Hey there, Chicago margarita lovers!
Summer’s finally here, and you know what that means – it’s time to grab your friends, find a perfect patio, and sip some killer margaritas while soaking up the sunshine. After enduring another legendary Chicago winter, we think we’ve all earned the right to celebrate with salt-rimmed glasses and good vibes.
We’re the Ben Lalez Team, and while we spend most of our time helping families find their perfect Chicago homes, we’ve also become experts at knowing where to grab the best drinks in every corner of the city. After all, many of our best client conversations happen over perfectly crafted cocktails!
Here’s our guide to the best spots for margaritas in Chicago with outdoor seating in 2025. By the way, if your venue serves delicious cocktails and we’ve left you off the list, make sure to contact us to be included in the next article!
Finding The Perfect Patio For Margaritas In Chicago
Let’s talk about what we think makes for the perfect margarita spot. Of course, the drinks need to be awesome, but the whole experience is what counts.
First, the patio itself has to deliver. We’re talking about comfortable seating, some shade options for those brutal July afternoons, and enough space that you don’t feel like you’re sitting in your neighbor’s lap. The best spots also have that indefinable atmosphere that makes you want to settle in for a few hours.
Then there’s the margarita program. Chicago’s gotten way more sophisticated about agave spirits over the last few years. We look for places that prioritize quality tequilas and mezcals, offering creative variations beyond the basic lime, and obsessing about the final presentation.
And the service and vibe need to match. Some places are more casual where you can roll up in flip-flops. Others are definitely more upscale, so you’re going to have to get dressed up. Both vibes work, but they need to commit to their concept.
North Side Neighborhood Favorites
Big Star – 1531 N Damen Ave, Wicker Park
Big Star has been the neighborhood margarita spot since 2009. The honky-tonk vibe with bright yellow chairs and umbrellas creates a fun vibe.
What we love about Big Star is that it’s not pretentious. It definitely gets busy at times and you might wait for a table, but it’s all part of the Big Star experience. They do pitcher service for groups, the patio is dog-friendly, and everything feels very “Chicago summer.”
Their food program has expanded over the years, but honestly, you’re here for the margaritas and the vibe. Just know that it’s first-come, first-served seating. Plan ahead if you’re coming with a big group.
Lonesome Rose – 2101 N California Ave, Logan Square
Here’s a spot that’s earned some serious recognition – Michelin Bib Gourmand status and James Beard Award recognition for design. But don’t let that scare you off, because Lonesome Rose has decent pricing while delivering a great experience.
Their rooftop patio offers skyline views, and they’ve got sidewalk seating that welcomes dogs. The Tex-Mex concept works really well, and their house margaritas are available by the pitcher. Their happy hour is every weekday from 3-6 PM with $6 margaritas, and we think it’s a steal.
The Logan Square location puts you in one of Chicago’s most central neighborhoods, so you can bar hop and check out other venues nearby.
Cesar’s Killer Margaritas – 2924 N Broadway, Lakeview
With a name like that, they better deliver on the margaritas – and they absolutely do. They have over 20 flavors including mango, strawberry, guava, and seasonal specialties. If you’re a bit more adventurous and want to try something different, this is where you should definitely go.
They have a multi-level setup that includes an outdoor patio, rooftop deck, and three indoor areas, so they can handle groups of any size. It’s located in Boystown with a welcoming LGBTQ+ friendly vibe that makes everyone feel at home.
Their Super Mega-Rita sharing drinks are perfect for groups, and their happy hour pricing runs Monday-Thursday from 3-6 PM with $8 lime margaritas.
West Side Trendsetters
La Josie – 740 W Randolph St
La Josie brings authentic Mexican flavors to Restaurant Row with three bars, including a dedicated rooftop space. What we like about this family-owned spot is their emphasis on extensive agave menus featuring both tequila and mezcal.
Their corner location on Randolph means you’re in the heart of the action, but the multiple bars help spread out crowds so you’re not fighting for space. The modern casual atmosphere hits that sweet spot between approachable and elevated.
Aba – 302 N Green St, Fulton Market
Aba owns the Fulton Market rooftop scene with their 4,000 square foot terrace, and while they’re Mediterranean-focused, they’ve been doing some great tequila events with premium brands, so they definitely understand agave spirits.
The terrace has nice greenery, fire pits, and heated seating, which means you can enjoy it even when the weather isn’t the best. The third-floor location has great skyline views.
This is definitely an upscale experience, and you’ll be paying for the location, ambiance, and high-end service. But if you want to feel like you’re somewhere special for a night, check them out.
Downtown And Riverwalk Stars
CocoBar – 316 N. Wabash Ave
Let’s start with what might be Chicago’s most exciting margarita destination right now. CocoBar sits right on the Chicago Riverwalk with that bright pink facade you can’t miss. What sets them apart is their absolutely ridiculous margarita menu – we’re talking over 50 different options.
But here’s what makes CocoBar special: they’ve created a build-your-own margarita program that actually works. You can choose your tequila or mezcal (they’re featuring Mexican-owned brands like La Gritona), pick your agua fresca flavor, and customize your rim. You also get that vacation vibe without having to leave Chicago.
The pricing starts around $15, which isn’t cheap, but the quality and creativity justify the cost. Their happy hour is from Monday through Wednesday, 5-7 PM with $10 frozen margaritas. No reservations required, so it’s first-come first-served.
LH Rooftop at LondonHouse – 85 E Wacker Dr
If you want to impress someone, this is your spot. LH Rooftop spans three floors (21-23) with the main action happening on the 22nd floor terrace. The views are stunning. You’ll be looking out over the Chicago River, Lake Michigan, and the Magnificent Mile all at once.
Their cocktail program is more upscale, and that means you’re paying premium prices. But the experience is worth it for special occasions. The outdoor terrace gets packed during prime times, so you want to make reservations if you want to snag an outdoor spot.
Remember… this is more of a dress-up venue. Dress code is smart casual, so you can’t show up in your favorite summer flip flops.
Terrace 16 at Trump Tower – 401 N Wabash Ave
For the most luxurious margarita experience in the city, this is the spot you want to check out. Their 16th-floor rooftop terrace seats 200 people and you’ll get Instagram-worthy views of the city and the river.
What’s cool here is their Tornado Tower Cocktail that serves up to six people and features Don Julio Añejo. It’s a bit costly, but if you’re celebrating something big with a group, it’s worth the story and the photos, right?
The atmosphere is business casual, so it’s a great place to impress clients or celebrate a big sale. Just know that you’re not just paying for the drinks – you’re paying for the views and ambiance too.
Hidden South Side Gems
Osito’s Tap – 2553 S Ridgeway Ave, Little Village
This might be Chicago’s best-kept margarita secret. Osito’s Tap has earned incredible reviews (4.7/5 on Google, 4.8/5 on OpenTable) while staying under the radar for most downtown crowds.
The speakeasy-style atmosphere in a historic greystone building creates this intimate patio experience with modern Latinx flair. What sets them apart is their educational approach to craft spirits and genuine community connection.
Little Village isn’t where most people think to go for craft cocktails, but that’s exactly what makes Osito’s special. Plus, free parking – when’s the last time you found that at a great cocktail spot?
La Vaca Margarita Bar – 1160 W 18th St, Pilsen
Pilsen’s most accessible margarita experience comes with $9 Margarita Mondays and $30 bottomless brunch service. This family-owned spot brings 50+ years of Pilsen history to their modern Mexican menu.
It’s a walk-in only policy. Their pricing is very reasonable, and the atmosphere feels like you’re drinking with locals rather than tourists. Highly recommended.
What’s Trending In 2025
The Chicago margarita scene is a lot of fun this year. Pitcher culture is huge – almost every spot offers shared service alongside individual cocktails, which makes sense for our group-oriented drinking culture.
Frozen specialties and slushies are all over summer menus. When it’s 90 degrees and humid, nobody wants a warm cocktail, so these ones just really hit the spot. The best places are getting creative with frozen variations that aren’t just sugary mush.
We’re also seeing more venues emphasizing Mexican-owned spirit brands. Places like CocoBar specifically highlight distilleries like La Gritona and Yola mezcal, which reflects a broader trend toward authenticity and supporting Mexican producers.
The outdoor space game has stepped up too. Fire pits, games, retractable roofs, and serious weather protection help extend Chicago’s notoriously short patio season. Some places are operating outdoor spaces almost year-round now.
Pro Tips For Your Margarita Tour
Reservation policies vary wildly. CocoBar and La Vaca are walk-in only, while LH Rooftop need advance booking for terrace seating. When in doubt, call ahead or check their websites.
Pricing ranges from $8 happy hour specials to $30 premium flights. We find that most places hit that sweet spot around $12-18 per margarita, and that’s pretty reasonable for quality cocktails in a big city.
Make sure to think about timing to get the most out of your night. Early happy hours (3-6 PM) offer the best deals, and you’ll almost always get outdoor seating. Once you get into the prime dinner hours (7-9 PM), you’ll start finding the patios packed with slower service.
And of course, you have to think about the weather. Many rooftops are weather-dependent, but places with retractable roofs or heated patios are the ones that are super busy when the weather isn’t the best.
Making The Most Of Margarita Season
Whether you want CocoBar’s creative riverside selection, Big Star’s neighborhood energy, or Osito’s Tap’s hidden gem status, Chicago has a ton of world-class agave experiences.
The emphasis on quality tequilas and mezcals, seasonal ingredients, and enhanced outdoor amenities shows how far Chicago’s cocktail culture has come. We’re no longer just competing with other Midwest cities – we’re holding our own against traditional margarita strongholds.
So grab your friends, download some good playlists, and start exploring. Summer in Chicago is short, but margarita season is here, and these patios are waiting for you.
Ready to find your new favorite margarita spot? Give the Ben Lalez Team a shout! We know every corner of this city, and we’re happy to share more of our favorite local spots with you.
Cheers to summer in Chicago!
