The Best Fall Restaurant Specials in Chicago

Fall is indeed foodies’ favorite season. The weather is perfect and the view only helps boost our appetite. After looking at our recent feature on this year’s fall specialty menu and drinks across Chicago, we sure hope you’re ready to indulge. After all, that’s why we gathered all these amazing fall restaurant specials running in October so you can get the most out of this delicious season!

Did we mention October is both National Pizza Month and National Pasta Month?


2001 Price at all 4C Restaurants on October 14th

On Thursday, October 14th only,  Four Corners (4C) is hosting a one-day celebration across all concepts featuring 2001 prices on select items from open to close, including:

  • $2 All Beers (will receive limited-edition 20th anniversary, color-changing stadium cups with purchase)
    • If your stadium cup turns green, you have a chance to win! Post your green stadium cup to Instagram tagging your location with #4CTurns20 to enter a contest to win $200 in My4C rewards.
  • $2 White Claws & Trulys
  • $2 Tots
  • $20 Select Bottles of Wine

Participating restaurants include 80 Proof (Old Town), Benchmark (Old Town), Federales (West Loop), Fremont (River North), Gaslight (Lincoln Park), Highline (River North), Kirkwood (Lakeview), Porter Kitchen & Deck (Loop), Ranalli’s (Lincoln Park) and Budweiser Brickhouse Tavern (Wrigleyville).

The Loyalist

177 N Ada St #001, Chicago, IL 60607

Available Tuesdays through Thursdays from 5:00pm to 7:00pm, diners can enjoy the “Burger, Beer, & Shot” special for just $19.00. Indulge in Chicago’s, and one of the country’s best burgers served with an ice-cold beer and a shot!



205 N Peoria St, Chicago, IL 60607

This West Loop hotspot features a special for pretty much each night! On Monday, diners can Every Monday from open to close throughout the month of October, diners can now enjoy a specialty pizza of their choice and a bucket of 312 for $30.00. In honor of Taco Tuesdays, diners can order their specialty “Taco Pizza” featuring Marinara, Chorizo, cheese mix, lettuce, white onion, sour cream. Also available on Tuesday through Thursdays, diners can order ½ off specialty cocktails and pizzas for happy hour!


Heritage Restaurant & Caviar Bar fall resaturant specials
Image Credit: Caroline Manrique

Heritage Restaurant & Caviar Bar

2700 W Chicago Ave, Chicago, IL 60622

  • Join the Tuesday Pizza parties this month and get one personal pizza + one bottle of wine for $22 at Heritage Restaurant & Caviar Bar! Pre-order for pick-up or delivery and/or enjoy while dining in-person. Current Choices of Pizza include:
    Sunday Gravy with Smoked Prime Rib, House Kimchi Polish Sausage and Giardiniera
    Clam, Bacon and Confit Potato with Paddlefish Roe
    Smoked King Trumpet Mushroom with Roasted Corn and 8 Month Cotija

Pair your pizza with some Excelsior, Sauvignon Blanc or Excelsior Cab. Having a big party? Order additional pizzas for $12!

The Smith

400 N Clark St, Chicago, IL 60654

In addition to their incredible happy hour offerings, head over to River North for “Red Sauce Sunday.” Priced at $45.00 for two, diners will receive a Chicken Parmesan, Caesar Salad, Rigatoni alla vodka, Parmesan garlic flatbread, and finish the meal out with rainbow cookies. Making it the perfect date night dinner for two. Half-priced chianti by the glass, carafe, or a big carafe is also available for purchase as an add-on. Red Sauce Sundays are available for indoor or outdoor seating on The Smith’s expansive patio.


2075 N Lincoln Ave, Chicago, IL 60614

Start your weekend off right at Gemini. Brunch begins at 9:00 am on both Saturdays and Sundays. Gemini also offers a $25.00 bottomless brunch. Guests can choose from Bellini’s, Mimosas, Pauly G’s Bloody Mary’s, Margaritas, wine, and many more! Starting at 4:30 pm on Sundays, diners can indulge in Gemini’s “Fried Chicken Sunday” special, featuring Southern Fried Chicken, coleslaw, cornbread, and housemade hot sauce for $28.00.

Old Pueblo Cantina

1200 W Webster Ave, Chicago, IL 60614

In addition to Taco Tuesday, Old Pueblo Cantina offers guests “Mariachi Monday” featuring live music starting at 5:30 pm. On Tuesdays, diners can enjoy specialty offerings including $7.95 margaritas, $29.95 margarita pitchers, and $10.00 taco platters!

El Che Steakhouse & Bar

845 W Washington Blvd, Chicago, IL 60607

For all of the carnivores out there, be sure not to miss Parrillada Tuesday at El Che Steakhouse & Bar. One of the restaurant’s signature dishes, this platter of hearth-grilled meats like sweetbreads, chorizo, morcilla, tira de asado, sirloin cap and marrowbone is normally $105. However, on Tuesdays guests can spoil themselves with this hefty platter for the low price of $60.


1709 W Chicago Ave, Chicago, IL 60622

Offered daily from 5:00 pm to 6:00 pm, Funkenhausen is the hotspot for happy hour in Chicago’s West Town neighborhood. Guests can enjoy 1/2 Priced Bar Snacks, $5 Beer, and $7 Select Cocktails.

stan's coffee box office package fall special
Image Credit: Stan’s

Stan’s Donuts & Coffee

As morning traffic returns to Lakeshore Drive and offices welcome employees back – Stan’s Donuts & Coffee is making office celebrations easier with their new “Wake Up Wednesday” package.

Starting October 27, Stans is making ordering breakfast for the office easier with a new package available every Wednesday featuring a dozen assorted donuts, six pretzel bagels, and a box of coffee for just $50. The new package will be available for pre-orders starting October 25. Anyone interested in the Wednesday deal can place their order via the Stan’s App or online by Tuesday’s close of business.

Farm Bar

1300 W Wellington Ave, Chicago, IL 60657

The weekends at Farm Bar in Lakeview are the perfect time to indulge in a little bit of down-home comfort food with their select Supper Club menu items. On Fridays guests can find a taste of the heartland with the Wisconsin Style Fish Fry. Additionally, guests can cozy up with the Short Rib Pot Roast on Saturdays, the perfect dish to warm you up as we begin to venture into the colder months.


3335 N Halsted St, Chicago, IL 60657

Every Wednesday, diners can experience “Hump Night All Night” at the bar which includes select entrees from Chef Devin Kreller and a drink of choice for $19.00. Entrees include:

  • Double Cheeseburger & Frites – slagel farms beef, american cheese, baby gem lettuce, pickles, special sauce, toasted brioche bun + hand-cut beef fat frites w/garlic aioli

  • Pastrami Reuben & Frites – house-smoked pastrami, caraway rye, sauerkraut, gruyere, house-made pickles, thousand island + hand-cut beef fat frites w/garlic aioli

  • Roasted Mushroom & Onion Wood Oven Flatbread – house-made dough, creamy mornay, caramelized onions, baby arugula, lemon, mushrooms, alpine cheese

  • Hand-Made Porcini Radiatore Pasta –  wood oven-roasted maitake mushrooms, spigarello, roasted garlic truffle butter, parmesan cream, fines herbes, mushroom bread crumb

Also available with this special, diners can sip on a glass of Henri Bourgeois French Sauvignon Blanc, Montrose French Rosé, Solitude Côtes du Rhône French Red, 2 Towns Blackberry Cider, and Great Lakes Brewing “Eliot Ness” Amber Lager.