Chicago Staycations: The Wonders at the Tip of Our Nose

  |     |   Chicago Living, Things to Do


Alright guys, we made it. It’s June, the sun is shining, we can finally put away our winter coats, soak in the sun and soak in the fun. I know quite a few of us are already daydreaming about an endless stream of pina coladas, losing track of time while on a white sandy beach south of the border, but let’s face it, between work, the kids, or whatever other obstacles life has thrown in the way of our travels, that might be more of a dream than a reality this summer.

But there’s no need to fret, we live in Chicago. All we have to do is look out our window, and voilah, plenty of space to plan our escape in our own backyard. Let’s take a peek at a few ideas to kick your Chicago summer off with a staycation that you won’t soon forget! Also, for the sake of budgeting, there are a couple options listed, one for a modestly priced staycation, a moderately priced staycation, and one for a splurging staycation. Every option has its perks, and you can’t go wrong no matter the decision.

A true staycation means not staying at home! Whether it's booking a room at a hotel, or staying in an airbnb, pretending like you're a tourist in your own city is the way to go. Check out some ideas on where to stay in the city!

  • Modest – Holiday Jones Hostel: If you want to try something that most Chicagoans have never thought of, then the Holiday Jones is for you. This delightfully and unique hostel is located in Wicker Park and offers a bike rental for a small extra amount. In the day, cruise around the neighborhood and take in the burgeoning culture or stop in to one of the many newly opened restaurants for an affordable drink or bite. At night, catch one of Chicago’s up and coming musical acts at one of the neighborhood’s many live music venues. The Jones is a steal for anyone who is trying to get closer to the hip, bohemian side of Chicago.
  • Moderate – The Congress Plaza Hotel: Don’t let the fancy decorative interior fool you, book in advance for this historically robust icon and you’ll be in the center of all that Chicago can offer for a bargain. Walking distance from Museum Campus, the shops at the Magnificent Mile, and the loop, The Congress will situate you perfectly for your staycation. Even if you’re just looking for a nice little jaunt to take in the scenery, The Congress is nestled in the heart of Chicago with spectacular views of Lake Michigan.
  • Splurge – The Freehand: The Freehand is interesting in the sense that it is a great option if you want to stay in luxury accommodations with a group. Without a doubt, it is the most unique of the lodgings on this list, and perhaps the best part of the Freehand is that since there are both private and group rooms, getting a group together to split the cost and having a staycation party will dramatically lighten the load on your pocketbook. The decor in the rooms and in the lobby is one of a kind and you will feel like you’re in another world at the Freehand.

Perhaps the greatest part about Chicago is the sheer amount of stuff there is to do in the city. What makes it even better is that most of the fantastic activities are easily accessible even while you’re strapped for cash.

  • Modest – Lakefront Trail: I don’t know about you, but nothing beats breathtaking views while getting the heart pumping. The Lakefront Trail offers just that. 18 miles of pristine Chicago views on the water is sure to kick off your summer stay-K the right way. If you’re not in the mood for dealing with other riders and joggers, no problem, for more of a secluded bike ride, try the South Shore portion of the trail. When it’s sunny, there is no better way to kick off a summer day than a beach side cruise that shows you multiple sides of the city.Side note: For a rainy-day getaway that costs nothing, try the Garfield Park Observatory. (It’s free and it smells great) Also, the fern room is great for anyone who’s interested in Illinois history.
  • Moderate – Chicago Architecture Foundation River Cruise: Chicago is known for its amazing architecture but do you know the background behind some of our infamous buildings? What better way to learn than on a cruise!? In partnership with the Chicago Architecture Foundation (CAF), volunteers give you a detailed narrative of Chicago's various architectural styles and their stories.
  • Splurge – Wrigley Field: Wrigley Field is truly one of the most iconic ballparks in the nation and is great place to see a ballgame or a concert no matter where you are from. I mean really, who doesn't like ball park dogs or big summer concerts? And since we are Chicagoans, what better to fork over a little extra cash for than something that is about as organically Chicago as it gets. Don’t let the extra cash turn you away, though. If it’s a ball game you’re catching, you can easily find cheap seats!

Chicago is obviously known for its deep-dish pizza, and its Chicago style hot dogs, Both of which, are easily found around the city, but where is the best bang for your buck? Where is the most memorable experience? And where, if you want to splurge a little, are you guaranteed to leave with a satisfied stomach as well as a clear conscience about your decision to splurge?

  • Modest – Daley's Restaurant: Daley's is a Chicago staple as it has been in business since 1892 in the Woodlawn neighborhood! It is one of the older restaurants in the city. This historic diner serves breakfast all day and soul food. It's inviting and warm atmosphere, and of course the delicious food, makes it a must visit during your staycation.
  • Moderate - Au Cheval: Au Cheval isn’t entirely honest, and I like it. A “single” has two patties, and a “double” has three. I was instantly sold. Unfortunately, so was everyone else, which is why it’s a good thing that Au Cheval is located in the West Loop. Plenty of time for you to hop to a nearby bar while you wait for your top notch burger.
  • Splurge – Montverde Restaurant and Pastificio: If you’re on a stay cation with your significant other, what better to share an experience with them at a classy West Loop Italian restaurant with great food and a personal atmosphere? Top Chef runner up Sarah Grueneberg brings all of her accolades to Montverde without overpricing. Plan to splurge a little, but Montverde is well worth the extra cash.

What's your dream staycation?


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