Holiday Shopping Happy Hour Guide – Chicagoland

Chicago's annual Magnificent Mile parade 

It’s no secret that I love to shop just about as much as I love Happy Hour.  For that reason, JB & I have composed Happy Hour shopping guides for our new homes of Chicagoland and Milwaukee for the busiest shopping time of the year.  This season, I’ve got you covered if you’re shopping around the 900 Shops on Michigan Ave, The Shops at North Bridge, or any of the many shops in between.

If you’ve been so kind to continue to follow us from the west coast, be sure to check out the shoppers survival guides for Los Angeles, too!

Happy Holidays!

Day: Daily specials features for “the 5 for $6 til 7pm menu”
Time: 5-7pm
Drink Deal: $6 cocktails, glasses of wine
Food Deal: $6 appetizers

PF Changs – 530 N. Wabash Ave.
Day: Mon-Fri
Time: 3-6pm
Drink Deal: $4-5 Beers, $6-9 Cocktails & glasses of wine
Food Deal: $3.25 dumplings, dim sum, and then some!

Pippins Tavern  - 806 N. Rush St.
Day: Daily
Time: All Night Long
Drink Deal: $3.50 Miller High Life
Food Deal: N/A

Pops for Champagne - 601 N. State St.
Day: Mon-Fri
Time: 3-7pm
Drink Deal: None listed on their site, but hopefully there’s a champagne deal or two!
Food Deal: $1 oysters

Seasons 52 - 55 E. Grand Ave.
Time: til 6pm
Drink Deal: $15-20 Wine Flights
Food Deal: Signature Flatbread included with your wine flight!

Streeter’s Tavern - 50 E. Chicago Ave.
Day: Daily
Time: All Night Long
Drink Deal: $5 Sailor Jerry rum drinks, $5.50 Jim Beam drinks
Food Deal: N/As

Weber Grill - 539 N. State St.
Day: Mon-Fri
Time: 3-6pm
Drink Deal: $10 Bourbon Flight
Food Deal: Half-priced Bar Bites


If shopping in suburbia is more your thing, check out on of my favorite shopping malls….

Oak Brook, IL

Days: Tues & Thurs.
Time: All Night Long
Drink Deal: $20 bottles of wine (Tues) / $5 Glasses of Wine (Thurs.)
Food Deal: N/A

The Cheesecake Factory 
Days: Monday - Friday
Times: 4-6pm
Drink Deals: $4 House Wines and Select Beers; $5 Specialty Cocktails (including Long Island Iced Teas, Mojitos, Margaritas, and more!)
Food Deals: Discounted Appetizers – many priced at $5 

Gibson’s Bar & Steakhouse - 2015 Spring Rd.
Day: Daily
Time: All Night Long
Drink Deals: $7 Absolut cocktails for “Absolut Friday”
Food Deals: N/A

Days: Sun-Thurs
Times: 4-7pm / 9pm-close (all day on Sun!)
Drink Deals: ½ off Draft Beers, House Cocktails, & Long Island IcedTeas
Food Deals: Appetizers starting at $6.95

Day: Friday
Time: 3-5pm / 9pm-close
Drink Deals: $7 Cocktails in Martini Lounge
Food Deals: Half-off Appetizers


Bolingbrook, IL

Days: Monday-Friday
Times: 4-7pm
Drink Deals: See calendar for daily specials
Food Deals: Half-off select small plates

Day: Sun-Thurs.
Time: 3-6:30pm / 9pm-close
Drink Deal: See current deals at location
Food Deal: See current deals at location

Day: Mon-Thurs
Time: 3-6pm for food / All Night for drinks
Drink Deal: $5 Margaritas (M&T), $5 Sangria (W&Th)
Food Deal: $5 Appetizers

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