Ranking Chicago’s Best Happy Hours Deals
In March, I kicked off a challenge: a 30-Day Happy Hour Series in Chicago. I know, I know—30 days?! That’s nuts! But relax, I’m not doing 30 back-to-back visits. The goal is just to try 30 different happy hours, on my own schedule, as life (and my liver) allows.
Brunch is out. Happy hour is in. There, I said it. People want great drink deals, solid apps, and a vibe—not paying $20 cocktails at 5 p.m. So I set out to find the spots that are actually worth your time and fit your budget. Because I am also on a budget lol.
Now that I’ve hit 10 happy hours, I’m ranking them—I’ll keep updating this list every time I hit 10 more. So how am I rating them?
The deal - obviously this seems like the most important because it’s what you’re here for
The food and drinks - I need the quality to be good. If the quality of happy hour is bad, then what’s that say about the menu as a whole?
The vibe - we, of course, want a good aesthetic
My overall experience - this incudes the service
If you’re looking for the best happy hours in Chicago, I’m your girl. Cheers to never paying full price again.
1) Itoko
Coming in at #1, and for good reason, is Itoko. This is probably one of the most popular happy hours in Chicago right now and here’s why. The vibes in here are EVERYTHING. A bright modern space with Japanese influence, not to mention they have a patio.
But you need to get here early or make a reservation because a line forms outside the door!! Everyone wants a piece of their infamous lychee martini’s (they are delicious btw). You can successfully have an entire meal and cocktails here for less - it’s why it’s such a hit.
Location: Lincoln Park
Happy Hour: see menu
Monday – Friday: 4:30 PM – 6:00 PM
The Deal:
$10 - $12 cocktails
$10 wine
$7 beer
Around 20-50% off their food
2) DJ’S GREAT ROOM
This is a newer spot that just opened in February. They also are planning to open a patio in late May. This place is precious, it has a living room feeling with big windows that bring in lots of light which makes for a perfect happy hour and lunch spot. My favorite thing about this place is the entry room that has a mini bar and booth, located just before the main dining room. I think it’s unique to offer a more intimate setting or a bigger space for people to be while you wait for a table.
You get FREE complimentary bread (do I need to say more?) The small bites were really tasty and the cocktails were top-notch. It is great for photo’s and just a warm, welcoming atmosphere, our server was also amazing. I really loved my experience at DJ’s Great Room!
Location: Old Town
Happy Hour: see menu
Tuesday – Friday: 4:00 PM – 6:00 PM
The Deal:
$11 cocktails (cosmo, dirty martini, negroni, manhattan)
$10 wine & sangria
$9 bites
3) DIEGO
As someone who could eat Mexican cuisine for every meal, this new restaurant deserves a spot at the top of the list. I love this place because it feels like you stepped outside of the city and are on a little taco hut on the beach.
Their happy hour cocktail is pre-made but it tastes fresh still - which is hard to come by. And I can’t rave enough about the chicken tacos. OH. MY. GOD. They are so good!! Come here sit on their patio after work and enjoy some great food.
Location: West Town
Happy Hour: see menu
Tuesday - Friday: 4:00 PM – 6:00 PM
The Deal:
Bites starting at $5 - $15
$11 coktails
$10 wine
$4 beer
4) YASEMI
I may be a bit biased on this one because I had such a great experience with our bartender. This is a new spot underneath the Godfrey Hotel. It’s a Mediterranean vibe and has one of the best happy hours I’ve ever been to. The cocktails were delicious and our bartender was able to make drinks off the menu that catered to our pallets.
What makes this even better is that their happy hour is every day of the week!
Location: River North
Happy Hour: see menu
Every day: 4:00 PM – 6:00 PM
The Deal:
$10 cocktails
$8 wine
$7 beer
Bites starting at $8
5) HURLEY TAP
This might be the best deal in the city, especially on Tuesday’s. This is definitely your typical neighborhood bar - but with great deals. Come here for their Taco Tuesday’s and eat some of the best authentic tacos. They make their meat fresh to perfection every day and when it’s gone, it’s gone. That’s how you know it’s good.
Location: Bucktown
Happy Hour: see menu
Taco Tuesday: $12 2 tacos + a Modelo
Monday - Friday (except Tuesdays): 3:00 PM – 6:00 PM
The Deal:
$6 drafts
$8 margs
$3 domestic bottles & $5 import bottles
$7 wine
$3 tacos
6) ABA
Aba is a tried and true staple that everyone knows! And it’s for good reason. They have such a great rooftop for the summer and it’s in a great location for people who go into the office. They don’t have a ton of food to offer on their happy hour menu but I think the drinks are worth it - plus the bartenders are super fun here!
Location: West Loop
Happy Hour: see menu
Sunday - Tuesday: 4:00 - 6:00 PM
Wednesday - Thursday: 3:00 - 6:00 PM
The Deal:
$10 margarita and martini
$8 wines
$15 spreads
7) SUSHI SAN
A great place to get sushi at a reasonable price - the only reason it’s lower on the list is because I didn’t love my experience. When I go out to eat, the experience is everything to me and I just felt like this place was missing the welcoming, friendly vibe. But the deals are good and the sushi was fresh! Get here early because it will fill up.
Location: Lincoln Park
Happy Hour: see menu
Monday - Thursday: 4:00 PM – 6:00 PM
Friday - Sunday: 3:00 PM - 5:00 PM
The Deal:
$10 cocktails
$6 snacks
8) CHEF’S SPECIAL
Don’t worry, I found you another happy hour that happens every day of the week (my favorite kind of deal). This American-Chinese spot has a line forming outside the door before they open for this deal. The deals on the food here are worth it alone. Not to mention, they have some of the most unique, fresh cocktails.
Don’t sleep on the green beans though!! They are so good!
Location: Bucktown
Happy Hour: see menu
Everyday: 5:00 - 6:00 PM
The Deal:
$6-$13 bites
$9 cocktail
$45 bottle of wine
9) BRASERO
A stylish, wood‑fired, Latin‑inspired lounge with a warm, modern ambiance. This might be one of my favorite restaurants in the city - the food is just always so amazing here. And the Caipirinhas are so refreshing and easy to drink. The steak and ceviche are cooked to absolute perfection and both melt in your mouth.
An added bonus is that their happy hour also exists on the weekends!
Location: West Town
Happy Hour: see menu
Everyday: 5:00 - 7:00 PM
The Deal:
$8-$20 bites
$10 cocktails
10) DIVAN
This place is a vibe. It’s giving speakeasy or some under cover bar in the prohibition era. The Persian‑Mediterranean flair makes it an ideal spot to unwind after work. Or even a pre-game for your weekends because happy hour is even on the weekends!
The cocktails here are beautiful and I personally think their cosmo is one of the best in the city (I had 2 to be sure).
Location: River North
Happy Hour: see menu
Everyday: 5:00 - 6:30 PM
The Deal:
$8-$20 bites
$10 cocktails
11) OLIVER’S
Can I just gush about this place for a second? It’s insanely aesthetic. Such girly vibes and I wanted to snap pictures of just about everything. Its decor is inspired by 1930’s LA with some retro charm. The ambiance, food, drinks were everything here.
Bonus points because they have 2 happy hours per night - see below.
The only reason it’s lower on the list is because of the pricing but I get it because it’s a more elevated experience. I would love to come back for dinner.
Location: South Loop
Golden Hour: see menu
Tuesday - Friday: 5:00 PM - 6:00 PM
The Deal:
$10 cocktails & wine
Snacks starting at $10
$16 tiny martini + truffle fries
Nightcap Hour:
Tuesday - Thursday: 8:00 PM - 9:00 PM
Friday - Saturday: 9:00 PM - 10:00 PM
The Deal:
$9 tini cocktails
Dessert starting at $9
12) QUEEN MARY
This spot is for the girls (and for dates) but mainly for the girls. The people who work here are so fun and love to play Sabrina Carpenter which you know is an A+ in my book.
They are famously known for their raw happy hour bar and if you like oysters, it’s the place to be.
Location: Wicker Park
Happy Hour: see menu
Sunday: 3:00 PM – 7:00 PM
Monday: 5:00 PM - 7:00 PM
The Deal:
$9 martinis
Deals on oysters, shrimp, and other shellfish (prices may vary)
13) LILAC TIGER
If you like vibrant, unique cocktails, this is the place for you. This is a lively, street-like atmosphere playing hip-hop music and offering South Asian food and drinks. Their cocktails are so unique and fun. Not to mention, their happy hour extends through the weekend!
Location: Wicker Park
Happy Hour: see menu
Every day: 5:00 PM – 6:00 PM
Sundays: 5:00 PM - 10:00 PM
The Deal:
$5 shots
$10 drinks
Snacks starting at $5
14) THE WHALE
Casino Royale meets Logan Square. This decor here is fun and they have an outdoor patio! TBH, I think the food could use some improvement but I really enjoyed their specialty drink which is a Gin & Tonic (pictured here).
Location: Logan Square
Happy Hour: see menu
Monday - Friday: 5:00 PM - 7:00 PM
The Deal:
$10 cocktails
$10 wine
$10 bites
$16 burger & fries
15) TAMA
Located inside an old house so it’s very charming, is a mix of Mediterranean, Asian, and South American traditions. The menu changes often but happy hour is always at the bar. I got the margarita and my friend ordered the cheri cheri lady which was delicious. The reason they are lower on the list is because it’s only offered 3 days a week and I’d love to see it extend through Friday.
Location: Wicker Park
Happy Hour: see menu
Tuesday - Thursday: 5:00 PM - 6:30 PM
The Deal:
$9 cocktails
$7 wine
$5 house beer
Snacks starting at $8
16) AMBAR
They have an extensive happy hour menu but I would not recommend the margarita. It was pure sour mix so opt for a glass of wine or beer. They have a lot of snacks to offer on their list but I think the presentation of the food could improve. I was pretty disappointed. Good spot for just drinks though if you’re in the area. Just wasn’t the best experience.
Location: River North
Happy Hour: see menu
Monday - Friday: 4:00 PM - 6:00 PM
The Deal:
$8 cocktails
$7 wine
$6 house beer
Snacks starting at $5
Whether you're a local or just visiting, these spots offer some of the best happy hour deals in Chicago. Once I complete the next 10, I’ll keep updating the list. CHEERS!!
