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6 Tips for a Perfect Staycation at the Hotel Chicago

A perfect Chicago staycation

Thanks to the new Hotel Chicago (formerly known as the Hotel Sax), my husband and I were offered a weekend’s stay in a beautiful suite with a view of State Street that would make you sick with jealousy (see our disclosure statement here).

Let me be clear: I tend to be the adventurous type. I sleep on floors, get up early to explore new places, and enjoy “roughing it”. But when planning a perfect Chicago staycation, I admit that my values were rather different.

I think this is true for many staycationers. During a staycation, you might be more likely to seek relaxation over adventure. You might even be more willing to splurge since you didn’t spend money on airfare. And your “travel” companion makes all the difference when you’re not distracted by new cultures and language barriers.

Staycationing is also a time when most travelers would agree that the hotel – or wherever you choose to hang your hat – is extremely important. It’s where we’re spending a good chunk of time (and probably the bulk of our change), isn’t it?

Here are six tips on how to create the perfect Chicago staycation for yourself:

1. Relax in luxury

My room at the Hotel Chicago

My room at the Hotel Chicago

Nothing could beat the modern elegance of the Hotel Chicago. When we checked into our hotel room, we were floored. Our suite welcomed us with two enormous rooms, floor to ceiling windows and two bathrooms – not to mention a tub that you could live in.

Not only this, but the décor was to die for – delicate vintage wallpaper embraced a faux snakeskin chair with chartreuse pillows in a combination that only a brilliant designer could dream up.

When you’re staycationing, so much of your time is spent in a hotel that you better really love it. Luckily, at the Hotel Chicago, we did.

2. Dine, Q style

Dinner, anyone? If you haven’t checked out Chicago Q for some urban BBQ, you haven’t seen enough of the Windy City. The expansive restaurant fills multiple rooms of what feels like someone’s southern home, complete with a living room and upstairs balcony.

The best part is, the prices are very reasonable – just expensive enough to take a new friend in town out to a nice meal, but cheap enough that you don’t feel guilty about footing the bill.

3. Plan your weekend right

The Chicago Marathon, viewed from the Hotel Chicago

View from our room at the Hotel Chicago of the Chicago Marathon

When we checked into the Hotel Chicago, we had forgotten that the Chicago Marathon was happening that very weekend – and we had front-row seats to the spot. The following morning, we were entertained for two hours as we watched thousands of colorful runners jog down State Street. The only difference is that while everyone else froze in the early Chicago morning, we were cozying up to a hot cup of coffee we prepared in our room.

How’s that for box seats?

If you’re staycationing, find a weekend when great things are happening in town – and make sure your hotel is front and center for the action. It’s one of the only times you’ll be able to really appreciate what it is to be a tourist in your own home.

4. Take a walk

Horse art dedicated to the Chicago Police Force

These cool horse sculptures are dedicated to the Chicago police force

How many times do you decide to take a cab into the center of your city and just stroll, especially on the later side of the evening?

Not often, I imagine.

There’s something magical about the Chicago River at night, and if you’re in the city after sunset, it wouldn’t be a complete staycation without a walk over a bridge or two. Look up and admire the skyscrapers in the evening sky, and watch as restaurant-goers transition into bars and lounges. Take advantage of being in the center of everything, and explore the city during an hour that you wouldn’t normally (of course, as all travelers should, do it safely).

5. Stay out late

Crimson Lounge at the Hotel Chicago

Crimson Lounge at the Hotel Chicago

Yes, we’re all adults and we can stay out late as much as we want anyway. But there’s something to be said about spending the wee hours of your morning at a local bar and then walking no more than five minutes in order to get to your bed. Unless you already live in downtown Chicago (or happen to have a bar for a neighbor) this probably isn’t your regular life.

But when you’re in a hotel, you’ve already got a few bars within arms’ reach. Even when we’re not staying at the Hotel Chicago, my husband and I regularly frequent the Crimson Lounge, just off the lobby. This sultry delight is decorated to the nines with gold trim, ornate lounge chairs, red velvet sofas – pure opulence.

It’s also the scene of many a Go Girl meetup, if you find yourself in the Chicago area from time to time.

The best part is, if you’re staying at the Hotel Chicago, you literally don’t need to travel any farther than to the elevators to get cozy inside your plush king-size bed after one-too-many luxurious martinis.

6. Brunch, brunch, brunch

You may have noticed that food is an important part of Chicago culture, and a hearty brunch can’t be beat – especially after a night of strolling and martinis. Wake up early and get your butt over to a neighborhood spot like Tweet or check out the egg-celent options in Streeterville and River North like Eggsperience or Yolk. You won’t regret it, even if the night before was rough.

Or you could sleep in – many of these places serve brunch until 3pm, if not all day long.

What activities would you recommend for a fabulous staycation in your town?

Beth Santos
Founder and CEO of Wanderful, creator of the Women in Travel Summit, enthusiastic lover of ice cream, picnics and art.

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