Chicago Must-Sees From a Chi Town Girl


If you’re from Chicago, you never refer to it as the “Second City,” maybe second to none!

There is so much to do in Chicago, but you can get a good taste of it (anyone get the pun?) even if you have just a long weekend. I grew up in the suburbs, was down town frequently, and I went to the University of Illinois at Chicago. So… I know my stuff. Really, everyone has their preferences, but here are a few of my tips and must-sees/dos if you will be stopping by the Windy City. Let’s start off with tips:

  • Think staying down town is too expensive? Stay in a suburb then and take the Metra down town! That’s what I often do and I always find the train ride enjoyable. In my experience, it is on time the majority of the time.
  • Public transit is your friend if you want to go to say, the Lincoln Park Zoo from the Loop. I found it relatively intuitive to understand the “L” (elevated train) system and the buses aren’t bad either. There are apps to track where the buses are and when they will arrive.
  • Chicago is a very walkable city if you are decent shape. A lot of what I am going to recommend I find is in walking distance from the Loop. So if you aren’t going to be in Chicago for a very long time and plan on just staying in the Loop area (believe me, there is more than enough to see just in that area), put on your walking shoes and explore.
  • Yes, there are homeless/street people. Yes, some of them will try to talk to you. I usually don’t make eye contact and keep walking just because if I stopped for everyone that tried to talk to me, I wouldn’t get to my destination! No, I am no an uncaring callous person. I have given people the other half of my sandwiches from Subway. Just be aware. I have never been pick-pocketed down town Chicago in my 5 plus years living down town, but I recommend to have zipped purses and not open totes for the ladies. Guys should keep your wallets in your front pocket or a zipped backpack.

Now for must sees/dos/eats:


  • You’ll need to take the standard tourist picture at the Bean which is located near Michigan Avenue. Near this you will also find what I term the “Face Fountains” (Crown Fountains) and Millennium Park! Take a stroll. Make sure on your walk you also hit Buckingham Fountain (pictured below) and you can walk along the lake toward the Aquarium.


  • If you’re in the mood for shopping there is North Bridge Mall or Water Tower
  • Deep. Dish. Pizza. Get it, love it, worship it. Try out Uno’s, Giordano’s, and/or Lou Malnati’s. I find the last one is my favorite.
  • If you’re up for a stellar view and a bit of a scare, you can always do the Sky Deck at the Willis Tower… if you’re brave… do “the ledge” experience where you will get a very intimate view of the city.
  • If you’re not from the area, I thoroughly enjoy Potbelly sandwiches as well as Argo tea (mint chocolate is the best!)
  • Check out the beaches in Chicago. That’s right, beaches. Even if you don’t want to swim in the lack, they are nice places to relax. There is a secret lagoon I recently discovered behind the Planetarium and I will always be partial to Ohio Street Beach (pictured below). DCIM100GOPROGOPR1200.JPG
  • Navy Pier oftentimes has a lot of fun things going on. You could take a speed boat ride or go on a dinner boat cruise! You can take a ride on the ferris wheel and I believe there is a free trolley that will bring you back toward down town.
  • Strolling along the riverwalk is a nice way to spend a sunny day in Chicago.DCIM100GOPROGOPR1198.JPG
  • If you’re looking for a swanky place to go to dinner, check out the Walnut Room, located in Macy’s on State street. I would definitely make reservations just in case. If you’re looking for great steak, go to the Chicago Chop House. It’s expensive, but very very good. Now if you’re up for a really different (and expensive!) eating experience, go to Alinea. I haven’t been there (yet!) but have heard rave reviews.
  • You could enjoy a tour by land or sea (er…. river). If that’s not your thing, but you still want to take a water ride, take a water taxi along the river. You can get some great pictures and it’s always fun.
  • There are no shortage of museums in Chicago … The Art Institute of Chicago, Museum of Contemporary Art, Museum of Science and Industry, Field Museum of Natural History, Adler Planetarium … to name just a few.
  • There is a FREE zoo (Lincoln Park Zoo)


Anyway, I hope that gives you some basic ideas of things you may want to add to your itinerary. Whenever anyone asks me what to see in Chicago, these are some of my go-to things. What are yours?

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