Living in downtown Chicago can be expensive. But if you’re willing to dine a little early, you’ll find some of the best Chicago food and wine at great prices! These are all a short walk from our place. If there are any you think should be added to the list, let me know!
405 N Wabash Ave (Between Trump and Wrigley), M-F 3-6
$8 Wine and Cocktails, $3-$9 Nibbles
Bernie’s Lunch & Supper
660 N Orleans, Mon-Fri 4-7
$5 Wine, $5 Snacks (Lamb Hashwi, Eggplant Caponata, Pan Con Tomate, Handcut Fries, Chicharónnes)
663 N State St Mon-Fri 4:00-6:00
1/2 OFF All Beer and Wine, 1/2 OFF Non-premium Liqueur, 1/2 OFF All Appetizers
The house wine isn’t bad, and at half-price it’s only $3.50 per glass! One nice thing about Bijan’s is you can enjoy the happy hour in the restaurant or even outside. You don’t have to sit by the bar. Bijan’s is open 10AM-4AM 365 Days a year! The steak salad (on the dinner menu) is fantastic! Say hello to Rolf.
The Boarding House
720 N Wells, Daily 4:30-6:30
Half price wine, $10 Pizzas
508 N State St, Mon-Fri, 3:30-6:30pm Upstairs
Half-off casaritas, house wine, draft and bottled beer
111 W Hubbard (First Floor Bar Area), Tuesday-Friday 5-8
$8 Wine and Cocktails, Half Price Select Dishes
Doc B’s Fresh Kitchen River North
55 E Grand, 4-6 Every Day (Updated Happy Hour 11/17)
$4 Beer, $6 Wines New Kitchen Items ($6-$9): Burgers, Chicken Sandwiches, Fried Chicken, Wok Bowels, Brussels Sprout Salad and more. The fried chicken is amazing. So is the brussels sprout salad. I like the Thai Veggie Wok Bowl, but usually ask them to kick up the spice level. MJ was our server and did a great job. Now, $5 burger night every Sunday at River North Doc B’s.
Spicy Crispy Chicken Sandwich – $6 at Doc B’s
127 W Huron (Godfrey Hotel), Mon-Fri 5-7:30
$8 wines and $8 Appetizers (Tuna Tartare, Salad, Calimari, Pizzas, Caprese, Ricotta Cappelletti)
521 N Rush, Every Day 4-6
$8 premium wines, $7-$19 appetizers
Emerald Loop Weeknight Specials
216 N Wabash $5 Draft Beers
Monday $11 Turkey Salad
Tuesday $8 burger
Wed $12 Rosemary Chicken
Thurs $11 Tacos, $12 Grilled Chicken Salad
Fri $13 Salmon or Ahi Tuna Salad, $13 Tilapia
25 E Ohio, Every Day 5-7
$7-8 wine and cocktails, $8 appetizers, $8 Prime burger
George is the managing partner, and he runs a great place. You’ll usually find Lonnie behind the bar making sure happy hour runs smoothly. Julia and the other servers will make sure you have a great experience.
Calamari at Flemings
15 W Illinois, Weeknights 5-8
Wednesday Wine Bottles $30, $15 Taco Trays
Thursday Rose and Oysters $20 All you can eat
The Hampton Social
353 W Hubbard, Weekdays 3-6
Half-price wood fired pizzas, Half-price specialty cocktails & rose
33 W Kinzie, Mon-Fri 4-6 (at bar only)
$7 Wine, $5 Half order calamari or meatball, $6 Margaritas $8 Martinis
169 W Kinzie, Wed 7-10 $20 bottle of wine and flatbread
Sunday $25 Brunch Buffet
110 W Hubbard, Mon-Fri 4-7
$2 shrimp cocktail, Scallop Crudo, King Crab Leg, $1 Oysters
59 W Hubbard, Mon-Thurs 4-6
Small Sandwiches $3.95, Drinks $6.95 (Prosecco, Sparkling Rose)
112 W Hubbard, Mon-Fri 3-6
$4 Sliders (assorted)
316 N Clark on the river, Weekdays 3-6,
Pulled Pork Sliders
445 N Dearborn, Now Every Day 4-6
Half-Price Appetizers, (Sausage & Peppers, Calamari, Pizza, Chicken Parmesan, etc.) The entire menu is half price including wines! Some of the items are “dinner sized”. This happy hour is not on their web site, but it’s a good one! We visited 1/9/18 and Jo Anvyn did a fantastic job serving. Having a great service experience is rare during happy hours and Mama’s Boy does a great job. Here’s a tip… You can buy discounted Rosebud gift cards at Costco… Save even more!
Calamari and Meatball at Mama’s Boy
108 W Kinzie
Tuesday 5-7 Tacos 2/$6.50
65 E Wacker Place, Mon-Fri 4-7
$8 wine, $8-9 bar bites
Tenderloin Sliders at Pinstripes – $7
435 E Illinois, Mon-Fri 3:00-6:30
$4 Beer, $4 Wine, $5 Well Drinks, Appetizer Specials including Sliders, Flatbreads and Pizza. Pinstripes is especially nice in the summer when you can dine outside.
315 N LaSalle, Mon-Thurs 4:30-6:30 in the bar area
$5 Bites, $5 Beers, $7 Cocktails
456 N Clark, Mon-Fri 5-6 in the lounge
$5 and $6 appetizers , $5 wines and sake
1 W Grand Ave, Mon-Thurs 3:30-6:30
$5-$7 Appetizers, $3 Beer, $5 House wines
720 N State, Weekdays 4-7
$7 wine and cocktails, $7 appetizers
Steak Sandwich at Ruth’s Chris Happy Hour
431 N Dearborn, Mon-Fri 4:00-6:30
$8 Prime Burger, Tenderloin Salad, Crab BLT, Steak Sandwich, Ahi Tuna, Spicy Shrimp. Limited wine selection. You can sit at the bar, but if you’re early you can ask for a booth along the window if available.
Sullivan’s Filet Wellington Bites – $7
415 N Dearborn at Hubbard – Formerly Thursday only, now six days a week!
Live music Thursday-Sunday.
Happy Hour Mon, Tue, Wed, Fri 5-7PM. Thursday 5-9PM. Sun 5-8PM
Sullivan’s Meat and Cheese Board – $7
$7 Select Wines, Cocktails, Bar Bites including: Filet Wellington Bites, Artisan Meat and Cheese Board, Cheesesteak Eggrolls, Tuna Poke Shooters. The place gets a little noisy and crowded when there’s live music. If you prefer a quiet time, visit Mon-Wed.
We visited March 5th and were greeted by our server Jessica and Manager Cole.
110 W Illinois, Mon-Fri 3:30-6:30
Dim Sum Happy Hour $4-$10, $7 Wine
Union Sushi + Barbeque
230 W Erie, Every Day 5-6:30
$1 Oysters, $2.50 beef filet skewers, $4 shrimp rolls, $5 Moscow mules
539 N State, Mon-Fri 3-6
$6 Wine, $4 Pulled Pork Pretzel Bowls, $5 Smoked Brisket Sliders