Elevate your dining experience in the Windy City with our guide to the premier outdoor dining in Chicago, where culinary delights meet al fresco elegance. From charming sidewalk cafes in bustling neighborhoods to rooftop retreats offering skyline views, Chicago’s outdoor dining scene is a celebration of diverse flavors against a backdrop of urban beauty. Each destination on our curated list promises a unique atmosphere and a delectable array of dishes, blending the richness of Chicago’s culinary heritage with the joy of dining under open skies. Whether you’re a food enthusiast or seeking the perfect ambiance for a special occasion, join us in savoring the top outdoor dining spots that transform every meal into a memorable and delightful experience.
If you love duck, this may be the restaurant you are looking for. I love how this restaurant manages to maintain a balance of upscale energy quality and cozy retro vibes. Nestled near the South branch of the Chicago River and South Loomis Street, this restaurant is perfect for a group outing or a sweet date. Every dish is carefully put together in sometimes deliciously unexpected ways. The restaurant makes it easy to order your whole rotisserie duck ahead of time. In addition to the delicious duck, I also loved the cauliflower tartare, the Brussel sprouts, and the sticky bun. They offer a great array of wines and some fantastically thought-out cocktails.
Located at the intersection of Grand, Milwaukee, and Halstead, this Italian restaurant offers one of the cutest outdoor dining spots in the city. The enclosed garden area contains beautiful vines and other plants. Piccolo Sogno has all of the rustic Italian favorites that you love. From pasta to pizza to some tasty Secondi, I deeply enjoyed everything I ate at this restaurant. The gnocchi, in particular, is my favorite. If you are a wine lover, you are sure to love this place. They have a robust wine list covering Northern, Central, and Southern Italy.
I have been to a few Parson’s locations, and they are all great for a group hang-out. Visit the Andersonville location after picking up a few plants at Gethsemane Garden Center or visiting the other local Andersonville shops. The Logan Square location provides beautiful views of the grassy boulevard. I loved all the food I tried here. I recommend the hush puppies and the fish sandwich. I was excited to find that the vegetarians at our party also had some delicious options. If you can only get one drink here, you must try one of their slushies.
Frontier is one of my favorite outdoor dining spots in Chicago, especially if I am getting together with a group of friends. The idea behind Frontier is that nature is what is behind the menu. So it seems only correct to have your meal in the open air. The wood-burning fireplace in the outdoor area brings everything together. While Frontier has plenty of familiar favorites, you can also get some more unusual offerings such as alligator and wagyu. If you love meat, you can also choose Frontier’s whole animal experience.
Big Star is one of my outdoor dining staples if I want to get a group of friends together. There are locations in Wrigleyville and Wicker Park. The Wrigleyville location is the perfect spot for a bite and some booze before or after a cubs game given that the restaurant is across the street from Wrigley Field. The Big Star on Damen Avenue is in the heart of Wicker Park. I love grabbing a few tacos and a pitcher of margaritas with friends after a stroll through the shops and sights of Wicker Park. Do not skip the queso fundito!
Beatnik On The River is a fabulous choice for a bite after work or after a stroll around the Loop. This restaurant’s outdoor seating is right on the river, so you can enjoy waterside views while enjoying Mediterranean cuisine. The decor is cozy and immensely well thought out. While this is a fun date spot, I love coming here with a group since it is an excuse to get enough food that you can try everything. The scallops and stuffed dates are two of my favorite dishes here. Beatnik also has some delicious large-format cocktails and some unique no-proof cocktails.
If you are craving Italian food and fresh air in Bronzeville, Truth Italian is where you want to be. The outdoor dining area is always full of energy and excitement. I always prefer coming here with a group and getting a few mimosas. Sometimes all I want is breakfast. When that mood strikes, I head over to Truth to take advantage of their all-day breakfast. That is not to say that their other options are not delicious. The shrimp and grits are my favorite thing here, but the french toast hits the spot if I want sweets.
When you hear “Gibsons” in Chicago, you know there has to be some steak around. Gibsons is a Chicago steak institution, and Gibsons Italia continues that tradition with an Italian spin. This restaurant has three levels, and the outdoor seating overlooks the gorgeous riverwalk and the river. This restaurant is another great place to grab a bite or drink after work, after a stroll around the Loop, or for a celebration. The Raviolo Carbonara was delightful, and their steaks do measure up to the hype. I also always love their side dishes.
The West Loop neighborhood is known for its amazing outdoor dining, and Aba makes a big contribution to this reputation with its gorgeous rooftop patio. While this restaurant is undeniably upscale, it still manages to feel comfortable and cozy. Aba offers several delicious Mediterranean dishes, including a lot of gluten-free options. Both the brunch and dinner are delicious at this restaurant. At brunch, I love the khachapuri, and at dinner, my go-to is the wild striped bass. This restaurant also has several uniquely put-together cocktails, both with and without alcohol. I also highly recommend the ancient civilization wines. Check out other rooftop bars in Chicago if you want to enjoy the outdoors with a view!
This Logan Square gem puts a lot of work into cultivating a thoughtful farm-to-table menu in a comfy, pub-like setting. The charming outdoor seating options allow you to do some people-watching as you enjoy dinner or brunch. It is really difficult for me to pick a few favorite dishes here because everything I eat and drink here is exemplary. Plus, the menu usually changes seasonally. I have enjoyed the green beans, the butternut squash, the mackerel, and the mushroom and raclette dumplings. You can always count on creative and intelligent cocktails at Longman and Eagle.
Soak in the lovely Lincoln Park neighborhood as you enjoy Sapori Trattoria’s fun outdoor dining. This spot is an adorable restaurant for date night or a cozy happy hour. The restaurant is a true neighborhood Italian restaurant that always makes me feel at home. The menu is not gigantic by any means, but that is because the emphasis is put on quality rather than quantity. The quality of the ingredients and preparation is apparent with every bite. The risotto alle funghi is one of my favorite dishes, along with the rigatoni caprese.
This restaurant may be on busy Armitage Avenue, but it still manages to feel cozy. The open-air patio is the perfect accompaniment to the amazing arepas offered by Rica Arepa. Choose this restaurant for a fun date or friend to hang out with. When I go here with a group, we order a bunch of different apps, and chicha venezolana is a must. The tequenos, tostones, and cachapas are the perfect way to start a meal. Next, we usually get a selection of arepas. Every single arepa I have had here was amazing. There are different kinds to suit any palate.
Enjoy dim sum under the sky at Shanghai Terrace. This restaurant is right off Michigan Avenue in the Peninsula Hotel. The decor is a beautiful balance of vintage and bold. The terrace itself is framed with a beautiful garden which makes it a beautiful spot for a summer dinner. The cuisine is Cantonese and Shanghainese, and the restaurant is consistently given many accolades. Take a few bites, and you can see why so many people love this restaurant. The xiao long bao is a delicious burst of flavor, while the fried rice with abalone sauce provides warmth and complex flavor.
While only some seating at The Dawson is outside, even the inside of the restaurant feels light and airy. The actual patio is large and full of energy. It is located at the intersection of Grand, Milwaukee, and Halsted, which places it in between West Town and the Loop. I love coming here with a group of friends. Brunch and dinner are equally delicious here. The food ranges from butter chicken pot pie to empanadas. Everything is delicious. I especially enjoy the cocktails here. Chai Times is the perfect cozy hot toddy.
Logan Square is one of my favorite neighborhoods to spend time in, and Pizza Lobo is often where I like to eat when I go there. The outdoor area is populated by retro seating and fire pits. This restaurant is another place that is great for a group of friends or a date. This restaurant offers plenty of amazing deals, including specials every day of the week. I could probably eat one of everything from the menu here. Some of my favorites are the fried cauliflower, the Amatrice’ Yo-self, and the Barracuda. Pizza Lobo also has some fun brunch options, including an old-fashioned cinnamon roll, a breakfast sando, and some drinks. I highly recommend having a frozen drink to accompany your meal.
While Monteverde Restaurant & Pacifico is in the bustling West Loop neighborhood, it manages to maintain a cozy, neighborhoody feel for its patio. I enjoy coming here with a group of friends so we can all steal off of each other’s plates. This restaurant is also the perfect spot for a first date. If you love fresh pasta, you should try Monteverde. You can taste the quality of the pasta in a simple dish like cacio whey pepe. I also adore the gnocchetti con pesto. The cocktails are delicious. My favorite is the banana standard.
While The Press Room is primarily known as a cozy basement wine bar with tasty food, it also has an adorable patio. I have dined in both settings, and I love them both. The restaurant is in a historic building that lends a vintage air to everything. The cuisine is simple but delicious. All of the vegetables used at this restaurant are sourced from a nearby farm. Some of my favorite dishes include the sourdough cavatelli and the scallops.
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