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Illinois' best

Rooftops with sandwiches

Made for those who believe a midday sandwich is best enjoyed away from the sidewalk crowds and up on a roof.

Based on 678 Opinions
+675
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Updated April 2026
01
Shannon's Deli image 1
Shannon's Deli image 2
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Rooftop seating offers nice views and a chance to watch trains pass by, creating a lively backdrop. The atmosphere feels friendly and familiar, with many regulars knowing each other by name. Evenings bring varied music and a bar area featuring video gaming, adding to the casual vibe.

A nice rooftop patio offers seating with a view. It can get loud from train traffic but provides a pleasant outdoor spot when the weather is good.

Sandwiches come big enough to split and include options like pastrami, chicken salad on a croissant, and turkey jam. They are ready quickly and pair well with homemade soups and salads.

People are saying

"I found the chicken salad to be fantastic."

"The rooftop patio seating is really nice."

"I thought the sandwiches here were great."

Good to know

1

Reservations are required for large groups, especially for special events.

2

The pastrami sandwich costs $14.25 without any side.

3

The restaurant lacks online ordering, which may affect convenience.

02
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.

A 16th floor rooftop offers a stunning city view with an outdoor seating area. The space creates a memorable evening atmosphere for dining.

Pork sandwiches stand out with pulled pork and prosciutto paired alongside ceviche with chicharrons and olives. Small sandwiches deliver solid flavors across the board.

People are saying

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

"The food on the Rooftop was delicious and flavorful."

"I found the pork sandwich to be delicious."

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.

03
The Garage Bar & Sandwiches image 1

Rooftop seating with a garden and balcony offers great views and a lively atmosphere. Music and sports bar vibes create an energetic environment that gets busy late. Activities like darts and shuffleboard add to the casual, family-friendly setting.

A killer rooftop sitting area offers a great spot to enjoy the weather. The patio and rooftop provide a nice space even when busy, with staff managing well.

Michelangelo and O. M. G. Chicken sandwiches stand out for their flavors. The Carmela and Dolly sandwiches offer excellent blends, while the biscuit sandwich adds a delicious twist.

People are saying

"They have a great, long list of beers to choose from."

"The rooftop is really nice and perfect for a sunny day."

"I found the chicken sandwich delicious."

Good to know

1

Trivia night happens every Wednesday at 8pm.

2

Bingo is hosted every Tuesday night with fun themes.

3

The brunch special is available on Saturdays and Sundays.

04
Villa D' Citta Bed & Breakfast image 1

Chicago mansion offers cozy, romantic atmosphere with beautifully appointed rooms featuring fireplaces and private terraces. Shared spaces include rooftop hot tub, fully stocked kitchen, and patios that encourage gathering. Unique amenities like wine on tap and build-your-own cannoli station add distinctive charm.

The rooftop features a hot tub and a fire pit with direct access from the Venetian room. Rooms connected to the roof offer a jacuzzi for added relaxation.

A fully stocked kitchen offers a variety of sandwich fixings including Italian ingredients and panini options. Fresh fruit, homemade banana bread, and snacks complement the sandwich choices.

People are saying

"The homemade breakfasts, especially the banana bread, were delicious."

"The rooftop hot tub was amazing."

"I loved the make-your-own Italian sandwich fixings."

Good to know

1

The property is in a safe neighborhood with many walkable restaurants.

2

Villa D' Citta is suitable for various events, including weddings.

3

Rooms feature luxurious amenities, including hot tubs and beautiful decor.

05
Reggies Chicago image 1
Bar & grill

Multilevel bar and grill with live bands and a rooftop deck featuring a basketball hoop creates a punk rock vibe. Atmosphere is lively and energetic, often very loud with dark, moody lighting. Seating includes comfy balcony spots and ample bars throughout the venue.

A three-level dive bar with a rooftop deck that offers a fun outdoor patio to chill, watch trains pass by, and enjoy entertainment before shows.

Pulled pork sandwiches come topped with fried onions and pair well with fries. Chicken sandwiches are huge and the menu includes creative burgers and nuggets alongside other sandwiches.

People are saying

"The bar food, especially the pulled pork, is some of the best I've had."

"The Rooftop has great drinks and casual eats."

"I loved the atmosphere and friendly vibe of this place."

Good to know

1

Parking can be challenging; consider using public transport or rideshares.

2

The venue hosts live music events almost every weekend.

3

Food service ends at 10pm, so plan accordingly.

06
One Lake Brewing image 1

Rooftop patio offers a beautiful city view and a lively atmosphere. Space feels open concept but can get noisy, especially with large groups. Beer selection includes some in-house brews with mixed reviews on quality.

Lively atmosphere fills the rooftop with a beautiful city-like view. The rooftop patio offers a nice spot to enjoy beer and food.

Chicken sandwiches stand out here, including BBQ and classic styles. Pulled pork and meatball sandwiches also appear, though portions can be small and temperatures inconsistent.

People are saying

"The beer here is great and enjoyable."

"The rooftop patio here is really nice and lively."

"You have to try the pulled pork or BBQ chicken sandwich."

Good to know

1

Happy hour features half-price bottles on Thursdays.

2

Trivia night occurs weekly with fun entertainment.

3

Extra charges apply for toppings on burgers, like a $2 upcharge for cheese.

07
First Draft Grayslake image 1
Traditional American restaurant

Indoor, outdoor, and rooftop seating create a versatile space with large windows and a fireplace adding cozy touches. The atmosphere stays casual and inviting, with multiple TVs and a lively bar area featuring games like darts and pool. A rooftop bar offers a unique experience with views and a fun social vibe.

A unique rooftop bar offers a casual vibe with indoor, outdoor, and rooftop seating. Service on the rooftop is consistently excellent during events and casual visits.

Italian beef, Cuban, and BBQ brisket sandwiches stand out here. Fried pickles often accompany these hearty, flavorful options.

People are saying

"They have a great beer selection here."

"The Rooftop staff were so friendly and attentive, even when it was busy."

"The brisket sandwich here is perfect and delicious."

Good to know

1

Happy hour runs from 3 to 6 pm with great specials.

2

Sunday brunch is highly praised and considered amazing.

3

Half-price pizzas are available on Sundays.

08
Homewood Brewing Company image 1

Spacious brewery with stylish decor and a laid-back charm combines a lively atmosphere and welcoming energy. Features include an open-air rooftop patio with a stunning mural, ping pong tables, and a photo booth. Serving robots add a unique touch to the modern, clean environment.

A stunning mural covers the rooftop wall, creating a striking visual. The rooftop offers a nice space for summer dining and cocktails, with a patio that invites relaxation.

Chicken sandwiches stand out with juicy, tender meat and pickles from heaven. The spicy chicken sandwich pairs well with creole fries that many find exceptional.

People are saying

"I thought the food was excellent and properly cooked."

"The chicken sandwich is crispy, juicy, and delicious."

"I want to sit on the rooftop when I come back."

Good to know

1

Reservations are recommended for dinner service, especially on weekends.

2

The kitchen closes at 8 PM, so plan your visit accordingly.

3

Parking is ample and free for all customers.

09
Avenue Ale House image 1
American restaurant

Large indoor wrap-around bar and rooftop patio create distinct spaces for different moods. Atmosphere shifts from quiet early evenings to hectic Friday nights with a lively sports bar vibe. Music blends classics and modern songs, complementing a crowd drawn to craft beer and unique cocktails.

The rooftop offers an excellent atmosphere and a real vibe that stands out. It works well for summer nights and feels like a top spot to hang out.

Grilled chicken sandwiches come big, juicy, and crunchy with fresh buns. Buffalo chicken sandwiches serve at the perfect temperature and can be made on request.

People are saying

"The bar staff, especially Jon and Karyl, are so welcoming and attentive."

"The rooftop has such a great vibe, especially on summer nights."

"I had the best grilled chicken sandwich ever."

Good to know

1

Trivia night happens every Wednesday at 8pm with a $5 entry fee.

2

Happy hour offers discounts on select drinks, including domestic beers.

3

The venue has a history of cleanliness issues, particularly in the bathrooms.

10
VU Rooftop image 1
Restaurant

Rooftop restaurant offers spectacular city views and a lively atmosphere with live jazz music and fire pits for warmth. Seating includes a cozy lounge area ideal for relaxing with friends. The venue combines indoor and outdoor spaces, creating a vibrant setting for group gatherings.

Spectacular views of the Chicago Lakefront and skyline create a breathtaking backdrop. The rooftop offers a chic ambiance with great food and drink options, making it a unique spot in the South Loop.

Hot chicken sandwich stands out with strong flavor and crunch but can be greasy and over-fried. Breakfast sandwich offers a solid option, though the heat level on spicy sandwiches stays moderate.

People are saying

"The food here is great, and the staff are so friendly."

"The rooftop views of the city and lakefront are impressive."

"The hot chicken sandwich has amazing flavor and crunch."

Good to know

1

Reservations are recommended, especially on weekends due to high demand.

2

A 20% automatic gratuity is added to all bills, regardless of party size.

3

Security checks are similar to TSA procedures before entry.

11
JoJo's Shake Bar - Naperville image 1

Whimsical setting includes a treehouse patio and rooftop swings, creating a playful vibe. Entertainment features free retro arcade games and an interactive mixology class. Drinks stand out with creative alcoholic shakes and unique shots.

Incredible views come with a rooftop patio that features swings and cute, kitschy decorations. The outdoor area is accessible by elevator, making it easy to reach with kids.

Honey-drizzled chicken sandwiches stand out with their crispy fried texture and sweet glaze. The New Yorker corned beef sandwich comes with an option to keep the coleslaw separate to avoid sogginess.

People are saying

"The shakes here are amazing and visually appealing."

"The sandwiches here were delicious and looked very good."

"Liz made our Rooftop evening special with her warmth and attentiveness."

Good to know

1

Mix It Monday event occurs every Monday, allowing guests to create two popular drinks.

2

Parking can be challenging; consider arriving early or using nearby garages.

3

Expect a lively atmosphere, especially during weekend evenings and special events.

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