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
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.
508 N State St, Mon-Fri, 3:30-6:30pm Upstairs
Half-off casaritas, house wine, draft and bottled beer
*NEW* – Chicago Chop House
60 W Ontario, 4-6 Every Day (even Sat & Sun)
Half price wines by the glass and cocktails (up to $20 reg price)
Half price appetizers including Crab Cakes, Lollipop Lamb Chops, Ahi Tuna. Definitely high end food, not scaled back “happy hour” versions.
The new owners have started a $1 Million renovation.
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. And, $5 burger night every Sunday at River North Doc B’s.
521 N Rush, Every Day 4-6
$8 premium wines, $7-$19 appetizers
Emerald Loop Weeknight Specials
216 N Wabash $5 Draft Beers
Monday $10 Turkey Salad
Tuesday $8 burger or $10 Quinoa Bowl
Wed $12 Rosemary Chicken
Thurs $10 Tacos, $12 Grilled Chicken Salad
Fri $17 Blackened Tilapia, $13 Lobster Wrap
25 E Ohio, Every Day 5-7
$9-12 wine and cocktails, $9-$14 appetizers, $10 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
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, Every Day 3-6
Well, unfortunately Mama’s Boy revised their happy hour. Gone are the Chicken Parmesan, Eggplant Parmesan, Meatball Pizza. New items include $5 sliders… chicken and waffle, philly cheese steak and burger. The chicken slider is a piece of chicken on what appears to be an eggo toaster waffle. The new items aren’t bad, but they don’t represent Rosebud like the previous more traditional Italian items. fortunately they still have the meatball and sausage w/peppers. There’s a selection of wines ($7-$10) and cocktails.
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.
Saturdays and Sundays – Blues Brunch
$15 Happy Hour Charcuterie @ River Roast
315 N LaSalle, Mon-Fri 3-5
$35 – Bottle of Rose and 12 Oysters
$3-$7 Bites, $10 Burgers, $10 Cob Salad
$5 Beers, $7 Cocktails
River Roast has a great location on the north side of the Chicago River at LaSalle. Be sure to arrive early for Happy Hour to get a great riverside seat.
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.
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