Best Happy Hours Deals in Chicago
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 have been to 30+ happy hours in the city, this is my roundup of the best ones. 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 a year ago. 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.
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) MACELLO
I liked this happy hour so much, I’ve been back multiple times! Feels like a home-y Italian living room with a wood fired oven right within view of the entire restaurant. Not to mention, some of the best espresso martini’s!
Location: West Loop
Happy Hour: see menu
Sunday 3-6 pm
Tuesday 3-6 pm
Wednesday 3-6 pm
Thursday 3-6 pm
Friday 4-6 pm
The Deal:
1/2 off wines, cocktails, and apps!
$8 espresso martini’s btw :)
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
17) FORMENTO’S
Formento’s brings the nostalgic Italian vibe with the dim lighting and cozy leather booths. Their patio is huge so it’s perfect for the summertime. With a happy hour that is every day, it’s kind of hard not to stop in to it.
Location: West Loop
Happy Hour: see menu
Everyday: 4:30 PM - 6:00 PM at the bar or patio
The Deal:
$10 cocktails
$10 wine
$5 beer
$2 oysters
Apps starting at $4
18) OAKVILLE
If you are looking for a little taste of Napa in Chicago, this is your spot. Calling all wine lovers to this happy hour! They have endless wines available and they are always on rotation.
Location: West Loop
Happy Hour: see menu
Mon - Fri: 4:00 PM - 6:00 PM in the bar
The Deal:
$6 wines
$7 margs, $8 spritz, and $9 martinis
$6 beer
$2 oysters
Apps starting at $6
19) EIGHT BAR/MAPLE & ASH
Eight bar is the bar downstairs Maple & Ash and they both offer a happy hour special. Personally, I prefer the Maple & Ash vibes/staff over Eight bar but to each their own.
Location: Gold Coast
Happy Hour: Eight Bar Menu / Maple & Ash Menu
Daily: OPEN - 6:00 PM
The Deal:
$15 cocktails
$8 mini martinis
$8 handrolls
$45 seafood tower
20) LA LUNITA
This modern Mexican spot in Logan Square, blends bold traditional flavors with seasonal ingredients. It’s such a lively environment with records on the wall and DJ’s on the weekends. Perfect spot to start or even end the night!
Location: Logan Square
Happy Hour: see menu
Tues - Thurs: 5:00 - 7:00 PM
Fridays: 4:00 - 6:00 PM
The Deal:
$8 cocktails
$10 wines
$5 shots
$8 Guacamole
$10 Esquites
$10 Chicharrón
The Daily Specials:
Tuesday
$5.00 Tacos ALL DAY!Wednesday
$1.50 Happy Hour Fresh OystersThursday
1/2 Bottle Wines ALL DAY!Friday
$5 Happy Hour Tequila & Mezcal Shots
21) TRINO
Diego’s sister restaurant - This modern Latin‑influenced steakhouse blends Galicia, Northern Mexico, and Argentina. The space is stylish yet warm, like walking into a speakeasy library. Did I mention they also have a speakeasy? It’s called Laberinto. I love a happy hour at a Steakhouse!
Location: West Loop
Happy Hour: see menu
Tues - Fri: 4:30 - 6:00 PM
The Deal:
$9 cocktails
$6 wines
Apps starting at $8
22) RPM SEAFOOD
One of the most beautiful views of the river is at RPM Seafood. Unfortunately, happy hour is only available at the bar and not on the patio but it’s still a decent happy hour! Great martini’s for $10? You can’t beat it!
Location: River North
Happy Hour: see menu
Mon- Fri: 4:00 - 5:30 PM
The Deal:
$10 cocktails and wine
$5 beer
Apps starting at $10 including rolls
23) KAYAO
Kayao blends Peruvian, Japanese, and Chinese influences into fun, inventive dishes. As does their sister restaurant, Matilda. The space is small but stylish and they have a late happy hour which is ideal! Amazing pisco sours and ceviche!!
Location: Old Town
Happy Hour: see menu
Mon- Fri: 4:00 - 7:00 PM
The Deal:
$10 cocktails and wine
$6 beer
$12 bites
24) BANGERS & LACE
A cozy, lodge-inspired Wicker Park staple known for its extensive craft beer list and a great after work spot - especially on those nice nights. A neighborhood favorite for casual hangs, late nights, and beer lovers but with a good happy hour.
Location: Wicker Park
Happy Hour: see menu
Mon- Fri: 4:00 - 6:00 PM
The Deal:
$4 shots
$6 beer
$9 wine and cocktails
25) CHARLIE MARTIN’S
This intimate supper‑club–style spot in River North brings a nostalgic Hollywood vibe with moody lighting and a gorgeous central bar. The cocktails are ever changing and fun! And the most important part, the happy hour extends into the weekend!!
Location: River North
Happy Hour: see menu
Tues - Sat: 5:00 - 7:00 PM
The Deal:
$10 martinis
$12 cocktails
$10 wines
Apps starting at $9
26) TAVERNA 1821
A modern Greek restaurant in Fulton Market that started as a pop up but was so successful so it’s here to stay! delivering warm Mediterranean food with fresh mezze, signature gyros, and an amazing happy hour (it’s on the weekends too!)
Location: West Loop
Happy Hour: see menu
Tues - Sat: 4:00 - 6:00 PM
The Deal:
$10 martinis
$12 cocktails
$5 beer and seltzer
Apps starting at $5
27) MONEYGUN
This high-energy cocktail bar has some of the best music! Neon lights, hip hop, lush booths, and elevated cocktails. Not only do they have a good happy hour but they also have just all over good vibes for the weekend.
Location: West Loop
Happy Hour: see menu
Tues - Fri: 5:00 - 7:00 PM
The Deal:
$10 martinis & Waffle Fries
28) HIRO IZAKAYA
Bringing Tokyo to the city of Chicago! The interior design in here is to die for - I love it so much. It’s a vibe in here with fun music, unique cocktails, and a happy hour where you can try it all at a discount.
Location: West Town
Happy Hour: see menu
Tues - Fri: 5:00 - 6:00 PM
The Deal:
$12 cocktails
Apps ranging from $7 - $14
29) TAO
I know what you’re thinking… the club has a happy hour? And yes, it does. They have a separate bar and dining area that is absolutely stunning. A pretty extensive happy hour that goes pretty late on week nights. I was thoroughly impressed with it and my favorite dish was the sashimi pizza!
Location: River North
Happy Hour: see menu
Tues - Thurs: 5:00 - 8:00 PM
The Deal:
$10 cocktails
1/2 wine and beer
$5 Sake and $9 Sake cans
Apps ranging from $7 - $28
30) SELVA
Located in the Emily Hotel, this Mexico inspired rooftop lounge is known for it’s agave cocktails and has some great city views. And their happy hour includes the weekends!
Location: West Loop
Happy Hour: see menu
Fri - Sat: 5:00 - 7:00 PM
The Deal:
$10 cocktails
$5 beer
Whether you're a local or just visiting, these spots offer some of the best happy hour deals in Chicago. CHEERS!!
