If there is one thing the millennial generation knows how to do, it is travel. Regardless of the budget or the schedule, we always find the time to squeeze in a quick trip somewhere. Over the last few years, Chicago has become a popular destination for the traveling millennial trying to squeeze in a destination over a long weekend. Between the ever-changing food scene and the array of entertainment options, Chicago continues to maintain its status as an incredible city for those in search of a destination with all the trimmings. Intrigued? Here is just a mere sampling of the Chicago highlights that you do not want to miss!

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Chicago Athletic Association

Located near Millennium Park, this 1890’s refurbished hotel and hang-out spot delivers upscale accommodations, refined refreshments and copious nightlife talent to both guests and evening visitors. From the architectural detail found in the grand marble staircases to the views from Cindy’s rooftop terrace, restaurant and bar, the Athletic Association is one of the best places to both play and stay in Chicago.

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Girl and the Goat

Born from the culinary creativity of local chef, Stephanie Izard, in 2010; Girl and the Goat is a relatively new face on the Chicago food scene, but has quickly become a staple of the West Loop. Open seven days a week to those with and without reservations, the Girl and the Goat features a globally influenced menu with a mix of dishes for every palate – from vegetarian to the devoted carnivore. Paired with a mixed collection of international wines, local beers, crafted cocktails and an incredible atmosphere, this meal is sure to be an experience worth repeating.

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Field Notes

The Field Note obsession is real…enough to make Chicago a destination for fans looking to browse the first and only Field Note store in the country. Designed for a group of friends in 2006 before launching as a company, Field Notes has quickly become a pocket mainstay, a vintage reminder of list-making days past. And these days, a browse through their store is just the inspiration any journal lover needs to turn a new page and embrace the Field Note mantra.

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The Second City

As a comedy club icon for more than fifty-years, The Second City has turned out some of the greatest comedic geniuses of our time. Tina and Amy, Steve Carell and even Stephen Colbert all began their illustrious careers here on this stage. With three theaters performing multiple shows each week, and even their own full service restaurant, 1959 Kitchen and Bar, The Second City is a full experience all its own. Laughter is guaranteed.

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Community Tavern

Ever heard of a boutique steak restaurant? Chicago’s northwest side has! Opened by experienced restaurateur Quay Tao and Executive Chef Joey Beato in 2015, Community Tavern has emerged quickly to the brink of fame with numerous awards and accolades for their well-done cuts of meat. Combined with a quaint atmosphere and an approachable array of wines and cocktails, Community Tavern is doing Chicago steaks as deliciously as anyone else, but with a price tag that allows for an obtainable luxury steak dinner experience where everyone is a welcomed guest.

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WBEZ Chicago

Chicago’s local NPR station, WBEZ Chicago, is somewhat of a legend to the podcasting generation. From iconic shows like This American Life, Serial, S-Town and Wait, Wait Don’t Tell Me, our listening habits would not be the same without WBEZ. And while tickets to the weekly Wait, Wait Don’t Tell Me taping at the Chase Bank Auditorium are difficult to snag (but not impossible!), fans can still request a tour of the actual WBEZ studio to satisfy their curiosities.


Shaw’s Crab House

Weekend brunch in the windy city? Introducing Shaw’s Crab House, a Chicago classic known for, among other things, their Saturday and Sunday brunches. For $59, diners have access to a spectacular brunch buffet like no other. Choosing between four unique stations including the chilled seafood station, grand hot buffet station, the chef’s station and, of course, the sweets station requires multiple plates. And when it comes to the crab cakes, lobster mac and the cheese and malted Belgium waffles, seconds and thirds may be involved.


Piece Brewery & Pizzeria

If Anthony Bourdain thinks it is worth a stop in a city filled with pizza, why disagree with an expert? Opened in July of 2001 by Bill Jacobs of Jacobs Bros. Bagels, Piece Brewery and Pizzeria emerged with the intent to send the world of Chicago deep dish into a tailspin. Specializing in the thin crust memories of Jacobs’ upbringing in Connecticut, the restaurant keeps things simple with just five pizza options (additional topping available, of course). And don’t forget the house-brewed beer on tap!

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The Ambassador

In what was once the famed Ambassador East Hotel, Journey Hotels has reimagined this 1926 classic into a more modern, eclectic space, with small nods to its original namesake. As a frequent stop for famous faces in its glory days, The Ambassador now boasts a more approachable atmosphere without losing any of its original charm. With 285 elegant rooms, two new concept restaurants, views of Lake Michigan and easy access to shopping on Michigan Avenue, The Ambassador is quickly becoming a Chicago icon on its own terms.

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Hotel EMC2

Only a couple blocks away from the Miracle Mile, the brand new Hotel EMC2, part of Marriot’s Autograph Collection Hotels, offers a unique stay for the trend-seeking millennial. Featuring a modern room design with a minimalist flare, this hotel includes all the latest tech amenities from smart tv’s to robots! With an in room Amazon echo in lieu of the traditional bedside phones, guests can “Ask Alexa to ask EMC2 for” whatever they may need during their stay. The hotel’s pair of room service robots, Cleo and Leo, will then usher up your special request.

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