One Day In Chicago With Kids

Twentyfour days into our family RV road trip around the U.S. and finally, we’re ready to explore the Windy City. Here’s how we spent one day in Chicago plus we share tips to find RV parking in Chicago.

You can use the links in the table of contents to skip to the sections that interest you.

Chicago is the starting point of iconic Route 66, the home of Skyscrapers, the Twinkie, the hotdog, deep-dish pizza, Italian beef, notorious gangster Al Capone, and popular sports teams Chicago Cubs, Bulls and Bears.

Bet you didn’t know all that!

Plan Your Approach

First things first: approach Chicago with care. Here’s why.

The reason why you should spend time with some form of a map before driving to Chicago in an RV is the insane number of low clearance bridges you are highly likely to encounter around the city centre. Plan your route carefully to avoid losing the top of your motorhome, unless you’re using an RV specific GPS to navigate.

We used the RV Parky app to safely navigate these obstacles. However, we didn’t get too close to the main red triangle zone (pictured above) with our motorhome, which was frustrating at the time, but in hindsight, it was a blessing. We dry camped at the Hammond Walmart, a good distance south of the city, and used public transport from there.

Which brings me to my next point: RV Parking in Chicago.

RV Parking In Chicago

It’s difficult to find RV parking in Chicago because there aren’t many options. In fact, there’s only one possible option that we know of that will get you right in the middle of all the action within walking distance of Millenium Park and The Loop, Chicago’s main touristy area.

The only place suitable for RV parking in downtown Chicago is McCormick Place Marshalling Yard.

Unlucky for us, it was fully booked when we called ahead to reserve an overnight lot. We advise calling or going online to book your spot well in advance of your trip.

It’s worth every effort because this site is the ideal location from where to walk or cycle to the heart of Chicago’s tourist scene. There are complaints about truckers and the noise they make at all hours of the day, but I’d still use it if it’s available for a night or two.

RV Overnight Options In Chicago

McCormick Place Marshalling Yard is the closest overnight option for RV’s. 

Most of the Walmarts – and there are many – are marked as “no overnight allowed” and campsites in the area all have terrible reviews. From our experience, there are no good campsites within an hours drive of downtown Chicago.  Please correct me if I’m wrong? I’ll love to hear about closer RV campsites if you know of any.

We boondocked / dry camped at the Hammond Walmart, situated next to the Illinois / Indiana state borderline, 18 miles (29km) south of Chicago’s Navy Pier. For two nights we parked there so that we could spend one full day in Chicago. In the morning, on the day we went into the city, we moved the RV to an unmarked gravel parking lot across from the Walmart for the day. When we returned, we pulled back into the CCTV controlled Walmart lot for the night.

Did You Know? In 1917, writers Ben Hecht and Maxwell Bodenheim hosted the shortest known debate in history. The topic? “Resolved: That People Who Attend Literary Debates are Imbeciles.” Seeing a room full of people, Hecht argued, “The affirmative rests.” Bodenheim took to the podium and nodded. “You win,” he said.

Public Transport To Chicago

It was a risky move to leave the RV in an unmarked lot for the day, but RV’s are expected to leave the Walmart parking lots early in the morning. With no RV parking in Chicago, we had no other option.

We used good old Google to search for public transport options ‘near me‘ to get from point A to B and we just went with it.

To get to Chicago from Hammond/Whiting, we took an Uber to the nearest bus stop to catch the Nr 26 bus. Our Uber driver was an African American lady who drove with her bible on the dash, which I noticed and liked because I used to travel with my bible before I downloaded The Bible app on my phone. Then the bus driver, also an African American woman, with a quiet sideways nod of her head, let the five of us on for free when we didn’t have the exact change to pay the $5,75 bus fare. How nice!

You need the exact correct bus fare if you plan to travel by bus.

Altogether, it took more than an hour to get to Millenium Park from Hammond Walmart. Taking the local bus through the suburbs was entertaining in itself because we got to see another side of the city. People-watching may not be fun for everyone, but it works for me, especially in different parts of the world. Halloween is big in America so the kids enjoyed seeing all the decorated houses, kitted out and ready for the big night.

Some parts looked rundown and as if perhaps we were on the wrong side of the track, but we felt safe all the way. Plus we got to enjoy part of the South Lake Shore Drive views over Lake Michigan and savour the moment of first entry without having to navigate traffic or trying to find parking.

At the end of the day, we thought we were very clever to book an Uber to pick us up at Navy Pier and take us straight back to our RV. The journey back took twice as long. Chicago’s peak traffic is not something to take lightly guys! Avoid. Avoid. Avoid.

Perhaps we should’ve looked at taking a train from Millenium to Hammond station and an Uber from there. Or better yet, booked an overnight parking space at McCormick Place before we booked our flights to America!

Things To Do In Chicago

I can promise you that one day is by no means nearly enough to even get a glimpse of what Chicago has to offer, but we got quite a bit under the belt, on foot and with three kids in tow.

The one thing I would’ve like to add to this visit would be a Chicago Cubs baseball game at the Wrigley Field stadium, but that would have to be left for another time.

We jumped off the bus somewhere near Grant Park and started to explore the area on foot. It was really cold and overcast with light rain showers catching us out every now and then. Not the ideal weather to wander on foot, but it’s not every day that we get to see a world-class city such as Chicago.

Pictured above is the route we followed on foot, roughly. We walked a lot more around Grant Park and Millenium Park than I could show on the map, so our total distance should be closer to four or five miles.

Deep Dish Pizza & Italian Beef

The first things I think of when you say Chicago, are the faces of Catherine Zeta-Jones and Renee Zellweger and then, deep-dish pizza. And we had some for breakfast. In the heart of Chicago no less, at Luke’s on West Jackson Boulevard. We ate Chicago style pan pizza and the famous Italian Beef in a bustling little restaurant packed with a bunch of locals, most of all workmen on their mid-morning coffee break. To me, that’s always a clear sign that we’ve found a winner when you find the spot where the locals eat.

We highly recommend Luke’s Italian Beef. The food was great. You can see that the staff have been doing this a long time because things happened like clockwork when it got very busy. I asked the cashier to give me what they are best known for and she gave me the Italian Beef. It was incredible and I totally get why Chicago is famous for it. It’s an Italian roll filled with beef and various toppings – a favourite being pickles – of your choice and sauce.

I was only sorry that we could not go back for more before we left the city and I regret not being able to eat a deep-dish pizza, Italian Beef and a traditional Chicago style hotdog, all in one sitting. They are apparently also known for great Mexican food. You need more days here just to sample all the staple foods Chicagoans love so much.

Willis Tower Skydeck

The Willis Tower’s Skydeck is about as high as you can get in Chicago, the city where tall building engineering methods were invented. The Skydeck is located on the building’s 103rd floor – 1,450 feet (443m) high, and is the highest public viewing platform in the United States. Just going up in the elevator is a bit of an experience as you reach the top in under 60 seconds!

This is one B was looking forward to. At nearly $100 (+- R 1400 or £74) for the five of us, we weren’t sure if we all should do it, but in the end, we decided to go together and I’m glad we did. Not because the Skydeck is such an amazing experience, but because we would’ve been waiting hours for B to get back if we hadn’t gone along. Not my idea of a good time. Anywhere.

Do I recommend the Chicago Skydeck? That depends. I’m not sure it’s the best attraction for families, especially if you have limited time in Chicago. It might be worth it for solo travellers or couples.

I’ll share the facts and you can decide.

The Skydeck view over Chicago is absolutely amazing. Standing inside the glass box so high up over the city, watching the tiny cars scooch around like minute ants, does get your pulse racing. It is exciting.

Twenty-five thousand people enter the Willis Tower EVERY day. We went on a Friday morning mid-October and it felt like all of them were in our queue.

It takes many hours of close quarter queueing and shoulder-rubbing with tourists before you finally reach the Skydeck viewing platform. Let’s just say there will be many moments of awkward eye-contact, uncomfortably polite smiling and eavesdropping on conversations while you wait your turn. Disney World queues seem short compared to this!

When you eventually reach the Skydeck, you better be prepared for the big moment. Plan those exuberantly creative and pretty selfie poses. I’ll go so far as to say, even practice them while you queue because when you get there, as unprepared as we were, after having had hours of mindless queueing, you may be disappointed with your shot.

You only get 60 seconds in the Skydeck viewing box. Yes. That’s it. In total. Groups of four or more get 90 seconds – a generous 30 seconds extra – visiting time. The five of us got lucky this time. Why do 60 seconds sound longer than 1 minute, and 90 seconds sound forever? Clever Jedi mind tricks that work when you buy your ticket.

There will be a member of staff to take a photo of you with your phone on the Skydeck.

Once your time is up, you will join another very long queue for the elevator to get back down and out of the building. You can spend time in the large lounge areas on the Skydeck floor, have a drink, something to eat and shop for trinkets before you head to the elevator queue.

As a single traveller with more than one day to spend in Chicago, I might pay $24 to stand in the highest viewing point in America. However, in my humble opinion and with the benefit of hindsight, there are better and more fun things for families with young children to spend their money and precious time on than The Skydeck.

Millennium Park

It was well past lunchtime when we finally left the Willis Tower. Good thing we had a big breakfast at Luke’s before going up the Skydeck, because we were good to continue exploring after a quick stop at Dunkin Donuts for coffee and, of course, a variety box of doughnuts.

I was expecting warm scrumptious doughnuts, but we must’ve made a mistake when we ordered because they were rather dry and literally needed to be dunked. We’ll be more picky with our next order.

Millennium Park is built on top of Millenium Station and a car park, which arguably makes it the largest rooftop garden in the world!

Our next point of order was to find The Bean. This set us off on a delightful galavant around Millenium Park, a 24,5-acre piece of art and culture set in larger Grant Park on the shores of Lake Michigan. The park is filled with impressive public art, the Lurie Gardens, The Crown Fountain and the famous Cloud Gate aka The Bean, all of which we explored.

Watch out for the punters at The Bean who sell their bracelets and trinkets. Don’t dare stick your hand out towards them or let them get hold of it. The minute they do you’ll have a bracelet slipped over your hand and hear them repeatedly demand, “twenty dolla, twenty dolla, twenty dolla”. They targeted the kids, but we gave the stuff back to them and made it clear that their trick would not work on us. Very cheeky.

Navy Pier

At Chicago’s Navy Pier, you’ll find a 200-foot Ferris wheel called the Centennial Wheel, the city’s only real IMAX screen, Chicago Children’s Museum, Chicago Shakespeare Theater and plentiful dining options.

Our walk from Millennium Park to Navy Pier took us over the historic DuSable Bridge – a drawbridge with beautiful decorative work – and along a small part of the Magnificent Mile on North Michigan Avenue. Truly jaw-dropping skyscrapers and prominent businesses plastered with famous names towered all around us.

We stopped for a quick spot of shopping, a bit further down from Michigan Avenue mind you, and reached Navy Pier late in the afternoon. We one hundred percent wanted to be back at the RV before dark, which unfortunately did not leave us with time to do much at Navy Pier.

After a walk around the Pier to see all its attractions and the view of Michigan Lake, we called an Uber to pick us up. By this time we had enough of the weather and were ready to get the kids fed and settled for the night.

Chicago’s Own Bucket List

This is the bucket list proudly displayed on a wall in the Willis Tower Skydeck in Chicago.

1. Experience Skydeck and get a photo on the ledge.
2. Try a Chicago-style hotdog
3. Get inspired at the Art Institute
4. See the city via Segway or double-decker bus.
5. Walk the magnificent mile
6. Take a photo at Cloud Gate (The Bean)
7. Fill up with a few slices of deep-dish pizza
8. Glide along the river on an architectural boat cruise
9. Attend a Chicago sporting event.
10. Admire the Chicago skyline from Museum Campus or Montrose Point
11. See the white beluga whales at Shedo Aquarium
12. Ride the Centennial Wheel at Navy Pier
13. Ice skate at Maggie Daley Park’s skating ribbon
14. Catch a concert or movie at Millennium Park
15. Experience the taste of Chicago: Blues Festival or Jazz Festival
16. Experience the inside of a submarine at the museum of science and industry.

Final Thoughts About Chicago

There’s so much to do. We could’ve spent the whole day just making the most of what Navy Pier had to offer: sightseeing cruises, water taxi, carnival rides, a 4000 square feet sensory maze, The Children’s Museum and The Imax. Or we could’ve spent time at one of the many world-class museums and aquariums in Chicago I’m not too happy about the chunk of time wasted at The Skydeck, but it is what it is.

Considering that we only got to see a small part of Chicago, it was surprisingly clean for one of the largest cities in the States. It doesn’t have a particularly bad smell like many other cities sometimes have. Took me weeks to shake the smell of Parisian streets.

Even though there was a beggar (notice the singular noun) on a few street corners, there weren’t many. The beggars I saw all somehow looked like they were doing well for themselves, just another guy doing a days work, almost neatly dressed, some even quite cheerful.

These guys looked smart compared to other homeless people I’ve seen. I know it’s a strange observation, perhaps even controversial, but I always notice them as it shows how a city cares for their desperately needy citizens. It’s one of the reasons I don’t care much for most cities because it can be a heartbreaking sight. Of course, I have no idea how Chicagoans treat homeless people in general and I’m not trying to generalise, but for what it’s worth, this is just the impression I got as a complete foreigner in this part of town.

We felt safe in Chicago. Considering how hard it is to find RV parking in Chicago, we got around without too much hassle, apart from peak-hour traffic. With the hope to return and experience a more authentic Chicago, we enjoyed being in one of the most famous cities in the world for just one day, even on a rainy one.

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