Chicago Travel Guide

A visit to Chicago is a visit to a city known for its beautiful skyline that frames Lake Michigan, its sports teams and its relationship to hot dogs and pizza.  Chicago’s nickname, Windy City, dates back to the late 1870s.  Then editor Charles A. Dan of the newspaper the “New York Sun”,  wrote that “Chicago was windy because of its politicians being full of hot air.”  Still, known for its exciting political scene, There are a lot of things to do in Chicago for the older woman solo traveler.  And if you are a foodie, you’ve landed in the right place.



I will be breaking down my city into mini-guides based on the best places to go for the older woman traveling solo in Chicago.  I will be your guide to the best that Chicago has to offer a first-time solo visitor or a repeat solo traveler to the city that I’ve had the pleasure of living in for 27 years.  My Chicago Travel Guide is an insider’s look at some of the 200 or so neighborhoods that make up the Windy City.

Chicago is so huge and diverse that it’s impossible to capture all of it in one post or travel guide. I will be discussing in my Chicago Travel Guides what to see in Chicago, both on and off the beaten path.  I will be focusing on what makes my city special.  It’s a beautiful city with plenty of things to do and see.

Tips for the Older Woman Solo Traveling to Chicago

Yes, Chicago does have a reputation for crime but so do a lot of cities in the United States.  But with a little street-savvy and awareness of how you’re presenting yourself, you will be fine. Most areas of Chicago are well patrolled by the City of Chicago Police, Chicago Transit Police and private security.

Here are some things to remember:

  • Be aware of your surroundings. Don’t stray down an alley. When walking at night (and Chicago is beautiful at night), stick to the well-lit streets with plenty of pedestrian and street traffic.
  • Make sure you’re not a target for pick-pocketers – leave that huge ass purse back at the hotel.  Instead, take only the essentials when going out.  Use a daypack or small purse with straps that you can wear across your body.  Don’t take large sums of cash with you and for God sake don’t pull out a wad of cash when paying for something – you never know who’s watching.  Instead, pay by credit/debit card. Take $20-$40 in smaller bills and stash them inside pockets of your small purse/daypack.  I personally like wearing jeans and storing a couple of bills of cash in my pockets, in case I have to tip or if I want to drop a couple dollars in street performer’s hat.
  • The next tip is a personal preference – I prefer to travel with small travel camera that tucks away in a small bag or slips into my pocket instead of taking my nice, big professional looking Canon.  That professional camera hanging around your neck, screams “I’m a tourist”.  Be a travel anthropologist.   Observe without being obvious.
  • I absolutely love Google Maps.  I have a horrible sense of direction and Google Maps have saved me plenty of times when I didn’t know where the hell I was going.
  • Have a planned itinerary – every day know what you’re going to be doing.  It’s okay to change it up once you get to your destination but have at least have a rough draft. I learned this lesson the hard way after wondering about Charleston, SC with no plans, no research about the city.  I had a horrible time.

  • Chicago has an amazing public transportation system.  Don’t be afraid to utilize it. Parking in Chicago is expensive. Parking in Chicago’s neighborhoods is nonexistent or restricted to residents.  So take a bus or train (the “L”) to your where you’re going.  It’s a cool way to see the city.  If you’re going to be going out late, use Uber or Lyft.