5 Mistakes on a Weekend Trip to Chicago

Chicago is quite the fan favorite, especially in the fall. The leaves are changing, sweaters are on sale, and the air has a chill in the morning. Walking through the city with a hot cup of coffee never feels better. There are a few things, though, that make a Chicago weekend a little more stressful than it needs to be.

One: Not Accounting for Tolls

This was a big mistake on our part. On the way to Chicago, we didn’t hit a single toll. On the way out, we drove through more than five, and we had cash for one. So now, we have to go back through the Illinois Toll website and try to figure out which ones we need to pay so we don’t get fined. Save yourself the trouble and throw $30 in assorted bills into your glove box before you leave.

Two: Wearing the Wrong Shoes

This one seems like a no-brainer, I know. I did consider that my feet might get tired from walking, but I didn’t realize HOW MUCH walking we’d be doing. We easily walked five miles on Saturday; it’s so much easier to walk than catch a Lyft. (Lyft is fairly cheap to use in the city, though, which was a big surprise to me.) If we had only gone out for dinner and a show, I could’ve made it in my shoes. But we went to the Art Institute of Chicago, Millennium Park, The Magnificent Mile, several restaurants, and then to The House of Blues for the LANY concert. By the time the concert was over, I was DONE walking around in those shoes, so we did get a Lyft to the last stop of the evening. I did feel very cute in my booties, but by 2pm, I would’ve done anything for some arch support. When you’re packing, choose shoes wisely.

Three: Not Having an Itinerary

I considered making an itinerary before the trip, but I knew Sam would turn it down, as he’s a go-with-the-flow kind of guy. Well, I should’ve made one anyway and just not told him. We still would’ve gotten to choose where we went and what we did, but the choices would’ve been taken care of before we were there. It got stressful to always be deciding where to eat and mapping the walking route to hit all of the places we wanted to go. If you’re going, I’d definitely recommend doing your research and planning ahead of time. It’s a big city with tons to do, and it can feel pretty overwhelming if you don’t have much of a plan.

Four: Missing the 96th Room

Luckily we didn’t make this mistake, because my mom texted me while we were there and told us we should go. Most people go to the Willis Tower to the Skydeck. I have been there, and it is cool, but the John Hancock building was way better in my opinion. It’s free entry, (the Skydeck is $23) and there is a restaurant and a bar at the top. We went on a Saturday, around 10pm, and only waited in line for 20 minutes tops. You ride an elevator up to the 96th floor to the Signature Room to have a drink overlooking the city. I’d recommend going after it gets dark, because the city lights are absolutely beautiful.  (p.s. the best view is in the girls bathroom…sorry boys.)

Five: Only Hitting Huge Tourist Attractions

Everyone knows the biggest spots in Chicago. I think it’s important to check out the smaller, local spots, too. Both days, we got brunch in little, family-owned restaurants in the outskirts of downtown, and I loved that. We went to the Windy City Cafe and The Breakfast Club and Grill. Both were incredible. While most major attractions are in the city, don’t forget that Chicago also has a beautiful beach right along it. We drove about 30 minutes to Roger’s Park for a less-crowded afternoon at the beach. Chicago is quite the city, but it can be peaceful, too. We also used Airbnb to stay in a woman’s apartment on the outskirts of town, which was a really cool way to see how the locals live. Also, her place had a private rooftop with an absolutely incredible view. I’m a huge advocate for airbnb. I think it’s just the best way to meet someone local and learn about the city from that perspective.


Have you ever been to Chicago? Any Secrets for me for the next time I go?

view from our airbnb rooftop
She also had champagne for sale to pair with the view;
the booties that almost made me cry on the Magnificent Mile
don’t forget to notice the street art
the beach at Roger’s Park
drinks and mochi at a Japanese speakeasy
Admiring at the Art Institute of Chicago
streets on the outskirts of downtown

1 Comment

  1. Taylor

    October 23, 2017 at 4:09 pm

    This is super helpful! All things you wouldn’t think of (especially the shoes) but so good to know for a future trip!

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