Chicago: Travel guide, prices and free housing · 2026

DUDaria Udalovaudalova.darya · Dec 9, 2019Read

Where I stayed: Holiday Jones Hostel It took me 8 hours by Greyhound bus to reach my dream city from Columbus, Ohio. I enjoyed traveling with them; the buses are comfortable, rarely full, the trip is cheap, and you can choose any seat, plus use the onboard restroom while moving. Definitely bring a jacket or a sweater, as it is very cold on the buses due to the air conditioning. In general, be prepared for the fact that in all public places, transport, and taxis, the air conditioning is often running at full power. I already wrote that you shouldn't take a large suitcase, and well, it was inconvenient for me to get around with my suitcase, a rolling bag, and a backpack because the subway is absolutely not designed for people with luggage: no elevators, no escalators, only stairs! If you are staying at the same hostel, keep in mind that there are no elevators. The receptionist helped me carry my suitcase (I didn't tip, I don't even know if I should have). The hostel is clean, the bathroom was shared per floor, but it locked from the inside. I was disappointed by the lack of a power outlet on the top bunk of the double bed. To say that I dreamed of visiting this city is an understatement. Since I was 12, I've had a photo in my memory of my friend's older sister who left for the States back in 2008 on the Work and Travel program, which I knew nothing about at the time. In the photo: her, skyscrapers, and a strange mirror object - a bean... At that moment, I felt a burning desire to visit that very city and that very place; I literally saw myself in the photo... All this time, I was sure that one day I would come to this city and see its strange futuristic symbol. First thing after checking in, I headed to Millennium Park; that's where the most popular attraction is located in the very center of Chicago - Cloud Gate. On the way, it seemed to me that very soon, the photo, already quite blurry in my memory, was about to become reality, only I would be in it. When I saw it in person, my smile knew no bounds; I couldn't believe it wasn't a dream. But it was, which made me shine and glow. Many might find such admiration for public sculpture strange, but for me at that moment, it meant only one thing - dreams come true! The next morning was foggy, and I thought it would prevent me from visiting the observation deck on the 103rd floor of the Willis Tower, so I headed to Lake Michigan. On the way, I was surprised by the number of ducks and seagulls freely walking around in the parks near the lake, like pigeons in our cities. The lake turned out to be very clean and blue, which was unexpected for urban conditions. Chicago is a city with an illusion of crime. Why? Because when you hear about it, the persona of Al Capone pops into your head, and personally, I immediately remember the Russian film Brother-2, which takes place in Chicago. The music from the film was playing in my headphones and accompanied all my walks around this city, creating a special mood and the impression that I am here, in a completely unfamiliar city, not alone, like the main character, and Chicago is not a stranger to me. But that's a plot for another movie. Closer to noon, the fog cleared, and I accomplished what I had planned - I went up to the observation deck. The view from there is impressive; you don't even believe or feel that you are so high up, of course, if you are not afraid of heights. The windows with a glass floor protruding from the building are such a popular place for photos that visitors are given only 60-90 seconds depending on the number of people in the group. What I like about such tourist places are the good souvenirs: beautiful, original, high-quality, a little more expensive - so what?! On the evening of the next day, I went to Navy Pier. Admission is free, and the view from there is worth a million dollars - a beautiful night city shimmering in lights. Look at it from the Ferris wheel – the sensations are indescribable! Three days of endless

VPValeriia Platonovalera.platonova1998 · Dec 9, 2019Read

Two weeks later, I left Walker, leaving letters for all the people I had grown to love. Andrey and I took a bus to Minneapolis. On the day of my arrival, I arranged to meet a waiter from our restaurant to sit in a cafe and wander around the city. Coby showed me the outskirts of Minneapolis and St. Paul. We ate incredibly delicious ice cream, and the next day I spent with Ariel—a girl who agreed to host me at her place for free. We visited galleries in Minneapolis and walked through what felt like the entire city. By the way, on the first day, Ariel gave me the keys to her apartment and went to stay with her boyfriend so as not to 'make me feel awkward,' as she put it. Tip! Use the CouchSurfing service; you can save a huge amount of money and see the city through the eyes of a local, but choose your host carefully and thoughtfully, and pick a location that is convenient for you. Be sure to pay attention to the reviews that your chosen host already has. In the evening, I headed to Chicago, where another host, Omar, met me. At 6 a.m., we were sitting on the shore of Lake Michigan watching the sunrise. Then we walked around the city, and afterwards, we went to his apartment. I thought there wouldn't be anything better than Ariel's apartment, but this was something else: downtown Chicago, 17th floor, panoramic windows, a small balcony where we had breakfast. Three guys prepared breakfast, and I was just an observer. After breakfast, we watched a movie. Omar asked if I had a list of places I wanted to see; my list consisted of only two museums. He showed me Chicago, explained the location of all the shopping centers and museums, and then I went to explore Chicago on my own. Again, I ate unrealistically delicious ice cream, wandered around the city, and enjoyed the atmosphere. I didn't take any pictures; it all remained only in my memory. After my walk, I returned to Omar's apartment. He had already finished working by then and told me we needed to leave quickly because there would be a perfect sunset today. We went cycling along the waterfront. He was right; that sunset was perfect. We reached the place where the morning of that day had begun; now Chicago was completely different—familiar, bright, and dear. We danced barefoot in the lake to music and laughed loudly; it was simply unforgettable. In the evening, I lay alone on a double bed and recalled the moments of this summer. Outside the window was Chicago. In the morning, Omar was no longer in the apartment; his work started at 6 a.m. I packed my things, had breakfast, and set off for New York. In New York, I visited the 9/11 Memorial. I won't say anything about my feelings at this place; I think everyone should visit it. For every person, this monument carries a different meaning that is close to them personally. My flight was at 5 p.m. In my headphones, a song was playing that Michael and I used to listen to when we went out in the evenings to talk by the lake. Tears of happiness streamed down my cheeks. I had completed the brightest and most difficult quest of my life.

SSSaniya Shonbayevashonbaeva99 · Dec 6, 2019Read

Chicago is my love. Yes, it is my favorite city. A city I fell in love with at first sight. The city where my trips across America began. Chicago is an insanely beautiful city. I compare it to New York; they look very similar, probably because of the large number of skyscrapers, but it is much cleaner and not as hectic. When I said I wanted to stay and live in Chicago, everyone replied, "Come on, Chicago? Have you seen the winds there?" And you are saying this to a person who lived in Astana with its harsh frosts? Believe me, that doesn't stop me. In Chicago, I brought along a couple of my close friends, which made this trip unforgettable. But besides them, we met several other J-1 participants from Ukraine and Romania, with whom we had a blast. You know what you absolutely must do while in Chicago? Try deep-dish pizza and go up to the 103rd floor of Willis Tower. This pizza is made only in Chicago, and it is incredibly delicious. By the way, it is one of the tastiest pizzas in my life. I am telling you this as a pizza connoisseur. There is one place that makes the most delicious pizza in Chicago; you must go there. Address: 130E Randolph Street Willis Tower is the tallest building in Chicago, and most likely in America. The ticket price is $23, but this is not something you should save money on. You know those pictures of skyscrapers from Pinterest? Well, you will see them with your own eyes and take such pictures yourself. And you will also have the opportunity to stand on a glass floor. I thought it wouldn't be that scary, but... Have you heard that among all the skyscrapers there is a prison skyscraper? I still can't understand how a prison can be in the city center. I was so curious about what was happening inside that building that I examined it from top to bottom. And suddenly, a prisoner started waving at me from a window on the 8th or 9th floor. It was the strangest and at the same time eerie feeling. I couldn't make out his face, but I saw his silhouette and hairstyle. When I walked past, I was left with an unpleasant feeling. But in my opinion, it is worth seeing and experiencing those emotions. And, of course, at night, don't miss the opportunity to walk around Chicago at night. Such a number of lights create a romantic atmosphere. Go to the waterfront, walk around Lake Michigan. Its size is impressive, and the water is crystal clear. Perhaps, after this, you will fall in love, just like I did.

ALAnastasiia Lebedevamylene-farmer96 · Nov 27, 2019Read

The city that stole my heart 2 years ago. My biggest fear was that I would come back and not feel that same thrill. But as soon as we stepped off the plane, I realized: "Home." Delight and anticipation spread through my body, my heart beat faster, and my eyes sparkled with happiness. Arriving in the center, I couldn't stop smiling, because everything was so familiar, so dear, so much my own. And, keeping with this summer's tradition, on the very first day we went to watch the sunset. To the stunning 103rd floor. You, the sunset, and 412 meters below you in a glass cube. My favorite city was sinking into darkness so beautifully that I couldn't look away. Then there were dozens of kilometers walked, thousands of calories of deep dish pizza, and a sea of lights enveloping Chicago. I was drowning in this blissful calm and beauty. Every part of me was rejoicing and admiring. My soul begged to stay. I said goodbye to the city just as beautifully as 2 years ago: sitting at the bar on the 96th floor of The Signature Room, watching the sunset sun reflect in yellow-red rays off the skyscraper windows. The city, shrouded in lights, gave off an atmosphere of mystery with hints of danger. I'm not saying goodbye.

NONatalia Oshaninanatalia.oshanina · Dec 14, 2017Read

Our big trip started on September 1st. We decided in advance that we would go as a group of six, booked a large car in California and all our accommodation (well, almost all of it), and planned our movements day by day. If you are short on time but want to visit as many interesting places as possible, do the same. We used services like Kayak (flights), Airbnb (accommodation), Turo (car rentals), Recreation.gov (camping rentals across America), TripAdvisor (interesting spots), and Couchsurfing (a community of people ready to host guests for free). Walmart was, of course, the sponsor of our food and camping gear. I hope this doesn't count as an ad – just a tip in case it's useful to someone :) So, we quit our jobs five days earlier than planned, did a "big checkout" at home (after all, a team of professional cleaners was on the job), packed our bags, and rented a car again to get to New York. I could talk about this trip endlessly, so I'll leave only fragments. Everyone will decide for themselves how and where they will go anyway. Chicago. The plane from New York lands at midnight, and in just 30 hours, the next one awaits us to California. Was it worth flying in for just a day? Absolutely, yes. This city struck me to the core – I have never seen such beautiful skyscrapers, such urban parks, or such cool subways anywhere else. I could never have imagined how one could build a multi-layered metropolis. Just imagine: the lower level is parking, the level above is high-speed highways, and above that are skyscrapers propping up the sky. Everything is drowning in greenery and buzzing with life. Panorama of the city from the planetarium World-famous Chicago Bean If you happen to visit Chicago, be sure to go to Millennium Park and walk along the embankment to the planetarium, then head back and take a boat ride along the inner canal from Navy Pier to the Willis Tower. You can see the "layers" of the city especially well from the water. You can also take a loop on the subway – the entire Loop is above ground, a kind of roller coaster right between the skyscrapers. Subway line winding between buildings The next point on our route was Los Angeles – that's where we rented a seven-seater car and set off on our own. This city left us with very strange impressions. You won't see a city as such – it's spread out over the territory like butter on bread, and it's completely impossible to get around here without a car. Looking at the skyscrapers after Chicago wasn't interesting – they don't even come close. Besides, there are a lot of homeless people in the center, and even as a large group, we felt very uncomfortable walking around. I was afraid to take out my camera, and there was nothing to shoot anyway. Literally every bench in this seemingly cozy central park is occupied by homeless people But this is the best place to meet the Pacific Ocean. We were at Venice Beach, named after the district where you can feel a bit like you're in Venice. Surfers, palm trees, lifeguards – this is exactly how we usually imagine Los Angeles. The ocean itself is very different from the Atlantic. It is much more powerful; you can't miss a single wave, and you definitely won't be able to fight them. A bit of Venice 200 meters from the ocean Pacific Ocean in all its glory Our trip was not without adventures. In Los Angeles, we rented accommodation on Airbnb, just like everywhere else. At night, it turned out that the landlady was mentally ill... We listened in horror to her screams and the same phrases repeated dozens of times. It's good that it all ended with just a ruined night's sleep. But as it turned out, that was only the lesser of our adventures... The road from Los Angeles to San Francisco would have taken us a whole day, so we decided to split the journey into two parts and spend the night near the town of Monterey. Nothing foreshadowed trouble, but five hours behind the wheel took their toll: at some exit from the main highway, at a very low speed... I s

GIGera Iakuninajakunina.g · Nov 30, 2015Read

Part 2. Chicago. JFK again, everything is clear again. Departure, an hour of chatting with my neighbor in economy class, and I'm there. Chicago didn't welcome me with good weather... it was cold, a fine, terribly nasty rain was falling, and my rather large body was being blown away by gusts of wind. Well, that's understandable! Windy City, duh!)) And since Her Carefree Highness Hera didn't bother to check the weather in the arrival city beforehand and dressed in shorts and a tank top, she unpacked her suitcase right at the airport to get warmer clothes. In the Chicago subway, for some reason, I felt a pleasant sensation of traveling alone for the first time. That feeling when you realize you are alone on another continent, with not a single Russian speaker around you... it's an indescribable feeling. And yet, you feel completely safe. As one guy said later: "This is America! What is there to be afraid of?!" - and that's true! I only had one incomplete day in Chicago, and it was wet and cold. So I left my things at the bus station and quickly trotted to Lake Michigan and back, just to catch a glimpse of the great lake. At the station, I met some girls from Kazakhstan, and I spent the day with them. By the way, we are still in touch!) I returned here on my way back and fell head over heels in love with this beautiful city of skyscrapers, trains rumbling overhead, metal curbs, and a fresh breeze. When my bus arrived, and it was 5:40 AM, it was starting to get light... I, as a person not on friendly terms with common sense, tired, frozen, with all my belongings, firmly decided to watch the sunrise on the shore of Lake Michigan. And so, this frozen, homeless-looking girl drags herself across the entire Loop to watch the sunrise! I will never forget this sunrise!! It was probably the most beautiful thing I have ever seen! I watched as the sun slowly rolled out from behind the horizon, illuminating the coast with a reddish light, while the seagulls, in their characteristic manner, walked around with an impudent look and disturbed the dawn silence with their cries... it was delightful. Afterwards, I wandered to the hostel, finished all the formal business, and went for a walk again. I will say it again, and perhaps a thousand more times, THIS CITY IS MAG-NI-FI-CENT!!! With its architecture, its rhythm of life, its air!! People here have a spark in their eyes; they are different from New York residents! After watching the locals, I wanted to have lunch not in a cafe, but on the street, well, in a park, for example. I took my lunch and went to the coast, and just as I had settled on the lawn under a tree and started devouring my delicious meal, I was attacked by geese!!! GEESE, Karl!!! (Beautiful ones, black and white) A horde of geese surrounded me and filled me with fear! A minute later, miraculously not pecked by the birds, I was already running for my life to a safer place. Evening Chicago is a different story. The lights of the high-rises here replace the stars, which, like in any metropolis, are practically invisible. You can look at the coastline in the evening endlessly. Well, you'll see that in the attached photos. The whole next day I wandered around again, and in the evening I had a trip planned to probably the most famous landmark in Chicago - Willis Tower (Skydeck). You have to see it!! A panoramic view of this wonderful city from a height of 412 meters! The emotions there are just off the charts! I was very afraid that I would be sad and bored when I was going to Chicago, but this is not the kind of city where moments of sorrow can strike... here you enjoy every minute spent on these streets and every breath of always fresh air. So, let's get back to our sheep... that is, to my further journey to the workplace... I waited for my bus, loaded into it, and we headed towards Minneapolis, where my employers were supposed to pick me up in the morning.

ВВадимTantric · Dec 12, 2025Read

Description: This was at one of the best restaurants in Chicago - Roof (Hotel theWit)! Earned: $8172.00

SSSagynysh Sovetsagynysh1704 · Dec 12, 2025Read

Sagynysh Kuatkyzy💫 on Instagram: "In Chicago … zhelsiz tunde zharyk ai with Kazakh national instrument - Sazsyrnai Inst: @iec.kazakhstan https://www.instagram.com/iec.kazakhstan/profilecard/?igsh=MWc3a2x2ZWg3OG16ZQ== TikTok: iec_1989 https://www.tiktok.com/@iec_1989?_t=8rnZQ6QHP5a&_r=1 YouTube: IECRiga https://youtube.com/@iecriga?si=ZqLWJYa0cptlKb0H" Видео: https://www.instagram.com/reel/C_gKHYvP_ez/?igsh=MTY4MnEzcTE3ZTZtZw==%0A%0A2