After planning the trip for months, the day finally came to go back to Chicago.

Since graduating college, I’d been going back to Chicago once a year. That is, until the pandemic hit.

I didn’t feel comfortable traveling anywhere between 2020 and 2021, so I didn’t go back until 2022. That trip was for a concert too. I met up with my friend who lived close to the city and we went together.

This year, my sister joined me. The last time we were in Chicago together was 15 years ago.  We were just 12-years old.

She didn’t get a chance to visit me in college because she was also in college so I took this as opportunity to be a tourist and relive my college days with her.

Getting to the City

We met at the airport after I got through security and headed straight to our gate. I’m definitely going to get TSA Pre-Check or Global Entry soon.

We flew into O’Hare, one of Chicago’s two airports. This is the bigger one but if I’m being honest I prefer to fly in to and out of Midway. When we originally booked our flights, O’Hare provided the earliest arrival but they changed the flight time twice on us.

We (really I) got a little turned around finding the blue line station but after asking an off duty security guard we found our way. I forgot to follow my own advice: look at the airport maps before the trip.

Tip: If you’re visiting Chicago, it’s more cost effective to use the CTA (public transportation) so I suggest downloading the Ventra app and/or getting a Ventra pass for however many days you’re in the city. They have 1-day ($5), 3-day ($15), 7-day ($20), or 30-day ($75) passes.

I helped my sister download the Ventra app to get a digital version of the Ventra pass. This app can also be used to buy Metra tickets (a commuter train). It can also show when the next bus or train is coming for whatever stop you’re at.

The train ride took about 40 minutes to get downtown. It felt like forever, honestly (which is why I don’t typically fly into O’Hare).

The Hotel

The hotel was just a couple blocks from our stop which was great.

We stayed at Hotel Blake. I’ve stayed here before so I already knew it was a good hotel but it must’ve been recently renovated because I didn’t remember the rooms (specifically the bathroom) being so nice.

I’d booked the hotel through Delta with a new feature they added that’s separate from Delta Vacations. I was worried checking in early would be an issue, but we were able to check-in and get to our room with no problem. The front desk receptionist even called to check on us when we got settled which was nice.

I forgot to take pictures of the room but there will be video on the YouTube channel.

By this point it was 12PM and we were starving so we set out for lunch. Well…I got my eyebrows done first. I went to Threading Plus, a place I would go to all the time in college. They’ve gone up in price since the last time I was there – $15 – but they still have great service. I was able to walk in and get serviced immediately.

We stopped there first because it was close to our first food spot of the trip: Lou Malnati’s.

Lou Malnati’s

When someone mentions deep dish pizza, I think of Lou Malnati’s. This was first place I had deep dish pizza when I visited Chicago just to see if I even wanted to go to college there. I had it again freshman year and at the time I just thought it was okay.

My sister wanted deep dish at some point during the trip so I thought having it as our first meal would be great. It was the closest deep dish pizza place that I was fine with eating (Gino’s East is across the street from the hotel but I didn’t like what I had last time I was there).

Since we were in Chicago during October, the restaurant had Halloween décor all over. Our server Shay who was an absolute pleasure.

We both ordered own personal deep dish pizzas. I got the Malnati Chicago Classic ($14.89) and my sister got cheese pizza with two customized toppings ($18.34).

Shay told us it would take about 30 minutes for the food to be ready. Since we were so hungry, my sister and I decided to order the Stuffed Spinach Bread as an appetizer ($12.19). While it was really good, we’d regret this later.

By the time our pizzas came out, we were already kind of full. That being said, the pizza was probably the best I’d had from them yet! The extra cheese and the sausage just hit different.

Even though we were enjoying our pizza, we only ate half of it and saved the other half for dinner later that night.

I guess it was for the best because we saved money on a meal. Once we got our to-go boxes, we headed out to our next stop.

Grant Park and Millennium Park

 From the restaurant, we walked to the Buckingham Fountain. Along the way I pointed out which buildings my classes were in or places I visited often to my sister.

We walked along Grant Park, seeing statues and art installations. The weather was surprisingly decent for it to be October in Chicago.

When we reached the fountain we took it all in: the lake, the city skyline, the fountain itself. After taking our pictures, we continued towards Millennium Park.

We walked past the Art Institute and saw the Crown Fountain. I’d seen it before with the screens but I had never witnessed the “fountain” part on since I’d usually walk past it in the winter time.

From there we’d made our way up to get to the Bean but unfortunately, it was closed off due to construction. I mentioned this in the ‘7 Free Things to Do’ post as well. We ended up trying to stick our phones between the fence to get a picture but it just wasn’t the same.

My sister hadn’t see the Bean before so she’d been excited for it. Needless to say, we were upset.

With the Bean being a bust, we walked back to the hotel so we could rest a bit before we got ready for the SZA concert.

Be on the lookout for the concert post next week! Since it will have its own post, we’ll end day one in Chicago here.

The corresponding YouTube video will be up on Tuesday!

What would you do on your first day in Chicago? What’s your favorite thing to do? Let me know in the comments!