When it comes to traveling, I like to say I’ve been to more places than some people and not as many as others. Not that I’m in competition. I doubt anyone cares about which states I’ve traveled to and which ones are still on my bucket list.
In the summer of 2025, though, I got to tick a major US city off of my travel bucket list: Chicago. I went for a horror convention but factored in enough time to do some sightseeing of the city during this extra long weekend. Check out my three days in Chicago below.
Arriving in Chicago
My sister and I left Pittsburgh in the early afternoon and landed around 2:00 pm. The flight was fast, but we found ourselves circling the airport for a bit while waiting for an open runway to land.
I was excited to see O’Hare after watching the McCallister family sprint through it several times over the years during my rewatch of Home Alone and Home Alone 2. The chessboard floor and cylindrical ceilings looked just like the movie, but I was surprised by how narrow it was and how tightly they packed people into those narrow spaces.
It was Thursday, July 31st, and we’d be there until Monday morning. I like to create a loose itinerary before I go anywhere. I basically pick out a few destinations and then look for what all can be done within walking distance of that area. I also make sure any museums or attractions we want to visit will be open on the dates and times that we plan to go. Then, we wing it from there.
The hotel
We stayed in Rosemont, IL near the airport because that’s where the convention was being held. There was a free shuttle that took you from the airport to the hotel, and there was a lot of construction going on around the airport. So, it was nice to have this shuttle that knew exactly where to go to travel around it.
The convention didn’t start until the following afternoon and ended on Sunday afternoon. So, I knew we had that evening, the next morning, and Sunday night to explore the Chicago area. Once we checked in and dropped off our stuff, we called an Uber and headed into the city.
The first commute into downtown Chicago
The city is technically only a half hour away from the airport, but when you factor in traffic, particularly rush hour traffic, the travel time increases greatly. I considered using the El Train. I could even see a station within view of the hotel, but it basically required you to cross a highway, and I saw no practical way to get over there. So, Uber it was.
The ride into the city that first evening, a Thursday night around 5:00 pm, was over an hour long. It was gridlocked the whole way. I remember staring out the window the entire time as we crawled along the multi-lane highway and thought, this road is just too small for this city.
Pittsburgh can be a nightmare too. It’s small and essentially situated on a peninsula. So, traffic can back up fast, and one accident in the tunnels or on a bridge or even a big event, such as a concert or a football game, can put you in a standstill.
I don’t know what it’s like to travel into Chicago from any other direction other than Rosemont, but I can say that every Uber driver we used during the trip warned us of the traffic in advance, no matter what time of day it was. I could also see the frustration in having to drive this route, even though it was a pretty worthwhile one in the end.
There was a lot of honking, a lot of fender benders, and a lot of cars that just seemed to be rusting from the inside out. I later looked up to see if Illinois required annual vehicle inspections the way Pennsylvania does, and I was unsurprised to learn that they don’t. I saw vehicles zip tied together, windshields with spiderweb cracks in them, and tires so bald I wondered how they were able to even function in the stop and go traffic.
The river walk
I had the Uber driver drop us off on a random street corner, just so we could be near the river walk. The initial plan was to just take in the downtown area before stopping for dinner.
The Chicago River felt familiar and comforting. It was super narrow, though compared to the ones at home. I felt like I could easily swim across it if I needed to, not that I thought I would need to. The water gave off a greenish cast, which I was surprised to see, thinking that was more of a St. Patrick’s Day thing, but it was still pretty green in late July heading into August.
The river was lined with walkable and drivable bridges. I liked the ability to easily cross over the river from one side of the city to the other using these bridges. The bridges were also low, so the boats in the water had to be small to fit beneath them.
The river walk was a little crowded and confusing. Being a Thursday night. The college kids were out in full force, hanging out on the steps that lined the front of the restaurants.
The actual walkway was very narrow, and the pace of the Midwesterners and even the tourists was well below the pace that I was used to walking in the east. There was more of meandering and less of sense of purpose which irritated me the entire trip. I knew the Midwest would be more laidback in general, but I thought the big city of Chicago would be the exception to that rule.
Navy Pier
After a few blocks, we got back up onto the street and crossed a bridge to the other side of the river to head to Navy Pier. Navy Pier sits right along Lake Michigan. I’d been to Lake Erie a few times before, so I felt like I knew what to expect from this side of town. It would be breezy like the ocean but not salty. There would be a boardwalk with a Ferris wheel and other touristy things to do.
What I wasn’t anticipating was the windiness of the area. Yeah, Chicago is called the Windy City, but it wasn’t nearly as gusty near the river as it was by the lake.
It felt very family friendly in this area. There were rides and theaters and places to eat. A stage was set up, and people were listening to a band play as the sun set.
There was an awkward, though expansive view of the city at the edge of the lake. The buildings felt scattered with no distinct skyline like New York has. They also felt very modern for such an older and larger city, not that eclectic mix that I’ve seen in other cities.
The sunset was pink, though hazy. There were wildfires burning in Canada at the time, giving off a smoky hue.
First meal
While trip planning, I had seen a restaurant in the area called Ed Debevic’s, a 1950’s themed diner that looked like a cute place to eat. We headed that way, and when we got inside, the music was blasting, but the hostess was nice and said that it would be a 10-minute wait.
We stood in the entryway with about a dozen other people. As we did, we could see the waiters wearing grass skirts and acting crazy. Sometimes they’d get on a little platform made up to look like a stage and make the diners clap and scream obnoxiously.
I then looked around at the signage in the area and realized that this was one of those restaurants where the staff is intentionally rude to and roasts its customers. As hungry as I was, I wasn’t about to be made to wear a weird hat or be mocked while I tried to eat a hamburger. My sister’s subtle nudge let me know she felt the same, and we left before our names were called to be seated.
I try to eat local when I’m in a different place, but when in a bind, we go for the chains. We have Shake Shack at home, but I’d never tried it before. It was nearby. So, we headed there.
It was nearly 8:00 pm when we finally got our food. I hadn’t really eaten since lunch. So, I was ready to dig in. It was good, even if I did feel a little guilty about eating a chain place.
Ending the first night
From there, we walked back towards the river to look for a safe place for an Uber to pick us up. It was still super windy, and there wasn’t a lot of foot traffic which made me uneasy.
The El train runs above the roads. So, it makes you feel like you’re in a tunnel as you walk beneath the tracks. It reminded me of Christopher Nolan’s Dark Knight trilogy which was largely filmed in Chicago. The films utilized these streets to create a dark maze of a cityscape, which was cool onscreen but very creepy to a tourist who saw dark corners everywhere from which you could be jumped.
We ended up at this turnaround on North Michigan Avenue near the Tribune Tower. There was a wide sidewalk there where you could stand and where cars could pull over to drop off and pick up people. I called for an Uber and watched our driver get confused and circle the area at least once before he picked us up.
A fender bender occurred in front of us not long after we got underway. The two drivers got out and began a shouting match as our driver weaved around them. The ride back was not nearly as long, though the highway was still a bit backed up. I was relieved when we got dropped off at the front door.
Being so close to the airport, I expected to hear low flying planes all night. Surprisingly, it wasn’t all that loud. Most of the planes seemed to head in the opposite direction of the hotel, and those that did come that way didn’t feel like they were about to land on the roof or anything.
The second day
The next morning, we headed out early to sightsee before the convention started late that afternoon. We decided to start at Cloud Gate, located in Millennium Park, just a few blocks back from where we had gone the night before.
It was a Friday morning, so a lot of people were heading to work. Of course, we got caught in commuter traffic, but it wasn’t as bad as the night before, and I was beginning to accept the fact that there was no such thing as a half hour ride into the city.
Millennium Park was pretty dead at this time of morning, but there were still some people hanging out. The bean-shaped statue of Cloud Gate looked just how I thought it would from seeing it on TV and in travel vlogs on YouTube. We got a ton of good photos without hoards of people gathered around it. We were also able to stand under it without being shoulder to shoulder with other tourists.
From there, we traveled through Millennium Park, taking the various paths through the gardens and the past the outdoor pavilion. I always look for green spaces when I sightsee through a city, and this was a good one. It wasn’t a big park, and it wasn’t isolated from the city the way that Central Park can be, but it was nice.
Afterward, we walked down to a nearby Dunkin Donuts, got some breakfast, and brought it back to the park to eat it on a bench. We then ventured over to the river and did some more of the river walk again.
The cinematic corner
I found out that if you followed the river west and followed the curve south, you could end up at the corner where Heath Ledger’s Joker was first introduced in The Dark Knight. We had a few hours to kill before The Art Institute of Chicago opened. So, we decided to head there on foot and see what we could see along the way.
The walk was about two miles, and it seemed to take forever, even though the roads are flat. Surprisingly, there wasn’t a lot of foot traffic. You also didn’t see a lot of scary people around. There was one man sitting on the sidewalk who appeared to be having either a major drug trip or a psychotic episode, but he wasn’t hurting anybody or in anyone’s way, and he didn’t seem to be in any kind of major distress. It was a far cry from New York, or even much smaller cities, which are just lined with homeless people.
Eventually, we made it to the spot, located at 404 West Harrison Street. It’s a pretty unassuming corner. A parking garage is located cattycorner across the street, and we matched up the angle in the movie with our cameras and snapped away. The El train was off in the distance, and now it’s what I look at every time I see this scene, such an obvious reference to Chicago which is unconvincingly standing in for Gotham City.
On the way back, we took a different route and ended up walking past a branch of the Chicago Public Library. We went inside to use the bathroom, and here is where I found that old school architecture I was looking for. We explored all five floors of the building before continuing on our way.
The Art Institute of Chicago
Back at Millennium Park, we sat and watched families play in the Crown Fountain, which has these LED towers that display images of smiling people. At a certain point, the towers spurt water from a hole placed at the mouth of the person displayed on the screen.
Lollapalooza was taking place that weekend. So, a lot of the nearby streets were blocked off at the time, and Grant Park was essentially off limits.
The Art Institute’s main doors were the only ones accessible at the time. So, once it opened, we ordered some tickets online and then headed in.
This museum is huge with multiple buildings and floors. Even with a map, we had trouble finding every exhibit, and we ended up missing a large chunk of famous paintings there, including pieces by Edward Hopper that I would have liked to have seen.
However, we were able to see “A Sundy on La Grande Jatte,” by Georges Seurat, along with some Van Goghs and Monet. I was even surprised to see Figure with Meat, the Francis Bacon piece that The Joker saves from destruction in 1989’s Batman. It turned out to be a very Batman heavy day in Chicago.
Giordano’s
After hours of exploring the museum, we decided to head to Giordano’s, a famous pizza place in Chicago known for deep dish pizza. I chose this place because it was so close to Millennium Park, and I really wanted to say I tried deep dish, even if I didn’t like it.
The Lollapalooza crowd was out in droves by then. The sidewalks were packed, but it didn’t feel overwhelming or like we were at a standstill.
When we got to the restaurant, there was a line out the door, but it moved fast. Once inside, we were instructed to order our pizza right off the bat and then wait for a table. They explained the reason why they have everyone order first is because it takes at least 40 minutes for each pizza to cook. So, this cuts down on the wait time.
We ordered a small cheese pizza to split between the two of us and were seated within 15 minutes. Once there, we were allowed to order sides and drinks. I got a side salad to hold me over until the pizza was ready. It took a while but getting that heads up ahead of time made the wait seem not nearly as long as it could have.
When the pizza came, the waitress served us and got us ready for the “cheese pull,” which felt like a magic trick despite it just being a mundane string of cheese that kept itself attached to the pie as she slid under a cut slice with a metal spatula.
The sauce on a deep dish pizza is on the top, and the cheese is in the middle. So, it seems like you’re going to just get a mouthful of tomato. Instead, it’s mostly cheese, which was right up my alley. It tasted like a crusty lasagna, and it was so filling.
We could each only eat two pieces, and we got the rest to go. Our hotel room really only had a refrigerator for drinks. It wasn’t meant to keep food cold. It also didn’t have a microwave, though I later discovered one at the snack bar downstairs that we could have used. So, I never ended up eating my final piece of the six-cut, but I was so glad that I had tried what I did while it was still fresh out of the oven.
The ride back
From there, we headed back to North Michigan Avenue to catch an Uber in the same place we had the night before. We got picked up by a guy named Steve who was by far our chattiest driver of the trip.
Steve warned us that he was going to take us on the scenic route to avoid the highway. It wouldn’t get us there any faster, but it would keep us moving versus sitting in irritating traffic. We also got a backyard tour of the city, including his home turf.
Steve was an older guy but a newlywed. He told us his wife was a voice actress, and I wish I’d pressed him for more details on her so that I could listen for her voice in commercials or cartoons. He said he decided to pick up a few driving jobs for the afternoon while she got her studio space ready in their new home. He also suggested a good Italian restaurant for us to try, and I kept it in mind for our final outing on Sunday.
The drive was long. I nearly dozed off in the car during the stretches where Steve wasn’t chatting to us.
We got back to the hotel and got in line to get our convention tickets. From then on out, we were in convention mode until Sunday afternoon. We left the hotel only to head to a nearby mall in Rosemont to get some dinner on Saturday night.
Sunday afternoon
After the convention ended on Sunday, we decided to head to Graceland Cemetery. I wanted to see some of the famous graves there.
Still decked out in our convention gear, we caught an Uber to Graceland, which was about 13 miles from our hotel. Our driver was confused as to why we were going to the cemetery.
“Are you going to a funeral?” He asked.
“No,” I said, “Just visiting.”
“Oh. Do you have a family member buried there?” he wondered.
“No,” I explained, “We’re just going to explore.”
He still didn’t get it.
This driver was the craziest of them all. He made crazy U-turns and crossed over medians to get to where he needed to go. I think he could sense my anxiousness because he asked me to tell him if I wanted him to slow down.
Graceland Cemetery
When we got to the cemetery, I was a bit rattled from the ride in. It took a long time for me to get my focus back and to be in the moment.
The famous statue, Eternal Silence, was easy to find. It’s near the front entrance with the El train tracks elevated in the background. The trains were so loud as they went by. It frequently broke the peacefulness of the grounds.
There were your standard mausoleums and various gravestone styles. A muddy pond with a weeping willow draped over it brought a sense of ease to my uneasiness.
At one point, I took picture of a gravestone with a yellow disc mounted above it. This was the only photo I took in the cemetery that blurred, but it didn’t blur in the usual way. Instead, it looked hazy and streaky, and I didn’t know what to make of it. I also took multiple shots and couldn’t get a clear one, but photos I took before and after of other parts of the cemetery turned out fine.
Almost locked in
There were other people in the cemetery but not a ton. It’s pretty standard to be only one of a few people traipsing through these places these days. It was close to 4:30 in the afternoon when we were winding our way through the back of the property and a vehicle approached. A man called to us and politely, though firmly, told us that the cemetery had closed at 4 pm and that he’d meet us at the front.
I was shocked. I couldn’t believe that the cemetery would close so early. It was hours from dusk, and most cemeteries I visited were not locked at night.
We were a long way from the front entrance. So, we cut straight through, walking as fast as we could. I was relieved that he had warned us before locking us in, but I was also worried that if we took too long, he would lock us in anyway, and then we’d have to call for help.
My tendency to fear the worst got the better of me as I rushed my sister to the front entrance. On the way, we watched a young guy on an electric scooter speed past, and I felt less guilty for being in the cemetery after hours, but I hated that he had a much faster way of getting out than we did.
I was relieved to find that the gates were still open when we got there. There was even a sign posted at the entrance with a number to call if you did get locked in. So, we had options, other than trying to climb the iron fence that surrounded the property or calling the police.
Right next door to Graceland was Wunder’s Cemetery, a much smaller cemetery which I had also been planning to visit but which had also closed. This cemetery was pretty overgrown and had a much lower chain link fence surrounding it which became more dilapidated as it ran along North Clark Street. So, I wasn’t that upset about missing it in comparison with Graceland Cemetery.
Wrigley Field
We had a ghost tour to go to at 8:00 that evening. So, we had time to kill. The plan was to walk from Graceland Cemetery to Oz Park. It was a two and a half mile walk which would only take about an hour. We planned to stop to eat somewhere along the way as well as stop by Wrigley Field and whatever other sights we might run into.
Wrigley Field was only about a half mile south. While we were in Graceland Cemetery, we could hear cheering from the stadium every so often. So, we knew there was an afternoon ballgame going on at the time of our visit.
The game was letting out as we headed towards the stadium. So, as we were walking towards it, everyone else was walking away from it.
A sea of blue Cubs shirts filled the sidewalks as people filed out. The neighborhood was very residential. So, a lot of these fans seemed to be walking straight home from the game. Still decked out in our horror-themed hoodies and backpacks, we were two black dots in a sea of blue, but the crowd was pretty friendly and in a good mood.
As we neared the stadium, we got swallowed in the bustle of vendors selling merchandise and food and crowds of people standing around and socializing. A large electronic sign on the front of Wrigley Stadium confirmed that the Cubs had won.
The stadium had a lot more character in person than it seemed to on TV. It has an interesting design and feels very personal and lived in rather than dilapidated and ugly as it appeared in movies and on the baseball games I’d watch on TV. It felt good to be around that positive energy, and I liked the safe feeling of the neighborhood.
Dinner time
Just past the stadium, the area became even more residential. Once the crowd cleared out, it was just couples walking their pets or pushing babies in strollers. There were old, stone houses and brick apartment complexes. It felt historical but also livable and convenient with shopping areas just down the street.
On North Halsted Street, we found Sapori Trattoria, a restaurant that our Uber driver, Steve, had recommended to us on Friday afternoon. The business was small, and the front entryway appeared to be packed with people.
So, we kept going, and further down North Halsted, we found a Raising Cane’s. Again, this is a chain that we have at home but not in super convenient spots. So, we decided to try it while in Chicago. The place wasn’t too busy, and we barely had to wait for our food. It felt good to hang out there for a while and rest up for the ghost tour.
Oz Park
The restaurant was only a five-minute walk from Oz Park, and we were still super early. So, we headed in there and explored for awhile while we waited for our tour.
Oz Park is a Wizard of Oz themed park with tennis courts, a baseball field, a pickleball court, a playground, and garden. The park itself is square shaped, and on each corner, there’s a statue based on one of the four main characters from The Wizard of Oz.
The ghost tour was scheduled to meet in front of the Tin Man Statue. Of course, we walked every corner of the park before we found it on the fourth and final corner at the intersection with West Webster Avenue and North Larrabee Street.
Just across the street was a Target where we were able to use the bathroom and load up on drinks and snacks for the evening. We then headed back to the park to wait for the ghost tour as dusk fell. You can read all about the ghost tour in my post, US Ghost Adventures Chicago Ghost Tour + Discount Code.
Last moments in the city
The tour ended right where it began. After we left our guide, we headed back across the street to the Target to call for an Uber to take us back to the hotel. We got our first female Uber driver which was such a relief, considering it was after dark. The ride back was the smoothest of any we had, likely because we didn’t have to pass through the heart of the town this time.
We got back to the hotel a little after 10:00 pm and then got ready to catch our flight early in the morning the following day. That morning, we waited for the shuttle to pick us up to take us to the airport.
I thought we’d be the only ones on the shuttle that early in the morning, but instead, the turnaround was so full of people with baggage that the shuttle filled to the brim, and we had to wait for the next one. We had time to spare, so we hung out, and the next shuttle came relatively quickly.
I remember a large family waiting with us. There must have been five or six kids, each with their own suitcase, but they seemed to be pretty self-sufficient and knew the drill when it came to traveling. They took up a large chunk of the shuttle, and I have a feeling not everyone made it on that time either.
The airport was packed as well, but the security line moved so fast that I felt like we had lucked out in comparison to other people who have had horror stories about traveling through O’Hare International. The flight was on time, and we were heading back east, towards the eastern time zone and the comfortable familiarity of home.
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My wife and I lived in Chicago for 5 years…as you know, as windy as it is, the moniker is based on the verbose politicians of an earlier time – non-stop “windy” talkers….everything you did was the perfect way to discover this city, the riverwalk, the lake, the food…so glad you had a great time and thanks for sharing!