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New Yorkers 1st Choice
Local picks in the Loop

Modern date spots

A sleek environment makes the evening feel intentional. It is time to step away from the routine and focus on the person across the table.

Based on 715 Opinions
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Updated April 2026
01
Drunk Shakespeare Chicago image 1
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Performing arts theater

Small, intimate theater with benches opposite each other and bookshelves on all walls creates a cozy, engaging space. Performers deliver high-energy, hilarious Shakespearean plays while interacting closely with the audience. Drinks and food arrive at seats via QR code ordering, enhancing the relaxed, lively atmosphere.

The show blends centuries-old text with modern culture and humor. The cast delivers Shakespeare with sharp modern quips that connect well with today's audience.

Performances blend Shakespeare and improvisational comedy for a lively, fun experience. Personalized moments like singing happy birthday add a unique touch to date nights.

People are saying

"It's hilariously fun and unpredictable."

"It's a hilarious and fun choice for date spots."

"It's a modern show that's super dope and hilarious."

Good to know

1

Must be 21 to enter; ID checked for all ages at the door.

2

The show is rated R and not suitable for the faint of modesty.

3

Expect a fun and unique experience with a comedic twist on Shakespeare.

02
Ayayay - Mexican Eatery image 1
Mexican restaurant

Urban, modern space with Tulum-inspired decor and stunning interior architecture creates an authentic Mexican canteen vibe. Great music energizes the atmosphere, while seating ranges from stools at larger tables to intimate spots for two. The setting feels like a slice of Mexico City with a lively, welcoming energy.

Urban and stylish design creates a modern vibe that feels like Mexico City. The space combines warmth with a contemporary ambiance.

Grilled portobello mushroom and steak tacos stand out as unique taco options. Tuesday nights at 6 PM offer a great date atmosphere with appetizers that impress even picky eaters.

People are saying

"I found the food here to be delicious and well-seasoned."

"The guacamole and chips here are amazing for Date Spots."

"The modern Mexican food here is delicious and unique."

Good to know

1

Happy hour runs daily from 2 to 6 pm.

2

$3 Taco Tuesdays offer great value for visitors.

3

Wednesday features a special margarita deal.

03
Hotel Blake, Ascend Hotel Collection image 1

Spacious rooms offer breathtaking views and artistic, upscale decor with comfortable beds. The lobby and dining areas present a classy, elegant atmosphere while city noise and sirens create a lively urban backdrop. Amenities include a well-equipped gym with views, a cafe downstairs, and convenient valet parking.

Rooms feel clean and modern with all the expected amenities for a 4-star stay. The building keeps its historic look outside but surprises with modern touches inside.

Rooms offer a cozy vibe with quick, friendly service for any issues. Couples can enjoy thin crust pizza with customizable toppings and a relaxed atmosphere for a quiet night.

People are saying

"The hotel staff were fantastic, so friendly and helpful."

"The breakfast here is fabulous, right in the heart of the city."

"The staff here are so thoughtful, they even left a birthday card in our room."

Good to know

1

Parking costs $60 per day, so plan accordingly.

2

The hotel is within walking distance to Grant Park and Soldier Field.

3

Rooms are clean, modern, and comfortable for a pleasant stay.

04
Momento Cantina image 1
Mexican restaurant

Space features vibrant Mexican-inspired decor with colorful lights and intricate metalwork. Atmosphere feels fun and lively, enhanced by live mariachi music and reggaeton beats. Unique self-serve tequila and mezcal stations invite guests to sample drinks at their own pace.

A modern atmosphere sets a lively and welcoming tone. The menu blends traditional and modern dishes with generous portions, and staff explain the flavors and preparation behind each item.

Dinner offers a curated experience that suits date nights well. The fish tacos stand out as a memorable dish to share.

People are saying

"The food here is delicious and fresh."

"The food here is delicious; I loved the ribeye tacos and tuna tostada."

"The modern twist on traditional Mexican fare is unforgettable."

Good to know

1

Happy hour runs from 4-7pm with great deals on drinks and appetizers.

2

Friday night features live Mariachi performances starting at 8pm.

3

The venue plans to host live DJ performances in the future.

05
Staypineapple, An Iconic Hotel, The Loop Chicago image 1

Historic building blends modern amenities with charming style and comfortable rooms featuring exceptional views. Atmosphere stays fun and welcoming with a calm, chill vibe throughout. Complimentary treats and a friendly bar add to the inviting experience.

Rooms blend modern comfort with historic charm. The building keeps its old-time charm while offering modern amenities.

Attention to personal details creates a thoughtful atmosphere for couples. Friendly staff greet guests by name and suggest local spots to explore, enhancing the date experience.

People are saying

"This hotel's location is great for walking everywhere."

"The beds and furniture felt so comfortable and modern."

"The staff went above and beyond to make our stay special."

Good to know

1

Happy hour offers a burger and beer or soda for $10 from 4-6 pm.

2

Every afternoon, enjoy a cookie hour with complimentary beverages.

3

Valet parking is expensive and can be problematic during busy events.

06
Chicago Athletic Association - The Unbound Collection by Hyatt image 1

Venetian-Gothic architecture shapes a stylish hotel with ornate woodwork and intricate carvings. Lively atmosphere fills public game rooms and a rooftop bar with great views of the lake and park. Athletic-themed amenities include basketball, bocce, and yoga, blending historic charm with active recreation.

Rooms blend historic character with modern comforts, creating a unique and comfortable space. The building features Gothic-era architectural details alongside modern functionality.

People are saying

"It's a striking historical site with authentic charm and artistic details."

"It's a restored historic building with modern touches and contemporary comfort."

"It's a charming, historical venue, perfect for date spots."

Good to know

1

Happy hour runs daily from 4-6pm with discounted drinks.

2

Expect wedding crowds on weekends due to the hotel's wedding venue status.

3

Reservations are required weeks in advance for dinner at Cindy's Rooftop.

07
The LaSalle Chicago, Autograph Collection image 1

Hotel combines old-fashioned charm with a modern twist in a sheek, elegant setting. Rooms are quiet, cozy, and spacious with attention to detail throughout. Public spaces include a quieter bar with jazz and offer great city views.

Rooms feel modern and spacious with clean lines and all essentials for comfort. Interiors blend upscale design with a touch of old-world charm, keeping halls and spaces fresh and inviting.

People are saying

"The hotel staff here is so friendly and helpful."

"The interior feels modern, luxurious, and elegant."

"Stan went above and beyond assisting us with our dog walk."

Good to know

1

The Grand Ballroom on the 22nd floor hosts weddings and events.

2

Jazz nights occur every Friday and Saturday at the in-house restaurant.

3

Check-in is located on the 21st floor, right outside the elevators.

08
Hyatt Regency Chicago image 1

Hotel offers modern design with spacious rooms featuring river views and comfortable beds. Common areas buzz with activity, creating a lively atmosphere despite occasional crowding. Amenities include a top-notch gym, club level access, and convenient on-site services like car rental and security.

Spaces show a modern elegance with a classic touch. Rooms stay clean and modern throughout.

Rooms offer excellent views that set a memorable backdrop. The setting suits celebrations and meaningful moments, making it a spot where relationships have deepened.

People are saying

"This hotel's downtown location is perfect for walking everywhere."

"The rooms felt fresh, modern, and offered beautiful river views."

"It's perfect for Date Spots, with the river and Magnificent Mile nearby."

Good to know

1

Restaurants remain open until 1am for late-night dining options.

2

Valet parking costs $80 per night, which is quite high.

3

The hotel does not offer shuttle service to O'Hare Airport; taxi costs around $60.

09
citizenM Chicago Downtown image 1

Hotel offers modern, eclectic design with vibrant colors and creative communal spaces including a bar and terrace with city views. Rooms feature smart home technology and blackout shades, providing a quiet, well-insulated environment. Gym and workstations add to the functional, trendy atmosphere.

Rooms feature iPad controls for lighting, TV, and curtains, blending tech with comfort. Spaces show a European flair and a unique, creative design that feels cozy and modern.

Rooms feel small but cozy, designed with a modern, unique touch. The space suits couples looking for an intimate setting.

People are saying

"I loved staying at this hotel; I'll definitely return."

"It's the perfect location for Date Spots, with attractions and shopping within walking distance."

"This modern hotel's location is great for walking everywhere."

Good to know

1

The hotel is located in the heart of Chicago, close to major attractions.

2

Parking costs around $50 a night and is located a block away from the hotel.

3

The gym is one of the best hotel gyms available.

10
The St. Regis Chicago image 1

Towering skyscraper offers spacious rooms with epic city views and an elegant atmosphere. Amenities include a large indoor pool, well-equipped gym, and personalized butler service. Dining spaces provide luxurious settings with rooftop views and unique breakfast options.

Rooms feature modern design with luxurious furnishings and standalone tubs. The entrance and overall architecture show modern sophistication combined with warm elegance.

People are saying

"Vince at the Hotel concierge desk went all out to make everything exceptional."

"The staff went above and beyond for our special occasions."

"It's so modern, with a chic and warm elegance."

Good to know

1

Every evening at 5 pm, they do Sabrage (Champagne Sabering) for guests.

2

There is a daily champagne opening ceremony with a saber starting at 5:30 p.m.

3

The hotel is located near Riverwalk, providing easy access to attractions.

11
Sports Illustrated Resorts Chicago image 1

Hotel offers great views and modern, comfortable rooms with thoughtful amenities like in-room kettles and a well-equipped gym. Rooftop bar and club create a loud atmosphere with bass noise permeating halls late into the night. Design is upscale and clean, but overall vibe is not warm or welcoming.

Rooms feature modern design with thoughtful details that support both work and relaxation. Panoramic city views and vibrant energy add to the lively vibe.

Rooms feature a sliding door that helps couples with different wake-up times. Staff often go the extra mile to make special occasions memorable. Comfortable stays suit couples looking for a relaxed getaway.

People are saying

"The hotel staff went above and beyond to make me feel welcome."

"The rooftop has stunning city views and is a great place to unwind."

"The rooms here are great Date Spots with super comfortable beds."

Good to know

1

Rooftop parties occur on weekends, featuring house music and a vibrant atmosphere.

2

Happy Hour offers complimentary drinks for guests from 4-5pm daily.

3

Reservations for special events like birthday celebrations are recommended for personalized services.

12
Renaissance Chicago Downtown Hotel image 1

Rooms offer spacious layouts with spectacular river views and maintain a quiet atmosphere despite nearby city noise. Rooftop bar provides a comfortable setting with heaters and fire pits, creating a pleasant spot to relax. Central bar stays lively, attracting a steady crowd, while the overall vibe remains luxurious and calm.

Rooms feature modern technology and nice decor. The atmosphere feels fresh and upscale with a clean, lively vibe throughout.

People are saying

"The hotel staff were so kind and professional."

"It's a clean, modern hotel right in the heart of the action."

"The staff here are so friendly and helpful for your date spots."

Good to know

1

The hotel charges $80 for overnight parking.

2

Valet parking is available for $88 per night.

3

The hotel is located right off the river, providing great views.

13
Pendry Chicago image 1

Historic building with Art Deco design offers spacious rooms featuring city views and luxurious amenities. Lobby and rooftop lounge provide a resort-like atmosphere with music and entertainment. Downtown location brings loud street noise at all hours, affecting room quietness.

Rooms show modern elegance with a clean, trendy design. The atmosphere blends cozy and elegant elements smoothly.

Suites offer a plush king bedroom and two bathrooms, fitting for a couples retreat or family. The setting suits both first dates and anniversary getaways with a comfortable, intimate vibe.

People are saying

"The hotel staff were so friendly and helpful."

"The service here is top tier and made our trip memorable."

"The modern staff here are so warm and make you feel special."

Good to know

1

The Cadillac experience is available only on select days and hours.

2

Escalade service operates on Fridays and Saturdays for rides within a two-mile radius.

3

Happy hour is offered daily at the restaurant.

14
theWit Chicago, a Hilton Hotel image 1

Hotel offers lively rooftop bar with great city views and vibrant atmosphere. Rooms and common areas feature funky artwork and a comfy, eclectic design. Nighttime brings street noise and energetic crowds, especially near the club and light rail.

Rooms feature modern furnishings and stay spotlessly clean. The overall vibe is comfortable and efficient, making it easy to settle in.

The rooftop offers a celebratory atmosphere with staff who go out of their way to make occasions special. It creates a memorable setting for couples with personalized service and a lively vibe.

People are saying

"The hotel's five-star service made my day better."

"The rooftop bar has a lively atmosphere and great skyline views."

"The staff here makes it a great spot for a date."

Good to know

1

The rooftop bar hosts a brunch buffet on weekends.

2

Private events frequently close the rooftop bar, limiting access.

3

Valet service is recommended as there is no parking available.

15
Silversmith Hotel Chicago Downtown image 1

Historic building blends modern comfort with classic design in a quiet atmosphere despite city noise. Spacious rooms feature floor-to-ceiling windows and high-quality amenities. Lobby bar offers a chill vibe with excellent service and drinks.

Rooms combine modern comfort with historic charm. Spaces feel spacious and clean with updated amenities and comfortable beds.

People are saying

"The Hotel staff made my stay feel welcoming and personal."

"The staff here are so warm and welcoming, making it a great spot for date spots."

"The rooms felt modern, spacious, and comfortable."

Good to know

1

The hotel charges a $30 historic preservation fee at check-in.

2

Happy hour at the bar features discounted drinks and appetizers until 7pm.

3

The bar closes at 10pm, so plan your evening accordingly.

16
JW Marriott Chicago image 1

Historic architecture blends with modern amenities in a quiet, peaceful setting despite urban surroundings. Spacious rooms offer old school luxury with plush beds and large bathrooms. Public spaces include an elegant lobby and a large bar with ample seating.

Rooms feature clean and modern design. Historic architecture blends with modern amenities throughout the hotel.

Rooms and facilities offer a perfect getaway vibe for couples. Front desk adds a personal touch by embroidering special dates on bathrobes and mailing them home.

People are saying

"I found the hotel to be absolutely beautiful and gorgeous."

"The staff here are so helpful, it makes for great date spots."

"The rooms felt clean and modern."

Good to know

1

Check-in is at 4pm and check-out is at 12pm.

2

Valet parking costs $88.00 per night.

3

Self-parking is available for $68.00 per night.

17
Canopy by Hilton Chicago Central Loop image 1

Quiet, spacious rooms with luxurious decor and modern amenities create a cozy, home-like atmosphere. Heavy carpeting and thoughtful design keep noise low despite nearby urban sounds. Facilities include a well-equipped fitness center, free water refill stations, and a rooftop restaurant open for dinner.

Rooms feel spacious and modern with a clean and comfortable design. The overall aesthetic is unique and beautifully crafted.

Amazing staff create a welcoming atmosphere. Parking is safe and just a couple blocks away.

People are saying

"This hotel's decor is beautifully designed and visually appealing."

"The rooms felt modern, clean, and beautifully designed."

"It's a cute boutique hotel, perfect for Date Spots."

Good to know

1

Parking at the hotel costs $75 a day, which can be high on weekends.

2

The hotel is located just 2 blocks from Union Station, making it accessible.

3

Wi-Fi issues may occur, as some guests reported authentication problems.

18
Fairmont Chicago, Millennium Park image 1

Hotel offers amazing city views and a quiet workspace with beautiful decor. Gold Lounge provides a relaxing retreat with light food and drinks. Efficient elevators and a well-equipped 24-hour gym support convenience and fitness needs.

Rooms feature modern design with comfortable beds and great showers. Cleanliness and essential amenities meet contemporary standards.

Offers a spot for date nights especially around hockey games. Experiences vary, with some finding it memorable while others suggest it may affect the mood for couples seeking leisure.

People are saying

"The city views from the room are amazing."

"The staff here really make your romantic weekend feel special."

"The rooms felt modern and were really clean."

Good to know

1

Reservations are required for the holiday bar during the festival.

2

Parking can be confusing; plan to arrive early to find the garage.

3

Expect extra charges for amenities, even if not used.

19
The Blackstone, Autograph Collection image 1

Historic hotel with classic charm and artistic decor creates an elegant and lively atmosphere. Rooms offer spacious layouts and great views, though noise from hallways and street is noticeable. Fitness center shows signs of wear but remains a notable feature.

Blends historic charm with modern style through beautiful touches. Rooms feel large, comfortable, and well equipped.

Offers a quiet setting for couples seeking a night away from the kids. Provides a comfortable space for a one night stay focused on relaxation and connection.

People are saying

"The hotel rooms here are spacious and impeccably clean."

"It strikes a nice balance between historic charm and modern comfort."

"The historic lobby feels so warm and inviting, perfect for Date Spots."

Good to know

1

Parking is available at a garage across the street, but no valet service is offered.

2

The hotel charges a nightly resort fee that is not disclosed at check-in.

3

Breakfast and snacks are served Monday through Friday at the hotel restaurant.

20
Swissotel Chicago image 1

Rooms offer panoramic views of the lake, river, and cityscape, creating a striking backdrop. The atmosphere feels upscale and spacious, with a large gym featuring impressive equipment and scenic views. Efficient escalators connect floors smoothly, supporting a steady flow of guests.

Rooms feel spacious and well-appointed with a clean, modern design. The elevator features high tech elements without being overdone.

Weekend stays often mark special occasions like birthdays and anniversaries here. Rooms accommodate couples and small groups, making it a solid choice for celebrations and quiet time together.

People are saying

"The hotel staff were lovely and accommodating."

"The Modern staff is super friendly and always ready to help."

"The views from the rooms are spectacular, perfect for Date Spots."

Good to know

1

Expect hidden fees like a $25 resort fee not disclosed at booking.

2

Parking costs $87 per night, which is considered high.

3

The hotel bar closes at 10:30 PM on weekends.

21
Nutella Cafe Chicago image 1

Nutella-themed decor creates a bright and inviting space with personalized Nutella jars as a unique feature. The cafe feels cramped and crowded, with small tables placed very close together, often leading to a noisy atmosphere. Outdoor patio seating offers an alternative to the tight indoor space.

Bright, modern decor fills the space with a cozy vibe. A Nutella jar-shaped door adds a playful touch to the inviting atmosphere.

Outdoor seating offers a comfortable atmosphere with pleasant evening temperatures. Sharing a crepe works well for couples not very hungry, and the menu includes Nutella options that appeal to fans.

People are saying

"You have to try the Nutella Crepe with bananas; it's very tasty."

"These Date Spots are perfect for sharing sweet crepes and Nutella treats."

"The Nutella latte is rich, chocolaty, and perfectly balanced."

Good to know

1

Expect a wait time of 30-45 minutes during peak hours.

2

The cafe opens at 8 am daily.

3

You can personalize your Nutella with your name for a unique souvenir.

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