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New Yorkers 1st Choice
Guide to the Chicago Loop

Outdoor spaces

An outdoor space that offers a genuine escape, not just a few chairs shoved onto a cramped concrete slab.

Based on 801 Opinions
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Updated May 2026
01
Grant Park image 1
Grant Park image 2
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City park

Urban park features panoramic city skyline views and a huge central fountain perfect for relaxation. Stretching 2.5 km along Lake Michigan, it offers wide open green spaces for picnics and play. Vibrant events and a lively skatepark create a dynamic atmosphere for all ages.

A green space axis stretching nearly 2.5 km along Lake Michigan offers wide open areas for picnics, hiking, and outdoor exercise. Kids find plenty of room to run and play, making it a hub for outdoor activities and a peaceful escape within the city.

People are saying

"It's a beautiful, spacious park with great walking trails."

"I loved the nice view of the skyline and lake."

"I loved the open green spaces and walking trails here."

Good to know

1

Parking costs $30 per day near Grant Park.

2

Public restrooms are not available in Grant Park.

3

Consider using Uber or bus transportation when visiting Grant Park.

02
Maggie Daley Park Ice Skating Ribbon image 1

Skating ribbon offers a unique track shape with hills for fun and suits all skill levels. City skyline views create a lively atmosphere with music and lights at night. Families enjoy a friendly outdoor space that feels like skating through woods.

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."

"The ice skating ribbon at these parks feels like skating on a river in the woods."

"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.

03
Kasey's Tavern image 1

Classic dive bar with extensive beer selection and a friendly vibe draws a lively local crowd. Outdoor patio offers nice street seating perfect for warm days. Rock music from a jukebox adds to the down-to-earth atmosphere.

Outdoor seating includes a nice patio on the street. Both outdoor and indoor areas provide good space. The patio works well in warmer months.

People are saying

"They have a great beer selection with tons of options."

"It's a chill, no-frills spot to catch a game and hear your friends."

"The outdoor seating here is really nice, especially in the summer."

Good to know

1

Contactless pay isn't available at Kasey's Tavern.

2

Customers can bring in outside food if they prefer.

3

Kasey's Tavern has several gluten-free options, including ciders and beers.

04
Rivers Restaurant image 1
American restaurant

Outdoor seating features a large covered patio with stunning river views perfect for watching boats. Atmosphere shifts from quiet and romantic to lively during happy hour. Space suits both casual dining and upscale event receptions with a fun vibe.

A large covered patio sits right on the river, offering stunning views and a spot to watch boats pass by. The outdoor space feels open and perfect for seating guests comfortably.

People are saying

"It's the perfect spot for your wedding reception or anniversary."

"This lunch spot has a great view of the river and boats."

"The patio has a nice view of the river."

Good to know

1

Reservations are recommended for larger groups, especially during busy hours.

2

The kitchen closes at 7pm, so plan your visit accordingly.

3

The restaurant can be busy after work hours, especially on Fridays.

05
citizenM Chicago Downtown image 1

Hotel blends modern design with smart home tech for comfort and style. Rooftop and patio provide relaxing outdoor spaces perfect for unwinding. Vibrant communal areas like the bar add a trendy atmosphere for socializing and work.

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

"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.

06
Nando's PERi-PERi image 1
Chicken restaurant

Spacious chicken restaurant offers modern decor and a relaxing atmosphere with city views. Guests enjoy meals on a lovely outdoor patio surrounded by a brilliant garden. Futuristic ordering makes dining smooth and casual.

A lovely outdoor patio and a brilliant garden create a great spot for dining outside. The outdoor seating area offers a nice place to enjoy meals when the weather is good.

People are saying

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

"The staff kept kids calm and safe during a scary incident."

"I loved the lovely outdoor patio for dining."

Good to know

1

Parking is validated, making it free if you park in the garage.

2

You order at the counter, which makes it easy for a quick bite.

3

Expect smaller food portions than what the menu images suggest.

07
Cafe Michelle @Dusable Harbor image 1
Mediterranean restaurant

Small Mediterranean spot boasts a breezy patio with gorgeous flowers and stunning views of Lake Michigan and Navy Pier. Atmosphere feels like Europe, perfect for relaxed people watching. Crowd is upscale, matching the high prices.

Outdoor seating feels nice and breezy with a cute patio decorated by gorgeous flowers.

People are saying

"The outdoor seating felt like a European escape, decorated with gorgeous flowers."

"The nice view of Lake Michigan and Navy Pier is amazing."

"The outdoor space is decorated with gorgeous flowers and is nice and breezy."

Good to know

1

Prices for food and drinks are generally high, with some items costing over $10.

2

Expect to pay around $40 for four ice creams.

3

Credit cards are accepted, but check for any additional charges.

08
Bandol Brasserie & Raw Bar image 1

Space blends art deco style with southern France beach vibes for an upscale feel. Outdoor terrace offers oysters and brunch with bottomless mimosas. French pop and chill house music create a lively vibe while cocktails and dishes bring a luxurious dining touch.

Outdoor seating includes a patio and an outdoor terrace where oysters and brunch are served. Bottomless mimosas are available for $30 during patio brunch.

People are saying

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

"The service at these dinner spots is excellent and attentive."

"I enjoyed brunch on the patio with bottomless mimosas."

Good to know

1

Reservations are recommended for dinner, especially on weekends.

2

Happy hour runs from 4 to 6 PM with great deals on drinks and appetizers.

3

The rooftop menu starts at 3 PM, perfect for afternoon gatherings.

09
Brews & Bites Riverwalk image 1

Outdoor seating under shade trees offers stunning views of the River Walk and urban bridges. The vibe is chill and cozy, perfect for casual gatherings and larger groups. Scenic river views blend with a relaxed weekend atmosphere.

Plenty of outdoor seating sits under shade trees with a nice view of the River Walk.

People are saying

"I loved the gorgeous view of the river."

"I thought the lamb burger was the best I've ever had."

"The outdoor space has plenty of seating with nice shade trees."

Good to know

1

Happy hour features a special menu with discounted drinks and appetizers.

2

The venue is seasonal and only operates for a limited time each year.

3

Outdoor seating is plentiful, providing great views of the river.

10
Casa Bonita at Millenium Park image 1

Enjoy outdoor seating under umbrellas with views of the Bean sculpture and city skyline. The place offers Mexican fare and refreshing margaritas with table service in a relaxed, tourist-friendly setting.

Outdoor seating includes tables under umbrellas with views of a bean sculpture. Food and drinks come with table service despite a self-serve setup.

People are saying

"The food here is good, especially the tacos."

"The Mexican food, especially the tacos, had just the right amount of kick."

"I enjoyed the outdoor seating and the marvelous view."

Good to know

1

The entry and venue are accessible for all visitors.

2

Restrooms in the park area are also accessible.

3

Expect to spend around $35-$50 per person for dining.

11
Seville Chicago image 1
Restaurant

Rooftop restaurant boasts stunning city views through floor-to-ceiling windows and a patio seating area facing the Sears Tower. Friendly staff create a relaxed atmosphere perfect for quiet meals or lively happy hours. Enjoy cocktails and small plates in a charming setting.

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 food here is delicious, super juicy and flavorful."

"The outdoor rooftop space offers a beautiful view."

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.

12
Forno Mauri image 1
Pizza restaurant

Wood-fired pizzas shine with high-quality Italian ingredients and thin crusts that taste authentic. Cozy, laid-back vibe feels welcoming and family-friendly. An adorable patio offers a peaceful outdoor spot, perfect when indoor air conditioning makes it muggy.

An adorable patio offers a pleasant outdoor seating area. Outdoor seating often serves as a fallback when the inside gets too hot due to air conditioning issues.

People are saying

"The pizza here has an incredible, authentic Neapolitan crust."

"I should definitely have the tiramisu; it's like being back in Italy."

"The patio was adorable and provided a pleasant outdoor space."

Good to know

1

Reservations are not accepted; seating is first-come, first-served.

2

The restaurant does not offer takeout or phone orders.

3

Pizzas are only available in one size, which is 12 inches.

13
Millennium Hall Restaurant image 1

Frank Gehry's dancing metal design creates a unique vibe with both indoor and outdoor seating offering great views of the ice rink and city. Atmosphere shifts from festive and chill to lively with big screens showing sports, making it perfect for groups and casual dining with a bar-focused vibe.

Outdoor seating offers a beautiful setting with a nice ambience. Both indoor and outdoor options exist, providing flexibility after events like concerts.

People are saying

"Chef David's pizza making class was so fun and awesome."

"I found the beers here to be excellent and tasty."

"The outdoor space here is beautiful and great for people watching."

Good to know

1

Reservations are recommended for pizza-making courses and private events.

2

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

3

Karaoke night starts at 10pm on Thursdays with a two-drink minimum.

14
Senoritas Cantina On Dearborn image 1

Small Mexican spot shines with fantastic margaritas and underrated vegetarian options. Quiet patio offers nice outdoor space on a calm street. Inside, loud music sets a lively Latin vibe.

A quiet patio sits on a calm street, offering a nice size outdoor space. Seating options include both indoor and outdoor areas, creating a relaxed ambiance.

People are saying

"The Mexican food here is authentic and delicious."

"The ambiance is eclectic and vibey, a great spot for photos."

"The outdoor patio is a nice size."

Good to know

1

Happy hour runs from 3-6pm with a 20% discount on drinks.

2

Brunch is now offered on weekends with a special menu.

3

A 3% surcharge applies for credit card payments.

15
Grant Park Bistro image 1

Bright, clean decor and natural light create a lively brunch vibe with bottomless mimosas. Outdoor patio offers great views of Grant Park and umbrellas for shade. Atmosphere shifts from chill to loud during events, making it perfect for both relaxed lunches and vibrant gatherings.

A beautiful patio offers great views of Grant Park with umbrellas for shade. The outdoor seating area feels lovely and inviting for lunch or drinks.

People are saying

"I thought the food here was amazing and excellent."

"The breakfast service here is amazing, especially from Alfredo."

"The patio is beautiful and great for people-watching."

Good to know

1

Happy hour runs from 4-6pm with affordable drink specials.

2

There is a one and a half hour limit for bottomless mimosas during brunch.

3

A 20% service charge is added for tables of more than four people.

16
Chicago French Press at Roosevelt Collection image 1

Small coffee shop shines with bright outdoor seating and a sunny patio featuring a fire pit. Cozy, luxurious vibe makes it welcoming but busy, so not great for working inside. Unique coffee flavors and tasty pastries add to the fun atmosphere.

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."

"The cafe staff are super kind and helpful."

"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.

17
The St. Regis Chicago image 1

Towering skyscraper boasts epic city views and spacious rooms with an elegant vibe. Guests enjoy a large indoor pool and a patio deck perfect for sipping chai lattes outdoors. Personalized butler service and rooftop dining add luxury and charm.

A small cafe outside serves very good chai lattes and other drinks. The patio deck and outdoor terrace offer lovely spots to enjoy city views and drinks.

People are saying

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

"The city views from the pool and terrace are amazing."

"The outdoor terrace offers amazing views of the city lights."

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.

18
Lea French Cafe Michigan Avenue image 1

Cozy terrace offers plenty of outdoor seating with a lovely view of the Bean. Quaint Parisian decor and warm lighting create a charming atmosphere. Self-service ordering and cashless payment make visits quick and easy despite crowds.

Cozy terrace and patio offer plenty of outdoor seating. Breakfast often enjoyed outside when weather is nice.

People are saying

"I loved the delicious, authentic French pastries and croissants here."

"I thought the ham and cheese baguette was perfect, just like Paris."

"The baked goods here are delicious, especially the croissants."

Good to know

1

Parking is available nearby in an underground garage.

2

Expect a wait time of 15-30 minutes during busy brunch hours.

3

The menu features a variety of pastries, including croissants and รฉclairs.

19
Radisson Blu Aqua Hotel, Chicago image 1

Modern hotel by Jeanne Gang offers breathtaking views and a rooftop pool open until 11 pm. Spacious rooms with wall-to-ceiling windows overlook an outdoor park and trail on the third floor. Expect a lively atmosphere with some noise from guests and city sirens.

An outdoor park and trail sits on the third floor, paired with a swimming pool that stays open until 11 pm. Rooms feature wall-to-ceiling windows and patio doors with sweeping views of the outdoor space.

People are saying

"The Hotel wedding coordinator handled every detail for peace of mind."

"The outdoor pool was nice and stayed open after Labor Day."

"The rooms have modern designs and great city views."

Good to know

1

Parking costs $63 per night with no re-entry or $80 per day with in/out access.

2

The hotel has a poor cleanliness record, with reports of dirty rooms and maintenance issues.

3

Expect long lines to enter the hotel, especially during peak times.

20
Franklin Tap image 1
Restaurant

Expansive layout with dog-friendly patio offers a relaxed outdoor spot for casual hangs. Over 100 beers on tap and an affordable menu keep the vibe lively. Multiple TVs show sports, drawing a diverse afterwork crowd to this casual, inviting place.

The dog-friendly patio offers a great spot to hang out with your pup on sunny days. Outdoor seating feels relaxed and inviting for casual gatherings.

People are saying

"The food here is excellent, tasty, and solid."

"I enjoyed the great beer selection here."

"I loved their cider options, especially the pineapple and pear."

Good to know

1

Happy hour runs every day with great deals on drinks.

2

Weekend brunch is available with special menu items.

3

Daily drink specials make it easy to unwind after work.

21
Fontano's Subs & Pizzeria image 1

Classic deli and pizzeria shines with brick oven pizza and cozy sidewalk patio. Well-worn wood paneling and black and white photos create an authentic atmosphere. Outdoor seating offers city views that enhance the chill, welcoming vibe.

Cozy sidewalk patio offers a nice spot to eat outside. Outdoor seating lets you enjoy the city views while dining.

People are saying

"The staff here is so friendly when making your sandwich."

"I enjoyed the cheesy, satisfying deep dish pizza."

"It's nice to have outdoor seating available."

Good to know

1

They charge a 3% admin fee for credit card payments without informing customers beforehand.

2

Getting the pizza by the slice saves time and avoids long waits.

3

It can be busy during lunch or dinner rush, making seating challenging.

22
Pittsfield Cafe image 1

Old diner in a 1930s building offers a cozy atmosphere with architectural charm. Outdoor seating on a terrace with amazing views of the Pittsfield Building creates a calm oasis. Pets and service dogs stay outside, enhancing the peaceful vibe.

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."

"The breakfast here is delicious and the staff is so friendly."

"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.

23
The Marq image 1
Restaurant

Stylish restaurant with a modern interior and quiet bar area offers a classy yet laid-back vibe. Outdoor seating provides an amazing city view perfect for enjoying meals. Spacious rooms support group dining and socializing comfortably.

Outdoor seating offers an amazing view of the city. The patio lets you enjoy a good meal outdoors amid the city's hustle and bustle.

People are saying

"The food here is delicious and creative."

"I really enjoyed the burger; it was solid and flavorful."

"I loved enjoying the city view from the outdoor space."

Good to know

1

The Marq can host events for up to 100 people with excellent service.

2

Happy hour is available, making it a great spot for after-work gatherings.

3

Street parking is available around the corner on Dearborn.

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