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Our Chicago Staycation

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As you know, we’re still not really traveling. We have a road trip planned, but only because it looked like things were getting better and then as quickly as that came, it went back to being horrible again. So, yes, we will be going on that trip, but that’s probably it for the near future. For now, we’re continuing our Destination Date Night series. 

We’ve been wanting to visit Chicago for quite some time, and we’ve done a few virtual tours during the pandemic to help feel like we’re going somewhere and to support tour guides who are out of work for the time being. One was a haunted history of Lincoln Park and another was a cool haunted river tour. (Can you tell we like haunted stories?) So, while we’re waiting until we can really visit Chicago, this was the next best thing.


I chose a great evening view of the Chicago River, because I knew that would be a big part of our “trip”. I liked that we could see the skyline. I also chose a background with the Buckingham Fountain, a landmark of Millennium Park that isn’t The Bean (Cloud Gate) that is part of everyone’s photos. I thought this was a more interesting and unique view and didn’t make me think of Anish Kapoor and how he’s the jerk of the art world. If you don’t know this story, please take some time to read about it when you’re done here. 

A lot of my backdrop had a blue color, so I went full out and added a bight blue tablecloth to my table then added some Chicago mainstays: 

  • Ferris wheel, first built in 1892, and now an iconic part of Navy Pier (a different wheel was built for this). This was America’s answer to the Eiffel Tower. 
  • The Chicago flag. I didn’t actually know that cities within states had their own flags, but the Chicago flag is pretty good looking.
  • The Oscar Mayer Wienermobile. This was a fun one, since I love the Wienermobile and once looked into touring with it. Oscar Mayer moved from Germany to Detroit and then to Chicago where he started his famous deli brand. I figured I needed a mini version of the mobile, and all orders come with a Wienermobile whistle, which is what you see in the mums.
I also just threw out a jar of flowers that complemented the rest of the things.

I decided to order the things I would definitely eat when I visit Chicago, that I can actually get here at a Chicagoan restaurant.  


The first was a deep dish Chicago pizza with sausage, pepperoni, and mushrooms. Generally, we get thin crust or regular pizza, as I find that deep dish is too filling. Because of that, I only ordered a personal size to share. 




Next, I ordered a giant calzone. Okay, I didn’t have an option to order a size, but this was way more than 2 normal people can eat.


Chicago has tons of microbreweries now, so I know I would have stopped into one of those places and gotten a taster of some of those and tried some delish bar foods. 


Beer and pizza are great together. 

While we ate, we took a long, leisurely stroll along the waterfront. The video we watched was taken during Covid, so we had pretty unobstructed views of everything and that was nice. Then we moved onto dessert, because of course we saved room for that.



Make way for…cheesecake. Yes, none of these things we’ve eaten were anything super special, but it is what that region of the country is known for and easily found nearby where we live, and (bonus) was offered by delivery. It wasn’t life changing or super exciting, but it was nice and chill and we ended up with leftovers, too.

As we wrapped up dessert, we watched some videos of the must-eat foods and must-do things in Chicago. 


Cheers to a Chicago staycation. If you want to have your own, you totally can. Here are some ways to make it special:
  • Chicago Bean/Cloud Gate statue
  • Chicago flag
  • Ferris wheel
    • This is the wooden one I got, but it’s pretty bad for splinters, so this one might be better
    • And you don’t have to put this one together at all
  • Wienermobile
  • Beer tasting tray
    • This one has funky glasses, but nowhere to mark which beer is which
  • Chicago Bears merch, like this jersey
    • Or Cubs merch, like this hat
  • Plan your trip like a local with the Not For Tourists Guide
  • A YouTube playlist – this is mine that you can use
  • I won’t be making a follow-up post to this, because I have this 48-hour guide for you. Our next date will take us down under with a visit to Australia. 


    I hope you enjoyed this and are planning a fun staycation for yourself/your family. If so, let me know in the comments and/or tag me in any of your social media posts so I can see where  you went!


    Disclaimer: This post includes affiliate links, and I may be compensated should you choose to make any purchases through them. This allows me to keep this blog running for you. 


    Want to read more tips for traveling worldwide on a budget? Check out my blog at Shereen Travels Cheap or find me on Facebook or Twitter. You’ll also find product and website suggestions, packing tips, current deals and a whole lot more to help you travel better for less!


    Source: http://www.shereentravelscheap.com/2021/09/our-chicago-staycation.html



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