After New York’s natural beauty, more wonder – of a very different kind – befell me when Mark, Maya, and I approached the skyline of Chicago, Illinois. Yes, I had set foot upon its grounds twice before. Once on a wintry layover from Belgium, never venturing further than a hotel room after missing my connecting flight, and once a couple of years ago, when we swung by our friends Keith and Kavita’s home on the outskirts of the city. But I had never witnessed its majestic architectural beauty, strolled its waterfront, or parked in its quirky neighborhoods.
Chicago skyline
When our long-anticipated departure from Newburyport, Massachusetts, approached, Mark and I had to pick a route, or, at the very least, a first destination. We prefer a northern track across the United States for its scenic appeal, but we hate cold weather. Everything was dependent on when exactly we could start our journey. Luckily, that happened in mid-September and not October like last year, when a southern approach was required. So, we stated, “As long as the weather holds, we will stick to a northern course.” As I write this, we still haven’t made any southward progress! Soon…
Our goal was Chicago, a city I had heard a lot of positives about but never visited, and a place where three sets of friends would be located at the end of September… Our trio stayed in the city for four nights and had a jolly good time, without spending a dime!* 😊
(Click on the photos or hover over them to read the captions in galleries.)
Six tips for a free “long weekend” in Chi Town:
1. Stick to outdoor sights and activities
We easily filled a few days by checking out Lake Michigan – with a long waterfront bike/walking trail – and several areas in downtown. The first day, we walked all the way from Lincoln Park to Navy Pier and returned via skyscraper heaven.
The modern architecture of the skyline is mind-blowing and diverse; the parks and green spaces are abundant and well-situated. And all of it is freely accessible.
Our second day had us explore Lincoln Park and Wicker Park.
And the third day found us in the Southern part of the city, with Buckingham Fountain, Millennium Park, the start of Route 66, and a different view of the skyline as its highlights.
2. Walk everywhere
We totally lucked out with the weather! The temperatures were in the low to mid-seventies (twenties Celsius) and we explored the city in shorts and t-shirts. One can exercise happily, crisscrossing Chicago. We wouldn’t recommend driving in downtown, especially with a camper. Do your homework regarding bridge heights and overpasses if you do decide to venture into the city. The three of us averaged 8 miles of walking a day (11-5-8). Maya loved it!
Buckingham Fountain and Chicago skyline
3. Find free parking
Parking meters and underground garages (with a height limit prohibitive to anything bigger than a car) abound. Once, we thought we could find a spot at no cost near a small park, two miles from our intended destination. When we reached that area, we were surprised to still find parking meters – $4.50 an hour. Ouch! We circled back to the University of Illinois Chicago area, before we discovered free street parking. But it was a three-mile (unattractive) jaunt to the fountain from there. Free parking in Chicago exists, but it is a huge city and you have to be energetic enough to cover substantial distances on foot. Even after a few sleepless nights…
4. Commit to urban camping
Our free app iOverlander came to the rescue again when we tried to figure out where we could park overnight without any issues. There are – surprisingly – a few spots at the edges of downtown where this is possible without raising eyebrows. We settled on a street along Lincoln Park, near the zoo, and “camped” there – with a low profile – for two nights.
Our overnight parking spot at Lincoln Park
For our third night, we checked out the Wicker Park area, but pronounced it too busy and too sloped. So, we moved to Humboldt Park, got settled, marveled at the lack of traffic and people, and hopped in bed around 9:55pm, only to be rudely interrupted by… speakers from a police car. “This park closes in five minutes. If you don’t leave soon – and that’s also for this camper – you will be ticketed!”
“Camped” in Humboldt Park in a failed attempt at a quiet, undisturbed night.
We have never jumped out of bed and put clothes on and secured all the cabinets and stored all lose items as quickly as that evening. Then, we squeezed through the half-closed gate and headed back to Wicker Park in the dark. Not ideal! Luckily, we managed to find a parking spot along the tree-lined streets that was big – and high – enough for our truck camper. We left a note in the app about the changed circumstances of Humboldt Park, and tried to sleep in a tilted position.
Short night near Wicker Park
Our last night had the best potential: Smith Park in Ukrainian Village. This remains our favorite, because you can pull into a spot (backwards if preferred) instead of parallel park, one side of the one-way street is park, and the other a relatively quiet neighborhood.
5. Prepare your own meals
This is something a lot of campers – like us – are used to anyway, but not eating out in a city saves a lot of money. We usually cook our dinners at home, eat cereal, unsweetened almond milk, and fruit for breakfast, and make healthy sandwiches for lunch. This, of course, does cost money, but we always have a full fridge upon arriving in a place we intend to spend a few days. On the same level, we also don’t buy gas in cities, as prices often spike there and fuel stations are busy and tight. In general, we don’t show up empty-handed when being invited for a meal, unless we forget about that dessert chocolate in our pocket…
6. Have generous friends “in the neighborhood”
Friends were the main draw for our 1,000-mile drive to Chicago and we planned our stay, camping spots, and time frame around meeting them. We are grateful that all six took time out of their busy schedules for a meet-up. And, even better, everyone treated us to fabulous meals!
The reason we parked for two nights at Lincoln Park was that our location was in walking distance of where our good sailing friends Lisa (who blogs here) and Fabio lived – temporarily – at the time. Accomplished circumnavigators, they are currently on a break from their boat (which is hauled out in Mexico). We have managed to meet up with them occasionally over the years and over the world. After our one-mile walk through an exciting part of town, it was another blow-your-mind evening for me, as I’d never actually relaxed in a room on the 56th floor. We had a fabulous time catching up, seeing the sun set in this urban landscape, and enjoying a three-course dinner by Italian cook Fabio!
Our second day in the Windy City was dedicated to finally meeting fellow nomads and travelers Peta and Ben from the blog Green Global Trek. I have been following their blog forever and if there’s anyone who I would like to trade lifestyles with, it’s them. Their choices, travels, international living circumstances, swift decisions, adventurous tendencies, and karma situations have fascinated me for years. To be honest, I never thought we’d cross paths in the US – the least tropical of their locations. The couple was in Chicago for a month as part of their Live Anywhere on Airbnb participation. I wrote about that amazing opportunity and contest here not too long ago. I encourage anyone to subscribe to their blog and YouTube channel! You can watch their Chicago episodes here (part 1) and here (part 2).
We managed to connect for lunch in Wicker Park – a fun and interesting time that was over way too quickly. They treated us to a picnic of Asian food and a tray of diverse microgreens produced by one of their sons. Delicious! Maya was the center of attention, receiving loads of cuddles and devouring the leftover greens. To be repeated elsewhere in the world!
Blogging friends turned real friends…
*Disclaimer: A city never sleeps, and therefore, we didn’t either. Those four nights in downtown were pretty noisy – traffic, music, early risers, late partiers, dog walkers, gatherings, and even fireworks right next to our camper! If you require decent nights of sleep, urban camping is not for you. But if you don’t mind wearing earplugs (we do mind) or are adamant about being in walking distance of a city without spending money (that’s us), three nights is probably doable.
We slept in the house of our friends during a three-day stay in the suburbs: luxury!
As a side note: after our four days in the city, we drove about an hour west to Glen Ellyn, where our long-time friends Keith and Kavita live. There, we were spoiled with showers, laundry machines, a fantastic mattress, unlimited electricity and internet, and a full-size kitchen. We treated them with a take-out dinner, homemade American-Belgian chocolate chip cookies (with the last of our Belgian chocolate), and vast amounts of alcohol. Now you know how that category’s expense for October happened. 😊 Again, we had a lovely time catching up, doing our own things during the day, and socializing at night.
Just like New York state, Chicago was full of wonderful surprises. Stay tuned for many more adventures and photos!
View around dusk from the 56th floor
This post is linked to Natalie’s Weekend Coffee Share #42. Read her contribution of this week here.
October 20, 2021 at 16:08
Everything in a big city likes Chicago seems to cost a fortune. I still have a difficult time paying for parking anywhere, but I usually bite the bullet. My wife also has a a health condition that doesn’t allow her to walk long distances or be in extreme heat.
I’ve spent a lot of time in and around Chicago because that’s where my parents grew up. You do have to get lucky with the weather because it can be muggy or freezing, depending on what time of the year you are there. When I was 18, I spent Christmas with my family in Chicago, and there was a foot of snow on the ground. The following day, my cousin, his friend and I (being sensible teenagers 😜) drove 24 hours straight, rotating drivers, to visit our grandparents in Florida. (That’s what our excuse was, but it was probably more of an excuse to chase girls.) I’ll always remember being in snow one day, and swimming in the Gulf of Mexico a little more than 24 hours later.
October 20, 2021 at 17:21
Hi Pete!
I wouldn’t know about how pricey Chicago is, but it seems like visiting the with your own home on wheels is the cheapest way to go then! 🙂 Like you, we hate paying for parking. Usually, we can get around that by parking further away and walking. I’m sorry to read that this is not possible for your wife. But that does make pay parking worthwhile, I’d say. As for me, I can’t stand extreme heat either as it gives me terrible headaches and migraines. In those situations, I either don’t go anywhere or would gladly pay to park.
Each time I was raving about Chicago to Mark while we walked around, he’d pull me back to reality (a reality I haven’t really experienced), mentioning the icy, snowy winters, and sticky, humid summers – both climates I’m not a fan of. So, as with many visits to many locations, the weather and the mood make a difference as to how a place is perceived.
That sounds pretty cool, to have snow one day and a swim in the ocean the next one. A bit like California. Hey… wait a minute! 🙂
October 20, 2021 at 16:52
I love your tips here, Liesbet. Most of these are suggestions that we live by for our daily (retired) live – esp. gravitating towards outdoor activiites, using walking as transportation and preparing our own meals. I look forward to seeing where your adventures take you next.
October 20, 2021 at 17:23
Outdoor activities and home cooking are both so gratifying and healthy. That these choices are actually the cheap/free as well is a wonderful bonus! I’m hoping to post a bunch of photos on social media the coming days. Stay tuned! 🙂
October 20, 2021 at 16:55
Wow, I didn’t know you were able to see Lisa and Fabio too! How great is that? (Are they there just temporarily, or have they moved from Arizona?) Knowing how much you enjoy being out in nature (on land or off) I’m a bit surprised that you liked Chicago so much. Paul and I had a similar reaction to the city of Vancouver, Canada… we really loved it and hope to get back for a longer stay.
October 20, 2021 at 17:29
Hi Janis!
Once we learned that Fabio and Lisa would finish their visit to Chicago the end of September (that deadline has been adjusted – their plans are up in the air right now), we knew we had to get a move on and leave New York state in time to reach and see them. I had no idea they were staying in a high-rise! Initially, we were going to meet for a waterfront walk and dinner out, but she has been incredibly busy and overwhelmed, so it was easier for everyone to have a dinner at their place, which we could walk to – turning a 9-mile day into an 11-mile one. 🙂
Cities are intriguing for a short amount of time. We could never live there. Yet, they are vibrant and have a beauty of their own. Some cities anyway. My North American favorites are Washington DC, San Francisco, Monterrey (not really a city), Annapolis (small city), Toronto, Quebec City, Vancouver, and now Chicago (in the right weather). I hope all four of us can return to Vancouver one day…
October 20, 2021 at 17:14
Really enjoyed this since Chicago is one of my favorite cities. So much to see. Not sure I’d attempt to boondock there though. 😁
October 20, 2021 at 17:31
Haha! I wouldn’t boondock there in Beauty, for sure… 🙂 I actually read somewhere that RVs longer than 24 feet are not allowed to overnight park in the city. I can totally see now why Chicago is one of your favorite cities!
October 20, 2021 at 17:40
I’d add avoid the bad areas of Chicago and most of it after dark since the crime rate has tripled in the past year. And soon the police force will be even smaller, if not even almost non-existent.
October 21, 2021 at 12:58
Hi Alex! Good to know. Luckily, we didn’t experience anything like that and never felt unsafe walking around Chicago or parking wherever we did, day or night.
October 20, 2021 at 17:57
We stayed with our children when they lived in Chicago for graduate school. They gave us the grand tour and lodging off and on for the nearly 10 years they lived there.
Here’s to luxury living and meetups with friends. You fared very well! 😀
October 21, 2021 at 12:59
You must know the city in and out, Marian! And throughout different seasons. Nice! I hope we will be able to do a monthlong house sit in Chicago in the future, but it would have to be in the shoulder season! 🙂
October 20, 2021 at 18:48
Liesbet – so wonderful you were able to visit the fabulous city of Chicago! Seems you were just down the street from me! I live here – partly for the seasons – but mid-Sept to mid-Oct is likely to be the most perfect outdoor walking weather you can find. If you ever head back this way, let me know and I’ll try to point you to some other beautiful spots you don’t want to miss.
October 22, 2021 at 17:07
Hi Janet! I had no idea you lived in Chicago. Right now! We certainly lucked out with the weather this fall. Chicago seems like a great place to experience all the seasons. My mom loves that fact about living in Belgium as well. For us, usually, once the leaves start turning, it’s past time to head south. 🙂
October 21, 2021 at 02:03
I don’t know why but I’ve come quite late to following your blog Liesbet. Anyway here I am. I’ve been following Lisa and Fabio, and Ben and Peta for years, and I’m so jealous you got to meet them in person. One day . . . . .
Wishing you well for the rest of your trip across the north. Hope the weather holds for you.
Alison
October 22, 2021 at 17:13
Hi Alison!
Something must have gone wrong when you signed up to my blog before, if you have done this in the past. I know you have commented here before, but it seems like you must have used different email addresses or so as each time I see a comment from you, I have to moderate it first. This only happens the very first time someone new leaves a comment on Roaming About, usually. To avoid spammers…
I have certainly seen you around Lisa and Peta & Ben’s blogs in the past too. We met Lisa and her Captain when sailing in French Polynesia in 2013 and met up around the world since then by boat, plane, and campers. She was probably the first blog I ever followed and she got me started on Roaming About. Before that, I blogged for eight years on Blogger about our sailing journey (2007 – 2015). 🙂
I hope you will meet these two fabulous couples one day!! And I hope we will see them all again, for a less rushed time together.
October 22, 2021 at 17:25
I have the same as you – I only moderate the first comment from someone new. I haven’t changed email addresses, so that seems to be some weird WP glitch. Anyway hopefully it will be ok now. 🙂
It was so good to get a little news of Lisa and Fabio as I know she hasn’t been blogging for a while.
Alison
October 22, 2021 at 20:15
Lisa is taking a break from the boat as she is working to replenish the cruising kitty. She and Fabio hope to go sailing again the first half of next year. And there’s a lot more going on, but I’m sure she will explain that in her blog one day if she cares to do so. They are both looking great and healthy!
October 21, 2021 at 05:16
Some great tips there, Liesbet. It just shows that you can have a great time in the city without spending a fortune!
October 22, 2021 at 17:15
Thanks, and true that. I don’t think we have ever visited a place that required a lot of money, because of how we arrived (by sailboat or camper). Even exploring Bora Bora and Tahiti was free to us. Maybe there is an eBook in the making about visiting fancy places for free, haha. Chicago might be a little tough to visit with your new rig, though. We didn’t see any overlanders in town. 🙂
October 21, 2021 at 09:49
Our city! (Well, at least for 26 years.) I’m happy you got a great weather weekend to see one of the most beautiful cities in the U.S., and of course I am thrilled and envious that you got to spend time with Lisa, Fabio, Peta, and Ben. Chicago in the fall is a delight, and you are lucky to have had to traverse it on foot. It is a very walkable city (we were there in early September and managed 12 miles on a Saturday before a wedding!), and mostly quite safe (despite the media’s and some others’ frenzy about crime, which has its pockets just like in any other big city). I know you are farther west now – keep enjoying the road!
October 22, 2021 at 17:19
That’s right, Lexie, you lived in Chicago as well. Something else you have in common with Lisa. 🙂 I can’t believe I missed you there as well by a few weeks. Jeez… If it was that special wedding of the photo, I am impressed as it didn’t look like you walked 12 miles that day!
We had no issues at all in the city regarding crime. Of course, we are always careful and only ventured outside at night once, to visit Fabio and Lisa, but that all felt busy, vibrant, and safe. Fabio suggested he’d come pick us up, but it wasn’t worth his hassle.
Just crossed the border from South Dakota into Nebraska today…
October 21, 2021 at 10:28
You are absolutely amazing, Liesbet. I would have thought it impossible to do what you did in Chicago. I can’t believe how much you walked. I once hit 17,500 steps while touring Japan one day–a personal best. That’s about 7 miles or so. Mine was one day–you did it every day at 8 miles! You’d be hard to keep up with.
October 22, 2021 at 20:03
You always make me feel so good about myself, Jacqui! I used to have a Fitbit and kept track of my steps those years as well. One day, when a hike turned out to be much longer than expected (it was a scary few hours) in North Cascades National Park, because we didn’t have the right information, I once hiked about 30,000 steps. A personal record, I think. When my Fitbit broke, I didn’t replace it. I’m all about simplifying my life. Enough gadgets already…
By the way, I don’t have good stamina and don’t walk fast at all. Mark is the one who is hard to keep up with. Also, I like my terrain flat and not hilly, let alone mountainous. To the chagrin of Mark! And Maya. 🙂
I hope your road trip went alright. Where did you go? I’d hate to have missed you along the way.
October 21, 2021 at 22:24
Liesbet, good points regarding visiting cities. What grabbed my attention was the interactive fountain, what fun and by the lools of your big smiles so was being social with friends. Your camper looks much larger when your’re standing by side it.
October 22, 2021 at 20:07
Hi Suzanne!
Good point about the perspective of the camper. One of these weeks, I hope to provide a bit more info about our set-up and the differences with Zesty, our campervan. Oh, the other day, I took a photo of our vehicle next to a bison along the road. That would give a good perspective as well! 🙂
We had to have a bit of patience watching the interactive fountain appear again, but it was worth it. Especially to see the look on people’s faces who didn’t expect water to jump out of the wall. Haha.
I hope you and Les are doing alright. Enjoy the spring and summer as much as you can.
October 22, 2021 at 16:10
That digital fountain is amazing!! How fab! #Weekendcoffeeshare (and good tip on the height restrictions)
October 22, 2021 at 20:13
Thanks for reading and commenting, Lydia. That fountain was quite special. I had read about it in Lonely Planet, but then, as usual, forgot about it as we were walking through town and the park. So, we lucked out happening upon it, when spotting a huge crowd. It’s nothing I’d ever seen before. 🙂
October 22, 2021 at 20:51
Hi Liesbet, Good tips to enjoy big cities without breaking a bank. As you know, walking is my primary mode of transportation. I do it as much as possible when I travel, too. Stick to outdoors has an added bonus of more covid-safe these days. Home made meals save both on cost and calories. Did you see the Bean in Millennial Park, not far from the interactive fountain? So great that you got to meet your friends in Chicago. Good friends make a nice city even nicer. Glad to see Lisa and Fabio healthy and happy. Safe travels! Thank you for linking up with #weekendcoffeeshare.
October 24, 2021 at 12:39
Hi Natalie!
I love it that you don’t have a car. That would be a good reason to live in a city. If I were in your shoes, I’d be car-less as well. While it might sound contradictory to most, not having a car and being able to get “everywhere” on foot, by bike, or with public transportation is liberating! And for further trips afield, there are options. When walking around Chicago, I saw several parking lots containing cars for day rentals (forgot the name of the company) and bike stalls for bike rentals. We’ve come a long way…
I think we missed “The Bean” in Millennium Park. Darn. Now we will have to go back. We turned off to find the Route 66 sign.
Good point about being outdoors regarding less Covid-risk too. Mark and I still haven’t eaten inside a restaurant. We prefer take-out or patio dining (if we don’t cook ourselves). The added bonus: Maya can come. And we take that dog everywhere! 🙂
October 23, 2021 at 12:48
Hi Liesbet. Wow – I’m not a fan of Chicago, but have spent a few days in and around it. I’m surprised you got in and out with so little hassle, but then you’re better at this sort of travel than am I.
Hey, about being stuck parking and sleeping on a slope. I’d be tempted to stop at the next construction site you see and ask if you can grab some scraps of lumber to use as parking wedges. Even with where you show the photo of, leveling the camper by 2-6 inches might have added lots of comfort for little inconvenience. Fun share. Travel safe.
October 24, 2021 at 12:46
Oh Gary, I have had to hear several times from my husband – who did all the driving – how he hates getting around cities! Most of the time, we pass them by. We always try to avoid tight downtown areas, but city driving is still stressful – for the chauffeur!
Good tip about the leveling blocks. We have them, of course. We’ve been at this for several years. 🙂 In our campervan, we had store-bought plastic squares that came with the camper when we bought it. Nice, light, and easy. Now, we have scrap pieces of decking (which are too slippery and will be replaced by lumber soon). But, the idea is to be low-profile in cities. And there isn’t a lot of extra room to maneuver and get on blocks. So, we know that in those situations, we have to take the spots as they come. Or move. At 10pm, however, we didn’t have much chance to be “shopping around” for a spot, haha. Usually, in nature, we manage to find a relatively level place or we use our blocks if needed.
On a different topic, I did read that story on your blog, which you mentioned previously, and left you my thoughts there. 🙂
October 23, 2021 at 23:47
This was a great read, especially when you got to meet Peta and Ben, I love following them too!
Great honest advice about urban camping Liesbet 🙂 #weekendcoffeeshare
October 24, 2021 at 12:47
Hi Debbie! I’m glad you liked my Chicago post. It’s so funny how I’ve been looking forward to meeting Ben and Peta somewhere on our travels (most likely Mexico) for years, and then, all of a sudden, it happened here in the US on short notice, while they haven’t lived here in ages.
October 24, 2021 at 01:37
Chicago is on my bucket list as well as Route 66. Great advise re camping out in cities.
October 24, 2021 at 12:50
Hi Max! thanks for swinging by, reading, and leaving a comment! It sounds like you will have to start your Route 66 road trip in Chicago, at the official starting point! 🙂 And, then, the views will only get more expansive. There are cool places where the Mother Road passes through (like western Arizona), but there are many boring stretches as well (like Albuquerque, NM)!! I hope you get to experience it all one day soon.
October 24, 2021 at 07:44
I’ve never visited Chicago. Is it as windy as they say it is, Liesbet?
You had me laughing about being woken and jumping out of bed by that police announcement. Not so funny for you guys I know, but I guess it’s going to happen sometime.
The fountain is cool. And the walk along the lake looks amazing. I can only imagine what the views are like from those lakeside apartments. But I’m not even going to guess how much a lakeside apartment is going to cost. Glad Maya enjoyed the walks as much as you guys did.
October 24, 2021 at 12:54
Well, Hugh, the three of us got super lucky on our visit to Chicago. Not only was it shorts weather, but the wind was pretty much non-existent. I had no idea it was called the Windy City (certainly not when exploring the outdoor sights), but read this somewhere. We have spent weeks at a time in very windy areas in previous years and that is no fun, especially when dust, sand, and prickly tumbleweeds (in the desert) are involved. I’m sure living in Chicago is super expensive. We would only be able to afford it by house and pet sitting, staying with friends, or camper visiting! 🙂
October 24, 2021 at 10:34
I don’t think I’d be brave enough to tackle a city like you just did. We’ve had our camper for a few years now and still haven’t managed to wild camp yet!
October 24, 2021 at 12:57
Hi Alex! Boondocking or wild camping is not for everyone. But, we are very frugal people, don’t need much in the way of kitchen gadgets or electricity requirements (just the computer to work and devices to check emails and social media), and are used to “living off the grid,” having sailed and camped for almost two decades. If we stayed in paid campgrounds or RV parks, we wouldn’t be able to afford this lifestyle. Plus, we do like the peace, solitude, and quietness of boondocking in nature. It’s a transition, if you ever try it, but you might like the simplicity and beauty of it all. 🙂
October 24, 2021 at 12:56
I’m surprised you were able to find free parking anywhere near downtown Chicago. When I used to live in Calgary, there were a few times when I was forced to park downtown, at a cost of $30 for half an hour. Big cites aren’t my thing, but you make a short visit to Chicago sound like fun! 🙂
October 24, 2021 at 13:03
Hi Diane!
Big cities aren’t usually our thing either – especially not in a big vehicle – but Chicago was doable. I had to convince my husband to stay this long too. But we had friends to see – a perfect excuse.
The free parking in “downtown” still required a two- to three-mile walk to the sites we were trying to visit. Parking garages are super expensive and we wouldn’t fit in them, so we have to be creative – and fit. At least for those days, haha. Maya was happy about all the extra walking, that’s for sure.
$30 for half an hour of parking in Calgary is extremely expensive. In the US, quite a few lots let you park for free the first half an hour. I think. At least at the hospitals… Or they have Early Bird or Weekend Deals. When we saw later, on our tiring walk back to the car, that we could have parked for an entire weekend day (it was Saturday) at an open, uncovered lot for $7, we frowned. We had no idea. I would have had to come up with a different title for this blog if we would have discovered this earlier. 🙂
October 24, 2021 at 17:04
I’ve been to Chicago lots. Usually driving to the city from the south from St. Louis. It was always a terrifying experience in a car. I can’t imagine driving into and around Chicago in a big vehicle. So I’m pretty impressed. And finding free parking. Doubly impressed!
I love the pics from the highrise but I’m not comfortable being in a building that tall. I used to work on the 19th floor and wasn’t too crazy about that.
Looks like you’re trip to the big city mostly went well (despite getting chased out of the park – at least you had a backup spot). Thanks for the free tour of the city.
October 26, 2021 at 22:18
Mark – while not enjoying it – is pretty good driving in cities. He has a lot of patience, is aware of everything around him, and is an excellent and careful driver. Thanks to iOverlander, we were set for urban camping. 🙂
I never thought about fear of heights when being in apartment buildings, but now I realize this is a thing. Peta also mentioned she wouldn’t have been comfortable in Lisa and Fabio’s apartment. Did you ever go to the top of buildings, like the Empire State Building or other monuments with viewing platforms?
All in all, it was a successful city trip and stay, but you know all about being exhausted after four crappy nights. Seems like we are on another stretch of those in Nebraska/Colorado as we are trying to run errands and cover a bit of distance. You know… honking trains and loud traffic…
October 24, 2021 at 21:10
This looks like it was so much fun! I’ve never been camping like this before, I did a tiny bit of camping way back when while I was in Girl Scouts, but I’ve never stayed in an RV. If my kids were older I would definitely love to pick up and do something like this! That’s lovely that you have great friends that you were able to spend time with! It looks like it was a great time. 🙂
October 26, 2021 at 22:21
Hi Angie! Welcome to Roaming About! The place where you can travel in an RV virtually. 🙂 I used to camp in a tent when I was younger as well, but these days – and especially as full-timers – a bit more comfort is important. This is our house. Not just a weekend getaway. I do hope you will be able to do something like this in the future as well. While it can be challenging, this lifestyle is often rewarding and liberating. 🙂
October 25, 2021 at 05:05
I was fortunate to visit Chicago over twenty years ago when things were much different in the city. As Alex referenced, it’s sad how things have change. Thanks for sharing your terrific photos, Liesbet.
October 26, 2021 at 22:24
Wow, you visited over twenty years ago. I have to imagine that the Chicago skyline looked a little bit different then, Jill! The apartment where we met Lisa and Fabio was built in the eighties. And, the interior reflected that. Haha. I think many big cities have changed; we need to be aware of our surroundings in crowded situations. I’m glad you enjoyed the photos. Better to keep your good memories of the city and not go back.
October 25, 2021 at 10:05
I have not been to Chicago since I left. I was born there and we left in 1989 when my dad got a new job. It’s very pretty. I would love to visit one day.
October 26, 2021 at 22:25
Hi Julie! For a city, I think Chicago is, indeed, very pretty. I hope you manage to return one day and see how it has changed… That would be interesting!
October 25, 2021 at 19:15
Me thinks maybe you’ll have to write a new book with all your travel tips – cheap/no cost parking and same with sightseeing. You did fab considering it was expensive Chicago! I’ve been there a few times. One of my fav cities in the U.S. Wow, how much did your blood pressure rise when you thought you were safely tucked in for the night and the police car rang the siren? My gawd! <3
October 26, 2021 at 22:30
Hi Debby!
The adrenaline sure kicked in once I understood the police were talking to us! Initially, I had no clue what it was about. Then, Mark said “I was wondering if this park would close. We better get the heck out of here.” Aha that’s what they were saying through the megaphone! That’s when I immediately put my clothes back on and we were ready and out the door within minutes! A good drill, me thinks. 🙂
The more I think about our frugal ways, the more I realize most people wouldn’t be comfortable with the decisions we make, the challenges we face, and the sacrifices we “suffer” as a result of being so careful with money. But, it keeps us traveling and it is a cool writing concept nevertheless, especially since we have experience with many different lifestyles, not just RVing, house sitting, or sailing.
October 27, 2021 at 12:02
I can only imagine! Lol. Just keep in mind, there are many who may not prefer to live frugal, but many don’t have a choice. <3
October 27, 2021 at 12:41
True that. If life (on the road) keeps getting more and more expensive, we won’t have a choice anymore either… 🙁 Or, we need to get “real jobs,” work ten hours a day, have no time for our dog, and spend all our well-earned money on rent/a mortgage, utilities, and surviving in a Western society. Time to move to Mexico! 🙂
October 28, 2021 at 10:25
One step ahead you my friend. How long have I been saying move to Mexico? Lol But you’re right, because that’s how many live, working to get by, no more getting ahead 🙁 Enjoy while you can! 🙂
October 29, 2021 at 13:03
We will try to enjoy. Some days, that works better than others. Especially the days that we don’t need any food, fuel, or parts. Sitting still for longer periods of time would help the wallet. Once we get to warmer climes. 🙂
October 26, 2021 at 11:59
What a great update and awesome tips. My hubby and youngest have been to Chicago for a soccer tournament, but I have never gone. I guess I hadn’t thought about lack of places for campers to stay. But glad you found places that worked, though being rudely awakened like that would have my adrenaline going.
October 26, 2021 at 22:33
Hi Kristin! That announcement by the police was totally unexpected and did get my adrenaline going. It happens rarely that we have to move abruptly after settling down. I think the last time was in Mexico in 2006. But I might remember incorrectly. And, it’s the worst when this has to happen at night. But, this was the first time in many years, so we can handle that. 🙂
October 29, 2021 at 16:58
These are excellent tips Liesbet. I had no idea there would be places you could camp for free in Chicago. I had seen on social media that you met up with Ben and Peta. What a delight to see Lisa and Fabio too! I’ve missed her blog and photos since they took a break from travel.
October 31, 2021 at 21:16
Hi Sue!
The opportunity to see Ben & Peta and Lisa & Fabio is what made us decide to go across the northern route and put Chicago on the program. While both visits with friends were way too short, it was worth it to touch base with all of them. With any luck, Lisa and the Captain will be back aboard and on the blog in the spring of 2022.
The places we “camped” for free in Chicago aren’t camping spots per se. They are usually places where it is allowed to park overnight. So, you want to be low key and not overstay your welcome… The idea is that the neighbors are usually okay with having a camper parked in their streets for one night, maybe two. But more might be pushing it… It’s also not much fun and not comfortable as we are just parked in a parking spot, closed in by other cars and often quite crooked.