In case you missed it, my sweet husband surprised me with a weekend trip to Chicago a few weeks ago. It was perfect! We were only there for a little over 48 hours, but we definitely made the most of it. We were able to see, do, and eat so many amazing things in such a short time. We fell in love with the city and will definitely be making a trip back soon.
If you’re looking to get the most out of a quick trip, this travel guide is for you. Although I can’t really take credit for it, because Derek planned the whole thing. So here is a travel guide from Derek. haha.
Where To Stay
DoubleTree by Hilton – Magnificent Mile
Amazing. Amazing. Amazing. Gorgeous hotel, extremely clean, well taken care of, amazing service. I don’t have one bad thing to say. I definitely recommend getting a room on one of the higher floors for an amazing view like below. Its a little bit extra money, but so so so worth it! It was amazing to wake up to that view each morning. We also saved money in the long run by staying on Magnificent Mile, because we were literally able to walk to everything so there was no money spent on taxis, ubers, etc. Derek and I plan to stay at the exact same place next time.
Where To Eat
Great food, great atmosphere. Its a very mom & Pop/old school vibe with amazing food. They had great service too.
A must!! This one was actually found by accident. We kind of got turned around while walking and missed the original place we were headed. By this point I was hangry so we decided to just eat at the next place we saw that looked decent. We both spotted this place from across the street and said it looked promising…… AMAZING! Seriously the best food ever. I honestly can’t say enough good things. Its one of those places that doesn’t look great from the outside but surprises you on the inside.
The Signature Room at the 95th
Go grab your bucket list and write this one on it…I don’t even have words to describe it.
So this is definitely a splurge, but so worth it. Derek and I didn’t get the chance to celebrate our anniversary this year, so we took this opportunity to splurge a little and celebrate a little late. It rained a little while we were there, but it was still a breath taking view. I’ll let the pictures do the talking on this one.
The pizza is as good as it looks in the picture. It truly did NOT disappoint! Easily best pizza I’ve ever had. All I’m going to say is you HAVE to go. Its not an option. You HAVE to!
What To Do
Walk the magnificent mile. There are endless things to do and see. Seriously, endless. Make sure you stop and see the river too! Its prettier in person than in the pictures!
You could spend an entire day just at the pier. I definitely did not realize how big it is and how much there is to do. Endless shops, places to eat, games, & more. Seriously endless stuff to do here. I would definitely devote most (or if you have enough time, all) of your day here.
Much cooler than I thought it was going to be. haha. The truth is, we had no plans of going to see it because Derek & I were both uninterested. We were walking one day and realized we were super close so we said why not since we were already so close. We were both really surprised by how impressed we were. Its definitely one of those things you just need to go see.
Another thing we never really “planned”. Its in the same area as the bean, so you might as well see both while you’re there. Its a really pretty area and this fountain/wall/art thing (haha) in this picture is really really cool in person.
Oak Street Beach
Such a nice area. Theres tons of people out walking, riding bikes, walking their pups in the sand. I definitely recommend just walking up and down the little trail they have and taking some time to sit on a bench and relax. Its very peaceful.