Chicago in 48 hours

It was short, but man. Chicago did not disappoint. I went to Chicago not having many expectations, I was just excited to explore a new city with an old friend.

Short weekend trips are one of the best ways to make memories with old friends. Sara and I grew up together in middle school, high school, college, and now jobs. We have made many drives to see each other between Oklahoma and Kansas, but somehow it's not the same going to see your friend in their 'own' city. For so long we ran around together in our city and were able to grow together by getting lost, going to dance practice, talking to boys, and all the other teenage stuff. However, being in a city where we both have never explored before felt like we were back in high school figuring things out together. I say all this to say a weekend trip is perfect to take with a long distance friend! So stop planning and just GO!


Sara and I talked on the phone for about 2 hours trying to figure out the best flights that were cheap and had us arrive and depart at the same time. My go-to site for booking flights is Kayak. The site allows you to search through all airlines and pulls up the cheapest flight. The only airline it does not check is Southwest, so make sure you check them out too.

We arrived in Chicago around 8:30 am on a Saturday morning... at different airports. Classic mistake. Thankfully we figured this out a couple days before and there is easy transportation from both airports into the city. We decided early on that public transportation was the best way to go for us. First, it was cheap. And second, there is hardly any parking in the downtown area, plus you avoid the traffic jams by using the train. When you arrive in Chicago there will be signs pointing to CTA transportation, which is underground. Just follow the signs and they will lead you directly to the trains. Right outside the entrance, there are booths to get tickets. Sara and I got a three-day pass for $20! We were pretty pleased that we would only have to spend $20 on transportation for the whole trip, except for the occasional uber ;). Once you have your ticket, use it to get through to the train and hop on to any of them. There is only one train that goes from the airport to the city, so don't worry about catching the wrong one.

*Side note about transportation* We felt safe about 90% of the time using the public transportation. Be aware of who is in the train car and what part of the city you are in. There was one incident that we had to remove ourselves from the train because we felt unsafe and uncomfortable. If you EVER feel that way, just get off at the next stop and hop on the next train that comes. Also, I would recommend taking Uber's if you're going to be out late at night. Just be smart and play it safe.

Google Maps made navigating this busy city a breeze! Find the links below to download the app. All you need to do is type in your starting location and ending location and the app will pull up all the possible routes of transportation you can take with specific times for stops. Below is what I typed into my phone which led me straight to our hotel with walking directions once I got off the train. Some of you that have always used google maps think I'm crazy for having to point this out, but it took a good couple months of convincing from my husband for this Apple girl to switch from my regular maps feature.


Google Maps

Download for apple products in the app store here.

Download for android products here.


Once we both rode the train into the city, we arrived at our BEAUTIFUL hotel, Kimpton Gray, in the business district around 9am. They let us check-in when we arrived, #bless and I could not recommend this hotel more! We felt completely safe in the area. Not too busy, yet walkable to major destinations, like Willis Tower, and so close to multiple train stops. The hotel has a boutique vibe and you'll find gorgeous details in every inch. If you have the time and money to splurge, they also have a lovely spa. 

Photo's courtesy of Kimpton Gray


Our goal for Day One was to just enjoy the city and that is exactly what we did.

Once we checked in and put our suitcases away, we headed straight to breakfast. A couple train stops away and some walking, we headed to Chicago Waffles. They have sweet and savory options that were both to die for. Definitely check it out if you are looking for a good brunch place. Try to call in before though, because this place can get pretty busy.


After some brunch, we walked over to Grant park which is about a 5 min walk away. Think of Grant park as Chicago's "Central Park." It holds the famous Millennium park, gorgeous art throughout, museums, and of course all the weekend runners from the city. We probably walked for a good 8 miles around this park down to the magnificent mile and people watched as we caught up on each other's lives. The magnificent mile is the place to go if you want some good shopping. We didn't worry about getting lost or getting to a certain point, we just soaked in the city and each others company. We eventually found this amazing flamingo wall. 

Type in "The Flamingo Rum Club" in google maps to get to this location.

Type in "The Flamingo Rum Club" in google maps to get to this location.


We were completely exhausted after all the walking and being in the sun, so we headed back to the hotel to rest up and get ready for the night. We were also in the mood for food. Honestly, when are we not? We decided this would be our night for Chicago deep dish pizza. The big hype about deep dish pizza is it's buttery, flaky crust with creamy cheese and then topped with seasoned marinara sauce. If you haven't heard already, there is a lifelong debate between the best pizza in Chicago. The two that people fight over the most is Lou Malnati's and Giordano's. In my opinion, they taste about the same, you just gotta try one before you leave Chicago. We tried Giordano's and it was to die for, as expected. Pro tip: on a busy night, the restaurant has you place your order and then wait to be seated. Bring a game or have a place to walk to or go get goldfish like Sara and I did to curb the hunger. It can take awhile. I wish I could show you a picture of this amazing cheesyness, but we were too hungry and ate before even thinking to take a picture of this delicious pizza, so you'll just have to go see it for yourself. We packed up our little leftovers, Sara put them in her purse and we were headed to our entertainment for the night.


One of my favorite things we did in Chicago was go to The Second City. Second City is an improv comedy club that has been open for about 60 years now and is the originator of many of our favorite comedians. Think Tina Fey, Steve Carrell, Bill Murray just to name a few. We bought our tickets the morning of the show and got some of the last few tickets available. I would recommend planning out the night you're going to go and get tickets in advance. It can be a four-hour show, so block out your night and be prepared to LAUGH. Arrive early to get good seats as they place you first come, first serve. You can order drinks from your seat, so get cozy.


Our goal for day two was to hit all the touristy places that we would feel bad about not seeing.

The Willis Tower


Once we were up and ready for the day we headed straight for the Willis Tower also known as the Sears Tower back in the day to head up to the famous SkyDeck. We wanted to get there right as it opened thinking we wouldn't have to wait in any lines. When we arrived, people had already been standing in line before they opened. Honestly, just be prepared to wait when going to see the most frequented attraction in Chicago. The line kept moving, but also be aware that you go to multiple stories just to wait in more lines. Eat beforehand or bring snacks and wear comfortable shoes. However, it was worth it. It's just something you gotta do. Plan a good 3 hours (maybe 4 at peak times) to be in lines and enjoy the SkyDeck at the price of $24 for general admission.

After the Willis Tower we went straight for food because we were starving. A foodie friend of mine recommended a biscuit place called Bang Bang Pie and Biscuits which hit the spot for a sweet and savory craving with a big dose of coffee. It is a bit north from the main attractions, but it was fairly close to our next tourist destination.

Wrigley Field


Now, I will preface this by saying we did not go into the Wrigley Field. #cheap (you can pay to take a tour of the inside) But, the area around it was just remodeled and we had a blast hanging out outside and taking in the historical stadium while not actually being it. If you're wondering if the stadium is actually worth the visit... I would say if you have time for it, go enjoy it. If you already have a packed itinerary then don't stress trying to go see it. We also might have caved and bought matching hats.  

The Bean


Next, was The Bean (officially known as Cloud Gate, I like The Bean better). I think this picture above is hilarious because it truly shows what traveling can be like. Most of the time, you're around hundreds of other people trying to get the exact same photo as you at the same time. Many times, people have edited out others around them to make the picture look better. No hiding any of these people here. The Bean was great. A cool illusion and an iconic Chicago picture.  Plan about 30 min to stop by and see this attraction.

Navy Pier


We headed over to the Navy Pier after The Bean, which again was crowded on a sunny Chicago day. The Navy pier is kind of like a carnival with things for kids to do and options to pay for games. We paid $16 for a ticket on the ferris wheel and were off! The line didn't take too long for us, but that can fluctuate throughout the day. Advice: go do it! So fun to see Chicago from this angle. (It also had great air conditioning in the pods, which was a refreshing break from the summer sun).

After all this, we were pooped. We headed back to the hotel and put up our sore feet from walking all day. After a little rest, we headed out for one last view. Chicago at sunset.

The View


This was the perfect way to end our little Chicago getaway. These breathtaking views were captured at The LondonHouse Rooftop bar. To get to it just navigate your way to the LondonHouse Chicago hotel where they have an elevator designated for the rooftop bar. Soak in the beautiful views and your time in Chicago.

We headed out the next morning at different times feeling exhausted and fulfilled from the adventures and each other's company.

Leave any questions or advice you have in the comments below!