Chicago Summer Guide #1: Dining al Fresco


To eat or drink outdoors is one of life's simple delights, and although we (as Chicagoans) can only enjoy these delights for a few short months, this city boasts some incredible bars, restaurants and lounges that will satiate your desire to spend every possible moment in the open air.

This post will be the first in a series of 3 blog posts where Daniel and I are sharing our recommendations for what to do in Chicago during the (absolutely glorious) summertime.  Whether you live in the Windy City or are just visiting for a short time, we'll be covering all the bases.  Keep watching for our next two posts which will cover outdoor activities, parks, beaches, festivals, concerts and more!

When we think about the best things to do in Chicago when the weather first turns warm, our minds naturally turn towards food and drink because our Summers don't really get HOT until July....meaning June is the absolute best month to eat outside (though you could make a strong case for September too!). The evenings are usually balmy and bearable in June before the humidity and heat set in during July and August. We've put our favorite spots into 4 categories so depending on what you're looking for you can find the right spot.

If you'll be in the city this Summer, make sure you check out at least one of these spots- you won't be disappointed! If you do stop by, let us know which ones you liked best! 


FOR A GOOD TIME (the kinds of places we would go to hang out with friends for a whole afternoon or evening)


Neighborhood: Fulton Market

Why we recommend it: The Mexcal Margaritas, the location, and the overall energy of this place.  The whole restaurant is completely opened up in the summer (even the roof opens up!), so it's the perfect combination of downtown scene and outdoor chill.  It can get a little loud over here, so we don't recommended it for long heart to heart conversations ;) If you need a bit to eat with your cocktail, try the nachos - these unique nachos are always crispy never soggy and even a small order is big enough to share with a couple of friends!


Neighborhood: Ukrainian Village

Why we recommend it: Apart from being a 5 minute walk from our apartment, we love that Sportsman's is really relaxed and low key. when you're indoors you can play checkers on the checkerboard tabletops and when you're outdoors you can sip a drink under a mood-setting array of string lights.  No food served here, just good reasonably priced drinks, but you can order food to be delivered. Come here for good quality time and drinks with a few close friends.


Neighborhood: Ravenswood

Why we recommend it: The rooftop bar has a happenin' but laid back feel. The menu here is on point. While many of our recommendations in this category feature casual fare, Fountainhead is your fun/chill destination of choice if you're looking for a great dining experience as well!

Park and Field

Neighborhood: Logan Square

Why we recommend it: For a local neighborhood spot, the patio here is still sprawling.  Lots of seating, a very fun vibe, bocce ball, and good food. 

The Moonlighter

Neighborhood: Logan Square

Why we recommend it: It's by the same group that brought us the beloved Scofflaw - a fun/low-key gin joint cocktail bar. Need we say more? A big patio, cocktails by the pitcher, and a solid lineup of burgers makes it the perfect spot to meet up with friends and soak up Summertime!

Parlor Pizza

Neighborhood: Wicker Park

Why we recommend it: Good pizza and a massive outdoor patio, plus this place is always buzzing with activity! Best for when you're craving a high energy level and good wood fired 'za.

Whiskey Business

Neighborhood: Wicker Park

Why we recommend it: The rooftop patio here has some pretty fab seating - are they chairs or couches?? Try to go at a non peak time if you want to avoid the Bro crowd.

Kaiser Tiger

Neighborhood: West Loop

Why we recommend it: The beer garden is a great spot to hang out and play some bocce ball with the Chicago skyline in the near background.  In addition to drinks and games they also have a pretty good food selection to go along with your beverages.


FOR "THE SCENE" (the kinds of places we would go for a night on the town)


Neighborhood: River North

Why we recommend it: Rooftop. Pool. Lounge. Cocktails. Downtown Vibes. Definitely the place to go if you want to experience the scene this Summer


Neighborhood: River North

Why we recommend it: Very inventive cocktails at fairly reasonable prices. A swanky rooftop. Another great place if you want to experience the downtown scene.

The Robey (Cabana Club)

Neighborhood: Wicker Park

Why we recommend it: Like the aforementioned Devereux, there's a pool. On a rooftop! The pool is actually only for hotel guests but the surrounding area is open to any patrons of the establishment so put on some sunscreen, get yourself a refreshing cocktail, and enjoy the trendiest scene outside of River North ;)

Cindy's Rooftop

Neighborhood: The Loop

Why we recommend it: Although the outdoor area here is fairly small, the indoor area at this rooftop establishment is also very bright and airy thanks to lots of windows and sunlights. The view of Millenium Park from the outdoor patio is truly lovely.  This will be on any and every list you read of where to go when in Chicago, so expect the place to be BUSY. Still, I cannot NOT recommend it because.... those views! that decor! sighh....


Neighborhood: River North 

Why we recommend it: For a rooftop that's not just a bar.  Noyane is an upscale sushi spot in River North that has a classy rooftop where you can enjoy a tasty bite.


FOR ROMANCE (the kinds of places we would go for a date night)

Mi Tocaya Antojeria

Neighborhood: Logan Square

Why we recommend it: As the youths would say: for a little "low key" romance this is your spot. Charming. Lively. Latin. This place exudes lighthearted, summertime amor!


Neighborhood: River North

Why we recommended it: String lights and upscale Mexican food = the perfect Summer date night.  Dogs are also allowed at the patio, so bring your furry friend as third wheel!

The Duck Inn

Neighborhood: Bridgeport

Why we recommend it: The outdoor patio here is full of charm. Situated behind the restaurant it's also secluded from the street for a more intimate feel. what's not to love about good food, string lights, and a play on words!?


FOR JUST REALLY GOOD FOOD (the kinds of places we would go for delicious dishes)

Mott Street

Neighborhood: Wicker Park

Why we recommend it: Everything. Period. The 90s rap music, the painted walls, the lights, the personable servers, the damn good Korean-street-food influenced menu. Don't miss the brussel sprouts, kimchi empanadas, the everything wings, the pork jowl and the stuffed cabbage, but honestly, if you go with a big group just order the whole menu and thank me later!

Small Cheval

Neighborhood: Wicker Park

Why we recommend it: for the highly acclaimed Au Cheval burger in a less crowded environment. This is a darn good burger, people!

Parson's Chicken and Fish

Neighborhood: Logan Square

Why we recommend it: Good down home food and sides at affordable prices. The large open patio out back is the perfect hang out spot, plus the entire restaurant recently got a makeover and it's looking pretty fly ;)

Spacca Napoli

Neighborhood: Ravenswood

Why we recommend it: All ingredients at this neighborhood gem are imported from Naples.  They are one of very few Neapolitan certified pizzerias in the world, and you can tell when you taste the fresh burrata di buffala or a wood fired pizza topped with fresh san marzano tomatoes and mozarella di buffala. The patio is casual, so the ambiance is less romantic than you might expect, but on the flipside, what is more romantic than really delicious carbs?!

Mi Tocaya Antojeria

Neighborhood: Logan Square

Why we recommend it: Just read any article on the top restaurants in Chicago right now and you'll likely hear about the incredible chef behind Mi Tocaya Antojeria. Yes, we already recommended it for the "Romance" category, but it belongs in the top notch food category too! If you're after a great meal- don't miss this one!


If you've eaten outdoors in Chicago recently we'd love to hear what spots you're loving lately- we love adventuring to new places that we hear about through friends!!

With love from Chicago,

Daniel + Jennifer