Chicago, Illinois: Downtown Happy Hour specials you shouldn’t miss! (2023)

Downtown Chicago is a bustling city with lots of diverse food options, but most of them are going to cost you a lot of money! Thats why these Happy Hour specials at several downtown Chicago restaurants could really be appreciated! You’ll find these restaurants are purposely spread throughout downtown to give options in multiple areas no matter if you are visiting or live here!

Chicago is SOOOOOO big geographically! We will focus on other parts of the town like we do for other big cities in some of our other blog posts! If you have a specific area of town you want us to feature, please let us know by filling out our contact form!

Venteux Brasserie Cafe & Oyster Bar

Happy Hour at Venteux Brasserie Cafe & Oyster Bar is absolutely divine! Located directly on Michigan Avenue (inside the famous Carbide & Carmen building) you’ll discover this Happy Hour alongside the luxurious Pendry Chicago hotel. This chic French bistro offers multiple reasonable small plates and great drinks in a classy downtown atmosphere!

• Happy Hour: 4pm-6pm Tuesday-Saturday
• Where: 224 N. Michigan Avenue Chicago, Illinois at the bar or bar top tables only
• Drink Specials: Discounted house wines, well cocktails and draft beers
• Food Specials: Special pricing on small plates of oysters, escargot, baked brie and more!
• Phone Number: 312-777-9003

If the happy hour isn’t enough to get you here, how about heading over for brunch on Friday-Sunday? From 10am-3pm and for $20, you’ll get bottomless mimosa, Rose, or Bloody Marys! Just make sure you grab a room at the Pendry just in case you have a little too much to drink!

Grant Park Bistro

Also on Michigan Avenue, down by Grant Park and the Buckingham Fountain (the Chicago Landmark made famous by its introduction to the 80’s sitcom “Married with Children“), you’ll find Happy Hour at the Grant Park Bistro. This bistro is a trendy but very casual bistro with classic American dishes like Hamburgers, Chicken wings and fries. Their happy hour may be the best in town for great pricing and good ‘ole American comfort food.

• Happy Hour: 4-6pm Sunday-Thursday
• Where: 800 S. Michigan Avenue, Chicago, Illinois
• Drink Specials: Draft Beers $4.50-$5.50, House wine and Cocktail Specials
• Food Specials: Fries, wings, Burgers, Grilled Chicken Sandwich $3-$8
• Phone Number: 312-753-3420

Okay, I don’t know what the deal is with Chicago and Mimosas but I’m not complaining! You’ll find a brunch here daily (Monday-Friday 7am-11am and Saturday & Sunday 10am-3pm) that offers $18 unlimited mimosas with a food entree purchase!

Raised Bar Chicago

Located inside The Renaissance Chicago Downtown Hotel, this Happy Hour is great for a breathtaking view of the city! Raised Bar Chicago is an eclectic, industrial themed bar has a fabulous outdoor patio that is perfect for a spring, summer or fall day. In the winter they also have igloos with heat set up on the outdoor patio.

• Happy Hour: 4-7pm Monday-Thursday
• Where: 1 W Wacker Dr, Chicago, IL 60601
• Drink Specials: $8 Red, White and Rose Wines, $8 Select Local Beers
• Food Specials: none at this time
• Phone Number: 312-795-3444

Even though this restaurant doesn’t offer food happy hour options, they do offer a menu full of fresh ingredients that are locally sourced! However, I personally prefer to just have a casual pre-dinner drink here right in the heart of the city before headed out to dinner elsewhere.

Tanta Chicago

If you have never tried Peruvian food, this Happy Hour is the place to try it! With innovative but authentic Peruvian fare, Tanta Chicago is sure to deliver a new found cuisine favorite or fill the spot for your old time Peruvian favorites! The atmosphere is inspired by Peruvian style and seasonally there is an outdoor patio. The Happy Hour itself is located in the BAR ONLY.

• Happy Hour: 5-7pm Monday-Friday (winter). 4-6pm Wednesday-Friday (summer)
• Where: 118 W Grand Ave, Chicago, IL 60654
• Drink Specials: $10 cocktails/ $10 wines by the glass/ $6 beers
• Food Specials: Small Plates and Snack $5-$9
• Phone Number: 312-222-9700

I recommend the Chicken Skewer and the Empanadas! Although I’m sure everything on the menu is great here, these had great taste and leave me wondering how soon I can get back to Tanta next! They are also well known for their Pisco Sour cocktail! I did not try this but would love to know if you have! 🙂

The Loyalist

The Loyalist is an upscale stylish American Gastropub that is located in the basement of its sister property, Smyth (a 2 star Michelin-starred restaurant). Located in the westside loop area of town, it is a great option for a neighborhood style pub with casual fare that is likely to exceed expectations!

• Happy Hour: 5-6pm Tuesday-Thursday
• Where: 177 N Ada St #001, Chicago, IL 60607 (located inside Smyth)
• Drink Specials: $10 cocktails
• Food Specials: Discounted Small Plates
• Phone Number: 773-913-3774

This is a super short Happy Hour and only on 3 days of the week but honestly, its a surprise to even find one at such a great establishment! If you can get here during Happy Hour, you should do it! If you can’t and miss Happy Hour, I think you’d be well served to eat here anyway and cough up the extra cash! 🙂 This is a great find.