Connections and Destinations

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Whether you are a Chicago native or new resident, there are many historical, educational and recreational attractions offered throughout this city

Some insider tips for for navigating (on foot or with public transportation or with increasingly popular “uber”), makes getting around a whole lot easier. 

Laura&K-Field Museum-dino skeletonWhen my west coast daughter, Karla, came home for the holidays, we planned a super fun day downtown. She expressed interest in a tatoo exhibit at The Field Museum, so that was our main destination. And I had been wanting to see the Skydeck (aka the Willis Tower observation deck, located on the 103rd floor), so the plan was created. 

Even as a Chicago native, I can still find getting around downtown a bit intimidating. Fortunately, I have a best friend who is so savvy at getting around the city, who gave me some great tips for making our connections. With a bit of planning and looking at our options for transportation, we were able to save time and money, and just fill the day with our wonderful adventure!


  • For visitors and travelers to downtown landmarks, restaurants, theaters, shopping, and museums, the city was developed on a grid system, so you can move around like a pencil on graph paper. The 0/0 point is at the intersection of State Street and Madison, and eight blocks equals the distance of one mile.
  • Wherever you see Lake Michigan, you are looking east at downtown’s natural border.
  • Don’t park in two parking garages; it will cost you a fortune.
  • Buy tickets in advance, online, and you can usually find places offering good discounts.
  • If you haven’t already, give UBER a try! It beats waiting for the bus and is very efficient and economical around downtown.

L&K_Field Museum-elephantsWe found all day parking at The Field Museum ($22), then used UBER’s ‘share the ride’ program and got our ride over to the Skydeck at Willis Tower and back, for only $4 and some cents each way. 

We got back to Orland Park before rush hour traffic, and enjoyed more time together at The Cheesecake Factory, a favorite place of ours for fun and feasting.

Chicago... Your Kind of Town!