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!

Beacon Tavern
405 N Wabash Ave (Between Trump and Wrigley),  M-F 3:00-6:00
$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

Cantina Laredo
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

Chucks: A Kerry Simon Kitchen
224 N Michigan Ave, Mon-Fri 3-6
$6 Drinks, Snacks $3-5 (Calimari, Poutine, Flatbread, Mini Burgers)

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

Dolce Italian
127 W Huron (Godfrey Hotel), Mon-Fri 5-7:30
$8 wines and $8 Appetizers (Tuna Tartare, Salad, Calimari, Pizzas, Caprese, Ricotta Cappelletti)

Eddie V’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 $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 Fleming

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

Harry Carey’s
33 W Kinzie, Mon-Fri 4-6 (at bar only)
$7 Wine, $5 Half order calamari or meatball, $6 Margaritas $8 Martinis

Highline Lounge
169 W Kinzie, Wed 7-10 $20 bottle of wine and flatbread
Sunday $25 Brunch Buffet

Hubbard Inn
110 W Hubbard, Mon-Fri  4-7
$2 shrimp cocktail, Scallop Crudo, King Crab Leg, $1 Oysters

Il Procellino
59 W Hubbard, Mon-Thurs 4-6
Small Sandwiches $3.95, Drinks $6.95 (Prosecco, Sparkling Rose)

Joy District
112 W Hubbard, Mon-Fri 3-6
$4 Sliders (assorted)

Kinzie Chop House 
Tue & Thurs 4-6 at the Bar & Patio
Buy One-Get One Free Bar Menu Appetizers (here’s the Menu)

The Kitchen
316 N Clark on the river, Weekdays 3-6,
Pulled Pork Sliders

Mama’s Boy
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

McCormick & Schmick’s Wacker Drive
1 E Wacker Dr, Mon-Fri 4-6:30
This chain claims the best happy hour in the country.  Here’s the menu.
Kamilla and Diego are both great servers.

McCormick & Schmick’s Chestnut
41 E Chestnut, Mon-Fri 4-7PM, Sat & Sun 12-5, Sun-Thurs 9-10
This chain claims the best happy hour in the country.  Here’s the menu.

108 W Kinzie
Tuesday 5-7 Tacos 2/$6.50

65 E Wacker Place, Mon-Fri 4-7
$8 wine, $8-9 bar bites


Osteria La Madia
59 W Grand, Mon-Fri 4:30-6:30 at the Bar
$5 food and Wine


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

River Roast

315 N LaSalle, Mon-Thurs 4:30-6:30 in the bar area
$5 Bites, $5 Beers, $7 Cocktails

Roka Akor
456 N Clark, Mon-Fri 5-6 in the lounge
$5 and $6 appetizers , $5 wines and sake

Rock Bottom
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

Ruth’s Chris

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.

tucejnnj   Sullivan’s burger
415 N Dearborn  – Formerly Thursday only, now six days a week!
Live music Thursday-Sunday
Mon, Tue, Wed, Fri 4:30-6:30.   Thursday  4:30-8:30.    Sun 3:30-6:30
$7 Select Wines, Cocktails, Bar Bites including:  Steak Flatbread, Sriracha Glazed Shrimp,  Roasted  Meatballs, Loaded Potato Tots, Blue Cheese Chips, Bar Burger.  

   Sullivan’s blue cheese chips

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

Weber Grill
539 N State, Mon-Fri 3-6
$6 Wine,  $4 Pulled Pork Pretzel Bowls, $5 Smoked Brisket Sliders

159 W Erie Mon-Fri 3-6
$4-$7 food specials (Half price appetizer menu)