Day Trip to Chicago
- Kimi's Travel Thoughts
- Jul 22
- 9 min read
I've mentioned this before, but I am rather ambitious with my travel plans. This is especially evident in my Day Trips series and, most notably, any day trips that take me outside of Texas. For my most recent day trip, I decided to go to Chicago, Illinois.
Why Take a Day Trip to Chicago
You might be thinking to yourself, "How are you supposed to see Chicago in a day?". That's a question my friends and co-workers asked me when I told them I was planning this trip. The goal is to showcase how much one person can see in a day, not actually seeing everything in Chicago within 24 hours.
A year ago, I posted a poll on social media asking where I should travel to for my final day trip of 2024 and Albuquerque, New Mexico beat Chicago by a single vote. Given the popularity of Chicago in the results, I knew that I would have to make that the next location or an out-of-state day trip and added it to my 2025 travel preview. So, here is the recap of my day trip to Chicago!
Flights
To get as much time in Chicago as possible, I caught the first flight out of Austin at 5:00 AM and the last flight out of Chicago Midway. That return flight was supposed to depart just before 10:30 PM and the flight was delayed an hour which worked in my favor because I needed to charge my phone a bit longer. Both flights were direct and I flew Southwest, so I ended up with some additional rewards points from each 2.5 hour flight.
Navigating Chicago in a Day
How does one get around Chicago in about 12 hours doing all the tourist activities that can be squeezed into a short amount of time? The answer is by being constantly on the move! Here's how I managed to see and do as much as I did for this day trip:
Walking
Naturally, I walk at a faster pace, but I also had a very good sense of where I was going because I carefully studied the map of Downtown Chicago for the areas I planned to walk around prior to leaving for this trip. Basically, I was on the move from the moment I was ready to begin sightseeing and had my water bottle with me along the way. Walking allowed me to get some exercise, see some of the city at a slower pace, and save my battery from draining too quickly because I didn't rely too much on Google Maps for navigation. It also helps that the city is very walkable with pathways and signage to help you go in the right direction for locations such as the Riverwalk and Navy Pier.
Hop-On, Hop-Off Bus Tour
When I know I will only have a short time to visit a city (such as when I spent a day in Miami), I like to take a hop-on, hop-off bus tour. It's a guaranteed way to see the tourist hot spots and avoid paying for rideshares to get everywhere plus you can learn some local history while you ride. Since I wasn't familiar with the public transit system in Chicago, I also felt that this would be a better option for me. I got a day pass and rode the route about 1.5 times to see everything and get to a couple of stops along the route throughout the day.
Rideshare and Taxi
I used Lyft rides to get to and from the airport in Chicago and the pickup and drop off experience at Midway Airport was easy to manage. Midway is the smaller airport in Chicago located on the city's southside. For the times I arrived at and left the airport on a Saturday, it took somewhere between 20-30 minutes to get between the airport and downtown.
I took a taxi to dinner because I was at the Willis Tower and didn't want to attempt to walk the 1.2 miles to my dinner location. The taxi was already outside the building and that meant I didn't have to order another Lyft and further drain my phone's battery.
Food
Despite being in Chicago, I actually didn't try the classic food that the city is known for. While deep dish pizza, Chicago dogs, and Italian beef sandwiches were around every corner, I also recognized that those were all heavy meals that would limit how much other food I eat throughout the day. Had I been on a multi-day trip to the Windy City, I would have tried those foods. Instead, I opted for other restaurants that are unique to Chicago and/or the Midwest.
Eggy's Diner
With most of the tourist activities not really being active at 8:30 AM, I made plans to enjoy breakfast at Eggy's Diner which is located in a neighborhood just a few blocks away from Millennium Park and the Riverwalk. Almost everything on the menu is somewhere between $16 and $20 USD. I ordered the crab cake eggs benedict which came with a side of roasted breakfast potatoes and it was delicious! There were other menu items that I would have loved to try, so this is a place I would go back to. As a neighborhood diner, it was very full (as expected on a Saturday morning) but I was able to get a seat at the bar right away because I was solo for this trip.
Frankie's Pizza by the Slice at Navy Pier
I actually did end up getting pizza after all. It just wasn't a Chicago style deep dish pizza. I needed a midday snack after riding the hop-on, hop-off bus for a couple of hours and got off at the Navy Pier stop because I knew that would be a good location with food and restrooms which noticed when I walked around Navy Pier earlier that morning. I knew a slice of pepperoni pizza would be just the thing to give me the fuel I needed to continue the rest of the afternoon until it was time for dinner. This slice of pizza was excellent and the dough was the star of the meal. The slice of pizza was about $7 and I also got a fountain drink for about $5 to help cool me off after being in the sun for a while.
McDonald's Headquarters (McDonald's International)
There is a channel on YouTube that I subscribed to called Weird History Food and a couple of months ago I watched one of their videos that featured international food items for McDonald's franchises. At one point in the video, they mentioned that the McDonald's headquarters in Chicago was the only place in the United States to try the fast food restaurant's international menu items. The global menu apparently rotates on a six-week basis and I had no idea what I would be able to order until I got there for dinner. I was really hoping to see Twister Fries (seasoned curly fries) on the global menu because that was my favorite thing to order anytime I was near a McDonald's while on a trip to Europe ten years ago.
Lucky for me, Twister Fries was on the menu! The flag next to the item on the digital kiosk menu was for Malaysia which certainly surprised me when I've associated those fries with France for the past decade. They also had items from other countries such as India and Switzerland. Along with the Twister Fries, I added a McRaclette to my order which is a burger patty with a creamy sauce, pickles, cheese, and chopped onions on a ciabatta bun. I included a small lemonade in my order and within a few minutes I had piping hot curly fries (plus the rest of my order) brought to the table I decided to sit at. I haven't been inside of a McDonald's in many years and it's been at least a year since the last time I ate from a McDonald's, but I must say that this was quite the experience and something that I would interested in doing again just to try more items in the future on the global menu.
Chicago Day Trip Activities
I'm a fan of baseball and my favorite MLB team is the Houston Astros as seen on the Kimi's Travel Thoughts account on Instagram. While I would have loved to watch them on the road in Chicago (which I strongly considered doing something similar during my day trip to Denver a couple of years ago), the team was not in the Windy City while I was visiting and I opted to use my time to check out other things in Chicago.
Millennium Park
Cloud Gate which is best know as "The Bean" is located at Millennium Park which was just a few blocks away from where I had breakfast, so I walked over to get some photos of the sculpture. Unfortunately, they did not come out great on an overcast day. I decided not to go into the park because it was super busy and I didn't want to deal with all the people.
Riverwalk
I stayed on the lakeside stretch of the Riverwalk because that was a short walk from Millennium Park, so I was mostly enjoying the views of Lake Michigan, boats, the walking path, and the biking path as I took my extended morning stroll through Chicago. There is a direct path to Navy Pier, so I followed that route as I made the walk to that destination. Had I followed the pathway that took me back into downtown, I would have had more to see and do along the Riverwalk.
Navy Pier
There is a lot that can be done at Navy Pier. There are harbor tours, architecture tours by boat, boardwalk carnival rides and snacks, a theater, a children's museum, food, and so much more! I casually walked along Navy Pier to take in all the sights and enjoy the gorgeous view of the Chicago skyline. I also needed to take a break from the light humidity because I had been walking for a while and stepped inside the food court area for a bit to rest. Once I cooled down, I walked over to the hop-on, hop-off bus tour stop in front of the Navy Pier entrance to begin exploring the city by bus for a couple of hours.
Want to see more pictures and a recap video of this day trip to Chicago? Follow Kimi's Travel Thoughts on Instagram to view exclusive content not featured here!
Big Bus Tours Hop-On, Hop-Off Tour
I have the Big Bus app on my phone and took advantage of the online purchase discount to purchase a day pass for a total of $58. The tour takes about 2 hours or just bit longer depending on traffic. You get to see a mix of Chicago's tourist highlights while listening to pre-recorded commentary as the driver takes you along the route. While I decided to not take a dedicated architecture tour, I did see many of the same buildings and learned some facts about the history of architecture in Chicago while I rode the Big Bus. I also saw so much more of the city than I ever would have been able to in a single day had I chosen any other method of transportation -- and I managed to save money in the process.
Chicago Skydeck at Willis Tower
Something to know about me is that I'm not afraid of heights. I went up to the view deck at Rockefeller Center in New York City, spontaneously hiked up Arthur's Seat in Scotland, went up to the CN Tower in Toronto, the Skyview Tower at Niagara Falls, and the Space Needle in Seattle. It was only right that my final activity of the day would be the Chicago Skydeck at Willis Tower (formerly the Sears Tower). I bought a general admission timed ticket online in advance for $38 plus a $5 USD service fee. The bus tour had a stop in front of Willis Tower, so that was how I got to this location.
After checking in, there are security lanes immediately followed by a line for the commemorative photos that can be purchased at the end of the Skydeck experience. From there, there is a small, interactive museum to go through before the line for the elevator begins to form. Visitors will take the elevator up to the 103rd floor where the Skydeck is located and you initially get to enjoy gallery window views of every side of Chicago along with checking out the gift shop. Then, there is another hallway that leads to the Skydeck which faces west and has two separate viewing lines. I got in the shorter line and took an individual photo before the second party took their photo. The plexiglass box that extends from the building is large enough for two parties, so I took some photos in one corner with help from the attendant and as the larger group took photos on the other side of the deck. When I got all the photos I needed, I returned to the food court on the ground floor of Willis Tower to relax and charge my phone before getting in a waiting taxi to go to McDonald's for dinner and, from there, to the airport.
Wrap-Up
Chicago in a day is definitely ambitious, but I feel like I got a lot out of it and I love how being in the Windy City made me feel. It is a city that I felt lived up to the hype and had all the elements about city life that I love. However, I know that I missed out on so many other sites, activities, and food because I was only there for about 12 hours to experience the city. While on this day trip, I determined that I would love to make my next trip to Chicago at least 3 days and two nights to try to enjoy the things that I missed out on due to my limited time on this trip. That being said, it is possible to do Chicago in a single day when coming from another state -- just as long as you are strategic about your itinerary!