24 Hours in Chicago

Trips & Travel

24 Hours in Chicago

Chicago has been a city on my bucket list to travel to for quite some time. And even though it’s only a short road trip away, I’ve never made it there. Until recently! If you’ve been following along via Instagram, you know we’ve been going to a ton of hockey this season. Some good friends of ours had it on their bucket list to see a Blues vs. Blackhawks game at the United Center in Chicago, and this year it worked out that not only were they able to go, but we went with them! And we got to sit in some amazing seats. But besides the game-what else can you do with 24 hours in Chicago? Quite a bit actually! Here’s our rundown!


Our landing pad for Chicago was the DoubleTree by Hilton Downtown Magnificent Mile. I highly recommend checking it out as a place to stay for your trip! Not only is the design welcoming and warm, but the rooms also were clean and comfortable and the overall aesthetic is gorgeous. As far as location, we were only a block or two from Magnificent Mile and five or so blocks from Navy Pier.

One thing I will note is that there is very little free parking in Chicago. If you are driving yourself, be prepared to pay for parking, even at your hotel. We parked the car at the hotel and then Uber’d anywhere we needed to beyond what we wanted to walk. Luckily, Chicago has a ton of public transportation options from cabs to Ubers & Lyfts to trains.


While we were in Chicago for a limited time, we still managed to hit up a few good restaurants! Before the game we headed to the Chicago Starbucks Reserve Roastery, which is five floors of coffee goodness. They don’t have the typical Starbucks menu, but they do still use the app for payment. There’s a bakery and bar inside as well! After the game, we ate a late (LAATTEE) dinner at Timothy O’Toole’s which was essential right across the street from our hotel. I had the burger and it was amazing! Matt got the buffalo chicken spring rolls and they were top-notch as well. Before we hit the road, we enjoyed Chicago-style hotdogs at Portillo’s. It was a little after two when we got there, and it was still crazy packed! And I know what you’re thinking. I went to Chicago and didn’t get the deep dish? Well, rest assured that I did, but it wasn’t, in my opinion, anything to write home about. It’s on the list for a return trip though, we just ran out of time to try another pizza spot. I missed out on breakfast because I met up with a friend I haven’t seen in ages and we had coffee and a catch-up down on Navy Pier!


Obviously, we went to the hockey game, so if you go during hockey season and your team is there, check out ticket prices. We lucked out and snagged second row from the ice seats to watch the Blues take home a winner at the United Center. If basketball or baseball is more your sport, Chicago is home to both those sports as well. And don’t worry about Ubering to or from the United Center. They have it all figured out with a heated tent to wait in while your driver is pulling into the dedicated lot for pick-ups! There is of course the famous Chicago bean, but we didn’t make it there. Plus a litany of museums and other places to go.

Magnificent Mile holds all the shops you could imagine and Navy Pier is a great place to meet up with one of the riverboat tours. We did go up in the Willis (formerly Sears) Tower, which held some amazing views of the city.

Must Do Activity

If there is one thing you are going to drop $50 a ticket on, make it the Chicago River Architecture Boat tour! It grants you amazing views and historical insights about some of the most famous buildings along the city skyline. Plus, you get to see all the hidden gem restaurants along the riverwalk from your slow sailing point of view.

Don’t Waste Your Time

*This is strictly my opinion, don’t come at me for it*

The Tilt activity that is at the top of the Willis Tower is a waste of money. For the following reasons:
1. You barely lean out from the building, so there isn’t really a huge scare factor.
2. You literally just look down at the street. The views from around the rest of the floor are so much nicer.
3. It’s barely a minute that you are tilted out there.

It just seems like a lot of hype and money for something that isn’t exciting or novel. Save your dollars for something else, like the boat tour or a great meal!

And that wraps up my 24 hours in Chicago! I can’t wait to come back for a bit of a longer stay and see more of the city. We’re hoping to maybe go back sometime in the summer to see all the sailboats and the tilting bridges along the river in action. If you’ve been to Chicago and there is somewhere I need to add to my must-stop list, drop it in the comments below!

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