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)

Bijan’s
663 N State St Mon-Fri  3:30-6:30
1/2 OFF All Beer and Wine, 1/2 OFF Non-premium Liqueur, 1/2 OFF All Appetizers

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

Celeste
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
55 E Grand, Mon-Fri 4-6
All Wines and Cocktails $5

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-$19appetizers

Emerald Loop Weeknight Specials
216 N Wabash $5 Draft Beers
Monday $11 Meat Loaf
Tuesday $11 Chicken Pot Pie, $8 burger
Wed $12 Rosemary Chicken, $12 Guinness Beef Stew
Thurs  $13 Corned Beef and Cabbage, $13 Meatball and Califlower Tikka Marsala
Fri $14  Lobster Mac and Cheese,  $13 Tilapia

Flemings
25 E Ohio, Every Day 5-7, Then 8-9
$7-8 wine and cocktails, $8 appetizers, $8 Prime burger
clnfnozo
  Calamari at Fleming

Fremont
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, Weekdays 4-6
$5 Wines, $7 Appetizers, (Sausage & Peppers, Calamari, Pizza, etc.)
This happy hour is not on their web site, but it’s a good one!

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.

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.

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

Morton’s
65 E Wacker Place, Mon-Fri 4-7
$7.50 wine, $7-8 bar bites

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

Pinstripes

   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
Special Bites, Craft Beers and 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

Roy’s
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.

Seven Lions Club 
130 S Michigan, Mon-Fri 3-6
$8 Bites & Pours, $24 Wine Bottles

Sullivans
tucejnnj   Sullivan’s burger
415 N Dearborn, Thursdays 5-11
$7 Wine and food specials including:  Steak Flatbread, Sriracha Glazed Shrimp, Cheesesteak Eggrolls, Roasted Garlic Meatballs, Loaded Potato Tots, Blue Cheese Chips, Bar Burger.  Only Thursdays!

t3juvn1h   Sullivan’s blue cheese chips

Sunda
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

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