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Navigating Chicago (Pandemic Style)

With phase 4 being in full effect, for the most part, I know many of us are anxious about what's to come or eager to venture out but for safety purposes, it can be tricky to navigate what that looks like. So if you’re comfortable taking a short road trip and unsure of what to do or where to stay, I’ve got you covered, but before I start, let me first start by saying please be safe. COVID19 is real and in order for us to move forward everyone has to do their part and it starts with you already know.. I’m gonna say it. Wash your hands and WEAR YOUR MASK.. again for the people in the back WEAR YOUR MASK. I know there’s a lot of facts and statistics about wearing a mask but they only facts and statistics I’m looking at is common sense. Keep yourself safe from germs when in-doors, put a mask on.

Now let’s get back to the real fun, my parents came to visit this past weekend and while my Dad is a more of go with the flow guy, my mom is up and down for anything so we naturally had to do both, while under such circumstances.


My parents and I rented out an Airbnb in the Gold Coast of Chicago, our stay at Randy's was great! Perfect location, it came with a desinated parking spot, it was located next to some great resturants, a 5 mintue walk to a grocery store, and walking distance to downtown. When traveling most people stay near millennium parks or on Mag mile, but with all of that being closed I’d encourage you to stay in one of the many neighborhoods of the city, you can really see the beauty of Chicago. Places to search for Airbnb outside of downtown: River North, Lincoln Park, Lakeview, Wrigley Field.


Consider any trips you make during this time a road trip so come prepared. If you buy things when you get to the city it’s way more expensive AND the wait times are extremely long.

Packing List

  • Cleaning supplies

  • Cooler

  • Snacks (for the road and stay)

  • Pack of water

  • Bandages

  • Sunscreen

  • Wipes

  • Hand sanitizer

  • Trash bags

  • Lysol

  • Paper towel

  • Bath towel and wash cloth (if youd prefer your own)

  • Portable Phone charger

  • Carry along a sweater (AC indoors)


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Packing List

  • Swimsuits

  • Loose fitting dress

  • Dress shirt (Juts in case you stop by Carmines in Gold Coast) 

  • Shorts

  • T-shirts

  • Jeans

  • Waking shoes

  • Fancy shoes

  • Sandal/slide

  • Hat

  • Umbrella

  •  Sunglasses


Enjoy the outdoors, when staying away from the city you can actually see what Chicago has to offer, thrift shops, cool restaurants, murals that make up the city, and a mix of people.

- Wicker Park

- Lincoln Park

- Lakeview

- River North

- Gold Coast

- West Loop


For the most part, every dining place is going to be reservation only, Do yourself a favor and download the open table app and book there, you’ll set up a simple profile and you’ll see all your dining options there, search the locations I shared above. Don’t wait until the evening of or you’ll either be waiting for a long period of time or not getting in.

  • The Dearborn (Right next to the chicago theather, makes for a great picture)

  • City Winery

  • LuxBar

  • Lou Malnati's

  • Velvet Taco

  • Carmine's

  • Yolk (Wicker Park)

  • Colective Coffee (Wicker Park)

  • Johnson's Real Ice Cream (tried it for the first time and it was INCREDIABLE, try the Cinnamon Toast Crunch scoop)

  • Joe and the Juice (a bit pricey for smoothie but worth every sip)

  • Also, don’t forget to cook, yes I know you can cook at home.. but remember a lot of things are still closed to the public, enjoy time at the place you’re staying, stop by a Local Jewel, Trader Joe’s, Aldi’s or Marianos to grab food to make. DO NOT go to Walgreens, CVS, or any other random market, you’ll be paying an arm and leg for food. Check out the hot bar areas too you’ll be able to get a good deal on a family pack meal.


  • Spot hero is a great application to use. I'd recommend downloading the app prior to getting int the city or booking it oneline and printing the slip ahead of time. Spot hero shows you where to park around the city and the prices are a lot cheaper than pulling up to park in a random parking garage in the city. It saves you time and money, arrive early for your reservation some parking garages in the city can go unnoticed.

Hope you enjoy!

Xx Jas

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