Staycation. What is it and why is it the greatest thing ever? A staycation is a “vacation” in your hometown. It gives you the opportunity to be a tourist where you live and just enjoy all that your city or town has to offer. It’s a great idea for those who don’t have the time to travel elsewhere, but still want to have a break from their typical schedule.

This last weekend, one of my best friends from Connecticut, Shawna, came to visit me in Chicago. She came at the perfect time. The weather wasn’t too terrible which allowed us to do a ton of exploring! Of course I wanted to show her all of the typical Chicago highlights, just on a budget.

To make the most of a staycation, check out somewhere you haven't gotten the chance to see yet, or even head back to places you haven't seen in awhile.

Shawna arrived on Saturday and after dropping her things off, we decided to hit one section of the city – the loop. We went to The Cloud Gate, also known as The Bean, walked around Millennium Park, and then headed over to Navy Pier. Usually I avoid Navy Pier, as it’s very touristy, but we wanted to do the Architecture Boat Tour. I’ve done the architecture boat tour a few times, but it’s always great.

The day was sunny and warm, making it the perfect time to go. Sailing along the river was fun, even if our tour guide wasn’t the greatest. It really is hit or miss. I always prefer the tour guides that make it more personal and relaxed instead of just throwing out facts left and right. Regardless, it was still a pretty great tour.

After a little more exploring, we grabbed dinner at The Boiler Room, a gourmet thin crust pizza place. Shawna decided to call it a night early (she was up for almost 24 hours at this point!) while I ended up going out to some Logan Square bars with other friends.

A staycation should involve the best of both worlds - the fun things you enjoy at home along with something a little special.

On Sunday, we decided to do something Shawna enjoys doing at home – going to church. I don’t typically go to church, but I agreed that it would be great to go and keep with her usual routine. I actually really enjoyed the service and loved the community aspect. It really set a great tone to the rest of the day.  After the service, we walked down the street to grab brunch at The Kit Kat Lounge.

The Kit Kat Lounge has delicious food and an option to get bottomless mimosas, sangria, or bellini’s. Additionally, every half hour or so, a drag queen will come out to perform a song. She was so awesome. First, she performed some classics like “These Boots Are Made For Walking”. Then, she switched outfits and started singing the best of Lady Gaga. It was so fun and such a great experience. I definitely recommend going there if you’re in that neighborhood.

As far as food goes, I decided to order the chicken and waffles. I was nervous it was going to be so filling and too much, but it was the perfect portion.

After brunch we made our way over to Wrigley Field. I feel like you have to get a picture in front of the sign, especially now that there is the “World Series Champions” listed there. I’m not often over in Wrigleyville anymore, so it’s always fun to walk around. We made our way over to the park by the lake front before taking an uber to go get deep dish at Giordano’s. Deep dish is always yummy and delicious – a must for visitors to try!

A staycation needs to have some relaxation time built in!


I don’t know about you, but when I’m visiting somewhere new, I find it hard to fully relax because I want to see everything I can. Luckily, when you’re on a staycation, you don’t have to worry about that. Shawna was on board with relaxing at my apartment on Monday. We spent the day just hanging out, ordering chinese food, and binge watching 13 Reasons Why.  If you haven’t seen the show, I definitely recommend it. It’s interesting and kinda makes you think about the impact you have on people in your life. Anyway, spending a day in was so relaxing and definitely needed after a bunch of running around.

A staycation would be nothing without friends, new and old.

Tuesday was the last day Shawna would be visiting. We decided to hit anything that was still inexpensive but considered a Chicago must. First, we went to the Sears Tower. We decided not to go inside, but just to observe from below. It can be kinda expensive to go all the way up to the sky deck.

We then decided to head over to the Signature Lounge at the Hancock Tower. You get a similarly amazing view and can enjoy a drink or dessert while you’re up there (probably for less money). You do need to be 21 to head up there, which makes it a relaxing environment. This is nice compared to kids possibly running around or screaming.

Check out this view – it’s pretty spectacular.  Although I must say, for one of the best views of the skyline, you have to head to the ladies bathroom.  Sorry Guys!

After checking out this view, we had to pick up some Garrett’s popcorn. It’s a must for popcorn lovers. The best is the Garrett’s Mix, also known at the Chicago Mix. It’s cheddar cheese popcorn and caramel popcorn mixed together in one bag. It’s delicious and you have to try it.

Dinner time rolls around and it’s time to network. We met up with good friends of one of Shawna’s co-workers. Daynor and Marc are incredibly sweet and so smart.  They are both incredibly successful in their chosen careers (law and sports media, respectively). I am so thankful to have gotten the chance to meet with them and really loved getting their advice on how to advance in my own career and how to get to where I want to go.  Last weekend was awesome and I’m so glad to have gotten to spend it with one of my best friends!

Next time you’re in need of a vacation, consider having a “staycation” instead and enjoy all that your hometown has to offer.

 

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