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New Yorkers 1st Choice
Best of Chicago

Milkshake with outdoor seating

Made for those who want to enjoy a cold, blended treat while sitting outside in the fresh air.

Based on 739 Opinions
+736
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Updated April 2026
01
Cluck'N Wings image 1
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Chicken restaurant

Chicken restaurant combines elegant lighting with a cozy, welcoming atmosphere that balances comfort and luxury. A chic, rustic minimalist decor complements a patio with cooling mist, offering a calm yet vibrant space for casual or refined dining.

Oreo and peanut butter cup milkshakes stand out here. The strawberry milkshake also gets recommended often.

A hidden gem patio sits in the back, offering a nice escape from the busy street. It suits day parties and casual hangouts with friends, with great music vibes and friendly service.

People are saying

"These burgers are juicy, flavorful, and carefully stacked."

"The patio is perfect for hanging out with friends."

"I tried the Oreo milkshake and it was superb."

Good to know

1

The restaurant offers a full halal menu for all dishes.

2

Kids' meals are available for younger diners.

3

Expect a wait time of about 15 minutes for food after ordering.

02
Spoko image 1
Polish restaurant

Polish restaurant with an intimate, local vibe and a glass garage door that opens to a large beer garden and outdoor patio. Atmosphere ranges from relaxed to loud when busy, offering a friendly and comfy setting. Known for serving authentic Polish beers and dishes like pierogi and sausage made onsite.

Thick, rich milkshakes come in flavors like chocolate Oreo. Kids especially enjoy the creamy texture and bold flavors.

Nice patio and outdoor dining space offer a cool streetside vibe. Partial indoor/outdoor seating adds variety for meals on pleasant days.

People are saying

"The Outdoor Seating here is amazing, especially the Polish staples."

"The brunch here is so good, especially the pierogi Benedict."

"The milkshakes are thick, rich, and delicious."

Good to know

1

Happy hour specials are available with decent prices for drinks and small bites.

2

The portion sizes are large for the prices, offering good value.

3

Spoko is vegetarian and pescetarian friendly, with various menu options.

03
Grant's Wonderburger Grill & Gallery image 1

Small bar and grill combines intimate space with live entertainment and an open-able roof for fresh air. Atmosphere is loud and lively, filled with artwork and a Southside vibe. Menu features highly praised burgers and curly fries, attracting families and locals alike.

Milkshakes come in delicious classic and adult versions. The adult milkshake has a distinct flavor that stands out and is often recommended to try.

Open-able roof lets fresh air in while keeping the space covered. Patio seating includes wall scrabble and occasional live music, creating a lively outdoor vibe.

People are saying

"I thought the burgers here were fantastic and delicious."

"The Wisconsin Cheese Curds here are spectacular and attentive."

"You have to try the adult milkshake; it's delicious."

Good to know

1

The party room accommodates about 15 kids and 25 adults comfortably.

2

You can bring your own dessert for events held at the venue.

3

Parking is usually available onsite, making it convenient for visitors.

04
Devil Dawgs Rush St image 1
Hot dog restaurant

Small space with standing counter and outdoor patio seating creates a casual, local vibe. Atmosphere feels bombastic and lively, with a devilish-themed cashier adding character. Outdoor seating offers a chance to enjoy city life despite limited indoor room.

Milkshakes come with 100% ice cream and strong flavors like peanut butter and Oreo mint. They often include extras like a maraschino cherry and deliver a rich, satisfying taste.

People are saying

"I thought the American food, specifically the hot dogs, were the best ever."

"I enjoyed the great Chicago dogs at the outdoor seating."

"I thought the milkshakes were no joke, super rich and delicious."

Good to know

1

Devil Dawgs Rush St does not have indoor seating; only counter service and outdoor tables.

2

Expect a decent wait time during peak hours, especially on weekends.

3

They only accept credit cards and mobile payments; cash is not accepted.

05
Budacki's Drive In image 1
Hot dog restaurant

Classic 1950s drive-in with outdoor picnic tables and a friendly, chill vibe. Freshly painted walls and a mural create a welcoming atmosphere that feels like a neighborhood hangout. Small indoor seating gives way to a relaxed outdoor experience with movies playing during warm weather.

Milkshakes here are not too sweet and come in flavors like strawberry cheesecake. They pair well with classic Chicago eats like hot dogs and Italian beef.

Outdoor seating offers a clean space with tables set up for a relaxed vibe. The area feels like chilling in the neighborhood, making it easy to unwind outside.

People are saying

"You have to try the amazing American Food, especially the hot dogs."

"I loved the Chicago hot dog with Vienna Beef and Chicagoan toppings."

"You'll love their affordable Milkshake; the prices are the best."

Good to know

1

Budacki's Drive In requires cash payment for small orders.

2

Prices are reasonable, with five large wings and fries costing around $16.

3

You can call ahead to place your order for pickup.

06
Jr’s Red Hots image 1
Hot dog stand

Order-at-the-window hot dog stand with outdoor seating near a parking lot and a heated standing eating area. Atmosphere is mostly quiet with minimal indoor space, focusing on quick bites and classic Chicago food. Open late, it attracts those seeking late-night meals in a safe area.

Milkshakes here have a classic Chicago style vibe and come out with a rich, creamy texture. Preparation time stays reasonable, usually under 30 minutes.

Outdoor seating includes tables along the side and spots by the parking lot. A vestibule outdoor enclosure on the west side offers shelter during bad weather.

People are saying

"I thought the hot dogs here were the best I've had."

"I thought the milkshakes here were sooo good."

"The outdoor seating wasn't shaded and felt a little cold."

Good to know

1

Jr's Red Hots is an order-at-the-window establishment.

2

They are open from 10 AM to 12 AM daily, and until 3 AM on weekends.

3

Jr's Red Hots accepts credit cards and mobile payments.

07
Lucy's Fried Chicken & Smashburgers image 1

Rustic, low-lit space with 60s-themed decor and boozy shakes creates a cozy, casual vibe. Outdoor patio and communal picnic tables invite relaxed dining. Known for spicy fried chicken sandwiches and smashburgers with a neighborhood feel.

Milkshakes come hand-spun and malted, delivering a classic Americana vibe. Vanilla flavor stands out as amazing and pairs well with fries and fried chicken.

Great outdoor space offers a nice patio for dining. The atmosphere feels awesome on a gorgeous day with plenty of fresh air.

People are saying

"The chicken sandwich here is outstanding and amazing."

"I enjoyed the great outdoor seating."

"I loved Lucy's milkshakes, burgers, and beer on tap."

Good to know

1

Delivery took nearly 2 hours, so plan accordingly.

2

The wait for to-go meals is typically 30-45 minutes.

3

Dipping sauces cost extra, so factor that into your order.

08
Superdawg Drive-In image 1
Hot dog stand

Drive-in hot dog stand with car hop service and classic 1950s style creates a nostalgic atmosphere. Eating in cars or at outdoor seating offers a fun family vibe with an authentic old-school Chicago feel. Iconic giant hot dog on the roof marks the well-maintained location.

Real milk shakes and malts come with no skimping on ice cream. Carhops serve filling, amazing milkshakes that stand out.

Clean and well-maintained outdoor seating offers ample tables to enjoy food comfortably. The space provides a relaxed vibe for dining outside or even in the car.

People are saying

"I thought the hot dogs and cheeseburgers were great."

"This place is a fun, nostalgic drive-in diner."

"I ate outside; there was outdoor seating available."

Good to know

1

Superdawg Drive-In is a drive-in restaurant where you eat in your car.

2

Parking at Superdawg Drive-In can be challenging.

3

The bathroom is very clean and well-maintained.

09
Fatso's Last Stand image 1
Hamburger restaurant

Small hamburger spot with casual, no-frills vibe and smoky backyard atmosphere. Outdoor seating includes picnic tables and a large patio, popular for late-night bites. Burgers and boozy shakes stand out as phenomenal offerings.

Milkshakes come in classic flavors like strawberry and Oreo, both tasting rich and creamy. You can also create kooky combos to impress friends, and the shakes pair well with other menu items.

Plenty of outdoor seating fills a nice little patio perfect for dining outside. The space offers a no frills spot to enjoy meals like cheeseburgers and fries in the open air.

People are saying

"I thought the burgers here were great and juicy."

"I sat outside on a nice day, enjoying the patio."

"I had my double cheeseburger and fries outside in the dining area."

Good to know

1

Bring cash as they don't accept credit cards.

2

Combo deals offer the best value for your meal.

3

Expect limited indoor seating, especially during colder months.

10
Ghirardelli Ice Cream & Chocolate Shop image 1

Two-story chocolate shop offers stunning river views and a luxurious yet welcoming atmosphere. The space fills with lively energy and can get noisy and busy, especially with families around. Seating is limited and first-come, first-served, with an outdoor patio providing a more relaxed vibe.

Milkshakes come thick and creamy with real strawberry flavor or rich chocolate lovers taste. They stand out as refreshing and high-quality treats packed with delicious chocolate.

A lovely outdoor patio offers a spot to enjoy sunny days and watch people. Seating mostly stays inside, but a few tables sit outside by the river walk for dessert or drinks.

People are saying

"Jameson's service made the chocolate experience feel personal and joyful."

"This milkshake is thick, creamy, and packed with real strawberry flavor."

"I loved sitting on the patio by the river walk."

Good to know

1

There's a special offer on 7/25 for a mini hot fudge sundae at $7.25.

2

Seating is first come, first serve and can be sparse during peak hours.

3

Finding a seat can be nearly impossible during busy times.

11
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.

Creamy and sweet, the Fruity Pebbles milkshake offers a fun twist. The vanilla milkshake tastes like drinking whipped cream. Staff often provide milkshakes to help cool down in the heat.

Outdoor seating features a colorful vibe with impressive decorations on the patio. Staff assist quickly with orders outside, and there is plenty of space to sit and enjoy the atmosphere.

People are saying

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

"The spicy chicken here is flavorful and perfectly cooked."

"The chicken here is so crispy and juicy."

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.

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