Last updated on February 15th, 2019 at 05:35 am

Last weekend I woke up extremely early to embark on an adventure to Chicago. Even though I only had two days, it was an incredible experience that gave me a small taste of the city I am now itching to explore again soon!

Chicago is huge, so here is my two day itinerary for the Windy City. For a quick list of my favorite parts, click here!

Table of Contents

Day One:

Getting There

At about 3:30 am on Friday, we got up and headed to the airport to catch a flight at 6:30. We landed at O’hare airport around ten and hopped on the Blue L line that goes into the city. The fare was five dollars a person. The train car we ended up in was pretty crowded so we had to stand for most of the way. As someone who is not used to trains, the subway in Chicago was one of my least favorite so far, old, grungy, and very loud. However, it’s a very simple way to get into the city and much cheaper than taking an Uber or Lyft.

Greetings from Chicago

I was on a mission to get a picture of the Greetings from Chicago street art, just outside of Logan Square. The train goes right by it, but it’s impossible to get a picture while it’s moving. We got off at the California stop, and then the famous sign is only a few blocks up at Milwaukee Avenue and Prindiville Street.

I was not aware that this sign was in front of a parking lot. Luckily I was mostly able to get the full sign in the picture.

There is some other street art in the area, it would have been fun to explore more, but we were supposed to meet our Airbnb host so we got back on the train.

Where We Stayed

Our Airbnb was not as central as I would have liked, but since we booked so late this was one of the only good options. I have heard that people have good luck booking hotels in Chicago as well, so in the future I would check that out. I did love our place, however, which was about 7 minutes from the Shedd Aquarium. Here’s the view:

Exploring Chicago

I wanted to get a peek at Lake Michigan, so we headed east. Some great views of the city can be captured from Lakefront Trail near Museum Campus. We started here and walked north along the trail and then veered off through Grant Park to see the Buckingham Fountain. Unfortunately it was turned off for winter, but it was still beautiful. From the Lakefront Trail you could also continue north and check out the Navy Pier.

We made our way to Millennium Park to see the Cloud Gate, also known as the bean. The reflection of the vibrant autumn leaves in the bean was spectacular! There were a ton of people, as expected.

I got a pretty great matcha cupcake from A.Sweets Girl food truck. It was beautiful, but messy!

The Skydeck

Skydeck Chicago was our ultimate destination. It was a pretty long walk from Millennium Park to the Skydeck, but we enjoyed the walk through the city. In the shade of the buildings it was pretty chilly so we stopped to get some tea at Argo Tea and charge my phone. We purchased the Chicago City Pass, which I highly recommend doing if you are interested in more than three of the attractions (more on this later). But of course, my city pass was on my phone which was dead since I had been up since 3 am… typical.

Argo Tea is not originally from Chicago, but it was still a nice place to stop and sit. They had bubble tea, specialty drinks, and loose leaf. All of the options were good (we may have stopped more than once on our trip).

Back on track, we arrived at the Skydeck. Using the Chicago City Pass, we skipped the huge line and went right to the elevator to head up to the 103rd floor. Be prepared to be crammed into an elevator and have your ears pop.

The view was worth it.

The ledge, the famous attraction at the Sky Deck of Willis Tower, is pretty scary but awesome. There are multiple edges but the best is the farthest left. People get really creative with these pictures, so you can spy for some inspiration!

The Speakeasy

There are many speakeasies in Chicago that I would have liked to try, but we chose The Drifter for several reasons:

The space was used as a speakeasy in the Prohibition.
There are several speakeasies that would be pretty impossible to get into because they require paid memberships or passwords.
They have rotating drinks on tarot cards.
They have a performance on the hour.

The Drifter is located in The Green Door Tavern. Just walk downstairs and there is a door that leads to this cozy, classic bar. There is a cover charge on Friday and Saturdays, but it’s only 4 – 6 dollars. Once inside, the host hands out the tarot cards and you select a 1920’s themed drink.

I got something similar to a daiquiri and then a drink with mezcal and an egg white. Both were good! They also have food so we ordered the Devil’s on Horseback. A bluesy, swing band performed to fit the theme.

Ramen at The Slurping Turtle

Josh always has to get ramen when we travel. I found this spot randomly because it was near The Drifter and it was amazing. We ordered steamed buns and I got the spicy pork ramen which included meatballs and pork belly. So good!

360 Chicago

Our last stop for the night was 360 Chicago in the John Hancock building. We went around ten o’clock, so there was no line. However, this attraction is also available with the Chicago City Pass so you can skip the line if need be.

There were beautiful views of the city lit up from here.

Also in the John Hancock building is the Signature Room (restaurant) and the Signature Lounge (bar). The view from here is the same as 360 Chicago, so I don’t recommend doing both. If you don’t plan to purchase the Chicago City Pass, it is about the same price for a general admission at 360 Chicago ($20.50) as it is for one drink at the Signature Lounge ($17.50/drink plus tip). There is also a one item per person requirement for the Signature Lounge. So pick your poison or grab the City Pass to view the observation deck.

Day Two

The Bean

We got up early to see the bean without the crowds. We arrived around 7:30 and there were less than 10 people. The resulting pictures were pretty great!

As we were leaving, it started pouring rain. Soaking wet and freezing, we ran for Wildberry Pancakes and Cafe. Warm coffee and food helped restore our energy. Wildberry was average in my opinion and I wouldn’t eat there again.

Second Breakfast

I had to make do with the little time we had left in Chicago so we trekked to Do-rite Donuts. Here I got a cinnamon raised donut and it was amazing. Large and fluffy with a great crunch on the outside. They had fewer choices than Stan’s but I think the donut was better quality.

The Art Institute

We stopped again to get some more tea and wait out the rain a bit. The next stop was the Art Institute of Chicago. On our way, we saw the Chicago Theater sign and several Macy’s Christmas windows. We also passed Garrett’s Popcorn, which is supposed to be really good, but they weren’t open.

We took the Nichols Bridgeway to the Art Institute.

This is another attraction that is included in the City Pass. It was a busy day at the museum because of the weather, so it was helpful to be able to skip the line. There are some really famous paintings at the Art Institute, as well as some beautiful lesser known works of art.

The Field Museum

Another long walk through Chicago parks (with a stop at Devil Dawgs again) brough us to the Field Museum. The entrance for City Pass holders is on the south side. Again, the pass allowed us to walk right in while others waited in horrible lines.

This museum is home to SUE, the most complete and well-persevered T. Rex ever discovered. Learn about evolution, animals, Ancient Egypt, and more at this museum. This museum is perfect if you are travelling with children. Although it was interesting, it was very crowded and I was a little bored.

The Shedd Aquarium

This was the last stop of our Chicago City Pass. The Shedd Aquarium is definitely magnificent and seems to be one of the more popular stops in Chicago’s museum campus. They house many marine animals, including dolphins, beluga whales, and sea lions as well as the more standard sharks, sting rays, and exotic fish. There is an abundance of critters organized by region of the world.

Deep Dish Pizza

Lou Malnati’s Pizza on State street is the place we visited next (after getting some more donuts from Stan’s for the morning). We put our name on the list and were told it would be an hour wait and that we should pre-order our pizza. While we waited, we drank some beer at Bulldog Ale House, simply because it was right down the street. The special just so happened to be a 5 dollar 23 oz Bulldog draft. What a great deal! The sunset wheat was great, very smooth and citrusy.

After our beer, we finally got a bite of classic deep dish pizza. Lou Malnati’s was very good and filling. We also ordered the Malnati salad, which was a great pairing.

Other recommended places for deep dish were Gino’s East and Giordano’s.

The Chicago City Pass

If it is your first time visiting Chicago, I recommend getting the Chicago City Pass. This includes skip the line passes to five attractions, including Skydeck Chicago, the Shedd Aquarium, the Field Museum, 360 Chicago or the Museum of Science and Industry, and Alder Planetarium or the Art Institute. I didn’t think we would have enough time in one weekend to tackle all of these attractions, but we did! This saved us a lot of time and money.

More Stuff To-do

Things that you should do if you have more time include shopping the Magnificent Mile, exploring the Navy Pier, seeing a game at Wrigley Field, visiting the Lincoln Park Zoo or Conservatory, and, of course, eating more donuts.

I loved Chicago! I can’t wait to go back again soon.

What was your experience in Chicago?

Need help packing for a fall or winter trip to Chicago? I sure did! Check out my guide.

Illinois, North America

Two Days in Chicago: Itinerary and Tips