Holiday Outings (Chicago Edition)

Enjoy, Celebrate, Reminisce…

Let’s face it, 2015, is coming to an end. You spent the entire year working hard, focusing on goals, or just cruising by. A fancy night out should be penciled into your planner. Toast with friends for the things you have accomplished, the failures that made you stronger, and the plans for the new year.

Pops for Champagne


601 North State Street at Ohio
Chicago, Illinois 60654

If you have lots to celebrate, and money is not an issue for a night, stop by Pops for Champagne. Located in River North, enjoy live music Sunday through Friday, and close to 250 champagne options.


Live Jazz Sunday – Tuesday at 9pm courtesy of the Joe Policastro Trio.



The Violet Hour


“At the violet hour, when the eyes and back
Turn upward from the desk, when the human engine waits
Like a taxi throbbing waiting . . .
At the violet hour, the evening hour that strives
Homeward, and brings the sailor home from sea”

T.S. Eliot, “The Waste Land” (1922)

If you haven’t already gone to a speakeasy this is your chance. This pre-prohibition style bar located in the heart of Wicker Park offers artisanal cocktails. And they have a few house rules, no cell-phones, no Budweiser, no jagger-bombs, and no bombs of any kind.


1520 N Damen Ave, Chicago, IL 60622
(773) 252-1500


Signature Lounge


This lounge is a must if you come into town, or as a Chicagoan you must go at least once. The cocktails aren’t anything out of the ordinary, but the view pays for itself. Perfect to bring friends coming into town for the holidays.


More Options…

RPM Italian

Owned by local celebrities. Enjoy the truffle garlic bread.

52 W Illinois St, Chicago, IL 60654
(312) 222-1888


The crisp calamari and don’t let the sangria glass run empty.

626 N State St, Chicago, IL 60654
(312) 698-5000

Girl and the Goat

809 W Randolph St, Chicago, IL 60607
(312) 492-6262


And if you’re on a budget…

It’s fantastic to go out for a fancy dinner, cocktails, and feel like a million dollars. If you’re only looking to spend a fantastic time with your closest friends without making a dent in your bank account, these are my favorite places:

Flaco’s Tacos

The frozen margarita’s are cheap and effective. Sit there for hours and let the conversation flow.

46 E Chicago Ave · (312) 266-8226


Enjoy a lychee or pear martini with a champagne topper. The kitchen is open, don’t forget to order wasabi fries.

3317 North Broadway, Chicago, IL 60657



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