Fashion that celebrates the return of Chicago’s Happy Hour

The scene at Terrace at Trump on Saturday, May 29, 2010 in Chicago. NOTE: ASSIGNMENT SAYS TERRACE AT SIXTEEN BUT WEBSITE SAYS TERRACE AT TRUMP. (Chris Salata/for the Chicago Tribune) B58468838Z.1, courtesy Jaunted.

For the past 26 years, Chicago happy hours may have been happy in name alone…

You probably hadn’t noticed, but up until just weeks ago, it was illegal for Chicago bars to offer drink specials to the after-work crowd.  This law was passed in 1989 as an effort to curb drunk driving.

But Governor Bruce Rauner recently signed legislation that allows bars and restaurants in the city to offer discounted drinks for up to 4 hours a day and 15 hours a week, as long as they give notice about the deals a week in advance.

Many on both the patron and owner side consider the change a victory – customers get cheaper drinks and establishments get more business.  And the good news for your liver and your mornings is that food can be included in the offers, so many places are offering deals that involve both dinner and drinks.

As Chicagoans celebrate slashed prices at their favorite neighborhood watering holes, you could see an increase in happy hour invitations from your friends and colleagues.  So, it’s probably wise to start thinking about how to dress for a day in the office that’s immediately followed by an evening out on the town.

Use this guide to help you find a few good deals and choose a look that works for both work and play.


River North  – Oak + Char

217 W Huron St

Oak + Char

  • The Deal: Every single day of the week and weekend from 4:30 to 6:30pm enjoy $2 High Life drafts, $4 craft drafts, $6 house cocktails $8 burgers, which is half the usual price.
  • The Scene: This River North spot feels at once masculine & feminine, comfy & upscale, rustic yet modern. It’s a full service restaurant, but they’ve got a great bar you can belly up to as well as a menu that easily lends itself to shared dishes and a few delicious drinks after work.
  • The Outfit: Go with a look that has the same union of opposites that the setting has.  This ultra-feminine, delicate top perfectly sets off the hard rockstar leather pants and studded leather bag in a subtle and sophisticated way.


Gold Coast – The Lodge

21 W. Division St.The Lodge

  • The Deal: There are $2 and $3 deals on various beers and spirits from 4 to 7pm every day of the work week.
  • The Scene: Sometimes after a long work week, all you want is to kick back at a dive bar with low prices and zero pretension.  When you do, you’ll be glad to find the drink specials, free peanuts and jukebox at The Lodge. But if you want to avoid a raucous crowd, you may want to jet out before 10 on Friday and Saturday nights.
  • The Outfit: Pretty much anything goes at a dive, but since you’re coming from work and still want to look stylish, opt for something like these tailored jeans, vibrant but easy top, and a blazer you can take off to embrace the casual atmosphere.


West Loop – The Izakaya at Momotaro

820 W. Lake St.


  • The Deal: Wednesday through Sunday from 6 to 8pm, get a two-course meal for $19 or a 3-course meal for $23.  Both deals include a Shochu shot or Tiger beer.
  • The Scene: The acclaimed Momatoro is definitely worth a visit if you’re a sushi fan. But for some relaxed sips and apps after work, head downstairs to their Izakaya, which is a Japanese term that refers to a casual drinking spot that serves food that pairs well with drinks. You’ll dig the cool, retro vibe that has a slightly Kill Bill feel to it.
  • The Outfit: Asian fashion is often known for leaning towards the avant garde and, sometimes, kitschy.  When you head to this hip, Japanese joint after you clock out, try something along the lines of this oversized bow top and bold, printed skirt.


Wicker Park – Frontier

1072 N Milwaukee Ave

  • The Deal: Every Monday through Friday, from 4 p.m. to 6 p.m. get $5 Rodeo Sweethearts cocktails, $5 Oskar Blues beer and $4 sparkling wine.
  • The Scene: If you want to venture a little further away from your downtown office, try this Wicker Park favorite. With its chic take on a Western lodge feel, deep respect for meat, and comprehensive bourbon menu, you may almost feel like you’ve escaped the city during your next happy hour.
  • The Outfit: Though it draws a cool crowd, this spot is not uppity in any way. You’ll fit right in at work and at Frontier with a hip, modern country look.  This is certainly the place to wear a flirty, floral dress, classic cowboy boots and a tailored, denim jacket to pull it all together.

The good news is that there’s a lot more where this came from.  Bars and restaurants all over the city are starting to roll out new happy hour specials, so find the ones that suit your style and prepare for some more affordable after-work revelry.

About the Author:  Liz Kores is the managing director of Oak Street Chicago, a business association that represents some of the finest designer boutiques, hotels, spas and restaurants in the Windy City.  She is also on the board of the Chicago Fashion Incubator and a frequent guest blogger on a variety of online style publications.  For more, visit

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