As the largest city in the Midwest and one of the largest cities in the nation, Chicago is a vibrant metropolis full of culture, architecture, and entertainment.
Chicago also has one of the best restaurant and bar scenes I’ve ever seen. There’s nothing better than enjoying craft cocktails and world-class food at half the price, so my most recent trip to Chicago had me looking for the best happy hours.
Read on to explore my long list of restaurants and bars with the best Happy Hour in Chicago to help you decide where to get drinks.
343 S Dearborn St, Chicago, IL 60604
Phone: (773) 216-3213
Brando’s Speakeasy is a hip karaoke bar in a vintage meets industrial-chic space in Printer’s Row across from DePaul University.
Brandos has a modern and laid-back cocktail lounge, while the rowdy karaoke lounge is decked out in 20’s-era décor.
660 N Orleans St, Chicago, IL 60654
Phone: (312) 624-9892
Bernie’s Chicago is a classy and welcoming cocktail bar and family-friendly restaurant opened by Chef Zack Sklar in Chicago’s River North neighborhood.
The seasonal menus draw upon locally sourced ingredients to create Spanish and Italian dishes. The cocktails are as spectacular, and chef-driven as the food.
With an emphasis on Spanish cuisine, I’d recommend the periwinkle-colored Bernie’s House Sangria.
Happy Hour Deals: Weekdays 4:30 pm to 6:30 pm – $9 wines, $7 Lite Thinking American Lager & Reprise IPA, $10 Moscow Mule, $11 Bernie’s Gin & Tonic, $11 Mood Indigo “Bernie’s House Sangria”, Turkey Burger Sliders $15, Chicken Wings $14, Tenderloin Sliders $15, Spinach and Artichoke Dip $15, and Crispy Brussels $15.
1709 W Chicago Ave, Chicago, IL 60622
Phone: (312) 929-4727
Earning the Michelin Bib Gourmand in 2021 and praise from Eater, Wine Enthusiast, and the Chicago Tribune, Funkenhausen is a Southern and German fusion restaurant in West Town.
The gorgeous dining space has wooden, arched ceilings tiled walls, and marble tables. Funkenhausen’s wine list is one of the best in the city.
I had a discounted glass of wine to accompany a house-made soft pretzel for Happy Hour.
Happy Hour Deals: Tuesday to Saturday 5:00 pm to 6:00 pm & Sunday 3:00 pm to 6:00 pm – $6–$12 snacks, $4–$11 sliders, $45 piggy plate, $8 beer, $8 combos, $5–$20 shots, $8 wine, $8 cocktails, and $16 smallcohol flights.
12 W Elm St, Chicago, IL 60610
Located a block from the shores of Lake Michigan in Near North Side, Sparrow is a cozy and charming cocktail bar with a beautifully designed interior.
The Sparrow is a longstanding cocktail bar that opened in its historic art deco building in 1927. Their happy hour offers unbeatable prices on craft beer from local breweries as well as cheap wine by the glass.
Happy Hour Deals: Monday to Friday 4:00 pm to 7:00 pm – $5 select draft beers and $10 wines/glass.
2024 N Halsted St, Chicago, IL 60614
Phone: (773) 935-5000
Café Ba-Ba-Reeba! Is a Spanish Tapas bar in Lincoln Park, a block from Oz Park. The authenticity of its Spanish cuisine and lively atmosphere has made Café Ba-Ba-Reeba a Chicago favorite since 1985.
As the first Tapas Bar in Chicago, Café Ba-Ba-Reeba! Sets a high standard. You won’t find a better Happy Hour in Chicago in terms of value for the money.
I recommend going with a group to order various tapas and a pitcher of red sangria.
Happy Hour Deals: Everyday 4:00 pm to 6:00 pm – $1.50 pintxos, $2.50–$3.50 tapas, $3–$5 featured drinks, and $20 pitcher of classic red sangria.
230 W Kinzie St, Chicago, IL 60654
Phone: (312) 464-9544
A gorgeous 1920s-era speakeasy and restaurant, Gilt Bar is an opulent and classy cocktail bar and New American restaurant that invokes the days of old.
Located a block from the Chicago River in River North, Gilt Bar offers a menu of classic cocktails and upscale bar fare as elegant as its ambiance.
Happy Hour Deals: Everyday until 5:30 pm – 20% off all orders placed online; 50% off all wine bottles for dine-in only on Wednesday.
1134 W Washington Blvd, Chicago, IL 60607
Phone: (331) 240-1914
Located in West Loop, The Press Room Chicago is yet another old-fashioned and sophisticated bar with a speakeasy feel.
The Press Room offers gourmet Italian and New American food to accompany a fine wine list and classic cocktails. Their happy hour deal of champagne with oysters was a wonderful start to my night out in Chicago.
Happy Hour Deals: Tuesday to Thursday 4:00 pm to 6:00 pm – $7 cocktails, $45 oysters & bubbles, $1 oysters ½ dz, and $20 board of daily selection of meats, cheese, and accompaniments.
2125 W Division St, Chicago, IL 60622
Phone: (773) 697-3522
Queen Mary is a cozy Wicker Park neighborhood tavern founded by Polish immigrant Maria Kafka in the 1940s.
Current owners revived the tavern in 2015 with Kafka’s blessing, and it remains a neighborhood favorite for excellent cocktails, maritime spirits, and Eastern European tavern fare.
I had a delicious dirty vodka martini at Queen Mary for a steal!
Happy Hour Deals: Mondays, 5:00 pm to 7:00 pm & Sundays 3:00 pm to 7:00 pm – $1 oysters and $6 classic martinis.
118 W Grand Ave, Chicago, IL 60654
Phone: (312) 222-9700
Receiving praise from Chicago Magazine, eater, Thrillist, Zagat, and more, Tanta Chicago is a fashionable Peruvian restaurant and bar with a picturesque rooftop location in River North.
They serve authentic Peruvian cuisine, from ceviches to empanadas, with an upscale presentation. My favorite Peruvian cocktail is the Pisco Sour, which you can get on the cheap at Tanta’s lively happy hour.
Happy Hour Deals: Monday & Tuesday 5:00 pm to 7:00 pm & Wednesday to Friday 4:00 pm to 6:00 pm – $10 cocktails, $10 wines/glass, $6 beer, and $5–$7 snacks.
1462 E 53rd St, Chicago, IL 60615
Phone: (773) 947-8831
Another Michelin Bib-winning fine dining restaurant, Virtue Restaurant is a proudly Black-owned Southern American restaurant and bar in an elegant setting in Hyde Park.
Owner and head Chef Erick Williams creates an impeccable menu of gourmet takes on Southern Classics to pair with a creative list of cocktails, beer, and wine.
I’ve never tasted more delicious fried catfish than on those perfectly crafted catfish sliders!
Happy Hour Deals: Wednesday to Friday 4:00 pm to 5:30 pm – $4 beer, $9 cocktails, $8 wines, $4 catfish slider, $7 buffalo mac & cheese croquette, $12 6-piece wings, $7 cheese & crackers, and $7 cup of gumbo.
845 W Washington Blvd, Chicago, IL 60607
Phone: (312) 265-1130
As the name suggests, El Che Steakhouse and Bar is an Argentinian-style steakhouse, using Argentina’s open-flamed “Asado” method to fire their prime steaks and seafood.
Located in a modern and elegant dining space in Greektown, El Che’s quick, hour-long Happy Hours are packed with incredible food and drink options.
The caramelized rum old fashioned was the height of richness, pairing well with the equally rich bone marrow small plate.
Happy Hour Deals: Monday to Friday 5:00 pm to 6:00 pm – $3 empanadas, $3 grilled shrimp, $3 grilled oyster, $6 beef fat fries, $6 chorizo, $10 endive salad, $13 bone marrow, $30 steak Frites, $9 house red wine or house white wine, $10 el che house sangria, $5 quilmes argentinian lager, $12 dona-cuca mule, $12 caramelized rum old fashioned, and $12 la sirena caipirinha.
2727 N Milwaukee Ave, Chicago, IL 60647
Phone: (773) 697-8726
The Walk In is a fun and casual bar in Logan Square with a divey atmosphere, great music, and gritty, industrial décor.
The staff and vibe is super-friendly and welcoming, guaranteeing a great time for all walks of life. I loved their happy hour cocktails, especially the spicy, citrusy mezcal drink called Lucy’s Explanation.
Happy Hour Deals: Monday to Friday 4:00 pm to 7:00 pm – $6 go-go gimlet, $6 old fashioned, $6 rosey cheeks, $6 lucy’s explanation, and $6 green light.
5553 N Clark St, Chicago, IL 60640
Phone: (773) 654-1432
Located in Andersonville, Uvae is a quaint wine bar and fusion kitchen from the owner and sommelier Lindsey Anderson-Perez.
The urban chic atmosphere makes it a fun place to get drinks. And the inventive gourmet cuisine pairs wonderfully with an expertly curated wine list.
I rang in the evening with a delicious glass of champagne and a plate of cold-boiled shrimp.
Happy Hour Deals: Wednesday to Friday 5:00 pm to 6:30 pm & Saturday and Sunday 3:00 pm to 6:30 pm – $2 oysters, $2 shrimp, and $5 bubbles.
3201 W Armitage Ave, Chicago, IL 60647
Phone: (773) 252-9700
Scofflaw is a fashionable gin-focused cocktail bar in a Victorian-style space in Logan Square. Chicago Magazine voted Scofflaw one of Chicago’s Top 10 Bars.
They source their unique spirits list from local distilleries, serving a decadent tavern menu till late. There’s nothing like packing in a burger and fries around midnight to give me a second wind.
Late-night eats at Scofflaw set their happy hour deals a cut above the rest.
Happy Hour Deals: Everyday 5:00 pm to 7:00 pm – $8 all cocktails and $20 Scofflaw Combo – burger+fries+cocktail (available after 11:00 pm).
1962 N Halsted St, Chicago, IL 60614
Phone: (773) 248-3000
Quality Crab & Oyster Bah is a New England-style seafood restaurant with a nautical theme and a family-friendly atmosphere that makes it a fun place to go out.
Another Lincoln Park favorite, Quality Crab and Oyster Bah offers a long list of oysters sourced responsibly from both coasts to enjoy with an impressive list of wine, cocktails, and beer.
I loved their silly nautically themed cocktail names. I tried the tropical Banana Hammock, a gin cocktail with ginger, coconut, banana, and basil.
Happy Hour Deals: Monday to Friday 4:00 pm to 6:00 pm – $2.50 oyster, $2.50 chef’s selection oyster on the half shell, $18 6-oysters & chef selection fries, $33 12-oysters & chef selection fries, $8 garlic shrimp, and half price for listed beer, cocktails, and wine.
675 N Franklin St, Chicago, IL 60654
Phone: (312) 445-4686
The Franklin Room is a high-end restaurant and bar in a stunning, two-story urban chic space in River North.
Self-described as a sophisticated speakeasy, The Franklin Room has an extensive list of whiskeys, perfectly executed classic cocktails, and gourmet New American tavern fare.
I don’t think you can find dollar oysters anywhere else in town.
Happy Hour Deals: Tuesday to Sunday 4:00 pm to 6:00 pm – $1 oysters and other listings available only at the bar.
5101 N Clark St, Chicago, IL 60640
Phone: (773) 942-7572
Bar Roma is a lovely Italian bistro and bar with a lively atmosphere and a bright and airy wooden dining space in Uptown.
They serve authentic Italian antipasti, hand-made pasta, and rich main courses to pair with an impressive list of Italian wines and Italian takes on classic cocktails.
Their beef cheek bucatini was the highlight of my happy hour.
Happy Hour Deals: Wednesday to Sunday 4:30 pm to 6:00 pm – $7 vini, $7–$9 cichetti, $10 ½ bucatini, $11 antipasti misto, and $10 gamberetto.
2683 N Halsted St, Chicago, IL 60614
Phone: (773) 348-9800
Aliveone is a funky Park West dive bar that is one of my favorite places to go out. It has bright red floors and ceilings, vintage light fixtures, a pool table, and great music.
A neighborhood institution since 1996, aliveOne is a great spot for delicious cocktails, beer, and a unique live-music jukebox.
Their craft cocktail menu is especially creative. I loved the Copernicus, with whiskey, Pimms, ginger beer, and lemon juice.
Happy Hour Deals: Sunday to Thursday 5:00 pm to 7:00 pm & Friday and Saturday 4:00 pm to 6:00 pm – half price for all drinks.
100 W Grand Ave, Chicago, IL 60654
Phone: (312) 836-0066
Located in a kitschy and cozy tavern in River North, Fado Irish Pub is Chicago’s favorite Irish Pub and sports bar.
They offer a long list of Irish and American Whiskeys, beer on tap, and authentic Irish pub fare, from shepherd’s pie to fish and chips.
If there’s any place to get a pint of Guinness and curry sauce topped chips, it’s Fado.
Happy Hour Deals: Weekdays 5:00 pm to 7:00 pm – $6 featured beer and wine, $7 select snacks, and $8 signature cocktails.
18 E Bellevue Pl, Chicago, IL 60611
Phone: (312) 642-3400
LUXBAR is an elegant, old-school American bar and restaurant in Chicago’s Gold Coast, a block from Oak Street Beach.
The stunning interior has checkerboard marble floors, a wood-burning fireplace, and wooden walls, creating a cozy early 20th-century ambiance.
The upscale food and drink menu has classics and creative items. I loved the avocado margarita, thickened with a rich avocado puree.
Happy Hour Deals: Tuesday to Friday 4:00 pm to 7:00 pm – $5 select food and drinks.
230 N Clark St, Chicago, IL 60601
Phone: (773) 219-0900
AceBounce is a giant cocktail bar and game room in an industrial warehouse space a block from The Chicago Theater.
Music is always blasting, and the numerous ping pong tables are always abuzz with alcohol-fueled tournaments. I loved their 5-dollar build-your-own kettle one vodka cocktails.
Happy Hour Deals: Weekdays 4:00 pm to 7:00 pm – $5 beer, $5 cocktails, and $5–$9 snacks.
19 E Ohio St, Chicago, IL 60611
Phone: (312) 940-3699
Broken Shaker is a funky and hip cocktail bar inside the fashionable Freehand Hotel in River North. The Broken Shaker is a James Beard Award semi-finalist for Best American Hotel Bars.
The décor and ambiance alone are James Beard-worthy, to say nothing of the incredible cocktails. A 13$ meal may not seem especially cheap, but the shaker happy meal has to be the most delicious meal I had in Chicago.
Happy Hour Deals: Monday to Thursday 4:00 pm to 6:00 pm – $8 daily cocktail, $5 beer of the month, and $13 shaker happy meal.
2483 N Clark St, Chicago, IL 60614
Phone: (773) 549-1132
Tin Lizzie is a casual and festive sports bar in Park West, a block from the beautiful North Pond Nature Sanctuary. There are 14 flat-screen TVs, board games, and booze galore.
You can even bring your pets to watch the game with you! I went for a 5-dollar shot and a beer to get me psyched for the night’s basketball game.
Happy Hour Deals: Monday to Thursday 5:00 pm to 8:00 pm – $5 draft beer well mixers and bite specials.
425 W Armitage Ave, Chicago, IL 60614
Phone: (312) 944-5087
Established in 1946, River Shannon has been a Lincoln Park neighborhood institution for over 70 years. River Shannon is an old-school Irish Pub in a historic old brick building that upholds the 1940s décor.
I’d come back again and again for a delicious domestic draft and cheap personal pizzas.
Happy Hour Deals: Monday to Thursday 3:30 pm to 7:00 pm – $10 specialty cocktails, $6 domestic drafts, and half-price pizza.
2165 N Western Ave, Chicago, IL 60647
Phone: (773) 666-5143
Chef’s Special cocktail Bar is a gorgeous mid-century modern cocktail and American Chinese fusion restaurant founded by Jason Vincent and Josh Pearlman.
Located in the hip Bucktown neighborhood, Chef’s Special has received praise from James Beard Foundation, and Chicago Magazine.
The utterly decadent cream-cheese-filled crab rangoons were the best I’ve had.
Happy Hour Deals: Everyday 5:00 pm to 6:00 pm – $6 crab rangoons, $5 draft beers, and other listings available only at the bar.
1954 N Halsted St, Chicago, IL 60614
Phone: (773) 634-4100
Bringing the beach-chic vibes of California to the Midwest, Summer House Santa Monica is a hip New American restaurant and bar in Lincoln Park.
Its skylight ceiling and plant-filled dining space feel like a fashionable greenhouse. The tropical cocktails and summer seltzers made me forget it was the dead of winter!
Happy Hour Deals: $7 seltzers, $9 cocktails, $4 bud lights, and other listings available only at the bar.
Broken English Taco Pub is a taco and Mexican cocktail bar with a vibrant, colorful interior and patio covered in Mexican-themed murals.
With locations in Old Town, Lincoln Park, and the Loop, you can enjoy margaritas and tacos no matter where you are in the Windy City.
I loved their top-shelf margaritas, which I augmented with a shot of mezcal. It was a happy hour indeed.
Happy Hour Deals: Wednesday and Friday 3:00 pm to 6:00 pm – $6 margaritas, $5 tradicional, $6 gran cent, and $7 meletti and mezcal.
Phone: (773) 384-3333
Voted best patio bar by Thrillist and the Infatuation, Parson’s Chicken and Fish is a family-friendly fried chicken and fish restaurant with locations in West Town, Logan Square, Lincoln Park, and Andersonville.
All locations are family-friendly, with massive outdoor patios and industrial-chic interiors. Negroni slushies with a plate of perfectly battered and fried chicken and fish croquettes for under 20$ was one of my favorite happy hour finds.
Happy Hour Deals: Monday to Thursday 3:00 pm to 6:00 pm – $10 fried sampler, $2 shots, $3 beer, $5 negroni slushy, and $5 highball.
694 N Milwaukee Ave, Chicago, IL 60642
Phone: (312) 846-6420
The Dandy Crown is an adorable cocktail bar with a huge brick-floored patio in River West. The Dandy Crown is proudly female-owned, serving elevated American fare and cocktails using seasonal ingredients.
I enjoyed the festive and fresh daiquiris, made using fresh juices and high-quality rum.
Happy Hour Deals: Everyday 3:00 pm to 12:00 am – $7 select draft beers, $7 cocktails, $12 wines/glass, and $7 old fashions & daiquiris.
15 W Division St, Chicago, IL 60610
Phone: (312) 600-9816
Hopsmith Chicago is a high-end sports bar and tavern in Near North Side with a lively atmosphere and an old-school marble bar.
They have plenty of TVs to watch the game and fun-filled trivia nights to accompany a large menu of regional American bar fare and an extensive beer, spirit, and cocktail menu.
Happy Hour Deals: Monday to Thursday 3:00 pm to 6:00 pm – $5 fatpours of all chicagoland drafts $7 ketel one, $7 beefeater, $7 bacardi, $7 olmeca altos tequila, and $7 jameson cocktails or shots.
169 W Kinzie St, Chicago, IL 60654
Phone: (312) 533-2742
A veritable adult playground, Highline is a cocktail bar, game lounge, and video arcade in River North.
They have an impressive array of indoor games like skee ball and pinball, along with old-school video games like Donkey Kong and Pac-Man.
I was impressed by their unique menu of mules. I chose a sazerac rye mule.
Happy Hour Deals: Tuesday to Thursday 4:00 pm to 6:00 pm – $6 4c old fashioned, $6 4c classic margarita, $6 traditional mules (svedka, cuervo silver, sazarak rye, and deep eddy peach), and half price for all draft beer.
Whether you’re looking for a classy speakeasy, funky dive bar, or adult arcade, you’ll find the best happy hour in Chicago at any one of the diverse locales on my list.
After imbibing in cheap cocktails and snacks, let me know which restaurant or bar you thought had the best happy hour in the comments below!
- Brando’s Speakeasy
- Bernie’s Chicago
- Cafe Ba-Ba-Reeba!
- Gilt Bar
- The Press Room
- Queen Mary
- Tanta Chicago
- Virtue Restaurant
- El Che Steakhouse & Bar
- The Walk In
- Uvae Kitchen and Wine Bar
- Quality Crab & Oyster Bah
- The Franklin Room
- Bar Roma
- Fadó Irish Pub
- Broken Shaker at Freehand Chicago
- Tin Lizzie
- River Shannon
- Chef’s Special Cocktail Bar
- Summer House Santa Monica
- Broken English Taco Pub
- Parson’s Chicken & Fish
- Lincoln Station
- The Dandy Crown