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How I Spent 24 Hours in Chicago

Last summer I spent a mere 24 hours in Chicago. You may be thinking I didn’t do too much in that amount of time. Rightfully so since there is plenty to do, see, and eat in Chicago. So it may surprise you to learn I did a lot. Or it may not because if you haven’t realized already I always do a ton in a short amount of time. Not everyone has the luxury of several days or more in one place. So here is the fun I had in my 24 hours!

How I Spent 24 Hours in Chicago ©2016 HollyDayz

Once arriving in Chicago, instead of taking the train, we took the green Go shuttle van. The round trip was about $25. It was faster and dropped us directly at our hotel in the River North section of Chicago. We were staying at Hotel Felix at it had a great location to get to all the things we wanted to see. We arrived a bit too early to get our room, but we were able to leave our little bag and grab some breakfast at the suggestion of the front desk staff.

Hotel Lobby ©2015 HollyDayz
Hotel Lobby ©2016 HollyDayz

We took a short walk over to Yolk for breakfast. There was so much goodness to choose from on the menu that I would happily go back without a hesitant thought. The staff at Yolk were very upbeat and positive which made for a great experience. I ordered strawberry and banana crepes, eggs, bacon, and sausage. It was absolutely delicious and filling.

Eggs, Bacon, Sausages, and a Strawberry and Bananas Crepe ©2015 HollyDayz
Eggs, Bacon, Sausages, and a Strawberry and Bananas Crepe ©2016 HollyDayz

Once we were done eating we walked back to Hotel Felix and our room was ready. The room was beautiful and spacious. Due to the early morning flight it seemed so easy just to stay in the room and relax. The bed was comfortable too, but with only 24 hours there was much to see and do. I wish we had stayed for longer! Chicago is a city full of amazing attractions and you can even purchase a Chicago CityPass to save some money on admission fees. If you plan on visiting lots of the local attractions, I’d recommend checking it out! If we had been in the area for more than 24 hours I would have definitely bought one!

Big comfy bed ©2015 HollyDayz
Big comfy bed ©2016 HollyDayz

The first thing we did was meet up with Chicago Crime Tours. We were extremely happy to get on the air-conditioned bus because it was a warm day. The seats were very comfortable. The tour was really informative and entertaining of the crimes that have happened in Chicago including the mob, drugs being sold out of a McDonald’s drive thru, and so much more. It was a lot of fun.

Area where the feds took out John Dillinger ©2015 HollyDayz
Area where the feds took out John Dillinger ©2016 HollyDayz

After having some fun on that tour we headed over to the Willis Tower, but for all those out there I know it will forever be the Sears Tower. I had to go up to the top and stand on The Ledge and explore the Sky Deck. The views from the Sky Deck were amazing! I was exited to stand out on The Ledge, just a word to the wise, don’t look down for too long. Gives you this weird, scary feeling after a while.

Hanging out on The Ledge ©2015 HollyDayz
Hanging out on The Ledge ©2016 HollyDayz

The lines to get up and down from the Sky Deck are pretty long. I would suggest a fast pass or to go very early, such as when it opens. Otherwise you need to allot more time as this could take up a good portion of it. Once we were finished at the Sky Deck we were able to enjoy the hotel for a little while.

On the Chicago River ©2015 HollyDayz
On the Chicago River ©2016 HollyDayz

We relaxed until it was time to head to the Wendella Boats Sunset Cruise. The cruise was great. They talked about all the beautiful architecture. Although we didn’t make it to Navy Pier, we did see it and many other things from the cruise. There was also alcohol and snacks on board. The cruise left the Chicago River and headed out to Lake Michigan. It was a chilly and I was very happy to have a hoodie on. We also moved from the top of the boat to the bottom because the wind was high.

Views from the sunset cruise ©2016 HollyDayz
Views from the sunset cruise ©2016 HollyDayz

Once we got off the boat we were pretty hungry. You can’t go to Chicago without eating pizza. So after a small debate amongst the staff at Hotel Felix we ended up at Giordano’s. I wish someone would have told me that you should order once you get there because it takes 45 minutes to make pizza. Sadly no one did and it took much longer than 45 minutes to eat. At that point we were pretty hangry. The pizza was delicious and I took the leftover back with me to the hotel.

Deep Dish Pizza ©2015 HollyDayz
Deep Dish Pizza ©2016 HollyDayz

The next morning before heading to the airport we headed over to Cloud Gate aka as The Bean. You can’t go to Chicago and not see The Bean! I quickly walked a bit and also spotted the Jay Pritzker Pavilion where they have events in the park. The Crown Fountain was also pretty cool. I could see people running through there on a very hot day. The fountain is interactive and has LED screens with faces that change. It is pretty cool and a sight to see.

Cloud Gate aka The Bean ©2016 HollyDayz
Cloud Gate aka The Bean ©2016 HollyDayz
The Crown Fountain ©2016 HollyDayz
The Crown Fountain ©2016 HollyDayz

After that we gathered our belongings and headed to the airport. A quick trip packed with so much. I look forward to going back to Chicago. There is much more to see and more to eat!

Have you ever been to Chicago? What did you do and how much time did you have?

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  • kemkem

    I’ve never been, but it’s one place l wouldn’t mind visiting. Loved your breakfast..looks yummy. I think l would enjoy that crime tour very much too. Fascinated with gangsters of old.

    • Holly Dayz

      It is a great city. I went often as a kid, but I got to really explore this time around. The breakfast was delicious. The crime tour was pretty cool. I highly recommend it.

  • Bijee

    There is this restaurant that we went to for breakfast there that I just loved!!! I have to find the picture to remember the name but it was so good we went both days! LOL and Girodonos is a must when we got there. That pizza is orgasmic!

    • Holly Dayz

      I would love to know where you went to eat. The pizza is good. I brought the rest back with me.

      • Bijee

        I’m gonna scroll through my pics and find it.

    • Ray

      It wasn’t Lou Malnati’s by any chance, was it? Because I was in Chicago just last month and had some deep dish pizza there. God, it was amazing!!!

      • KenyaRae

        I saw it in a picture the other day it’s called the breakfast club.

  • SocaMom® (@SocaMomDC)

    I haven’t been to Chicago in a few years, and even then we only hung out for the day. I will have to add this to my summer list of places to check out! The more blogs I read, the longer the list gets 🙂

    • Holly Dayz

      I loved it. I will happily go back. I enjoyed my time there as a kid too.

      • Staci

        Next time try Lou Manalttis Pizza on Rush Street

  • staciesayzso

    You saw a lot of Chicago in 24 hours! Love Giordanos. We have one here and it’s soo good!

    • Holly Dayz

      I did! It makes the time there seem longer because I spent the entire day moving around. Giordano’s is really good.

  • Tia @ FinanciallyFitandFab

    I’m from Chicago! I love Giordanos and Yolk. Looks like you did alot in a short amount of time.

    • Holly Dayz

      I really did! I wish I had some food from both places right now lol.


    I haven’t been to Chitown yet but it’s definitely on my list.

    • Holly Dayz

      Go soon. So much to see, do and of course eat.

  • mimicutelips

    Nice, I’m all about maximizing my time any where I go. Chicago is still on my list of places that I want to visit.

    • Holly Dayz

      So am I. I hope you get there soon. You will enjoy it.

  • Nathan

    Great post– you did a lot in 24 hours. The food looks amazing but I’d be a bit nervous about sitting on the ledge. I heard it cracked a few years back when people were on it!

    • Holly Dayz

      Thank you. I know huh lol. I heard the same thing, but I went out there a couple of times anyway.

  • prateekdasgupta

    I have never lived in Chicago but among all the cities I visited in U.S Chicago was my favorite!Outstanding food, warm and friendly people, Sears Tower and Shedd Aquarium were experiences of a lifetime, great travel guide!

    • Holly Dayz

      I have to check out the Aquarium. It is a great city with some good food.

  • Tandy | Lavender and Lime

    I did not know Sears Tower had changed its name! I can remember visiting a huge bookstore when I was in Chicago many moons ago 🙂

    • Holly Dayz

      Yea it changed it some time ago, but it will forever be known as the Sears Tower.

  • Krysten

    I haven’t been to Chicago is such a long time!
    Ugh, I want that pizza so bad, looks like you had fun! 😀

    • Holly Dayz

      I could go for some pizza too.

  • Kiwi

    I will be honest I am not as excited to travel to Chicago because of the crime rate. I think one day I would like to of course to visit the BEAN and maybe…maybe visit the infamous ledge!

    • Holly Dayz

      That shouldn’t be a reason to not travel to Chicago. There is crime everywhere and some worse than Chicago. You never know what is going to happen anywhere.

  • Sara Broers (@TravelWithSara)

    Some of my 24 hour Chicago favorites! I LOVE Giordano’s pizza and The Bean! Arriving early at Willis Tower is the best tip anyone can receive! The lines can be long, but worth the view.

    • Holly Dayz

      I saw the lines just to come back down. Smh craziness. The views are amazing.

  • Sarah Ebner (@sarahjebner)

    You certainly packed it in! I haven’t been to Chicago in years, but would very much like to go back – especially to do one of those crime tours!

    • Holly Dayz

      I used to go often as a kid, but of course never saw any of this stuff. It was so much fun.

  • Tonya Denmark (@DOTraveler)

    I LOVE Chicago and always glad to read more things to do in such a friendly city. I definitely want to check out the crime tour, sounds fun!

    • Holly Dayz

      It is a great city with a lot of beauty. The crime tour was a lot of fun. Leaned a lot.

  • Alyssa | Adjust Your Focus®

    I know a lot of people from Chicago, and have driven through on road trips, but it’s still one city I haven’t stopped in and really explored. That needs to change! Thanks for sharing.

    • Holly Dayz

      I hope you stop next to ride by. A lot to see and do in the land of the skyscrapers.

  • heyitskaysways

    I’ve never been to Chicago maybe one day. You accomplished & enjoyed plenty in your 24 hours!

    • Holly Dayz

      As you can see a lot can be done in a day.

  • Carly Moore (@girloutofbounds)

    The Sky Deck… that’s the nopest thing I’ve seen this week. You couldn’t pay me enough to sit on there lol.

    • Holly Dayz

      Well you can watch from afar then. Great experience that I am glad I was able to do.

  • Ray

    I just visited Chicago for the first time last month for a work trip. I decided to fly in the weekend before so I could get 3 days in while I was there, but even that wasn’t enough. So, I made it a “sports themed” weekend by doing a tour of Wrigley Field and Soldier Field, visiting the Chicago Sports Museum, and watching both a Chicago Fire match and a Chicago White Sox baseball game. Really looking forward to going back again in the future and explore more of the culinary and craft beer side of Chitown.

  • Holly Dain

    As a lifelong Chicagoan I must say you did well. I used to work at both Airport Express and Wendella so maybe we met up and didn’t know it. Next time you need to spend more time for sure. Be sure to check out , Shedd Aquarium, Lincoln Park Zoo, The amazing theater district and some ethnic food. Pizza is good but Chicago has So much great food you can really miss out. It is really cool how similar our names are.
    Holly Dain

  • Darvel

    Breakfast looked delicious! Didn’t get a chance to visit “the bean” when I was last there. Definitely plan on returning for a mini vacation. You covered a lot in a 24 hour span! Thanks for sharing!

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