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New Yorkers 1st Choice
Guide to the Loop

Unique spots with outdoor space

You want to be outside without sacrificing the character of the place.

Based on 715 Opinions
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Updated April 2026
01
Maggie Daley Park Ice Skating Ribbon image 1
Maggie Daley Park Ice Skating Ribbon image 2
Maggie Daley Park Ice Skating Ribbon image 3
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Ice skating ribbon features a unique track shape with varying elevations that create a more fun experience than typical oval rinks. Skating offers amazing city skyline views and a vibe that feels like skating on a river in the woods. The atmosphere is lively with music and crowds, especially during evening sessions when city lights enhance the scenery.

A ribbon-shaped ice rink with elevation changes creates a unique skating loop. The uphill and downhill slopes offer a different feel from traditional flat rinks.

Outdoor activities include a skating ribbon that suits all skill levels, even beginners. The space offers a family-friendly environment where kids and adults can enjoy an immersive outdoor experience.

People are saying

"The ice skating ribbon offers a fun, unique experience with slopes."

"I experienced a unique skating ribbon with slopes and hills."

"I loved skating the ribbon; it felt like skating on a river in the woods."

Good to know

1

Reservations are required in advance as time slots fill up quickly.

2

Ice skating is available from mid-November through mid-March.

3

The park has two entrances, one with lockers and restrooms.

02
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 high tech amenities and offer great city views. The overall vibe is cozy and modern, making it a unique stay for couples or solo travelers.

Rooftop and patio areas offer a very relaxing atmosphere. The outside patio works well for unwinding after a long day of walking.

People are saying

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

"It's a fun, funky, and unique place with a modern style."

"The outdoor patio and terrace areas are really relaxing."

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.

03
Seville Chicago image 1
Restaurant

Rooftop restaurant offers stunning city views and a relaxed atmosphere with friendly staff. The space features beautiful ambiance suitable for quiet meals or lively happy hours. Cocktails and small plates complement the setting, creating a charming dining experience.

Dishes feature unique and flavorful tastes that stand out. The Moroccan wings have a unique spice and fall off the bone, while the sea bass offers a distinct flavor that exceeds expectations.

Floor-to-ceiling windows offer beautiful city views inside. Outdoor seating on the patio provides a clear sightline to the south side of the Sears Tower during warmer months.

People are saying

"You'll love the inventive cocktails, many are sweet."

"The outdoor rooftop space offers a beautiful view."

"The food here has unique, flavorful tastes."

Good to know

1

Happy hour runs from 3:30 to 5:30pm on weekdays.

2

Happy hour offers great deals on food and drinks.

3

The restaurant is located on the 16th floor of the Hilton hotel.

04
Chicago French Press at Roosevelt Collection image 1

Small coffee shop with bright outdoor seating and a cozy, luxurious vibe. Atmosphere feels welcoming and fun, often busy and not ideal for working inside. Offers unique coffee flavors and a variety of tasty pastries.

Specialty drinks stand out with unique flavors. Coffee offers a distinctive taste not found elsewhere.

Sunny patio space offers mostly outdoor seating with a fire pit nearby. The area suits sipping drinks and working while enjoying nice weather.

People are saying

"I had some of the best coffee I've ever tasted here."

"Their specialty coffee drinks are truly unique and amazing."

"The outdoor space is a lovely patio, perfect for enjoying the nice weather."

Good to know

1

The cafe does not accept cash; only credit cards and mobile payments are allowed.

2

Free parking is available for up to 2 hours near the shop.

3

The menu is not fully available online, which may limit pre-visit planning.

05
ESPRESSO AND MILK image 1

Minimalist coffee shop with stark white interior and black-clad baristas behind a clean white marble counter. Atmosphere is bright and inviting but noisy with an echo, offering no indoor seating and relying on outdoor patio space for guests. Focus centers on high-quality espresso drinks and unique latte flavors, making it ideal for quick takeout visits.

Espresso and milk feature high quality espresso with unique latte flavors. They make their own syrups, giving each cup a distinctive taste.

Outdoor seating includes a small patio space with limited seats. The area sits on a busy street, which can affect comfort, and lacks convenient trash bins for disposal.

People are saying

"I loved the iced mocha; it was well balanced."

"I found the latte flavors here to be so unique and delicious."

"The outdoor patio seating was appreciated because the space was small."

Good to know

1

There is no seating at this coffee shop, so it is takeout only.

2

They are open from 7 AM to 3 PM on weekdays.

3

Expect long wait times during morning rush hours.

06
Pittsfield Cafe image 1

Old diner inside an elegant 1930s building offers a cozy atmosphere with a quiet morning vibe and architectural charm. Seating is ample, including outdoor spots with an amazing view. The setting feels like a calm oasis amid a bustling city.

Vintage building with unique architecture creates a distinct old-school dining vibe. The setting blends history and art with warm service for breakfast.

Outdoor seating features a cozy patio feel with a terrace facing an interior patio. Tables offer an amazing view of the Pittsfield Building, and pets or service dogs must stay outside.

People are saying

"I found this diner to have delicious, classic American food."

"I found the building's vintage architecture and amazing ceiling to be unique."

"The outdoor seating has a beautiful view of the Pittsfield Building."

Good to know

1

They have early bird specials until 11am every day.

2

Credit card payments incur a 3% charge without prior notice.

3

The bathrooms require a key from management for access.

07
Necessary & Sufficient Coffee - Printers Row image 1

Cafe offers spacious seating with large open windows facing the street, creating a vibrant yet cozy atmosphere. Live DJs and local art displays add to the creative and chill vibe. Both indoor and outdoor areas provide comfortable spots for work or relaxation.

Donuts and a cranberry hibiscus scone stand out with their unique flavors. The menu features seasonal items and a variety of colored cakes, chocolates, and drinks.

Outdoor seating includes tables and window spots that feel comfortable and cute. Games add a bit of fun to the space while waiting for food.

People are saying

"I found the coffee here to be good and smooth."

"The outdoor space is comfortable and cute with a wonderful view."

"I loved their unique pastries and drinks."

Good to know

1

They invest heavily in community events and support numerous local small businesses.

2

Sundays are lively with a DJ setting the tone for the day.

3

They automatically add a 15% gratuity to all orders.

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