TripAcross.net
Total Miles Traveled: 62,631
Her View
Chicago - Caywood's perspective
Chicago: a city of public parks. It is a huge city, but surprisingly I am totally in love with it. So much to see, always something to do, many public transportation options. I love this city.
We started Chicago in the morning with the typical downtown tourist things: Buckingham Fountain, Millennium Park, the waterfront, and Navy Pier. Unfortunately the one day we had in Chicago was super foggy, so we planned but weren't able to do 360 Chicago (previously the Hancock Building). Buckingham Fountain was gorgeous, even surrounded by a light grey curtain of fog. Millennium Park is never a disappointment. We got to take plenty of goofy pictures by the bean, watch little kids splash around in the Crown Fountain (Feliks thought it was the Clown Fountain), and walk through the colorful flowers in the Lurie Garden.
Driving bikes in Chicago was actually not bad at all. They have bike lanes and sidewalks all over the place. We biked over to the marina to look at the hundreds of sailboats, then headed to Navy Pier. FYI bikes are not allowed on Navy Pier. We walked up and down the pier, looked at all the fun boats, and got a drink. Really cool place. They actually had a Lobster Festival at the end of the pier while we were there, but we didn't go due to the $12 admission and the fact that I don't like seafood. After walking the length of the pier outside we went inside to walk through the stained glass museum, then up top to see the Ferris wheel. I love Chicago!
Lunchtime - we met a friend for Chicago dogs and Italian at Portillo's. So good! Feliks got a couple Chicago dogs and I got some amazing chicken alfredo. After lunch we drove over to Reggie's Music Joint, a bar and record store that I found online. Seriously one of the coolest (dive) bars I've ever been to. When you pull up to this place, you think it's going to be a grungy hole in the wall. It is a hole in the wall for sure - aren't those the best? Three stories tall, there is a regular bar on the first floor that has great food and drinks specials and live music very day. The second floor is an album store that has every genre of music you could imagine, movie soundtracks, bargain records, and so much more. Oh and they offer a 10% discount if you show your receipt from the bar, or a 20% discount with college ID. Feliks got The Wall record, I got the RHPS soundtrack, and we picked up a few quarter bargains albums. The third floor of this place is the rooftop bar, which was a whole different vibe than inside. All ages and types of people, including families, were enjoying the summer weather outside on this rooftop with good drinks, good music, a pool table, and a $10 all you can eat buffet. I can't wait to go back to Chicago and go to this bar again.
I wasn't feeling well in Chicago, so we chilled for the evening at our friend Andrea's place. The next morning on our way out Feliks found a great local breakfast joint called Johnnie's Snack Shop. I feel like this is one of those hidden gems. Our waitress said the place had been there forever, and under current ownership for six years. We saw the owner sitting down and walking around the restaurant. Cheap food, great breakfast, and fast service. I give it a solid A.
My advice from our experience:
1. Try the public transportation here. Don't drive. Biking is fine, or I think it would be great to try their bus or train. This city really had public transportation worked out solid.
2. GO TO REGGIE'S, and be sure to check out all three floors. Seriously, this place is awesome.
His View
Chicago - Feliks' perspective
The Windy City - was not so windy, rather foggy. At first glance, Chicago downtown didn't seem that big. As we kept going I realized what I was looking at was the suburb skyscrapers, and the real skyscrapers were hidden by the massive amounts of fog sitting over the downtown area. There was at least a dozen buildings I couldn't see the top of, which I always find fascinating that the people on those top floors are basically in the clouds. It took me a while to fully grasp the size of the downtown area. It was massive. We started off by going to the parks near the Chicago harbor. Grant Park: a huge area of green grass, fountains, bike trails, monuments, sculptures, and everyone's favorite... the bean. I love the fact that there were people running, biking, roller blading, walking, and how well the designated areas to do these activities were marked. We got really lucky with a parking spot, pulled down the bikes, and started riding around. The Navy Pier was only a few blocks away from Grant Park, so we headed there for a stroll down the pier. It was a pretty busy place. It looked like there was a good mix of locals and tourists, but the activities were definitely geared toward the tourist side. There were restaurants, shops, boat tours, and dinner yacht cruises. They also had a lobster fest going on, which was a bit more pricey than what I was expecting, but one of the workers told us it was really fresh seafood. We decided to skip this, as we were looking to get a traditional Chicago dog later for lunch. There was a nice gallery of stained glass windows inside the Navy Pier that we looked at for a few minutes.
Our lunch plans were to meet an old college friend Andrea for a real Chicago style hot dog. We were recommended Portillo's, which happened to be less than a mile from the Navy Pier. Portillo's was actually really cool; it was almost like three restaurants in one. They had the hot dogs, the pastas, the pizzas, and some desserts - everything looked delicious. I got two regular hot dogs, Chicago style with no ketchup. After barely making it out of lunch - I say barely because I was so full I could hardly move - we headed to Reggie's Music Joint.
At first glance, Reggie's Music Joint seemed like a straight biker bar. The bouncer that checked our IDs had to have been at least 6'5", 300 pounds, and covered from head to toe in tattoos and piercings. Inside the bar displayed memorabilia from White Sox to Cubs to local rock bands and big music stars. The bartender was the ultra skinny female version of the bouncer, and claimed that she pretty much had everything behind the bar. This was tested when Caywood ordered a mimosa, and a mimosa appeared in front of her. The bartender was not lying.
The second floor of Reggie's Music Joint was Reggie's Music Shop, where we found some twenty-five cent treasures and a couple must-have records that we wanted to play on the spot. If you hang on to your receipt from the bar, you get a 10% discount on your records. The third floor of Reggie's was by far my favorite, and it was the busiest. Pretty much the same bar as downstairs loaded with all the goodies, and a small buffet line with wings, beans, mac and cheese, burgers, and fries. It was a very local atmosphere type spot. There were people of all walks of life, and the diversity was very refreshing. While sitting with another round sharing stories, Andrea brought up White Castle. Since Caywood and I made a pact to get White Castle as soon as we saw one, and Chicago happened to have White Castles, we agreed to go there for dinner. As we were googling the nearest location, it just so happened that there was one right around the corner. The expression of excitement reached a new level in our conversation. Needless to say, we all got sliders. The evening closed out at Andrea's house, where another old buddy came to visit to reminisce on the college days.
Overall, even though we didn't get to do a whole lot of sightseeing in Chicago due to the fog, it was a very good experience. I did not think that Chicago would be a huge contender for a place to live, but it made its way to at least the top 5. While I would probably not want to drive in Chicago, I would be perfectly fine riding my bike. By far the most shocking part about a city of that size is the bike lanes that span through almost every street. I wish we could have done more sightseeing, but I definitely got enough to make me want to come back for more. Parking was difficult and the roads did get hairy in some places. I would recommend parking and biking, as it would be much easier than driving.
![]() White Castle fun | ![]() THE BEAN |
|---|---|
![]() Stained glass museum | ![]() Reggie's Music Joint |
![]() Portillo's | ![]() Our boston host Andrea |
![]() Navy Pier | ![]() Navy Pier ferris wheel |
![]() Navy Pier entrance | ![]() Lurie Garden |
![]() Lots of walking | ![]() Johnnie's Snack Shop |
![]() From under the bean | ![]() Foggy Chicago skyline |
![]() Feliks @ Navy Pier | ![]() Excitement for the bean! |
![]() Crown Fountain | ![]() Crowd at Navy Pier |
![]() Chicago love | ![]() Chicago Fog |
![]() Cheers @ Reggie's Music Joint | ![]() Buckingham Fountain and fog |
![]() At Crown Foutain |
Next stop: Louisville, KY






















