There’s nothing quite like sitting in a well-decorated bar or lounge and sipping on a fun cocktail with friends to kick off the weekend – or to take a much-needed, mid-week break! I love visiting new restaurants and bars as they pop up all over Chicago, so it’s not uncommon for friends to ask me for recommendations when they’re looking for a new place to try! It’s always fun helping them pick a new spot to check out and having a variety of suggestions.
Below, I’ve rounded up some of my favorite spots in Chicago to grab cocktails with friends or on a date as well as what I usually order! I’ve organized these by neighborhood and plan to continue to add to this list as time goes on! So, make sure you bookmark this post if you live in Chicago or plan on visiting any time soon.
Wrigleyville
Hotel Zachary – 3630 N Clark St, Chicago, IL 60613
I LOVE Hotel Zachary’s Bar (pictured above). I stop in about once a week since I live in the neighborhood and I’m a huge fan of the vibe. It’s Wrigley-themed, with a nod to 1920’s luxury. I’ve tried (almost) all of their specialty cocktails, but my favorite by far is The Rattlesnake. This drink is made with egg white, Bulleit rye, sugar, absinthe and lemon. The Rattlesnake used the be one of the featured drinks on Hotel Zachary’s bar menu, which is how I first learned about it. It’s not listed anymore, but they can still make it! 10/10 would recommend! If you’re looking to grab a bite while you’re there, I’m also a huge fan of their Little Gem Wedge Salad which comes with pickled red onion, bacon, avocado, and blue cheese.
Old Crow Smokehouse – 3506 N Clark St, Chicago, IL 60657
There’s also an Old Crow in the River North area, but I think that their Wrigley location is much more fun! I started going to Old Crow my senior year of college and it’s one of those places where it’s an odd night if I don’t run into at least one person I know from school or the ‘burbs. It’s got a very friendly feel to it! Old Crow is known for its live country music on Saturday nights and drinks served in branded mason jars. My favorite drink to get here is Front Porch Punch which is made with blackberry moonshine, elderflower, lemon, soda and finished off with fresh blueberries and raspberries sprinkled on top! I’m also a fan of their Peach Collins which is made with peach moonshine, Beefeater 24 Gin, peach puree, lemon, and soda. If you’re a country music fan this spot is for you!
Lincoln Park
Homeslice – 938 W Webster Ave, Chicago, IL 60614
Homeslice is one of three fun pizza-focused restaurants/bars in the Chicagoland area that my friends and I love to visit on the weekend! The other two are Happy Camper in Old Town and Paradise Park in Wicker Park, but the vibe at Homeslice is my personal favorite. It’s the perfect Sunday Funday spot! My favorite drink to get here is their Matcha Mamma which is made with vodka, matcha, and lemonade. Sometimes I’ll have them add some mango flavoring to it as well. (Shout out to a server I had last summer who made this great suggestion!) If I’m in the mood for a more “extra” drink, I’ll order the A-Lotta-Colada (shown above) which comes in a sparkly pineapple cup and is made with coconut whiskey and rum cream. They also have some fun and quirky pizza options that are worth checking out as well!
Old Town
The Vig – 1527 N Wells St, Chicago, IL 60610
The Vig in Old Town is one of my go-to spots for a night out with my girlfriends! It’s the perfect spot to get the night started. You can grab a late dinner in one of their tufted leather booths and people-watch as the dinner crowd transitions into more of a nightlife feel. Their Espresso Martinis and Cosmopolitans are both SO good. I also recently tried their Paging Betty cocktail made with vanilla-infused Tito’s, cran-raspberry shrub, lemon, and egg white. It tastes like a raspberry dreamsicle! The DJ at the Vig is usually solid and they play a combo of sports and music videos on the TVs around the bar as well as a mixture of current music and top hits from the last few years.
Downtown
Streeterville Social – 455 N Park Dr, Chicago, IL 60611
I had the pleasure of checking out Streeterville Social’s on the roof of the Loews Hotel on a July evening. It was the perfect spot to be in as the sun set! The view is great, but the drinks and food are even better! Drink-wise I had the Find Your Matcha cocktail (shown above) which is made with Capel Pisco, matcha, egg white, and lime. I also had Sweet Dreams which is made is Casamigos Añejo, triple sec, cucumber syrup, and lime. If you’re a mezcal fan, they have a sister cocktail to Sweet Dreams called Foggy Thoughts which is identical, except they swap out the Casamigos Añejo for Vida Mezcal. One of Streeterville Social’s managers also brought over samples of two of their frozen drinks to try: Mint to Be which is made with Ketel One Cucumber Mint, watermelon and lime and their Frosé which was more on the floral side. Both were SO good! If you’re going to get food while you’re there, definitely try out their King Crab Avocado Toast, Blistered Shishito Peppers, Calamari, and Ahi Tuna & Black Tea Watermelon.
Apogee Lounge – 2 W Erie St, Chicago, IL 60654
Apogee Lounge is one of the pricier spots on this list, but in my opinion the experience is worth it! It’s located in the Dana Hotel and known for their shared cocktails that come in fun drinkware like Macrodose (shown above) which is served in a mushroom “cup.” This drink features Hendrick’s Gin, watermelon, daily fresh herbs, and Secret Powder Mix #8. Apogee is a spot that’s a great for a date if you sit at the bar, but it’s also a blast to go with a larger group and sit at one of the tables with some shared drinks. One of the most popular shared cocktails they serve is Mr. Nice Guy which comes in a bong-like container stuffed with baby’s breath flowers and is made with Absolut Elyx vodka, cinnamon citrus smoke, ginger and pineapple. They also have a rooftop area that’s open during the warmer months!
Drumbar – 201 E Delaware Pl, Chicago, IL 60611
Drumbar is a great spot for a chill evening with a date or for a double date. This bar is located at the top of a hotel, but feels nothing like your typical hotel bar. The inside has a cozy and library-like feel to it including some quieter tables down a long hallway. Last time I visited with Jim and our friends Lexi and Bill we sat at the far end of the hallway in a cute little alcove and it had a more intimate feel compared to the main area of the bar. One of my favorite cocktails on their menu is the Apple Whiskey Sour made with “very old” barton bourbon, novo fogo tanager cachaça, fuji, apple, cardamaro and lemon. It reminds me of boozy cider but without it tasting too sweet or syrupy.
Three Dots and a Dash – 435 N Clark St, Chicago, IL 60654
If you’re going to talk about cocktails in Chicago, Three Dots and a Dash has to be on the list! This tiki bar has a speakeasy style entrance, “hidden” in an alleyway in River North and marked by tiki torches. The entire bar is decked out in tropical decor and their drinks are primarily rum-based. It’s always absolutely packed here so it can be hard to hear people if you’re with a group of more than 3-4 people in total. I prefer sitting at the bar because then you can watch their bartenders make all of the different, decorated drinks. Three Dots is definitely more of a sit-down spot vs. a stand, dance and walk around situation. My favorite drink here is the Jet Pilot (shown above) which is made with a Jamaican overproof rum blend, lime, grapefruit, falernum, cinnamon, absinthe and bitters.
Rock Bottom Restaurant & Brewery – 1 W Grand Ave, Chicago, IL 60610
Rock Bottom is my all-time favorite spot for happy hour because they have incredible deals and one of the latest running happy hours near my office building. Most happy hours downtown area go until about 5:30 p.m. At Rock Bottom, happy hour goes from 4:30-6:30 and includes the BEST deals. Their signature cocktails are only $6 and there are lots of discounted food options to choose from as well! I mainly focus on their cocktails, fried pickles and ballpark pretzels during happy hour, but I know that they also have plenty of beer deals and they have their own brewery on-site!
Fig and Olive – 104 E Oak St, Chicago, IL 60611
Fig and Olive is known for being a high-end restaurant, but their bar at the center is absolutely stunning! There’s greenery “growing” from the center of the bar that’s decorated with twinkle lights. It’s simply magical looking! When it comes to cocktails, they have one of the best espresso martinis that I’ve ever had! This is a favorite spot for me and my Aunt Mary when we go out to eat together for dinner.
Cindy’s Rooftop – 12 S. Michigan Ave, Chicago, IL 60603
Come for the cocktails, stay for the view of Millennium Park and Lake Michigan! Cindy’s is right on Michigan Avenue, at the top of the Chicago Athletic Association. (They also have a full menu, but I’ve only ever been here for drinks with friends.) It can be a very touristy spot due to the view and can get especially crowded in the summertime, but it’s worth it. I love the vibe here later in the evening.
Public House Chicago – 400 N State St, Chicago, IL 60654
If you’re going to check out Public House, you need to try two things. Their boozy Seasonal Cake Shake and their Crispy Brussels Sprouts! The cake shake is always super rich, but great for sharing with another person! They have a Chocolate Porter Cake Shake and a Vanilla Stout Cake Shake all-year round, but their seasonal cake shakes (like the one above) are always so creative!
LUXBAR – 18 E Bellevue Pl, Chicago, IL 60611
LUXBAR happy hour was one my favorites when I worked a bit more north on Michigan Avenue for a few years! They have happy hour Monday-Friday from 3-6 p.m. and everything on that menu is $5 or under! They has wine and beer options on the happy hour menu as well as a really good burger! In the summer, they also have outside seating which is so nice in the evening! It’s a great spot to grab cocktails or wine and sit with friends on the patio on a summer night.
Cerise Rooftop – 203 N Wabash Ave 26th floor, Chicago, IL 60601
I checked out Cerise for the first time a few weeks ago with my friend Emma and we loved it! The view is great and their Devil to Pay cocktail (above) has GLITTER in it! That drink is made with aviation gin, rose, lemon and La Croix. Would highly recommend this spot for some golden hour cocktails with a date or a few friends.
West Loop
Federales – 180 N Morgan St, Chicago, IL 60607
One tequila, two tequila, three tequila, floor! Federales is always a party and their Paloma made with grapefruit soda, tequila and lime is so good! I was first turned onto Palomas by my friend Hanna when I was in Austin, TX and they’ve been one of my favorites ever since! Federales is know for its infamous bell and ice shot glasses! You can order a shot of tequila that will come in a shot glass made of ice and then after you take the shot you throw the glass at the bell to try and ring it! Feds is also known for this cool mural on one of the exterior walls, shown below. Fun summer feature: their roof is retractable, so in the summer it’s like you’re outside! It’s always pretty packed(and sometimes you’ll have to wait in line) but it’s worth it since it’s always a party!
Soho House Chicago – 113-125 N Green St, Chicago, IL 60607
Soho House is one of many trendy spots in Chicago. Here, you need to be a member (or friends with one) to access the upstairs. I myself am not a member, but a few of my friends are! Soho House has special deals for members under a certain age. For example, on Mondays or after 11 p.m. on various days, food and drinks are 50% off! The last time I was here, I went with my friend Lexi and we grabbed a few cocktails at the bar. The general vibe is like an upscale lounge with dark wood, dim lighting at night and vintage light fixtures. The espresso martinis here are so good and they make them with Intelligentsia coffee! Whatever you do here… don’t take photos!!! Celebs like Chance the Rapper are members, so for privacy’s sake you aren’t allowed to snap photos in the members only areas.
If you’re not a member, Soho House does have an area downstairs that’s open to the public called The Allis! The Allis is stunning and feels more open compared to upstairs. With its high ceilings and multiple levels it has a much more airy, boho vibe compared to the vintage charm upstairs.
Punch Bowl Social – 310 N Green St, Chicago, IL 60607
I attended Punch Bowl Social’s grand opening when they first came to Chicago and I immediately knew I’d be back! Punch Bowl is a great spot for larger groups! They have a bunch of games you can play, inside, including bags and foosball. Their space is made up of multiple floors and has a retro-lodge vibe. As the name would suggest, Punch Bowl Social serves punch bowl style cocktails that are great for sharing! My personal favorite punch is the Watermelon Polo Bowl! It’s made with Sauza Blue Reposado Tequila, Teakoe’s watermelon spearmint tea, McClary Bro’s Watermelon Shrub, house-made strawberry syrup and fresh lime juice. You can order it in the large, group format or single-serve.
What’s your favorite spot to grab cocktails in your city? Let me know in a comment below or shoot me a message via social media! I’d love to add some new spots to my list for future travels.
Until next time!
