Top Rooftop Restaurants In Chicago: Your Ultimate Guide To Sky-High Dining

Chicago's rooftop dining scene is on fire, and we're not just talking about the summer heat. If you're looking for the best rooftop restaurants in Chicago, you've come to the right place. From stunning skyline views to mouthwatering menus, these elevated eateries offer more than just a meal—they deliver unforgettable experiences. Whether you're a local or a visitor, this guide will help you find the perfect rooftop spot to enjoy the Windy City's skyline in style.

There's something magical about dining under the open sky, especially when you're surrounded by the breathtaking views of Chicago's iconic skyline. Rooftop restaurants have become a must-visit for foodies and adventurers alike, offering a unique blend of fine dining, great drinks, and unforgettable scenery. But with so many options out there, how do you choose the best rooftop restaurants in Chicago? That's where we come in.

This guide is your go-to resource for discovering the top rooftop restaurants in Chicago. We'll take you through the best spots, their unique features, and why they're worth a visit. So grab your friends, put on your best outfit, and get ready to experience Chicago like never before. Let's dive in!

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Here's a quick table of contents to help you navigate through this ultimate guide:

• Introduction
• What to Look For in a Rooftop Restaurant
• Top Rooftop Restaurants in Chicago
• Seasonal Experience
• Menu Highlights
• Atmosphere and Ambience
• Drinks and Cocktails
• Reservations and Tips
• Costs and Budget
• Conclusion

What to Look For in a Rooftop Restaurant

When it comes to rooftop dining, there's more to consider than just the view. Sure, the skyline is a big draw, but you also want to make sure the restaurant delivers on food, drinks, and overall experience. Here's what you should keep in mind when choosing a rooftop restaurant:

First off, the location matters big time. Some rooftops offer better views than others, so do your research. Is the restaurant located in the heart of downtown or in a quieter neighborhood? Both have their pros and cons, so it depends on what vibe you're going for. Next up, the menu. You don't want to settle for average food when you're paying for the experience, right? Look for places that offer unique dishes or signature cocktails that elevate the whole meal.

And let's not forget the service. A great rooftop restaurant should have staff that's attentive but not overbearing. They should be able to recommend dishes, drinks, and even give you tips on how to make the most of your visit. Oh, and one more thing—check out the reviews. Yelp, Google, and even Instagram can give you a good idea of what to expect before you even step foot in the place.

Key Features to Consider

• Stunning views of Chicago's skyline
• Unique and creative menu options
• Excellent service and staff
• Comfortable seating and ambiance
• Availability of outdoor seating

Top Rooftop Restaurants in Chicago

Now that you know what to look for, let's dive into the best rooftop restaurants in Chicago. These spots are the cream of the crop, offering everything from gourmet dining to casual hangouts with friends. We've got you covered, no matter what kind of experience you're looking for.

1. Cindy's

Perched on the rooftop of the Chicago Athletic Association Hotel, Cindy's is a must-visit for anyone looking to enjoy the best rooftop restaurants in Chicago. The views of Millennium Park and the Bean are unmatched, and the menu offers a mix of classic American dishes with a modern twist. Oh, and don't miss their famous milkshakes—they're worth every calorie!

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2. The Terrace at Trump

If you're looking for luxury, The Terrace at Trump has got you covered. Located on the 16th floor of the Trump International Hotel and Tower, this rooftop restaurant offers panoramic views of the Chicago River and skyline. Their menu features a mix of American and international cuisine, and the cocktail list is extensive enough to keep you entertained all night.

3. The Roof on Two

For a more laid-back vibe, head to The Roof on Two at the Godfrey Hotel. This rooftop spot is all about good vibes, great drinks, and stunning views of the city. The menu is a mix of shareable plates and signature cocktails, making it perfect for a group outing or a casual date night.

Seasonal Experience

Chicago's rooftop restaurants offer something special year-round, but the experience can vary depending on the season. In the summer, you'll want to take advantage of the warm weather and outdoor seating. Many rooftop spots even have fire pits or heaters for those cool summer nights. As the weather cools down in the fall, the rooftop scene becomes even more magical with cozy blankets and seasonal drinks.

Winter might not seem like the best time for rooftop dining, but some places, like Cindy's, transform into winter wonderlands with heated igloos and hot cocoa. And don't forget spring, when the city comes alive with flowers and sunshine. It's the perfect time to enjoy a rooftop brunch or a late afternoon cocktail with friends.

Seasonal Highlights

• Summer: Outdoor seating, live music, and refreshing cocktails
• Fall: Cozy blankets, seasonal drinks, and stunning foliage views
• Winter: Heated igloos, hot cocoa, and winter wonderland vibes
• Spring: Brunch specials, blooming flowers, and sunny afternoons

Menu Highlights

One of the best things about rooftop restaurants is the food. Whether you're in the mood for a gourmet meal or something more casual, these spots have got you covered. Here are some menu highlights from the top rooftop restaurants in Chicago:

Cindy's

Cindy's menu is all about classic American dishes with a modern twist. Their fried chicken is a must-try, and the burgers are just as good. For dessert, don't miss the milkshakes—they come in flavors like peanut butter and jelly and s'mores.

The Terrace at Trump

The Terrace at Trump offers a mix of American and international cuisine, with dishes like lobster bisque and filet mignon on the menu. Their cocktail list is extensive, featuring both classic and signature drinks. If you're in the mood for something sweet, try the chocolate fondue—it's perfect for sharing.

The Roof on Two

The Roof on Two's menu is all about shareable plates and signature cocktails. Their fried chicken sandwich is a crowd favorite, and the truffle fries are worth every calorie. For drinks, the signature cocktails are a must-try, with options like the Godfrey Margarita and the Bee's Knees.

Atmosphere and Ambience

The atmosphere of a rooftop restaurant can make or break the experience. Some places are all about luxury and elegance, while others offer a more laid-back vibe. It all depends on what you're looking for. For a more formal experience, The Terrace at Trump is a great choice. If you're in the mood for something more casual, The Roof on Two is perfect for a fun night out with friends.

And let's not forget the decor. Many rooftop restaurants in Chicago have unique designs that add to the overall experience. Cindy's, for example, has a beautiful greenhouse-like structure that lets in plenty of natural light during the day. At night, the string lights and fairy lights create a magical ambiance that's perfect for a romantic evening.

Unique Features

• Cindy's: Greenhouse structure with stunning views of Millennium Park
• The Terrace at Trump: Panoramic views of the Chicago River and skyline
• The Roof on Two: Cozy seating areas with a laid-back vibe

Drinks and Cocktails

No rooftop experience is complete without a great drink in hand. Whether you're in the mood for a classic cocktail or something more unique, Chicago's rooftop restaurants have got you covered. Here are some of the best drinks and cocktails to try:

Cindy's milkshakes are a must-try, but if you're looking for something a little stronger, The Terrace at Trump has an extensive cocktail list. Their signature drinks, like the Trump Tower Martini, are worth every sip. At The Roof on Two, the Godfrey Margarita is a crowd favorite, and the Bee's Knees is perfect for those who love a good gin cocktail.

Signature Drinks

• Cindy's: Milkshakes (peanut butter and jelly, s'mores)
• The Terrace at Trump: Trump Tower Martini, Signature Margaritas
• The Roof on Two: Godfrey Margarita, Bee's Knees

Reservations and Tips

Getting a table at one of Chicago's top rooftop restaurants can be a challenge, especially during peak season. Here are some tips to help you secure a spot:

First, book early. Most rooftop restaurants fill up quickly, especially on weekends. If you're planning a special occasion, it's a good idea to make a reservation at least a week in advance. And if you're flexible with your timing, try going during off-peak hours. Many places offer happy hour specials that can save you some money while still giving you the full rooftop experience.

Another tip is to check out the restaurant's website or social media pages for any special events or promotions. Some places even offer exclusive deals for their loyalty program members, so it's worth signing up if you're a frequent visitor.

Costs and Budget

When it comes to rooftop dining, prices can vary depending on the restaurant and the experience you're looking for. On average, you can expect to spend anywhere from $20 to $50 per person for a meal, not including drinks. Cocktails and signature drinks can add up quickly, so it's a good idea to set a budget before you go.

Some rooftop restaurants also offer prix fixe menus or special deals during certain times of the year, so it's worth checking out their website or social media pages for any promotions. And if you're looking to save some money, consider going for brunch or happy hour. Many places offer great deals during these times, making it easier to enjoy the rooftop experience without breaking the bank.

Conclusion

Chicago's rooftop restaurants offer something special for everyone, whether you're looking for a gourmet dining experience or a casual night out with friends. From stunning views of the skyline to mouthwatering menus and signature cocktails, these elevated eateries deliver unforgettable experiences that you won't find anywhere else.

So next time you're in the Windy City, make sure to check out one of the top rooftop restaurants in Chicago. Whether you're a local or a visitor, these spots are sure to leave a lasting impression. And don't forget to share your experience with us in the comments below or on social media. Who knows, your review might just help someone else discover their new favorite rooftop spot!