Chicago, USA | Top 10 Sights for a 1 Day Itinerary
Below you will find a detailed itinerary for making the most of your one day in Chicago, Illinois. Chicago is a major city in the United States, so flying in or out of Chicago O’Hare airport can leave you with one day to explore the city. There are many highlights to this city, but if you have a limited time there, this is a list of some of the best things to do (in order) to make sure that you make the most of it.
My family and I were departing from Chicago O’Hare airport around 9:00pm. We are from Nashville, but we spent the night in Louisville the night before to make sure we could leave early and get to see some of Chicago before we left. After some minor car issues, we arrived around 1:00pm in the Windy City (yes, it is very windy).
First things first: if you are driving, make sure you park in a central location. Even though it might be pricey, it is worth it. You will be able to access most sights by walking if you do this.
Second thing: make sure to take time to notice and appreciate your surroundings. The most notable things about Chicago to me:
- Architecture: take in the sheer size of the buildings that surround you and take time to feel how small you are in comparison to this big world.
- Natural space: even in a giant metropolitan city, there is still room for so much nature surrounding the city with Lake Michigan, winding through the city with the Chicago River, and right in the middle of the city at Millennium Park.
- Vibe: while some parts of Chicago feel vibrant and new, there is an undertone of history that runs through its veins.
So, enough rambling, here’s the top 10 sights to see in 1 day in Chicago:
1. Park at Millenium Park
This is a central location to almost everything, and it will allow you to start your short time with the most iconic sight in Chicago: Cloud Gate (or, more common, The Bean). TIP: you can pre-pay online to park at any well-known spot. This saves you time and potentially money, because you will guarantee you have a spot, and you will be able to pay before you go to avoid any further charges for amount of time or events going on. This parking garage takes you underground from the street, and the signs are fairly easy to follow. The parking garage is huge, so there should be plenty of spots when you get there.
2. Cloud Gate (The Bean)
Starting off at The Bean just makes the entire day start off on the right foot. This is something you see in everyone’s Chicago Instagram posts or on the top sights to see in Chicago. In reality, it is just a giant sculpture that looks like a giant bean (or, cloud), but it is iconic so naturally you have to stop there.
The Bean is also part of Millenium Park, which is a beautiful green park in the middle of this giant city full of skyscrapers. While making your way to the bean, make sure you take advantage of your walk through this park since there are many cool things to see throughout the park. My favorite part was walking over the bridge that is bright and silver and curves around the side of the park. It took us straight from our parking almost directly to Cloud Gate.
3. Historic Route 66 Beginning or End Signs
While you most likely aren’t starting or ending a Route 66 drive, seeing the places where it starts and ends is pretty significant. It is an iconic part of the US of A, so being able to see those classic signs is a fun addition to this walking tour.
4. South Wabash Avenue
You have probably seen pictures of this street, and while you are walking to the next sight, make sure you take in the sights and sounds of this picturesque street. This street definitely classifies as windy from the rushing Chicago “L” that passes overhead – the rapid transit system that runs through the city.
5. The Chicago Theatre
It was the middle of the afternoon when we were there, but the giant sign still lit up in the daylight! This is a classic theatre that hosts different types of shows such as classic theater performances as well as live music concerts. While we didn’t get to see a show while we were there, the pictures of the inside are beautiful and I would highly recommend trying to do a tour of the venue if you aren’t able to make it to a show. Even if you can’t, the classic theatre vibe from the outside is enough to get the historic feeling of this theater as well as get a picture in front of a beautiful sign showing off where you are.
6. DuSable Bridge
While walking to your next destination, it requires you to cross over the Chicago River. While there are many different bridges that you can cross, I recommend taking one bridge one way and a different bridge another way. This way you can walk across DuSable Bridge and also get to view it in its entirety from afar on a different bridge – all while getting to take in the surprisingly blue water and the buildings that tower over you in every direction.
7. Magnificent Mile
Somehow I managed to get a total of 0 pictures of this street – probably because my eyes were staring straight up and my jaw dropped the whole time. Maybe I’m just not used to it, but it was pretty amazing to walk down a street that combined both historical buildings and the top brand-name stores that stretch for a literal mile! This is a great place to take in the historic architecture as well as get some good shopping in. I would definitely encourage you to do your research to know what stores you’re interested in and where they are so you can easily get to each place!
8. Riverwalk & Chicago Brewhouse
When you get back from walking down the Magnificent Mile, cross back over the Chicago River via any bridge and find a set of stairs that takes you down to the river. Once you are down by the river, there is a long path that lets you walk along the river and enjoy the view from below. Almost directly under the N. Wabash Street Bridge you will find Chicago Brewhouse. This is a great place to be able to sit down, have a great view looking out over the river, and enjoy a diverse menu and some Chicago craft beers!
9. North Avenue Beach
Since you will have to be heading to the airport or making your way out of the city, get your car and head to North Avenue Beach. I think if you were really adventurous you could walk, but it is best to drive to this spot. After you enjoy a cold beer on a hot day, you can walk back through Millennium Park and get your car. Drive to North Avenue Beach to check out Lake Michigan and see the beautiful Chicago skyline from outside of the city.
10. Lou Malnati’s
If you are from Chicago, you might hate that I’m saying this place, but it really is a quick and easy stop to make if you only have a short amount of time left but want to get a taste of the Chicago deep dish pizza. Since we were heading to the airport, we went to the Lou Malnati’s on Lincoln Ave. and were able to sit outside and admire the cute area of town that we were in. It really was delicious pizza, and we really enjoyed the style of the restaurant.
After you have eaten and feel too full to move, make your way to the airport or your hotel or out of town. While this only scratches the surface of Chicago, it is simply a way to see some top sights with your limited amount of time and minimal driving in the city!
Other Notable Activities:
- Skydeck Chicago at Willis Tower
You have probably seen the famous pictures of people standing in a glass box high above the city of Chicago. That is Skydeck Chicago, and depending on your style of travel, you could easily add this in to your itinerary! Tickets cost $26, so if you like to save money, this could definitely be skipped – and if you’re afraid of heights (like my mom), I would definitely steer clear of this one.
- Navy Pier
This is another famous spot in Chicago that we did not have time to fully explore, so we decided to skip it. While we will definitely go back again sometime, if this is something that is more your style, you should definitely try to visit. It boasts restaurants, rides and games, cruises from there, shopping, events, and more. You probably can recognize this from the giant ferris wheel on the pier. Definitely something to check out if you have the time!
Enjoy your time in Chicago!
