What I Loved Most About Chicago
- July 3, 2017
- Last Updated: December 23, 2024
- 18 Comments
- Travel
I hope you had a great weekend! As you guys may know, we just got back from our trip to Indy and Chicago. I realllly loved Chicago so wanted to share a little bit about our trip here.
My sister put together an awesome itinerary for us so it was like having our own private tour guide! Usually, I spend weeks putting together my bucket list of what to do, where to eat and where to run, but Becca made it so easy for us. It took some weight off my shoulders, and I feel like we experienced the best of it in our short time there.
We stayed in an air bnb in the Lincoln Park neighborhood. It turned out to be the perfect area, close to the lake front trail, easy access to transportation, and a good central location.
So, here are some of my favorite parts about Chicago!
The Lakefront trail
It’s gorgeous. After arriving and getting settled, the first thing we did was go for a run along here.
Lincoln park is on the eastern part of the city so near the trail. That was one of the reasons we looked at staying there.
Also, if you end up staying near Lincoln Park, you’re super close to the Lincoln Park Zoo, which is FREE!
The architecture
I did not know anything about the Chicago architecture until this trip! We did a boat tour on Lake Michigan and then through the Chicago River to learn about it and it was so beautiful!
Seeing some of these buildings up close was SO COOL. We learned some of the history and stories behind these sky scrapers.
Did you know Chicago has the 2nd tallest building in the US? The Sears aka Willis Tower.
The food
OBVIOUSLY. Deep dish pizza, donuts, “walking” tacos in Fritos bags, breweries, happy hours, french toast flights.


For deep dish pizza, my sister and many others recommended Pequod’s Pizza. They definitely didn’t let us down. I absolutely love thin crust, but I was pleasantly surprised at how much I enjoyed thick crust.
Tons of cheese and bread.


We checked out donuts at two difference places: Firecakes and Glazed and Infused.


If you have a sweet tooth for breakfast, then I definitely recommend stopping by Batter & Berries.
They are known for their french toast flights and have delicious waffles too!

We even got a reservation at Girl and the Goat, which is supposedly very difficult to get into. Thanks, Open Table! Though I did book two months in advance 🙂

We tried the roasted cauliflower, pan roasted halibut, goat roasted empanadas. and pork cheek (delicious!)


The “L”
Chicago is a huge city, at least compared to what we have here in Charlotte. But, there are great forms of public transportation, reasonably priced too! While we walked mostly everywhere, we also took busses and the L, an elevated train system. It’s a great way to see the city, too! Beautiful view from up above and easy to get to many of the widespread neighborhoods.
The Neighborhoods
We didn’t even get to see everything, but there are so many quaint neighborhoods right outside the city that feel like you’re much further away. The streets were clean and the buildings were beautiful.
The downtown area is very clean but not overwhelmingly crowded.






I.O (The Comedy Scene)
My sister is really into comedy (one of the reasons she moved to Chicago) so she suggested we check out I.O (Improv Olympic). We stayed for a few improv shows, as they offer shows nightly throughout the week. This is where the stars like Tina Fey, Chris Farley, Amy Poehler, Seth Meyers, etc. Definitely recommend checking this out!
Overall, we spent 3 days there. The weather was great, the views were amazing, and the food was very memorable.
Ever Been to Chicago?
Thin crust or deep dish pizza?
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Support Bucket List TummyI was in Chicago a couple of summers ago for a weekend and absolutely LOVED it. Definitely in the top three of my favorite US cities! Just walking around the city and taking it all in was incredible.
I too tried Firecakes & Little Goat Diner (sister restaurant of Girl & The Goat) and of course some deep dish pizza though I think I prefer thin crusts.
That thick crust pizza…and french toast…YUM. you have a knack for finding the BEST food while traveling!
That is amazing how much you fit into 3 days! I went to chicago in middle school and to this day it is one of my favorite memories. I want to return as an adult so badly!
You should – they have so much amazing food, culture and sights to see! Beautiful weather right now, too!
I *loved* the improv shows when we were in Chicago. I’m not gonna lie and say it was my favorite place–I’m just not a big city girl–but I’d go back just for the improv. Glad to hear you had an awesome time!
The Improv shows were pretty entertaining – it’s neat to think about all of the stars who started there. So much history!
Went to Chicago in early June and LOVED it! Great city…
Thin crust all the way from my point of view.
I’m a true thin crust fan 🙂 Thick crust was pretty good, though!
Chicago is really such a neat city!! The architecture is incredible and I feel like it’s pretty clean for a city. When I visited with my parent, we had the MOST amazing brunch a Wheat’s End Cafe. Those huge chocolate chips will always be on my mind…A few years back I had to take dairy and gluten out of my diet due to health issues so the fact that I could enjoy french toast, pancakes, and popovers with sausage gravy and poached egg, all gluten and dairy free, had me overjoyed 🙂 ! I’m actually going back to Chicago next week for a mission trip to work at a summer camp for disadvantaged kids. So excited!
xxMeah
I’m envious you’ll be there next week – awesome city with lots of good food. You are going for an excellent reason 🙂
If you feel the need to change away from dietetics, you know you could have a career in travel/food advising…
Seriously. I’m planning a states roadtrip for next year so when it gets closer, I’m coming to your blog to get reminders for all these cities. A huge thank you in advance!! Chicago was put on my list last year when I started hearing about how it has a really great music and theatre culture. Something I didn’t expect. Now after seeing that lakeshore (!!!) and hearing about its’ downtown it is most definitely a must go.
Also – “but I was pleasantly surprised at how much I enjoyed thick crust. Tons of cheese and bread”… this made me laugh. What’s not to love!!
Yes it does! My sister moved to Chicago just for the theatre – we went to an improv show while we were there, it was so fun!
Please come back and SEE ME?????
YES
I am live you in that I love the huge slice of thin crust! I love folding it and shoving it in my mouth 🙂 I’ve only had deep dish once and it was pretty tasty, although I bet if I tried Chicago I would have a tough time deciding what’s best.
The Windy City is on my list, any trails out there?
We didn’t find any trails, but I’m sure there are tons. It’s a huge running mecca. My husband works in running sales, so he was scoping out the plethora of running stores in the small radius.
Looks like a great trip! I went to Chicago 10 years ago, but it was February so we didnt do as much as I would have liked. If I go back I definitely want to run along the Lakefront Trail!
It is so beautiful. I’d live in Chicago just for that!