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Travel Guides

24 Hours in Chicago

Chicago

Chicago, IL

I’ve lived about 2 hours away from Chicago for the past 6 years. In all the time, the hubby and I have actually never spent a full day and night there. We’ve been there a ton and taken the kids a bunch, but always for day trips and made our way home at the end of the night.

It was funny also, no matter how many times we said, “let’s go to Chicago… but just for a couple hours… we need to be home before bedtime” we would always end up back home at midnight. Haha!

Now that we are officially moving to Dallas in a few months, we decided to take a day/night trip there just to get away for a little while.

Actually it was my mom’s idea because her and my sister were visiting at the time and she suggested we do it while she takes care of the kiddos. Why not?

So we booked a hotel and we were off! Our first and last 24 hours in Chicago.

Well, maybe not our last. I would definitely go back to Chicago to visit.

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Where We Stayed

168 N Michigan Ave, Chicago, IL 60601

Since it was such an impulse trip we didn’t really do much searching for a hotel. My sister just searched for an affordable option on Hotels.com or something and booked it. However, since it was in the middle of winter when we went (mid-February) there were a ton of options for great rates.

She found Hotel Julian right across the street from Millennium Park and Cloud Gate (or “The Bean”) that is right near downtown. It ended up being such a cute little boutique hotel with super cute rooms, a nice little hotel bar, and the perfect location for all the walking that we were going to do.

If we do ever end up going back to Chicago for a mini-trip, I would definitely keep on this on my list of places to consider staying.

What We Did & Ate

353 W Hubbard St, Chicago, IL 60654

This was our first stop of the day! We decided on brunch here because their menu looked amazing and I had been seeing all the cute pics of their “Rose all day” sign.

Judge away… I just went here to get a picture in front of the wall.

The food ended up being amazing. I had chilaquiles, Jamie had the Avocado toast, and Stefan had a sausage and potato hash along with some mimosas to wash it all down. None of us were driving anywhere that day so why not start the day off right?

After filling our bellies with food we dropped the car off at the hotel. We didn’t want to drive, since we knew we would be drinking, or continue to pay for parking especially when the hotel provided garage parking for the night of our stay.

If we decided to go anywhere that wasn’t in walking distance we would just take an Uber. Much cheaper and faster than getting our own car, finding parking, paying for parking, then doing it all over again.

Also someone would have to stay being the DD all day and that’s not fun when you’re kid free for 24 hours. Ha!

201 E Randolph St, Chicago, IL 60602

Since our hotel was right across the street from Millennium Park we took my sister to see The Bean. She had never been to Chicago before so we thought it only fitting to do all the tourist things we could. Plus, you can’t go to Chicago and not see the bean.

During the summer months there’s also a bunch more to do in Millennium Park. They usually have free concerts during the day and there are water fountains and places for kids to run around and play. However, since it was the middle of winter most things were closed. I was still surprised at how many people were still out and about though.

233 S Wacker Dr, Chicago, IL 60606

After taking all the pictures at The Bean, we decided to head over to the Sky Deck at the Willis Tower. Even as many times I’ve been to Chicago, this was the one ‘tourist’ thing that had not done yet.

I’ve heard that lines can get super long some days and was hoping to possibly beat the possible crowd by going earlier in the day. Well, to our surprise, there was absolutely no line and no waiting anywhere.

It’s a long walk to get to the ticket counter (probably line when busy) and then a super long walk to the elevator (probably another long line when busy) to get to the top.

I wasn’t really nervous about the whole thing until we got in the elevator. It was a short trip… because the elevator travels so fast… but there’s a little video that plays and tells you how high up you are in relation to other things and watching that made everyone in the elevator nervous.

Once we got to the top there were about 8 or so “sky decks” at various points and you could pick which one you wanted to go on based on where it looked out. We didn’t really care and just picked the one with the shortest line. Haha! We ended up just waiting about 60 seconds for the people in front of us to finish up.

They do give you about a 2-3 minute time limit once you are on the glass, which is smart, so that people don’t take a million and one pictures and take 30 minutes. Though if I’d have been waiting in line for over 4 hours I would have wanted more than 2 minutes. Thankfully we didn’t wait at all and the lady told us we could get back in line for more time if we wanted.

12 S Michigan Ave, Chicago, IL 60603

After walking the whole way to the Sky Deck we were starting to get a little hungry and wanting another drink. So we decided to walk back towards the hotel and stop at Cindy’s for an app and couple drinks.

Originally I wanted to go to Cindy’s for brunch because I heard it was fantastic but they didn’t have any reservation openings on such a short notice trip. When we arrived the kitchen was actually closed except for a small app menu but the bar was still open and the restaurant was pretty busy.

We grabbed a bartop table looking out over the terrace they have that looks over Millennium Park, The Bean, and Lake Michigan. We had a couple drinks and decided to head out to do some shopping next.

Shopping

N State Street, Chicago

I actually had a couple returns to do so we headed out over to State Street to do a little shopping. Since it was so cold outside we thought that heading in and out of a couple stores would be a good way to keep us warm while we waited for our dinner reservation.

Plus, my sister had never been to Chicago before and just walking up and down some of the streets was fun for her (and us) to see everything that is Chicago and how massive the city really is.

35 W Wacker Dr, Chicago, IL 60601

We got bored of shopping pretty quick and were all ready for some more apps and drinks and stopped here.

Originally we tried to go to The Dearborn but it was packed for a Sunday night and it had an hour wait and the bar was completely full.

However, this little place was just 2 blocks north so we ducked in here when it started to snow a little. We grabbed a couple drinks and a few apps to tide us over until our dinner reservation at 9:30p.

The food was great but the server must’ve been having a bad night or something and was really rude to us. I would go back for the food but not for the service.

Hotel Julian Bar

Since our Catch35 server was so rude to us, we paid our check and left. Tanta, where we were going to eat dinner, was more of a walk than we all wanted to make – in the snow – so we headed back to the hotel for a minute to warm up, dry off, and also sit at their bar instead.

This was a much better idea and they had some really great drinks! The bartender was also amazing and as we were chatting we found out she had just moved to Chicago from being in Tampa, Florida for a few years! What a small world that all three of us were from Tampa too! We chatted for a while then grabbed an Uber to dinner.

118 W Grand Ave, Chicago, IL 60654

I always let the hubby pick food places and he never disappoints! This place was amazing and I am definitely planning on going back if we are ever in Chicago again.

It’s a tapas style restaurant with Peruvian food that is to die. We ordered a bunch of different plates and ended up loving so many of them that we ordered second rounds of some things – the scallops and the octopus were a couple of our favorites.

The prices were also very reasonable and I would highly recommend to anyone!

Hotel Julian Bar

By the time dinner was over it was almost midnight but, despite normally going to bed earlier because kids, none of us were super tired. Unfortunately, it being a Sunday night, most of the restaurants were closing so we took an Uber back to our hotel and sat at the bar again. Had a couple more drinks each and chatted with the bartender for about an hour or so.

It was the perfect way to end the day.

The next morning we didn’t do anything at all and just slept in and then grabbed our car to head home. We probably could have stayed in the city a little longer but it had snowed a few inches overnight and we didn’t want to walk all over in the snow and sleeting rain. So home it was!

What We've Done Previously

8400 W 31st St, Brookfield, IL 60513

We’ve taken the kids here a few times and absolutely love it. Highly recommend for a fun family day.

Chicago Riverwalk, Chicago, IL 60601

Just a nice little scenic walk along the Chicago River. It has beautiful city views & dining, plus bridges, fishing piers & boat docks.

Magnificent Mile

Chicago, IL 60611

The Magnificent Mile is Chicago’s premier commercial district. The vibrant, bustling area is home to upscale shops, luxe fashion outlets, cool restaurants and posh hotels.

201 E Randolph St, Chicago, IL 60602

24.5-acre green space with a the Crown Fountain, Cloud Gate (The Bean), and outdoor pavilion where they have summer concerts.

600 E Grand Ave, Chicago, IL 60611

Former Navy training center draws crowds with carnival rides, restaurants, shops & fireworks.

1200 S Lake Shore Dr, Chicago, IL 60605

We’ve been here at least a half-dozen times. It’s a fun aquarium with a ton of things to do with the kiddos and even has their own little play space in the basement.

835 N Michigan Ave, Chicago, IL 60611

Shopping destination with glass elevator & over 100 retail stores, spas & restaurants.

There you have my recap of our 24 hours in Chicago! Hoping this blog post helps some of you easily plan a quick trip to Chicago.

No matter where you go, you definitely won’t be disappointed. Have you ever been to Chicago? Do you have any recommendations for me if we go back?

What are your thoughts?

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