Travel Guide: 5 Days in Chicago


Every year, my husband and I take a vaca for our anniversary, and this year (year 3!) was spent in Chicago! We choose to do trips/experiences rather than gifts, because the memories mean so much more to us than any gift could! I have a dear friend/business bestie who lives in Chicago, so I went a few days early to spend some time working + playing with her. It was actually perfect because she and I got to have went on a few super girly outings- ones that I know Josh would have endured, but probably not enjoyed. :) Once Josh made it into town, I had him meet me on Michigan Ave, and we hit the ground running like we always do.

Chicago is SO enjoyable because you get to experience a big city (like NYC), but is more relaxed. For one, it's easier, cheaper, and quicker to get around town which definitely helps take the stress off. Another thing I loved is being able to see the city from some very unique perspectives, such as the riverboat tour, and from Navy Pier. 

Below are my top 7 MUST-SEES for Chi-town!


1. Restoration Hardware / 3 arts club cafe

The 3 Arts Club Cafe inside a Restoration Hardware is a quaint little spot in the quaintest little neighborhood in Chicago. I went with here with Sarah, and it was the perfect spot for an early girls night after a long day of work. It's really cool that it's inside a furniture store. After we ate, we perused the floors of furniture, and dreamed of what our houses would look like one day :) We split the hamburger- definitely recommend!


2. Hampton Social

Rosè all day! I had seen the Hampton Social on Instagram (best place to find fun spots, right?!), and Sarah and I walked there from her condo! It was the CUTEST restaurant- even better than the pictures! It decorated very nautical, and all of the windows were open. They had live music, we got a spot right by the window, and stayed for hours!


3. Skydeck Chicago

The Skydeck Chicago is the place to go for city views! It has the window boxes with the glass floors (shown above in the picture of me and the hubs). We got right in with the fast pass. You can see it all in about 30-45 minutes.


4. Michigan Avenue

I have this tradition when I go out of town of waking up (semi) early and walking to local shops that I find usually on Yelp. The Peninsula Hotel on Michigan Ave. has a great little french cafe with a delicious latte! Michigan Ave. is also known as the Magnificent Mile, and it truly is! We walked Michigan probably every day during our stay. We were really close at our hotel, The Whitehall.


5. The Bean

The bean! Properly called Cloud Gate, is a sculpture in the Millenium Park area. We mentioned it to a few Uber drivers that it was on our list, and every time we got a little chuckle from them, ha! I guess it's not as much of a novelty for the locals. But, I was honestly pretty fascinated by it! It really is beautiful with the skyline reflected in it. I'm so proud of the artist for creating a piece that continues to fascinate so many people every day. 


6. Rosebuds

Do you ever have one of those days or nights when you feel like you are living inside a dream? When you look around and think "nothing could make me happier than this right now". That was our night at Rosebuds. We quite literally stumbled upon Rosebuds walking back to our hotel one afternoon. We made a reservation, put on our fancy clothes, and walked right in. They escorted us to a table outside, and there just so happened to be a man playing jazz music on the street corner. I think the jazz player may have been a coincidence because he wasn't there when we walked by the next night! Regardless, I definitely recommend sitting outside if it's warm! We wined and dined and topped it all of with Tiramisu- my favorite dessert!


7. The Riverboat Architecture Tour

The views from the Architecture tour, to me, are one of the things that sets Chicago apart. Seeing the city from the water is such a unique experience and the views are breathtaking. It reminded me of being in Venice, Italy (where I studied abroad)! We went around 6pm, so we were able to see it in the daylight, and in the dark. It was perfect for pictures, so I definitely recommend that time slot. When the sun goes down, the city GLOWS.


Check out the other guides, and let me know in the comments if you try out anything mentioned! Would love to hear about your travels!

Personal, TravelEmily Wells