Hitchhiking Out of Chicago is a B****

The day had arrived for Ben and I to say bye to the Windy City and hello to Minneapolis. We knew that hitchhiking out of Chicago wouldn’t be easy, but we weren’t expecting it to be impossible.

Little did we know that the last ride we would get in Illinois would be in the back of a cop car.

To avoid local traffic, Ben and I decided to go towards the outskirts of Chicago i.e. the suburbs. To get there we would have to take the local subway (CTA) for one and a half hours and then take the bus for about 25 minutes to the intersection of the US 41 and the I94. This was a great plan, so we thought.

It wasn’t after we got off the train and walked up to the CTA employee that we got our first bad news of the day. Apparently, buses don’t run on Sundays. How in the world did we miss that very important piece in our planning?

Welcome to Chicago where Buses don't run on Sundays
Welcome to Chicago where buses don’t run on Sundays

Anyway, Ben and I figured that maybe we could walk the distance, it couldn’t possibly be that long of a walk. WRONG!

According to Google Maps, it would take us about an hour to get there by foot. We were feeling pretty optimistic and decided to walk and try to hitch a ride along the way. As we walked along the street, cars after cars just passed us by. The drivers wouldn’t even glance at us, it was as if we didn’t exist. Forty-five minutes into our walk, someone finally pulled over and asked if we needed a ride. He told us that, “People around here are real snobby and they won’t pick up hitchhikers”.

In a matter of minutes, we were where we needed to be but of course it just so happened that  a cop car was waiting right at the intersection. The driver felt our concern and offered to drop us at the next exit on the highway, and we gladly accepted not knowing any better.

Usually when you get off at a highway exit, there is an entrance ramp close by, but not in this case. With our awesome luck the entrance ramp was an hour walk away. How do we know that, you ask? Because we had to walk it and no, this time nobody stopped to give us a ride.

To make matters worst, when we finally made it to the entrance ramp we noticed a cop car waiting at the end of the street. I barely had enough energy to put my thumb out to hitch a ride out of Illinois, let alone have a cop tell us we couldn’t hitchhike here. We were in the middle of nowhere. Fortunately, as we walked a little further down the street, the cop disappeared around the corner, giving us the chance to hitch our first real ride.

Three hours later, we were still in the same spot holding our thumbs out. The entire time we were waiting, only two cars stopped and unfortunately, they were headed in the opposite direction. We were getting restless, this was the longest we have waited so far. A few minutes later, a car finally stopped, but not one we were happy to see. The same cop that we saw early, had made his way back to inform us that we couldn’t hitchhike here. He asked us some routine questions and then pulled off. He didn’t even wait to make sure we left. It was as though he felt sorry for us.

So now we were even more desperate for a ride because we were on the cops radar, but that didn’t matter because 15 minutes later another cop pulled over to question us. The questions were no different. He told us that three people called us in because we were hitchhiking. So not only were the drivers ignoring us, but they were also calling the cops. This was just freaking epic.

Though this cop was friendly and tried to help us, he eventually gave us the boot and told us we had to get back on the street that ran along side the highway (same street we came from earlier to get on the entrance ramp) and head west until we hit the next town which was about 1.5 miles away.

We had no choice but to do it.

Twenty minutes into our yet again endless walk, a female driver that was actually on I-94 heading east, saw us and thought she would turn around and help us out. She took us to the next town and explained to us that this would be a better place to hitchhike from. Within 15 minutes of trying to hitch a ride from that spot, two cop cars pulled over.

They both seemed fascinated by our way of traveling but unfortunately they too had to give us the boot. Apparently, too many people were complaining about us hitchhiking in their little town. It was starting to get real annoying. People were snitching, and I couldn’t really understand why? If you don’t want to pick us up, all you have to do is keep driving. It’s that simple.

Just like the other cop before, these two cops told us it’s “illegal” to hitchhike in Illinois and we would have to leave this spot. They suggested we walk to the next town along the SAME damn street we came from but this time it was 5 miles away.

WTF, this couldn’t be real life. Yet again, Ben and I picked up our bags and started walking. As we headed towards a gas station to use the restroom, someone saw us and offered us a ride to another entrance ramp.

As we reached the entrance ramp, and placed our bags down, Ben started laughing hysterically. Barely able to speak he said, “There is another cop coming”. “You have to be shitting me, we weren’t even here for a minute.” Once again we were told that we can’t hitchhike here and we should keep it moving.

Sounds like your been reading the same thing over and over again huh? Well just imagine how we felt living through it.


It was now 5pm and we had gotten nowhere, we pretty much walked most of the way. We needed to figure something out because the area we were in, was way to busy for us to pitch a tent. Eventually, we decided it would be best if we just head back to Chicago and take a 6am bus to Minneapolis because there was no way we where getting out of Illinois by hitchhiking.

So we used google map to find the best way to get out of our little nightmare and it’s best suggestion was to walk four and a half hours to the train station we initially came from.

Though we had more than enough time to catch the 6am bus, the CTA trains stopped working at midnight and would start running again at 5:30am, which meant we needed to catch the train that night or else we would miss the bus.We had about seven hours to make our four and a half hours walk to the trains station with our heavy ass backpacks.

For the first two hours we stayed positive, we took breaks when we needed too, and gave each other high fives when we made it to our next break point. We even laughed about the situation we where in. Actually, I was laughing so hard I was crying because it was just too funny. Nonetheless, we were optimistic and sure we were going to make it.

By the third hour, our legs barely wanted to move anymore.

We got to the point where we started emptying out our bags and throwing away “useless” things just so our bags would weigh less. But that didn’t help much. With every step those bags got heavier, our legs were ready to give in, and to make matters worst it started to rain.

This was starting to feel like we were characters in Daniel Handler’s book a “A Series of Unfortunate Events”. At some point we were putting our thumbs out in hopes of someone calling the cops on us, just so they could give us a lift to the train station. But of course, when we actually wanted the cops to show up, none of them did. Matter of fact, about six cop cars passed us by but not a single one even acknowledged us.

It was 10pm and we still had an hour to go and Ben and I had lost faith in our legs. There was no way we were going to make it.

However, just as we were about to give up, a cop car came to our rescue.

With his flashlight pointing in our face and nearly blinding us, he asked us if we where hitchhiking, because some people called us in. Surprise, surprise!

Before we could even answer, three more cop cars with their flashing blue and red lights pulled over. Suddenly, there were 5 cops standing around us, asking us questions. It was starting to get confusing for both them and us. I felt like we were in an interrogation room, being questioned for a crime we didn’t commit. We were just too tired for all of this.

Eventually, they told us that they would give us a lift to the train station but we would have to ride in separate cars and be padded down to make sure we didn’t have any weapons on us. It seemed like the only reason they offered us the ride was because they wanted us out of their town, but who cares about the reason. We were finally off our feet, and we were going to make it to the train station before 12am.

But the best part was that we hitched a ride in a cop car :D.

When we finally made it to the train station, I swear a tear ran down my cheek. I felt like kissing the station floor, that’s how ecstatic I was.

We gladly got on the train but as we sat down, I felt a sense of disappointment. We wasted the whole day trying to get somewhere just to end up back to where we started, and not only that, we damn near walked the entire time. This day was just unbelievable and we will definitely never forget it.

Beautiful city but not for hitchhikers
Beautiful city but not for hitchhikers

Ben and I decided to sleep in Union Station that night, that way it would be easier for us to catch the 6am bus to Minneapolis. However, when we got to the station, we found out that Union Station closes at 1am and doesn’t reopen until 5:30am.

Great there we were with no place to sleep.

We tried contacting the person that hosted us the previous night to see if we could crash at his place but he didn’t answer his phone.

At that point I had no energy left, I dropped my bags and sat down on the floor. I was so exhausted I could barley keep my eyes open. The only option left for us was to sleep in the subway station for the night.

For the first time on our trip, I felt like a true hobo.

Just as we were about to get “uncomfortable”, a train heading to the O’Hare Airport stopped in front of us.

Light bulb. Why not sleep at the airport? We grabbed our bags and hopped on the train.

After finding a spot to sleep, I pulled out our sleeping bags and was ready to knock out when Ben had one of his crazy ideas again, “Baby, have you ever wanted to walk into an airport and just buy a ticket to wherever?”  “Yeah I guess, but …” “Then we should do it”, he quickly responded. Seconds later he was on the phone looking for cheap flights to well….wherever.

Eventually, we were down to two options, Cancun or Mexico City. We flipped a coin and Cancun won.

It was 4am when we booked our 8am flight to Cancun. One minute we are going crazy trying to hitchhike a ride out of Chicago, the next we are on a plane heading to Cancun, Mexico.

Ben is enjoying the fluffy clouds outside
Ben enjoying the fluffy clouds

We had a shitty ass day and because of it we landed in Mexico. Though things didn’t go according to plan and Ben and I have to put our hitchhiking tour of the U.S. on pause, we are really excited about being in Mexico.

Have you every had a shitty day that lead to a spontaneous travel decision? If so we would love to hear from you.

The Author

Jazzy is a professional travel blogger and the chief editor of Road Affair. She has been traveling around the world with her partner in crime, Ben, since 2012.

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  1. WOW! That sounds pretty crazy! It sucks that you all spent the day like that but its awesome that you made a snap decision to go to Mexico! I’m excited hear more about that adventure:) You all are living it up! Taking on life by the horns. Im really enjoying living vicariously through you all!

    1. Thanks Nic!! It was a crazy day but at least we can laugh about it now and say that that needed to happen in order to get us here (Mexico). We are loving the this city so far and we promise to keep the stories coming.

      Best wishes

  2. that was a difficult day, but you got a great ending. We had to changes travel plans once because of having to look for a hospital. I didn’t mind the plans, I just wanted my friend would be fine. She had to have an emergency surgery :(

  3. I’ve lived in Chicago my entire life – in the city, not the suburbs – and I can tell you that CTA buses DO run on Sundays. Service on a particular route may be suspended on Sundays but not ALL buses.

    If I’d known of your plan to hitchhike in/around Chicago, I would have advised against it. Chicago is seeing the worst crime in decades and people here are quite leery. Moreover, we hear over and over again that if we see anything/one suspicious, we should call the police. That might explain why so many police officers approached you.

    It is a crazy story but it seems to have had a decent ending for you.

    1. Hey Francesca,

      See that is what we thought, but maybe that is not the case in the suburbs because everyone has a car (totally assuming). We found that super weird.

      It’s funny because someone that lived in Chicago actually told us that he had some friend over that hitchhiked into the city and had a few run in with the cops and that it was illegal. But we ignored him because when we looked it up online, there was nothing that said it was illegal. We figured his friends must have been hitchhiking wrong. We would have saved ourselves a lot of trouble if we would have just listen to him.

      But hey, if we didn’t have people calling the cops on us, we would have never made it back into town plus we wouldn’t have made it to Mexico.

      Thanks for giving us the inside scope. It explains a lot. Mucho Gracias (Thank you very much)

  4. Great story! Absolutely LOVE the end! I feel your pain though about the whole day waiting and getting nowhere. I admire your optimism! And I can’t believe that people would call the cops just because they see somebody hitch-hiking!!! I’m sure you’ll be laughing about this story now sipping a cocktail on one of Cancun’s beaches! :-)

  5. WOW, what a crazy story. Actually, in the Caucasus cops give rides to hitchikers pretty frequently, especially in Georgia. I think it’s because they are trying to make their reputation a bit better and look friendlier as historically police in this region used to be very violent, corrupted and rather hated. I was super surprised when I got my first police car ride. It was less crazy than yours though…

    1. When we got pulled over, it’s was definitely a surprise for us to see how friendly most cops were, they were also excited about our mode of traveling, but they still gave us the boot, which clearly after awhile didn’t seem so nice to us. But hey,it got us to Cancun and we love it here.

  6. I lived in Chicago for a number of years so was troubled at the outset when I read your post title. You had a very rough day made no easier by the cops. It also didn’t surprise me that people called you in to the cops as a hitchhike in those parts is so rare it can, for some, only mean trouble. All that said though you an amazing experience and the reward is the sun and sand of Cancun. Make sure you go further south though to Tulum, or go inland. Cancun is kind of crazy. I did have an experince like this once while hitching in Italy. Got pulled over several times by cops. My day ended in the small town of Aousta by the French border. There was nowhere to stay but my pathetic puss must have made the bar keeper feel sorry for me so he gave me the keys to his bachelor pad in town. Apparently this was a place his wife knew nothing about; only his girlfriend. Had a good night sleep and hit the road early in the morning.

    1. Well, we learned our lesson about hitchhiking out of Chicago. We should have talked to you to see how plausible it would be to hitchhike in Illinois maybe we would have saved ourselves some trouble. But hey, who cares now, we can laugh about it as we soak up the sun and dig our feet into the white sand.

      We had a day trip to Tulum a week ago (post about it coming soon) and loved it, we went to the Gran Cenote and the Mayan Ruins.

      Thanks for sharing Tim, see everyone has a bad day sometimes it’s how we end it or use it to make other situations in the future better.

  7. Crazy that it’s illegal to hitchhike… Whatever happened to the adventurous North-American spirit? Kerouac must be turning in his grave. But at least you’re in Mexico, which is a-ma-ZING! Hope you’re having a great time!

    1. That spirit is long lost and is slowing trying to creep out of the grave. Hopefully, more people will be more open to it as they were before and they can make it an officially mode of travel. That would make Kerouac jump out of his grave in joy !!!

      p.s. In most states in the USA, it is not illegal to hitchhike.

  8. Blimey, you won’t be forgetting that day in a hurry! Talk about bad luck, but what an outcome, really impressed with the spur of the moment Mexico though, hope it turns out to be an awesome result of a rubbish day!

    1. Haha we most definitely won’t. Sometimes you just have to go with the flow and take it as it comes. So far it definitely has been awesome and we are looking forward to more awesomeness :D

  9. This story is crazy. While I was reading I wasn’t sure if everything would work out! Though I know you guys had a sucky time, I’m very glad for you that it DID work out. (Genius – sleeping at an airport!) Hope Cancun is great!

  10. Wow what a mission! I haven’t hitched in the US but had no trouble in Canada, think the longest we waited was 1 1/2 hours but usually got rides within 30 minutes.

    1. We had no problem hitchhiking rides until we got to Chicago. Our longest wait was 2 1/2 which wasn’t bad and we got most of our rides between 20-30 mins as well.

      Thanks for sharing those stats with us Katie.

  11. Seems like y’all really earned this Cancun trip, enjoy! ;) That was certainly a twist ending, I did not expect coming. However there is nothing more satisfying than buying a ticket from your smartphone as you lounge around the airport. As a permanent nomad who refuses to plan ahead I tend to do this a lot hehehe ;)

  12. This is hysterical! I mean, I know it probably wasn’t in the moment (even though you guys found a way to laugh about it) but it really does make for one of the more entertaining blog posts I’ve ever read! Made it all the better that I could so easily imagine myself in your situation…Love the ending!

    1. I am glad we can entertain you Bisbocci :) Even in the moment it was funny, because it seemed so surreal. But towards the end when our legs were giving in, we weren’t laughing anymore. The ending definitely made it all worth tolerating. And you are right, it did make a hell of a story to tell and write about.

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