Josh and I absolutely love travelling and one of our goals this year was to travel more. We created a little bucket list of places we wanted to visit this year with Tulum being one of them and the next up on our list? Chicago!
We headed down to Chicago with a few friends to explore the city, eat some amazing food, and most importantly…Lollapalooza! If you haven’t heard of Lolla, it’s a music festival, similar to Coachella, hosted in the middle of the city. It was an amazing and crazy experience that featured a wide range of artists from DJ’s to rock bands. We vlogged the whole thing so definitely stay tuned for that!
Before heading down to Chicago we of course had to book our flight and accommodations, not my favourite task. Luckily, Josh is a numbers guy and always searches high and low for the best bang for our buck. Out of all of the platforms we looked through redtag.ca was the most affordable with the best price options! No joke. The website was so easy to navigate and the customer service was beyond friendly making out booking experience a breeze.
I received a ton of questions about what to do and see when we were in Chicago and the answer is A LOT! The city reminded me of a mini New York City with the beautiful cityscapes and an overwhelming amount of amazing food options. I literally worked out 7 days a week before leaving so I could eat deep dish pizza and pasta all day. It was SO worth it!
If you’ve never been to Chicago, no worries I’ve got you covered! There are so many things to do, see, and eat, so brace yourselves for all of my top picks (sorry, it’s kind of a long one)…
Visit a rooftop patio. We went to Raised Bar as well as London House, which had ah-mazing views of the city and river. I heard Cindy’s rooftop is also amazing, a little on the pricey side but definitely worth going up for a drink.
Take a stroll down the pier. Visiting Chicago’s pier was a great way to spend an afternoon but it definitely wasn’t an all day trip. It was nice to be on the lake and take in all the boats and you also got a great view of the downtown core.
Grab a deep dish pizza, or two. The top two places we were recommended over and over again were Lou Malnati’s and Giordano’s, a definite must when in Chicago! It was my first time trying deep dish and now I don’t think I’d have it from anywhere but in Chi-town.
Visit Millennium Park and Cloud Gate. This is a very touristy thing to do but tourist or not it’s a pretty cool spot to visit! Cloud Gate aka “the bean” was a great spot for a photo op and Millennium Park was nice to walk around and check out some cool art installations.
Take me out to the ball game. I’m by no means a big sports fan, that’s totally Josh’s arena, but visiting Wrigley Field was so much fun! Whether you’re sitting in the nose bleeds or in the front row, you’ll have a blast. Wrigleyville is also a great area in general so be sure to make time before or after the game to grab a drink or a hot dog.
Check out the arts. I didn’t realize this but Chicago is filled with art! From installations, art tours, museums, and amazing music festivals- it’s everywhere! Between a four day music festival and many other bucket list activities we unfortunately didn’t make it to their art institute but there was a lineup outside the building every morning. I’d take that as a good sign!
Target. For all my fellow Canadians out there, this to do in Chicago, or anywhere in the United States, is pretty self explanatory ;)
Cafe’s all day. There were so many cute coffee shops and cafe’s it was almost a daily struggle to choose just one to visit everyday. If you’re looking for an instagram worthy spot definitely check out Goddess and the Baker for their cute treats and marble table tops. And if you’re REALLY looking for an insta worthy place with the best grilled cheese in the world, 3 Arts Cafe is your go to! Nestled in the middle of the most gorgeous Restoration Hardware you’ll ever see, 3 Arts is the perfect spot to shop, nibble, and fill your phone with endless photo opportunities!
We have a few smaller trips in the works but no major plans, so if you have any suggestions of your favourite spots of anywhere you’d like to visit I’d love to hear about them!