Tour Chicago in 10 Hours

Shane had been planning on visiting Chicago to see Lucky Boys Confusion play at the Taste of Lincoln Avenue with his friends. When his friends backed out, I was more than happy to step in and take him instead. I’d been looking for any excuse for a road trip and this was it!

I toured Chicago same weekend last year with my friend Fawn and had a blast. It’s a scintillating city with all of its history and architecture, movie scenes, and amazing food. So, I was thrilled to show him around. Read our sponsored post from that Chicago Trip here: Bang Bang Pie & Biscuits.

We drove 8 1/2 hours to make an overnight stop in Michigan where we camped and toured St. Joseph, an adorable beach town on the coast not far from Chicago. This was really just an excuse to mark another state off our list that we hadn’t been to, yet. And then on our way to Chicago the next morning, we also were able to mark a National Park off our list, The Indiana Dunes National Park. We finally got to Chicago just in time to get settled into our adorable AirBnB and make it to the Taste of Lincoln Festival to see Lucky Boys Confusion. So fun!

The next day, Sunday, we were able to take the whole day to just tour the city and have some fun before heading home to New York on Monday. If you are short on time, this is the perfect itinerary to Tour Chicago in 10 Hours! Most of it is walking, so I suggest you use the app Best Parking to find yourself a cheap garage to park in and take a Lyft to the places that are too far to walk. It will save you so much time and money! And who wants to deal with that traffic?! NOT I!

1.) First stop is Millennium Park. Home of Cloud Gate aka “The Bean”, The Crown Fountain, and other beautiful landscapes and artwork in the middle of the city. We suggest you get there early because as you can see, it gets really crowded! Don’t forget to stop by the beginning of Route 66 sign which isn’t far from the park.

2.) The Riverwalk is a short walk from Millennium Park and offers so many fun and interesting scenes of Chicago’s downtown. Not to mention its the most beautiful spot in the city. Read my article from last year to read some of my favorite stories, 10 Unique Facts About Chicago.

Free Tours by Foot gives an AMAZING tour of the Riverwalk if you want to learn more. I did this last year during my trip to Chicago, so when we went this year, we chose to do the Gangster Tour instead. Free Tours by Foot offer different tours throughout Chicago that are way better than doing any sightseeing excursions that usually cost an arm and a leg. With these tours, you pay at the end what you feel they’ve earned. And trust me, their tour guides should earn way more than those costly excursions.

3.) So with that being said, obviously our next recommendation is to visit Lincoln Park for the Free Tours by Foot Gangster Tour (or the Riverwalk Tour).

Learn about the hidden gems and hired guns of Lincoln Park while getting to see the famous sights such as The Biograph Theater where Dillinger was killed, the site of the St. Valentine’s Day Massacre, The Red Lion Pub (the most haunted place in all of Chicago) and so much more. It was so fun to get to walk in this well known neighborhood of Chicago and learn facts about the notorious gangsters and see their old stomping grounds.

4.) Get back to downtown Chicago and grab drinks at SafeHouse. SafeHouse is hands down the funnest place in the city and could easily be my favorite bar of all time! This unique place was recommended to me last year when visiting Chicago by one of our readers. Not knowing anything about the place, my friend Fawn and I figured we would give it a try. Little did we know, you need a password to get in unscathed and have to find your way back out of the restaurant when your ready to leave!

No, I’m not going to give you the password. I didn’t give it to Shane either because everyone needs the full experience for their first time to SafeHouse. During your time there, you will be able to hunt and explore through the place to figure out the password for the next time you visit. In the meantime, good luck finding your way out and enjoy.

5.) Eat deep dish pizza at Lou Manalti’s and/or Giordano’s. The reason I say and/or is because we ate at one, and then took home a frozen deep dish from another. Last year I ate at Giordano’s and it was incredible! There’s nothing like having deep dish pizza for the first time in the heart of Chicago. So, when we went this year we decided to try another city favorite called Lou Manalti’s. Shane loved the pizza, but I was still hooked on Giordano’s so after dinner we took a long stroll and grabbed a frozen one to take home and have for dinner the next night. Which ended up being the best idea EVER!

The verdict: He chooses Lou Manalti’s and I choose Giordano’s.

6.) After an exhausting day of touring, if you have the energy I highly suggest to end the day at Navy Pier and take an evening ride on the Ferris Wheel to see the skyline lit up.

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I hope this gives you a great idea of how to spend a day in Chicago! I know we didn’t talk about restaurants for breakfast or lunch and that’s because we ate a little outside of the city and skipped lunch that day! However, here are some recommendations:

Grab a Chicago dog in Millenium park. There are tons of food stands around the area to get your authentic fix.

Visit Bang Bang Pie & Biscuits for their amazing pie and biscuit meals. So filling and one of a kind. Luckily there are two locations for where ever you may be in Chicago! See our sponsored post HERE.

Stop in for a hearty breakfast at the local food chain, The Golden Nugget Pancake House. Yes, it’s a chain – but it’s delicious and cheap!

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Remember when visiting Chicago to be ALERT, but also HAVE FUN!