Chicago is one of my favorite cities to visit, as well as being my city of birth. Loaded with fascinating things to see and do, it is impossible to see all the highlights of Chicago in a day. Unfortunately, that was all we had, so we made some hard choices.
Dividing the city geographically, we opted for Chicago’s key downtown locations over the museums, as we have visited them before. Both are presented below. We began our day in the western suburbs and took the Metra train into Union Station.
Option 1 – Downtown Chicago in a Day
This 53 foot tall Alexander Calder sculpture called Flamingo is the image I have in my head when I think about Chicago. It sits outside of the building my father worked at for far too many years.
Our carefully planned route allowed us to hit what I believe are the downtown highlights of Chicago:
Skydeck on Wills Tower
Formerly the Sears Tower, it was once the world’s tallest building. It is now the second tallest in the USA. The views from the Skydeck on the 103 floor can include four states. However, it is the glass ledge that really got my heart pumping.
Sitting in the Ledge, a glass box overhanging on the 103 floor of the Skydeck.
Photo Credit: One of the professional shots taken by the team at Skydeck Chicago. Used with permission.
Read Next: Skydeck Chicago: I Walked Out on the Ledge – Would You?
Art Institute of Chicago
Considered to be one of the world’s best art museums, this not to be missed museum is loaded with famous works. Most noted as housing the world’s second largest collection of impressionists work, the museum actually has over 300,000 works from Byzantine to modern art.
- The Art Institute of Chicago is the second largest art museum in the United States (Metropolitan Museum of Art (The Met) in New York is the largest).
- There are three dining options inside the Art Institute including two cafes (lower and second levels) and Mediterranean fine dining on the top level.
- Audio guides are available for rent or use your smartphone and their free downloadable app. Check it out on their official website here. There is free wifi in the Art Institute.
The famous lions sit outside the Art Institute of Chicago
CAF River Cruise
Chicago is famous for an eclectic mix of architectural styles including being the birthplace of the American skyscraper. There is no better way to see the variety of architecture than from the Chicago River. The best of the cruise options appears to be the Architecture Foundation (CAF) River Cruise aboard Chicago’s First Lady Cruises.
Architecture Foundation (CAF) River Cruise aboard Chicago’s First Lady Cruises.
Photo Credit: Chicago’s First Lady Cruises
Read Next: Chicago Architecture: Enjoyed from the River
The Bean
This huge reflective sculpture in Millennium Park is the current number one tourist attraction in Chicago. The best part – it’s free.
The Bean
We are standing underneath The Bean Sculpture in Chicago – Can you spot us in the reflection?
Giordano’s Pizza
If you ask me, I will insist that the world’s best pizza is a stuffed mushroom and spinach pizza from Giordano’s. Honestly, I was so excited to have my favorite pizza that we gobbled it up before I remembered that I wanted a photo. The empty pie plate just wasn’t so attractive.
Chicago in a Day Option 2 – Take a Tour
Chicago in a Day Option 3 – Museum Row:
If you have two days, or if you prefer museums, my other favorite highlight of Chicago is Museum Row. Located a few miles away from the places we visited on this trip, the first three museums listed here are within walking distance of each other:
- Field Museum: The first in the row, it started as part of a part of the 1893 World’s Columbian Exposition. With the financial support of Mr. Marshall Field, the exhibit became Chicago’s first permanent museum.
- Adler Planetarium: The oldest modern planetarium in the Western Hemisphere, it also boasts the best views of the Chicago skyline, both day and night.
- Shedd Aquarium: Home to 32,000 animals including Beluga Whales and Granddad, Jellies.
- Museum of Science and Industry: Not on museum row, and a drive away, but certainly a museum worth visiting.
Tour Chicago’s Best Museums
One final image –this huge globe outside the Willis Tower. Notice anything missing? Hint: Where is New Zealand?
What do you consider to be the highlights of Chicago? Did you spot the problem with the globe?
If you enjoyed this article, please share it on social media including Pinterest:
Disclaimer: I was provided with a complimentary entry on several locations in Chicago to aid in the writing of this page. However, the opinions expressed here are strictly my own.
Here's the secret to packing light:
Download our free packing light checklist when you sign up for our newsletter.
Oh, we love Chicago. And, now that you mention it, Giordano’s may have something to do with that. And maybe Garrett’s, too. Mmmm…we are definitely overdue for a trip! Thanks for bringing back such fond memories. #TheWeeklyPostcard
Giordano’s is my favorite. I could barely wait until the pizza arrived.
Great choice of Chicago highlights. I live near Chicago and used to work a block from Millennium Park. I used to love walking over there on my lunch break and just hanging out for a while.
The Bean in Millennium Park is interesting on its own as well as from a people watching point of view.
I spent about a week in Chicago some years ago but I never “sat in the Ledge.” In fact I’ve never even heard of it, so I envy you for that. I would have liked to do it, but now I lost the opportunity. I don’t think I’m going back there again. I didn’t quite like Chicago to tell you the truth. Other then the Miracle Mile and the River Cruise, I didn’t find it too attractive.
I find big cities interesting for the culture, activity, and architecture.
It’s a beautiful city indeed. We should come back there, we were there briefly only for transit 🙂
Chicago can be a fun city as there is a lot to do.
I have never been to Chicago. I know it is a great city and am really interested to go. That photo in the Skydeck is insane. So cool!
It is a fun city. The Skydeck Ledge was awesome.
Having just left Chicago in the fall, this made me miss the city! Great suggestions as far as museums go–The Field Museum and the Art Institute of Chicago were my top choices! I also think it’s great you made it to the Skydeck. I was so afraid on the ledge and only took a pic of my feet, but I made it out there!
Well done getting out on the skydeck.
It’s weird that there are so many things that resemble things in NYC, they’re just on a smaller scale in Chicago. Except the bean. Nothing like that in NYC. I wonder if the sun’s rays and heat have the same problem as that weird glass building in London that melts people’s cars! Have a good weekend!
Interesting. When I was in New York I thought the same in reverse, a big Chicago. I haven’t heard of problems with the bean, but I don’t live there and now I am curious.
There is no way I could sit on that glass ledge/box. Just looking at that picture makes me toes curl
Mollyxxx
LOL – It was really incredible.
I have always wondered if Chicago should go on my to-do-list. Thanks for some insight!
It’s a fantastic city really requiring more than a day. (I was there for a few, but visiting friends and family).
I haven’t been to Chicago in years! It looks even more amazing than I remember. You definitely had a nice day. I think you are braver than me sitting on that glass!
LOL – I just did it, didn’t think about it. As for the day, we were really lucky.
Chicago is one of those places we visited but managed to miss almost everything. D and I were staying at St Charles and decided we would drive to a point north of the city with our bikes and then cycle along the lake. It was a beautiful day – but not for long. Just as we approached the city the temperature plummeted and we got hit by driving rain. It was a long, slow, wet, difficult cycle back to the car and then to add insult to injury we got caught in awful traffic heading back to St Charles. I do think of Chicago fondly though – as a city we have to go back to. Thanks for the post. It is going in my save pile.
After that story I am surprised you think of it fondly. Sorry you missed the highlights, but now you have a good reason to go back.
The two things I had to do when I went to Chicago was to see American Gothic at the Art Institute and eat the cheeseburger place that inspired the Saturday Night Live Skit — i think the latter dates me!
American Gothic is one of my favorites, but I wish I remember that SNL skit. (It dates me too).
I would have loved doing the river cruise. Okay, I’m a cruiser.
Have a fabulous day. ☺
Of course you would 🙂
I’d be up for some really good pizza.
According to that globe, your country doesn’t exist…
While most things from memory don’t stack up when I get then again, this pizza does. Giordano’s is still my favorite. And, pretty funny that New Zealand doesn’t exist.
I’ve only seen Chicago in movies and it’s mainly residential neighbourhoods and the airport, so thanks for my first real look at Chicago! 😀 It’s lovely, and I hope to visit some day. 😀
I never really think movies give you a fair look at a city.
I hear very good reports about Chicago, and her really great reports about its food culture. It is a pretty city, isn’t it.
It’s the town of my birth, so I think I am biased. It is a great city.
No photo of the Metra Train – it was one of the highlights of the day (especially with your new best friend – the train conductor entertaining us most of the ride)
It’s more of a guide for other people than a report of our fun day. However, I will agree that he was a highlight of our day.