How to Wander Chicago’s Rooftop Scene like an Insider.

Chicago is a city that never fails to mesmerize visitors with its stunning skyline, beautiful lakefront, and thriving food culture. And what better way to experience the city’s splendor than by exploring its rooftop scene? Rooftop bars, lounges, and restaurants have become a popular attraction among locals and tourists alike, offering scenic views and delectable food and drinks.

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As a native Chicagoan with a deep appreciation for the city’s beauty, I have discovered that rooftop adventures are a must-have experience when visiting Chicago. My favorite place to relax at home is on the patio, and nothing beats a rooftop when traveling. In this article, I invite you to join me on a tour of three of the best rooftops in the city, where we’ll discover insider tips and tricks to make the most of your rooftop adventure.

So, forget about balconies and patios and let’s explore Chicago’s rooftop scene together. From the best times to visit to the dress codes, reservations, and money-saving hacks, we’ll cover everything you need to know to make your rooftop experience part of your sightseeing adventure in Chicago. Let’s wander Chicago’s rooftop scene like a local pro.

Understanding Chicago’s Rooftop Scene

Chicago offers a diverse selection of rooftop bars and lounges, each with its unique vibe and atmosphere. Some of the most popular areas for rooftop venues include River North, the Loop, and the West Loop.

Additionally, rooftop venues come in different types to cater to a wide range of tastes and preferences. Some of the most popular types of rooftop venues include sports bars, hotel lounges, and restaurants. Sports bars offer an excellent atmosphere for catching the game while enjoying stunning views of the city. Hotel lounges, on the other hand, offer a more upscale experience, with exclusive access to hotel guests and VIPs. And lastly, restaurants offer a combination of delicious food and scenic views, making them a popular choice for brunch and dinner.

The best times to visit rooftop bars and lounges in Chicago vary depending on the venue and the day of the week. Weekdays are generally less busy, making it easier to snag a table or enjoy a more relaxed atmosphere. However, weekends are typically more lively, with events and parties happening throughout the night. The best times to visit also depend on the time of year, with summer being the most popular season for rooftop adventures.

Insider Tips for Navigating Chicago’s Rooftop Scene

When it comes to exploring Chicago’s rooftop scene, insider knowledge is key. To make the most of your rooftop adventure, consider the following insider tips:

Dress code recommendations: Dress codes can vary depending on the venue. Some rooftop bars and lounges require formal attire, while others are more casual. It’s always a good idea to check the dress code policy before visiting to avoid any surprises. In general, dress to impress, and avoid wearing athletic wear or beach attire.

Recommended times for visiting popular venues: The best times to visit popular rooftop venues vary depending on the day of the week and the time of year. Weekdays are generally less busy, making it easier to secure a table and enjoy a more relaxed atmosphere. However, weekends are usually more lively and offer an exciting party atmosphere. Additionally, some venues offer stunning sunset views, making early evening reservations a popular choice.

Money-saving hacks: Rooftop venues can be expensive, but there are ways to save money while still enjoying the experience. Many venues offer happy hour specials or weekday discounts, making it a great option for budget-conscious visitors. Another money-saving hack is to avoid peak hours and opt for brunch or lunch reservations, which are typically less expensive than dinner.

How to Save $$$ – Happy Hour Rooftop Specials 

(Always call to verify as changes can occur quickly.)

• Cerise – Every Thursday from 5 – 9PM.
• Kennedy Rooftop at Hyatt Place Chicago/Wicker Park Monday to Friday 4 – 6PM.
• LondonHouse Rooftop – Monday to Thursday 4 – 7PM $10 house champagne and discounted snacks.
• Upstairs at the Gwen – Monday to Thursday 4 – 5:30PM – $10 cocktails, $8 house wine, $5 fries + more.
• Roof on theWit – “Wind Down Weekdays” Tuesday through Friday 4-6 p.m. $7 CBD Spritzer, $10 Roof Sliders.
• I|O Godfrey Hotel Rooftop – Monday through Friday 3 – 6PM  – $10 Frose All Day, $7 house Rose, $7 Black Truffle Fries.

By following these insider tips and tricks, you can maximize your rooftop adventure and explore Chicago’s rooftop scene like a pro. So dress to impress, make reservations in advance, visit at the right time, and save money with happy hour specials and other discounts. Enjoy the breathtaking views and the vibrant atmosphere of Chicago’s rooftop scene.

Making Reservations

If you’re planning a trip to Chicago, the first thing you should know is that making plans is essential. This is especially true if you want to visit rooftop bars, restaurants, or other popular attractions on weekends or holidays. Chicago is a “make a reservation” city, and even the Lincoln Park Zoo, one of the country’s few free zoos, even required reservations during the pandemic.

To secure a spot at your desired rooftop bar or restaurant, it’s recommended that you make a reservation well ahead of time. Most restaurants and rooftop bars in Chicago can be found on either Open Table or Tock, which makes the reservation process more straightforward. A limited number of venues are also available on Resy. 

However, it’s essential to keep in mind that not all reservations are created equal. Some places have strict seating rules and only allow a maximum party size of 4, while others may let you book up to 10 people. Additionally, some places require deposits or have cancellation policies, so make sure to read the fine print before making your reservation.

By planning ahead and making reservations in advance, you can ensure that you have a great rooftop experience in Chicago. So be sure to plan accordingly, read the rules and guidelines carefully, and enjoy your rooftop adventure in the Windy City.

One helpful tip to keep in mind is that many rooftop bars and restaurants in Chicago use a contactless system to access their menus. Upon arrival, they will either hand or display a QR code that you can scan with your phone’s camera to view the menu. If you’re not familiar with this modern convenience, now is an excellent time to get comfortable with it.

If you’re planning to visit rooftop bars in Chicago on a Friday or Saturday night, be prepared for live events, DJs, or a club-like atmosphere at some venues. Additionally, it’s important to note that most rooftop bars automatically include a 20% gratuity in the bill. If you plan to stay out late, keep in mind that the kitchens typically close around 10 PM, so you won’t be able to order food after that time. However, you can still enjoy drinks and the ambiance of the rooftop bar.

Recommended Rooftop Venues to Visit

1.   LondonHouse Rooftop

85 East Wacker Drive, Chicago, IL 60601

LondonHouse Rooftop is a popular rooftop bar in Chicago that offers stunning views of the city’s skyline and the Chicago River. Located on the 21st floor of the LondonHouse Chicago hotel, this rooftop bar offers a luxurious experience with its upscale decor and ambiance.

One of the most notable features of LondonHouse Rooftop is its 360-degree views of the city. Guests can take in panoramic views of the Chicago River, Lake Michigan, and the iconic buildings that make up the city’s skyline. It’s a perfect spot to take in the beauty of the city during the day or enjoy a romantic evening under the stars.

The rooftop bar features both indoor and outdoor seating, making it a perfect spot to visit all year round. During the colder months, guests can still enjoy the views from the enclosed indoor lounge, complete with comfortable seating and a cozy fireplace. In the summer, the outdoor terrace is the perfect spot to relax and enjoy the warm weather.

LondonHouse Rooftop also offers an extensive cocktail menu that includes classic drinks, as well as unique creations. Guests can enjoy a variety of small plates and appetizers to complement their drinks, including oysters, charcuterie boards, and artisanal cheeses.

While LondonHouse Rooftop can be a bit pricey, it’s a must-visit spot for those looking for a luxurious rooftop experience in Chicago. It’s recommended to make reservations in advance, especially during peak hours, to ensure a spot at this popular destination.

 (Reserve on Tock)

2.   Upstairs at the Gwen  – 5th floor

521 N Rush St 5th Floor, Chicago, IL 60611

The Gwen Rooftop, located atop The Gwen hotel in downtown Chicago, offers guests an unforgettable rooftop experience. With stunning views of the city, a stylish ambiance, and excellent service, it’s one of the top rooftop destinations in the city.

The rooftop is split into two sections, the terrace and the lounge. The terrace is an outdoor space that provides breathtaking views of the Chicago skyline. The lounge is an enclosed space with a modern and sophisticated decor that is perfect for a night out with friends or a romantic evening with your significant other.

Enjoy the space year-round, regardless of the weather with their warm drinks and fire pits during the colder seasons. The rooftop also features comfortable seating, a full bar, and a diverse menu of small plates, salads, sandwiches, and desserts.

The menu at The Gwen Rooftop is designed to appeal to a variety of tastes, with options ranging from classic dishes to creative twists on traditional favorites. The cocktail menu is equally impressive, with an extensive list of craft cocktails, wine, and beer.

This beautiful rooftop venue in Chicago is easy to book and offers a variety of seating options. One of the most popular options is the firepit table, which can seat up to 6 people and requires a $75 deposit with reservation. The overall atmosphere of the Gwen Rooftop is relaxed and chill, making it easy to settle in and enjoy the beautiful surroundings. If the firepit isn’t for you, there are plenty of other seating options available both indoors and outdoors, and no deposit is required for those.

FROM THE MENU:

• JUNGLE BIRD $14

jamaican rum, campari, pineapple, lime, demerara syrup

• FRIDA’S GARDEN  $15

black pepper infused blanco tequila, lime, manzanilla syrup, strawberry

(Reserve on Open Table)

Cerise – 26th floor

203 N Wabash Ave 26th floor, Chicago, IL 60601

Cerise is a rooftop bar with a beautifully unique setting that is easy to book. If you’re familiar with Virgin Hotels, then you already know to expect something unexpected. The front door greets you with a red lip seat, and as you make your way inside, you’ll see a disco ball by the entrance and swings on the outdoor patio area. Every direction has something for your eyes to behold.

Cerise boasts the BEST service hands down. The servers are awesome, friendly, and fun. It could be the eclectic flare, the unpretentious vibe, or the welcoming atmosphere, but you’ll want to return to Cerise again and again. In fact, I’m already looking forward to my next visit.

FROM THE MENU:

• Grilled Octopus $17.00

fines herbs lemon salad, shaved shallots, gochujang aioli

• Purple Reign $15.00

hendrick’s gin, lavender syrup, teapot bitters, fever tree tonic, cucumber, lemon

• Summer Love Sangria $15.00

rosé, grapefruit new amsterdam vodka, grapefruit, lemon, lime

4.   Raised (Reserve on Tock)

1 W Wacker Dr, Chicago, IL 60601

Raised is a popular rooftop bar located in Chicago that boasts a unique view of the Chicago River, Marina City, and the Michigan Avenue Bridge. Despite having to cancel my reservation due to scheduling conflicts, I was excited about the prospect of enjoying the stunning views from the top. However, due to its popularity, rescheduling proved to be a challenge as there was no availability left for the weekend by Thursday.

5.   Offshore (Reserve on Tock)

1000 E Grand Ave, Chicago, IL 60611

Offshore is the perfect place to enjoy the picturesque views of the city from Navy Pier. With a comfortable seating area and fire pits, it’s the ideal spot to unwind and relax. However, if you’re planning on visiting, make sure you book in advance as it’s a popular destination and reservations fill up quickly. In fact, I missed out on a table for my group of four because I forgot to have someone else book another table. But I’m not giving up on this world’s largest rooftop bar and I will definitely visit Offshore the next time I’m in town.

6.   Roof on theWit – 27^th floor (Reserve on Open Table)

201 N State St 27th Floor, Chicago, IL 60601

Roof on the Wit is an amazing rooftop spot that offers stunning views of Chicago’s skyline. Although I had to cancel my reservation due to scheduling conflicts, I regret not being able to experience this one. With dozens of rooftops to explore in the city, each with its own unique skyline views and menus, I would have liked to visit them all. If you’re looking for the best hotel in Chicago, you can read reviews and find great hotel deals on TripAdvisor.

Whether you’re looking to party on the weekends or enjoy a happy hour with stunning views, there’s something for everyone. And if you happen to be in Chicago in the spring, don’t forget to take a stroll along Michigan Avenue to witness the vibrant display of tulips that adorn the city’s planters. With so much to explore and enjoy, Chicago is truly a city worth visiting.

Happy Wandering Chicago’s Rooftops!