View of Chicago from Lake Michigan near Navy Pier

Back in 2017, I was able to tag along on a trip to Chicago and instantly fell in love with the city. I had never been before, but since then, I've been 3 times! The river and Lake Michigan are beautiful and the food is hands down the best of any place I've traveled. This past trip, I tagged along with my mom on a work trip for a few days and got to experience even more places that I'm going to share with you all. I love Chicago with a fiery passion, so this post is long, but all of the food places and activities are hyperlinks, so you can click on them and research on your own! If you're headed to Chicago anytime soon or have any must try places for me the next time I go, let me know in the comments below!!


We were supposed to fly out of Atlanta and then have a connecting flight from Kentucky the morning we left, but got a text at 5:00a that the connecting flight was cancelled [insert mini panic attack]. Because of this, Southwest actually put us on the one way flight getting us there way earlier. We landed at 8:30a instead of 11:00a! Once we dropped our bags at the hotel,which was the Hilton Garden Inn near Magnificent Mile (aka the best shopping ever), we started to walk towards Millennium Park since I wanted to show my mom The Bean. Really quickly--I've stayed in 3 different hotels and they were all good locations. The Hilton on this trip was the best location, in my opinion, for all that we did, but as long as you're along the river running near Lake Michigan, you'll be good if you want to spend your time downtown! Everyone walks in the city and places are easily accessible by foot, so a car isn't needed. Parking is expensive everywhere anyways. You can always Uber/Lyft if you need to! I would also note that Chicago has a reputation for not being safe, but there is only one area (located on the south side) that people should avoid. Just look up a crime report map and it will show you the areas with the highest crime rate. Of course, always be aware of your surroundings and don't go sketchy places on your own, but I've done mostly everything alone when I've gone and never felt unsafe. Any-who, back to the trip haha...We checked out The Bean (Cloud Gate) and Lake Michigan. My mom was shocked how much the lake looks like the ocean. It's SO pretty! We also stopped at Nutella Cafe and had a breakfast treat. We mostly did sightseeing during the morning, but it was cold so we went back to the hotel to rest since we had been up since 3:00a. For lunch, we went to Portillo's. This is a Chicago classic and very busy tourist spot, but I think the "Chicago dog" is so good and affordable. My mom loved it as well!

We were scheduled to go on an architecture boat tour at 2:00p, but time got away from us and we missed the boat [insert bigger panic attack]. I have never ran so fast in my life. I had to leave my mom behind lol. Thankfully, we were able to reschedule to the 3:00p tour. Since it was cold, we sat inside and had spiked hot chocolate--yumm! I definitely recommend this tour as a way to see all of the major buildings in the city and learn about Chicago's architecture history after the fire. It's also an easy way to sight-see without walking all over the place. We ended the night by having pizza in bed from Pizzeria Unos and watching Game of Thrones. *Side note: As far as deep dish pizza goes, I've tried both Lou Malnati's and Giordano's. Giordano's is my fave by far. Mostly because I don't like huge pieces of sausage and both of the other places make their pizza that way.


The next day, my mom had to work so I was on my own. I started the day by taking an Uber to Left Coast Food + Juice. It was too early in the morning to walk that far without having coffee yet haha. Their Laguna Avocado Toast was delish and seriously so pretty that I didn't want to eat it. I did some shopping that morning and then stopped by Joe & The Juice. I asked the waiter for his recommendation, which was a great idea. I had the Herb Tonic and felt like the epitome of health. Next, I went to the Lincoln Park Zoo. I talked myself out of doing this on my first trip. BIG HUGE MISTAKE. This is one of my favorite things I have done in Chicago and I may do it every time I go. The zoo is a FREE ADMISSION zoo, which is one of very few in the entire U.S. I am a big outdoors person, so it may be why I loved it so much. It's along Lake Michigan and you just stroll through looking at animals. The weather was perfect and the zoo is so well maintained that it reminds me of a garden or park. The African Experience was my favorite, because the animals are so close to you! I could have reached over and picked up a meerkat. There are also polar bear, penguin and monkey exhibits ("Lions and tigers and bears, oh my!" Sorry, I had to). I ate a late lunch at Sweetgreen, which was kind of underwhelming to me? It's such a popular place, though. Afterwards, I got a coffee and macarons at a cute little shop called Alliance Patisserie. I roamed around until my mom got off work and we went to Navy Pier. You have to go here in Chicago. It's tradition and the end of the pier offers great views of Lake Michigan and the skyline. When it's pretty outside, this place is packed. We also stocked up on Garrett Popcorn--another Chicago classic. For dinner, we ate at Eataly. If you haven't been before (they're in New York too), it is a sort of grocery store with restaurants in it as well. You have to eat pasta here!!


On my last day my mom worked, so I flew solo again. I got coffee at Hero Coffee on Jackson Blvd. This coffee place has multiple locations, but this is the most "Instagram worthy." It's located in an alleyway and has a huge, illuminated sign above it that simply reads "coffee." I've also been to the location on Dearborn Street as well which has a more local feel. I shopped around and then headed to 3 Arts Club Cafe for brunch. I've seen this place on every Chicago "must do" list and finally got to check it out. It's a cafe in the middle of a restoration hardware store. I loved the atmosphere, but wasn't crazy about my meal (ribeye sandwich). I've heard this is a great place for happy hour or a cup of coffee. I think I agree. I didn't eat much, so I went to La Bodega Del Barrio for one of their famous churros and coffee. I got the fruity pebbles flavor. Oh my yum. I ended the day before my flight by sipping my coffee on the steps of the Riverwalk. It was so hard to leave!

I hope if you get the chance to go to Chicago that you love it as much as I do! If the winters weren't so brutal, I think I would have moved there already. Here's me gazing out the window like I own the place (LOL):



Fairgrounds - Must try! I had the lavender latte (seasonal).

Dollop Coffee - The coffee and scone with jam was awesome!


Beatnik on the River - So many reasons to try this place. You NEED to look at pictures of how cute this place is. You eat on couches that line the river, and the food was great. I had the baba ghanoush. The main dishes are pricey, so I suggest appetizers or going for brunch when it's more affordable.

Wildberry Pancakes - I would legit kill for the blueberry danish crepes. Seriously.


Beatrix - Great lunch spot! The salmon salad was incredible and their green juice was so refreshing.

Sushi San - I had the crunchy avocado roll!

Roti - Build your own Mediterranean bowl. Chain restaurant mostly in the Northeast.

Lou Malnati's & Giordano's - Two famous pizza locations. I tried both---I prefer Giordano's!

El Hefe - This was a last minute decision, but the place had great food and the decor is spunky.

Activities/Things To Do:

Chicago Theater Tour - OKAY. I just so happened to go to Chicago for the first time on the anniversary of the theater opening and they offered special tours all day so I was able to snag a ticket. This was so cool!! I learned so much and they even take you backstage where all of the performers have signed their names. The regular tour is only $18. Even if you don't like theater, this is a must do.

Willis Tower (formerly Sears Tower) - Best 360 views of the city and is one of the tallest buildings in the world. The skydeck gave me major anxiety, but it's another must-do. You walk into a glass box protruding from the building and look straight down (103 floors, 1,353 feet). The line is long for this, so be prepared. It also costs $25/person to go up.

Chicago Cultural Center - Worth seeing. They have exhibitions throughout the building. Free admission!

Riverwalk & Lake Front Trail - This was the most peaceful and beautiful thing I've ever done. I ended up walking miles without realizing.

Magnificent Mile - This is best known for shopping. There are high end stores, but affordable ones sprinkled throughout.

Shopping - If you're looking for other shopping options, the area near the Chicago Theater has all of the popular stores (Target, Old Navy, H & M, etc.).


Shedd Aquarium - The weather was awful the day I went here so I needed to do something inside, but I was disappointed. Especially after paying $40 for admission. It probably doesn't help there were a million toddler field trips going the same day so kids were literally everywhere.

Harold Washington Library - I thought this was going to be a stunningly beautiful library (heck, it takes up the entirety of the city block it's on) with old books and memorabilia, but it's just a public library haha. Apparently there is a glass ceiling atrium on the top floor where you can sit and read, but I didn't head up there.

Harry Caray's - We ate pretty late and stumbled onto this place. I had no problems with it, I just wouldn't say you HAVE to eat here. It was yummy, but pretty pricey. I had the salmon!

Peet's Coffee - Popular chain. I was not a fan of the coffee. The muffin was good though!

Stan's Donuts & Coffee - Full disclaimer: I am not a doughnut person. However, I have tried places before and liked them. This is not one of those places. The inside of this place is really pretty, but the icing/glaze was so overwhelming and I had it e v e r y w h e r e by the time I took one bite. Sorry, Stan!



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Emily Duggan

"Leopard print is my favorite color."

Jessica Graber

"No talkie before coffee."

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