West Loop Deals

Updated April 2018

Just because The West Loop is one of the most expensive neighborhoods in Chicago, it doesn't mean you have to spend a lot to have a great time here.  Enjoy some of our favorite DEALS!


In addition to creating West Loop Life - Brian builds websites!

I’ve been building websites since the 90’s and LOVE creating distinctive, easy to maintain, mobile friendly websites that are built with SEO from the start.  Let me take away the confusion, create your website and teach you how easy it can be to maintain and update it! Email me at info@westlooplife.com



  • Free Jazz at Wishbone Restaurant every Thursday 7pm


  • Free Wine Tastings at Madison Vine Wines - Thursdays 6pm - 1340 W. Madison
  • Free Beer Tastings at Madison Vine Wines - Tuesdays 6pm - 1340 W. Madison



Spring Rewards - Free Food

$50 in restaurant gift certificates with our Promo Code ZSKMFV for SpringRewards.com.  

There are $75 of free restaurant gift cards (credited back on your credit card) in the West Loop

My neighborhood favorites:


Our latest obsession is finding the Amazon Treasure Truck!

It brings deeply discounted deals right to your neighborhood!

Chicago Podcast
West Loop Life Podcast Treasures

Happy Hours

Checkout Episode 46 for all the details.

  • bellyQ - 1400 W. Randolph St - Bill Kim's West Loop Korean spot has specials from 4:30 p.m. to 7 p.m. on weeknights. $5 items include Sticky Smoked chicken wings, dumplings and more.
  • Urban Belly - 4-6pm daily $5 specials on Kirin Draft Pitchers, Spiked Lemonade, Sake & Wine
  • Cruz Blanca - 4pm-6:30pm Tue-Fri & Sunday
  • The Madison Bar and Kitchen - 4:30-6:30pm Every Day
  • The Loyalist - beer, shot and burger $15 Tuesdays
  • La Sardine french restaurant - 5-7pm Mon-Thur at the bar $1 oysters, $3 glazed halibut collars, $4 charcuterie $15 wine flights
  • Umami Burger - 4-6pm Mon-Fri and after 10pm
  • Beer Bistro - Daily specials all day like $5 pizzas on Mondays
  • Third Rail - Daily specials all day like $3 burgers on Thursdays
  • More specials all over Chicago from "The Eater Chicago Happy Hours Map
  • The best deals in Bars all over Chicago - http://smalltabs.com
 Mad Social  1140 W Madison St  - Happy Hour West Loop

Mad Social 1140 W Madison St - Happy Hour West Loop

   Green Street Local  -  130 S Green St

Green Street Local - 130 S Green St


The Madison Bar and Kitchen

1027 W Madison St
Chicago, IL 60607


Tuesdays 5-7pm : Half price sushi, Half price bottles of wine 

 The Madison Bar and Kitchen  1027 W Madison St

The Madison Bar and Kitchen  1027 W Madison St



Cruz Blanca

Cruz Blanca

 Bar Takito Happy Hours  - 201 N Morgan St. 

Bar Takito Happy Hours  - 201 N Morgan St. 

 Bar Takito Happy Hours  - 201 N Morgan St. 

Bar Takito Happy Hours  - 201 N Morgan St. 

Randolph Street.JPG

$4 – Randolph Street Market

With dozens of vendors offering antiques, clothing, global goods and gourmet foods, Randolph Street Market is one of Chicago's favorite weekend activities. We love this monthly event and suggest pairing it with a meal at nearby Restaurant Row.


Mix at six Harris theater  $10 theater performance and a cocktail!

Okay, Okay, this location isn't in The West Loop, but it's just a short walk to Millennium Park.  And being so close to Chicago's amazing theaters is one of the great things about living in The West Loop!

MIX at SIX, the series the Chicago Tribune said “ups the cultural ante considerably,” is known for offering some of the theater’s most provocative and innovative work, at a time of day that makes it one of the most accessible and engaging performance series yet.

https://harristheaterchicago.org Featuring four after work performances throughout the season. Beginning at 6PM, these performances see renowned artists from around the world performing fast - paced, one - hour performances after work. Enjoy signature cocktails, beer from Goose Island and food from Chicago’s most in demand food trucks, available for purchase on Lower Randolph outside the lobbies.

 Concerts West Loop Chicago

SOFAR Sounds

Underground concerts in intimate venues like apartments, cool office spaces, WeWork, Condo building party rooms...  

Skip the SOFAR waitlist using Promo Code: WESTLOOPLIFE-7265F  for guaranteed access to ticket sales.


This video from the West Loop Community Organization gives a fun sampling of The West Loop:


Save 10%

Use Promo Code WESTLOOPER2017

Via - The $3.95 black car ride share service

https://ridewithvia.com   It's only $3.95 a ride in Chicago.  Promo Code brian6j6b, gets you $10 of free credit.

ParqEx.com - The Airbnb of parking

Get $25 in free neighborhood parking with promo code WESTLOOPLIFE

Bare Feet Power Yoga  

https://barefeetpoweryoga.com/workshops/  30 days unlimited classes for only $30

Peapod.com grocery delivery

This service saves us 2 hours a week and only costs about $10 more than shopping at Mariano's.  Would you pay $10 to have an extra couple of hours in you weekend? We would! Get $20 off your first order. Use Promo Code for CHICAGO for 6 months free delivery too!

Everywhere Wireless $19/month internet

We've been using their 10MBps service for a year now and it's better, more reliable, and just as good as our old 50MBps from AT&T and Comcast.  Mention "Brian Bosak" for your first month free.

Happy Hours (Spring 2017)

Checkout Episode 10 for all the details.

  • Cruz Blanca - 4pm-6:30pm Tue-Fri & Sunday
  • The Betty - 4pm-6:30pm Mon-Fri
  • Nellcôte - 5-7pm Mon-Fri
  • Fulton Market Kitchen - SpringRewards.com $10 off anything. Promo Code ZSKMFV
  • The Izakaya at Momotaro - 6-8pm Wed-Sun
  • The Madison Bar and Kitchen - 4:30-6:30pm Every Day
  • Umami Burger - 4-6pm Mon-Fri and after 10pm
  • Beer Bistro - Daily specials all day
  • Third Rail - Daily specials all day


Daily Specials (Spring/Summer2017)

Beer Bistro 1061 W Madison  

  • $0.50 wings on Sunday
  • $5 pizzas, $2 PBR cans Monday
  • $5 Burgers with choice of side  Tuesday
  • $3 Craft Beer Cans  Wednesday
  • $5 Craft Martinis Thursday


Third Rail 1133 W Madison St

  • Tuesday $2 Tacos
  • Thursday $3 burgers
  • Friday $5 craft drafts, $8 Manhattans & Old Fashioneds