traveling back in time: chicago

One of my favorite things to do in my free time is plan trips and travel. I love the trips themselves but sometimes I don’t want to dedicate tons of time to the actual travel portion of traveling. From Louisville, Chicago is only four to five hours away, depending on exactly where you’re leaving from/going to. I’ve found this to be the perfect distance for a quick getaway and there are so many fun things to do in the city! I’ve gone to Chicago three times in the last year and had a different itinerary every time. The first time I went with my family for a weekend in the fall. Then, Gabriella and I went with some of our friends for a few days on spring break. Finally, I went again for another family weekend this summer. I love planning trips around concerts, so both family trips were entirely based on shows that weren’t coming to Louisville and happened to fall on a Saturday night in Chicago. By no means am I an expert on the city, but I have found some 10/10 sights and experiences to share!

Things to do

I love to stay busy when I take trips, so here are my top activity recommendations.

• Lincoln Park Zoo: I like to check out the zoo whenever possible when I visit a new place. This zoo is so cute and completely free! I definitely recommend going when it’s warm out because in the winter there weren’t many animals out, but it was still fun to walk around.

• Lincoln Park Botanical Garden: If you decide to stop by the Lincoln Park Zoo, you have to hop over to the botanical garden too. It’s right next door and also completely free! There are lots of beautiful plants to see and lots of great photo ops. There is a super cool and slightly eerie pond with bowls that float and make sounds in the middle of one of the rooms.

• 360 Chicago: One of the most touristy things in Chicago is the Skydeck at the top of Willis Tower. Think of this stop in the John Hanckock building as the lesser known, cheaper option. I got the Sun and Stars tickets, which allows you to go up to the top twice in 48 hours - once at night and once during the day. I went first at night and then again the next afternoon. I wasn’t sure what I was looking at at night but it was so cool to see the entire city lit up.

• Garfield Park Botanical Garden: This botanical garden is not in the middle of the city, but it’s well worth it to venture a little bit outside to experience. There were so many rooms with different terrains and unique types of plants to see and learn about. This is another free excursion and they also offer free parking!

• Underground Donut Tour: This one may sound a little out there, but hang with me! A tour of donut shops through downtown Chicago. This is a two hour commitment, but honestly worth every minute and every penny. Walk the streets of Chicago with local tour guides and get to try the best donuts in the city. You go to four different shops (the exact ones depend on the day you do the tour, but you won’t be disappointed)! I got to try a donut made with funnel cake batter and topped with pop rocks (pop rocks!!!), a pistachio cake donut, and so many more. My personal favorite, though was a vanilla cake donut with vanilla glaze, and topped with sprinkles.

• Oz Park: The Wizard of Oz has always been one of my favorite movies, so when I found out there was a neighborhood park with statues of the characters I just HAD to go. It’s in a super cute neighborhood and a nice place to hang out for a little while.

• Millenium Park: Millenium Park is probably the most typical tourist thing in this list. It’s the home of The Bean, The Crown Fountain, and The Art Institute of Chicago - just to name a few things. It’s also a huge park with walking paths, playgrounds, gardens, and all the people watching you could ever dream of.

Photo Ops

I love a good opportunity for a picture, so there was no way I could leave these spots out.

• The Bean: How will anyone know you’re in Chicago if you don’t immediately post a picture in front of the Bean??? It’s a necessity when touring the city. I definitely recommend taking a fun mirror selfie from underneath it, too!

• Millenium Park: I decided that the whole park needed to be on this list too. First, there are markers that you can take pictures with that say “Millenium Park” on them. The Crown Fountains are cool to watch, but also a great place for a fun photo! The iconic lions in front of the Art Institute are fun, too. There’s also lots of greenery and scenery to take some less touristy-pictures.

• Lake Michigan beach: I have yet to actually go to the beach for the sake of going to the beach, but I’ve gone for the sole purpose of pictures plenty. This adds another dimension to those vacation pictures, even though it’s not your average beach vacation.

• Obama Rock: This one is probably not for everyone, but I was super enthralled with it. It marks the spot of Barack and Michelle Obama’s first kiss outside of a Baskin Robbins.

Places to Eat

Food can make or break any trip, so make sure to pick some good spots.

• Pequod’s Pizza: Pequod’s is located in the same neighborhood as Oz Park and it’s absolutely a local favorite. They’re known for their caramelized deep dish crust and it is incredible!

• Lou Malnati’s Pizzeria: Self-proclaimed as Chicago’s best deep dish pizza and it was a big hit with my family. It’s so good that when I posted that we were there, my cousin immediately called me to ask if I would bring a large pizza back to Louisville. If that’s not a testament to the pizza quality, I don’t know what is.

• Heritage Outpost: This is the cutest little coffee shop and they had a great Americano! They’re all over the city, but I went to the one in Uptown. It’s located in the lobby of a super cool condo building and the atmosphere was perfect to take a break and enjoy coffee.

• Ann Sather: This breakfast spot with NOT disappoint. They have lots of uniques options and even some Swedish choices. Gabriella got a side of Swedish meatballs with her breakfast when we went!

Tips

• If you’re driving to Chicago and plan to drive around the city, make sure to investigate the parking situation in advance for every place you’re planning on going. Driving and parking in the city can be a pain. I’ve found the best way to get around depending on what your plans are, is to buy a parking pass for one of the Millenium Park garages in advance. You can leave your car there as long as you need throughout the day and walk/uber to other places.

• There are so many local food places in Chicago. Don’t go to the chains if you’re looking for true Chicago eats! Venture out into the area surrounding wherever you’re staying and see what the city has to offer.

Chicago is such a fun place to visit and it’s full of opportunities for adventure!

Let us know if you decide to try out any of these places.

See y’all soon,

Molly