Workation: 10 Getaways Near Chicago

September 10, 2015

2:00 pm

While Chicago is a great place to live and work – especially if you’re looking to build a company – sometimes you just need to take a small break. But, alas, sometimes living the startup dream is actually far from it, and going away for a full vacation simply may not work work when starting a company. In that case, maybe it’s time to get away on a “workation”.

Nowadays, it’s all too common to find entrepreneurs and other working professionals toting their work along with them. These “workations” give the benefit of some level of escape from the doldrums of everyday life without having to sacrifice too much on the business end. But what if you’re a startup founder in Chicago that needs to make sure you’re near your office or at least near the city in those “just in case” situations? Well, what better way than to spend that workation in some yet-unexplored nook of Chicago or some nearby attraction?

This celebration of the Chicago ecosystem is brought to you by @properties, the leading Chicago real estate brokerage serving both the city of Chicago and North Shore through dynamic marketing and innovation. Read more here. Tech.Co reached out to a few agents at @properties, did some of our own research, and reached out to some other professionals around the city and got them to share with us some of their favorite workation spots that aren’t too far away from Chicago (or even already in Chicago) – places where you can take some time to relax, and still manage to get your work done.

Whether you’re staying in the city for a staycation or hoping to find someplace near for a workation, here are 10 getaways to check out near Chicago.

The Spoke & Bird


What is it?

An American restaurant with a great outdoor space that makes you forget you’re in the city.

Where is it located?

Prairie District in the South Loop (205-209 E 18th St, Chicago, IL 60616)

Why come here?

According to @properties agent Colleen Harper: “[There’s] a quiet haven on the patio during the summer, Monday through Friday. The indoor cafe is also a great place to catch up on emails. The organic, locally-sourced ingredients for their unique meals and snacks are delightful and quite tasty. The friendly owners and employees leave you feeling connected to the neighborhood. They know lots of their clientele by their first names – four star pick.”

The Drake


What is it?

One of Chicago’s oldest luxury hotels.

Where is it?

Near North Side (140 E Walton St, Chicago, IL 60611)

Why come here?

According to Chicago-based attorney, Michael Helfand: “Staying Downtown in a hotel off of Michigan Ave is a true staycation because unless you are a tourist or work in that area, most Chicagoans don’t spend a ton of time there. I work in the loop and don’t have much reason to ever be there. But if there is an event in the city or we just want some quiet time, my wife and I stay at the Drake or Peninsula because they are world class hotels, one older, one newer, both with a great style. And when I need to get work done – which for me is every day – I can do so in their rooms, but have a breathtaking view.”

Union League Club of Chicago


What is it?

A renowned social club whose members are recognized for establishing many of Chicago’s major cultural institutions, such as The Art Institute of Chicago.

Where is it located?

In the Loop (65 W Jackson Blvd, Chicago, IL 60604)

Why come here?

According to @properties agent Diane Edelman, the Union League Club offers everything from free Wi-Fi and art exhibits, to food and exercise facilities. It’s a great escape from the city, if you happen to be a member. If you’re not, then you just need to find someone who is and get them to invite you over as a guest.

I|O at The Godfrey Hotel


What is it?

A lounge area that also serves as a great meeting and event space.

Where is it located?

On the fourth floor of The Godfrey Hotel in Near North / River North (127 W Huron, Chicago, IL 60654)

Why come here?

Writes VP of Wagstaff Worldwide, Carissa Remitz: “[It’s] a great place for a hideaway! Located on the fourth floor of the hotel, the indoor/outdoor rooftop lounge and meeting and event spaces offer free Wi-Fi (no codes needed), ample electrical sockets, and great food and cocktails. The Chef’s Cocktails are not to be missed – Chef Riley Huddleston creates them to order in the kitchen using scientific methods (like checking the pH to make sure the cocktail is the perfect level of sweet and sour).”

King Spa & Sauna


What is it?

A day spa and sauna that’s great for families.

Where is it located?

Niles, IL – just 20 minutes outside of Chicago (809 Civic Ctr Dr)

Why come here?

For @properties agent Mirlinda Vula: “This is a co-ed, true bathhouse with massages, body scrubs, facials, saunas, hot fresh food, Wi-Fi, movie theater, meditation room, and more. This place is hands down my only choice when it comes to getting some much needed R&R&R (rest, relaxation and rejuvenation).” Not only that, but there’s also apparently an option to stay the night in one of their meditation rooms for a mere $35.

Chicago Harbors


What is it?

A string of 10 harbors along Lake Michigan.

Where is it located?

There are 10 harbors total, each of which can be found here.

Why come here?

Heather Clark from Video Brewery suggests: “If your battery is fully charged and the weather is nice, [then] head to any of the harbors. There is open Wi-Fi serving all of the boats in the Chicago harbor system and picnic tables available for working at.”

Little Beans Cafe


What is it?

A cafe that doubles as a creative recreational space for kids.

Where is located?

There’s one location in Evanston and one in Chicago, right in Bucktown (1809 W Webster Ave, Chicago, IL 60614)

Why come here?

A great staycation spot for parents in the city. Write @properties agent Ressie Krabacher: “I come here with my kids and watch them play, learn, and imagine in their indoor playground. They get so busy that they don’t even come to look for me. [The] cafe has good Wi-Fi, [and it’s] not crowded at all so I’m able to catch up with client calls during the week. Wonderful staff too. I get hugs and kisses from my happy little rugrats, [and] get to play with them and be a kid too!”

The Long Room


What is it?

A joint coffee shop and bar.

Where is it located?

In Lakeview (1612 W Irving Park Rd)

Why come here?

It’s a unique hideaway space that offers both alcohol (known for its craft beer) and coffee, as well as food. They have a fully-enclosed beer garden outside, photobooths, free Wi-Fi, and plenty of outlets. If you’re planning a staycation, you may as well someplace comfortable that’s got a great vibe.

Marina Grand Resort


What is it?

A beachside resort on Lake Michigan.

Where is it located?

New Buffalo, MI – a few miles outside of Chicago (600 West Water St, New Buffalo, MI 49117)

Why come here?

According to Bill Fish, president of Reputation Management, it isn’t just a great resort offering all the amenities you need to do your work: “I happened to grow up in Valparaiso, Indiana which is roughly 30 miles from Chicago. As a kid, my parents would drive us just over the border to New Buffalo, Michigan. Its a phenomenal beach town and roughly an hour drive from Chicago (non-rush hour).” A good workation option that isn’t too far from home.

Four Seasons Hotel Lobby


What is it?

The lobby of the Four Seasons Hotel Chicago.

Where is it located?

Inside the Four Seasons, Near North Side (120 E Delaware Pl, Chicago, IL 60611)

Why come here?

Writes food and travel writer Amber Gibson, a staycation doesn’t mean having to keep locked up in your apartment: “I love working and meeting clients at the Four Seasons lobby. There is free and speedy Wi-Fi, several outlets, and they have a beautiful new contemporary art collection. It certainly has better ambiance than my apartment and is so much more peaceful and elegant than working in Starbucks!”

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Ronald Barba was the previous managing editor of Tech.Co. His primary story interests include industry trends, consumer-facing apps/products, the startup lifestyle, business ethics, diversity in tech, and what-is-this-bullsh*t things. Aside from writing about startups and entrepreneurship, Ronald is interested in 'Doctor Who', Murakami, 'The Mindy Project', and fried chicken. He is currently based in New York because he mistakenly studied philosophy in college and is now a "writer". Tweet @RonaldPBarba.

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