a top-tier tequila selection and include standout drinks like the Carrajillo de Olla. Staff provide superb guidance to help choose from an amazing menu during happy hour and beyond.

Sophisticated Mexican vibes set the tone with elegant lighting and beautiful decorations. The atmosphere suits date nights and refined after-work drinks.

People are saying

"The food here has flavor profiles that are above and beyond."

"The cocktails here are phenomenal, with recommendations that are spot-on."

"The upscale cocktails here are amazing, with unique flavors and flawless presentation."

Good to know

1

Happy hour offers $10 off cocktails and half-price appetizers from 4-6pm.

2

Reservations are recommended for large parties, especially on weekends.

3

The restaurant hosts a popup event with their sister restaurant every month.

03
Yasemi, A Modern Mediterranean Restaurant image 1

Spacious restaurant with modern, elegant decor and airy layout that avoids crowding. Atmosphere feels casual but chic, with loud music creating an energetic vibe. Tables require personal light to read menus due to dim lighting.

Happy Hour features unique cocktails at a very reasonable price. Drinks like the blood orange Paloma and kiwi kefi stand out for their delicious flavors and stunning presentation.

Atmosphere feels sophisticated and comfortable with an elegant yet warm vibe. Decor leans toward chic and stylish.

People are saying

"The Mediterranean food here is fresh and delicious, especially the hummus."

"I stopped in for happy hour and the cocktails were a great deal."

"I can't wait to return for the Upscale experience."

Good to know

1

Happy hour runs daily from 4-6pm with unique cocktails at reasonable prices.

2

Enjoy $2 oysters during happy hour, a great deal for seafood lovers.

3

The restaurant adds a 4% surcharge to all bills, so plan accordingly.

04
Hawksmoor Chicago image 1

Steakhouse offers a stylish and warm dining room with quiet sophistication and a relaxed but upmarket atmosphere. Cocktails are expertly crafted, complementing the coal-cooked steaks that define the menu. Private rooms and a dynamic space support both intimate and business gatherings.

Cocktails here pair well with the food, especially the great steaks. Drinks complement the menu with wonderful flavors.

People are saying

"The food here was delicious and cooked to perfection."

"The cocktails here were amazing and delicious."

"The upscale porterhouse steak is cooked flawlessly and full of rich, beefy flavor."

Good to know

1

Happy hour runs from 5pm-6pm with great deals on steak, burgers, and oysters.

2

Reservations are recommended for the Sunday roast, which is only available on Sundays.

3

The restaurant offers gluten-free options and is knowledgeable about dietary restrictions.

05
Akiro Hand Roll Bar image 1
Japanese restaurant

Counter seating surrounds chefs who handcraft sushi rolls in full view, creating a lively and social dining experience. The space combines chic decor with an elegant, downtown vibe that complements the fresh, high-quality sushi and thoughtfully paired cocktails.

Cocktails here stand out for being consistently amazing and well-crafted. The jasmine fizz offers a notable non-alcoholic option that complements the menu.

Elegant atmosphere blends with a relaxed, welcoming vibe. Food features sophisticated sauces and balanced flavors, especially in dishes like Tuna Tiradito.

People are saying

"The sushi chefs here are amazing and give great recommendations."

"The cocktails here were amazing and excellent."

"The ambiance here is elegant yet welcoming."

Good to know

1

Reservations are recommended for busy nights like New Year's Eve.

2

The restaurant specializes in Nikkei cuisine, blending Japanese and Peruvian flavors.

3

Expect tight seating arrangements, which may affect dining comfort.

06
The Alston image 1
Steak house

Dining room offers spacious elegance with a unique interior design and tableside presentations like duck press. Atmosphere blends pre-Covid hospitality with a lively, upscale crowd. Bar serves impressive cocktails alongside expert wine pairings.

Complimentary welcome cocktail sets the tone. Cocktails are consistently delicious and pair well with appetizers.

Elegant and thoughtfully designed space creates a sophisticated dining experience with a welcoming atmosphere and stunning views.

People are saying

"The steak here is outstanding, and the service makes you feel well taken care of."

"The atmosphere here is elegant and thoughtfully designed."

"The cocktails were just okay."

Good to know

1

Reservations are recommended to secure a table, especially during peak hours.

2

A 3% service charge is added to all credit card transactions.

3

Happy hour features a curated menu of food and drinks.

07
The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago image 1

Upscale hotel with a sophisticated design aesthetic and elegant yet comfortable atmosphere. Rooftop terrace and bar offer stunning views and a lively spot for cocktails and small bites. Central location attracts a bustling crowd, creating a vibrant energy throughout the day.

Rooftop offers a great outdoor space for cocktails with fire heaters for colder weather. Lobby bartenders craft excellent cocktails, and the rooftop bar serves high quality drinks alongside small bites.

Elegant furnishings and plush bedding create a refined luxury atmosphere. The design feels sophisticated yet relaxed, blending comfort with high-end amenities.

People are saying

"The hotel staff were so kind and helpful."

"The bathroom was spacious and had a separate tub and shower."

"It's so elegant, with sophisticated design and plush furnishings."

Good to know

1

Expect a Daily Destination Fee upon arrival, which may not be disclosed during booking.

2

Room service is unavailable after 10:30 PM, despite advertised hours until 11 PM.

3

The hotel is attached to the Shops at North Bridge for convenient shopping.

08
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.

Bartenders like Derrick craft amazing cocktails while servers such as Julio offer unique, contest-winning drinks. Staff show strong knowledge of cocktail preparation and pairings with food and wine.

Dark woods and old-world steakhouse charm create a classic, refined atmosphere. The space blends historic Chicago charm with an updated, elegant feel.

People are saying

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

"The upscale steaks here are outstanding and perfectly cooked."

"The cocktails here are amazing."

Good to know

1

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

2

Valentineโ€™s Day celebrations offer special menu items.

3

Reservations are recommended, especially during holidays.

09
Coco Pazzo Restaurant & Bar image 1
Italian restaurant

Open wood-fired grill and rustic decor create an elegant, cozy atmosphere with candlelit tables and heavy velvet curtains that reduce noise and separate diners. The space fills quickly, fostering a lively yet comfortable vibe suited for polite, discreet conversation without loud music. Views of the city through lovely windows add to the upscale, professional feel.

Offers tasty and reasonably priced cocktails with consistently great flavors.

Warm, candlelit tables and rustic decor create a cozy yet elegant atmosphere. The setting suits discreet and polite diners who prefer quiet over loud conversation.

People are saying

"The Italian food here, especially the pasta, is outstanding and delicious."

"The Upscale food here is fantastic, with rich flavors and fresh ingredients."

"The cocktails here were great and very good."

Good to know

1

Reservations are recommended during busy times, especially on weekends.

2

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

3

The average meal cost is around $150 for two, including drinks.

10
Tortoise Supper Club image 1
American restaurant

Elegant supper club blends live jazz music with a cozy, lively atmosphere featuring dark wood and colorful jazz-inspired wallpaper. Dining spaces include a private room with a bar, creating intimate vibes amid a bustling crowd. The setting combines elements of a jazz club and restaurant for a unique experience.

Skilled bar chefs craft creative cocktails that pair well with food. The blood orange harpoon stands out, and happy hour offers half-off cocktails plus $1 oysters and shrimp cocktail.

Elegant atmosphere blends with an intimate and welcoming vibe. Attentive service complements the elegant ambiance without feeling stuffy.

People are saying

"The food at these dinner spots was spectacular and delicious."

"You have to try the beef Wellington; it's expertly prepared and tender."

"It's an elegant, intimate, and stunning atmosphere here."

Good to know

1

Reservations are required for private events and should be made well in advance.

2

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

3

Valet parking costs $16 for three hours, making it convenient for guests.

11
Mastro's Steakhouse image 1
Fine dining restaurant

Elegant dining space features dim, cozy lighting and live music performances that create a romantic, upscale atmosphere. The lounge offers an upbeat vibe with talented singers and pianists providing background entertainment. Seating is close together, enhancing a lively, intimate feel.

Intricate cocktails blend pineapple juice and tequila with care. The bar manager offers personalized recommendations and occasional Port tastings at the table.

Warm and elegant atmosphere sets the tone here. Live music adds to the upscale and refined vibe.

People are saying

"The steak here is amazing, with attentive and friendly staff."

"The cocktails here are expertly made by attentive and friendly bartenders."

"The atmosphere here is upscale, elegant, and visually appealing."

Good to know

1

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

2

Reservations are recommended for dinner, especially on weekends.

3

Valet parking is available and recommended for convenience.

12
Lure Fishbar - Chicago image 1
Seafood restaurant

Seafood restaurant with quiet, elegant atmosphere and beautiful interior design featuring boat decor and funky wall art. Seating is comfortable and the space offers a small patio alongside plenty of indoor tables. The vibe suits a fancy dining experience rather than a casual, lively spot.

Bartenders Alex and Gabe serve friendly, fast service with great cocktails that taste very good.

The spot offers a quiet and elegant atmosphere with excellent seafood. It suits both casual dinners and elegant date nights.

People are saying

"The seafood here is fresh, high quality, and delicious."

"The cocktails here are fantastic and made by friendly, attentive staff."

"The atmosphere here is quiet and elegant."

Good to know

1

Happy hour runs daily from 4 PM to 6 PM, including weekends.

2

Enjoy half-off wine bottles during happy hour.

3

Reservations are recommended for dinner, especially on weekends.

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River North, Chicago

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