My City Adventures Guide to a Chicago Vacation – Getting Around Town

Marquee lights of the historic Chicago Theater. Some say it's not the destination, it's the journey. Well, our Chicago journey was full of getting lost. Hopefully, this will help you find your way around.

My City Adventures Guide to a Chicago Vacation – Getting Around Town

This post is brought to you through collaborations with ChooseChicago and Smart Destinations. I also included sponsored links which I believe will help you get the most out of your Chicago adventures.

Before I dive into our summer vacation I think I should begin by sharing why I chose Chicago, IL. With 20,000 cities in the United States, the options were almost endless. Yet Chicago has a diverse tapestry of architecture and is boldly pushing the boundaries of culinary art. Not to mention its greatest comeback story. All that made to a top choice. But what really sealed the deal was a quick google of what to do in Chicago during the last week of July. The Roots were playing at Northerly Island Park for the annual Tour de Fat. Whaaat!? I love The Roots! Sold!

Chicago's Riverwalk. Some say it's not the destination, it's the journey. Well, our Chicago journey was full of getting lost. Hopefully, this will help you find your way around.

Of course, my daughter Lily and I did more than go to a concert and look at buildings. Much more. For your benefit, I divided the post into three sections: transportation, food, and sightseeing. You can start here with “Getting To and Around Town“. Coming soon are sections on food and sightseeing.

When I Say First Things First I Mean Food!

More Fun than We Could Handle in Just Five Days!

Also here’s my first fun fact about Chicago. The city got its name from “Checagou”, the Potawatomi word for wild onions. This tribe of Native Americans were the first inhabitants of Chicago’s terrain.

Riding in a Most Peculiar Style

Some say it’s not about the destination, it’s about the journey. Well, not this time! My goal was to have a fantastic summer vacation so I wanted the journey to be as cheap as possible. Even though I don’t own a vehicle I had plenty of options. Plane, train, automobile, or bus.

Some say it's not the destination, it's the journey. Well, our Chicago journey was full of getting lost. Hopefully, this will help you find your way around.

Honestly though, I didn’t even bother looking into airline tickets or renting a car. I assumed either would be too much for my budget. Amtrak has free and half price days for children’s train rides. Plus a four-hour layover in St. Louis would have given us some time to explore the Gateway City. However, after calculating the cost of departure to Chicago and arrival back in Kansas City, Greyhound’s bus transit was the least expensive at $153 round trip for both of us. With our tickets booked we were off. And so were the other people who traveled on the bus with us.

I don’t know the Greyhound slogan but “Don’t start none, won’t be none” would be most accurate. This was the primary spiel I heard throughout our bus ride. Actually, the quote from the Greyhound drivers was “If a passenger becomes a problem, Greyhound does not transport them past the point that they become a problem.” Meaning if you act a fool on the bus, you will get left on the side of the road with the police. It could have been because our bus was scheduled to leave at 11 pm. You know who they say comes out at night. Clearly we were in for a colorful journey.

Public transit bus in Chicago. Some say it's not the destination, it's the journey. Well, our Chicago journey was full of getting lost. Hopefully, this will help you find your way around.

From the moment the bus pulled out of the station, the characters on-board gave me a surreal look into sides of humanity fit for a bizarre reality TV show. There was the woman meeting her boyfriend in St. Louis who spent over two hours in a phone conversation that would make a late night call girl blush. And it wasn’t with her boyfriend. A group of men sitting behind us were heading to a boys weekend and had started the party a little too soon. While traveling back home we met a woman in a nasty custody dispute with her children’s father. She spent most of her time sitting in her girlfriend’s lap sobbing loudly. I’d made the mistake of figuring that if we got a later bus we could simply sleep through the ride and wake up at our destination. I was wrong! But we made it. Safe, sound, and only mildly sleep deprived.

We Hit the Ground Running and Immediately Got Lost

My goal of keeping transportation expenses to a minimum meant using Uber was out of the question. I purchased a Ventra card, accepted on Chicago’s buses and trains. Ventra cards can be loaded with funds for 1 day, 3 days, 7 days, and 30 days. My seven-day pass cost $28. However since our trip was only five days it would have been nice to have a five-day option. No cabs or Uber also meant a lot of walking and quickly gaining some navigational sense of the local transit system. It just wasn’t quick enough. My GPS app was virtually worthless for most of our vacation. To get around we relied heavily on the kindness of local bus drivers and city maps posted throughout the downtown area.

State Street bridge in Chicago. Some say it's not the destination, it's the journey. Well, our Chicago journey was full of getting lost. Hopefully, this will help you find your way around.

Our hungry bellies dictated the first thing on the travel itinerary was to explore a nearby restaurant. I managed finding the way to Devon Seafood Grill on the Magnificent Mile with ease. After dinner was a different story. God must have decided I was better off lost because my GPS would not work and then my phone died. No big deal. Surely I can reverse my steps back to the train station where we got off. Wrong! The distance from the restaurant to the blue line train was only 10 minutes on foot. After 15 minutes of hopelessly walking up and down unfamiliar streets, I had a slightly panic inducing realization. I didn’t have a clue how to get to where I needed to be.

“Relax, Mama! We’re on Vacation!”

The first and only other time I’ve been to Chicago is with my mother when I was 10 years old. I’m 32 now. Luckily the small amount of research I did in anticipation of our trip began to serve me well. I recognized a few surrounding landmarks from travel guides. Wandering up one street, we came across a finely dressed couple looking in the window of a Maserati dealership. Aahhh! This is the Gold Coast neighborhood. Lily and I continued up that street then turned left. At the corner of somewhere and someplace we noticed a woman steering a horse-drawn carriage past the exquisite Sofitel Hotel. (I later learned it was the corner of Wabash Ave. and Chestnut St.) The stunning sight of the Sofitel’s half crescent-shaped glass first floor exterior left me awestruck.

Horse drawn carriage in front of Sofitel Hotel Chicago. Some say it's not the destination, it's the journey. Well, our Chicago journey was full of getting lost. Hopefully, this will help you find your way around.

Feelings of panic washed away. I told myself to temporarily abandon any sense of urgency to be at the next place. Switching gears to a more relaxed state and now primed for adventure mode, Lily and I started a game I call Which Way. The rules are simple. We start on a street corner and pick a direction to walk. Left, right, or straight. The way to win is by finding some new place or thing you haven’t seen before. It could be a new mural or a statue or anything. It’s the best way I know to explore sights I would otherwise miss if I stuck to the beaten path.

Feeling the Chicago Blues

Once night fell we got back on schedule. Thank God for those city maps and wi-fi hot spots! We finally found our way back to the “L” station we needed and hopped on the Blue Line. Can I just take a moment to talk about the amazingly wonderful Blue Line!? This train runs 24 hours a day from the Chicago O’Hare International Airport, through downtown, to Forest Park. Luckily, the AirBNB apartment we stayed in was only a five-minute walk from the South Halsted station. Eventually we rode on seven of the eight “L” routes and several bus routes with all we planned during the trip. Yet it didn’t take long to learn that the quickest way for us to get back and forth was on the Blue Line. Take my advice if you’re traveling to Chicago. Remember the Blue Line. It will be your best friend. Side note: The Red Line also operates on a 24 hour schedule.

Kayakers on Chicago's Riverwalk. Some say it's not the destination, it's the journey. Well, our Chicago journey was full of getting lost. Hopefully, this will help you find your way around.

I hope this helps you navigate getting to and around Chicago streets a bit easier than I did. Subscribe now so you won’t miss my upcoming posts on Chicago eats and Chicago sights. You’ll also be the first to hear about our latest adventures and amazing local giveaways. Thank you for reading!

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