8 Best Casual Outdoor Dining Spots in Chicago


Outdoor Dining in the Windy City

Some of the best casual outdoor dining in Chicago include meals that are eaten standing up at a counter or at outdoor tables. Here are eight of our favorite only-in-Chicago places where eating outside is the right thing to do on a beautiful spring day.

Chicago Dogs

  • For anyone craving a true Chicago red hot, Mustard’s Last Stand should be able to satisfy your hunger. Serving all-beef, Vienna-brand red dogs, these sausages are steamed before being placed on a poppy-seed roll and buried under condiments, they do not disappoint.
  • Although we tend to prefer steamed dogs, charred is the way to go at Wiener’s Circle. Cooked on a grate right behind the order counter, the flames add a crunch to the dog that steaming can not achieve. They also have some of the best French fries in all of Chicago.

Pies and 24/7 Breakfast

  • Originally a food truck, the Bang Bang Pie Shop has since opened a brick and mortar store. Six types of sweet pies are served a day, two fruit, two chocolate and two cream, as well as one savory pie. The Pear Brandy Mince Pie, made with pears, apples, raisins, cranberries and other fruits is one of the best we have ever had.
  • Operating 24/7, the Tempo Café, in downtown Chicago, serves excellent working class food at affordable prices. Breakfast is served around the clock, we enjoyed omelets that were presented in silver skillets. The ham and eggs was also an excellent breakfast dish, this too came in a silver skillet. For patrons looking for something other than breakfast, there is a full menu of sandwiches, hot dinners and stir fries.

Best Sandwiches in Chicago

  • A Roadfood reviewer once asked if Johnnie’s was “the ultimate Chicago sandwich,” we have answered “yes.” In our eyes, an Italian beef sandwich is a signature dish of Chicago so do not take it lightly when we say that it is one of the best sandwiches we have ever had.
  • Sandwiches at Corned Beef Factory Sandwich Shop are made with thinly sliced corned beef that is moist, tender, remarkably lean and dramatically flavorful. The beef is paired with your choice of mustard, yellow or spicy, pickles and homemade potato chips. They offer a few other meats and sandwiches, as well as honey puffs, which are fantastic balls of fried dough covered in honey.

Seafood, Gelato and Smoked Salmon

  • Pizza may be in the name, but we recommend you order anything but that at Freddie’s Pizzaeria. There is nothing wrong with the pies, it is just that everything else is so much better. From creamy gelato to a seafood salad to homemade gnocchi, everything offered here is fantastic. Be prepared to order what looks best because there is no formal menu posted.
  • Smoked foods are smoked in a small but colorful smokehouse behind the main building at Calumet Fisheries. The smoked salmon is infused with pepper and garlic and carries a deep smoky flavor with it, as it should. A variety of fried dishes are also offered including shrimp, oysters, scallops and, of course, onion rings.

Mustard’s Last Stand

Mustard's Last Stand in Evanston serves all-beef, Vienna-brand red hots steamed to plumpness, dressed to the nines & cushioned inside soft poppy-seed rolls.


Wiener’s Circle

The brash & sassy Wiener's Circle serves Chicago-style all-beef hot dogs topped with flawless condiments. French fries are some of the city's best.


Bang Bang Pie Shop

Bang Bang bakes 3 flavors of pie daily. They are among Chicago's best, exquisitely produced with fresh ingredients plus a helping of value-added love.


Tempo Café

Tempo is a 24/7 Chicago cafe with a full menu. It is best known for mighty omelets served in silver skillets on wooden trivets.



Is this the best Chicago sandwich ever? Johnnie's Italian beef delivers juicy garlic kick; add vibrant giardiniera and you'll hear angels sing.


Corned Beef Factory Sandwich Shop

A restaurant created by a genuine corned beef factory, this little gem makes great cured-meat sandwiches, plus Italian beef & Chicago hot dogs.


Freddy’s Pizzeria

A small corner grocery with an immense menu of sandwiches, hot dishes & superb gelato, Freddy's is a treasured destination for Italian food in Chicagoland.


Calumet Fisheries

Calumet is a tiny Chicago South Side seafood shack with a great smokehouse: catfish, chubs, eel, trout, salmon, shrimp, sturgeon, trout, whitefish and more.