How to Explore Chicago in 3 Days

As a midwestern born and raised, you might be shocked to hear I’ve never been to Chicago. My reason being, I’d rather spend my travel time getting away from the midwest towards sandy beaches and sunshine. However, after spending a 3-day weekend in the Windy City, I must say I now consider one of the top places to visit. I cannot say enough about this glorious city! Full of adventure and charm, Chicago never ceases to run out of places to explore.Here’s how we managed to see and do so much in a short, relaxing weekend trip to Chicago.

Chicago City Scape | How To Explore Chicago In 3 Days

Day 1. In one day, we walked through the shops and landmarks of the Magnificent Mile which brought us into downtown Chicago and along the bank of the Chicago River. We stopped in at The World-famous Billy Goats Tavern to eat. This hole-in-the-wall restaurant is filled with wacky old news clippings, photographs and other odds and ends. It’s a hard place to find but worth the search!


The gleam of the lake during golden hour was too irresistible, so we spontaneously hopped on a Sunset Cruise at Wendella. We got a narrated tour down the Chicago River on the way to Lake Michigan, where we arrived just in time to watch the sun set behind the skyline of the city and Navy Pier. It was some of the best city views I had ever seen.


We stayed at the Chicago Athletic Association which we’re pretty sure was made for us. I have a thing for themed hotels and rooftop restaurants and he has a thing for sports history and burger joints. The CAA had all of this and more. We played games in their old-school game room and walked around marveling the modern vintage interior. Check out their website for the history of the hotel and it’s striking amenities. I booked it through Hotel Tonight and got a great deal on a room.


Processed with Rookie Cam


Day 2. We had an easy start to the day with breakfast in bed, then hopped on the bus and headed to the Lincoln Park Zoo. We were entertained for hours by all the exhibits and laughed hysterically at gorillas playing hide and seek with a pile of blankets they had. Lincoln Park is such a nice zoo and so much fun!


A summer trip to Chicago wouldn’t be complete without attending a Cubs game, so we headed to Wrigleyville where we were met by an enormous crowd of people singing in the streets, shopping for Cubs gear, and socializing on the Wrigleyville rooftops that peer into the field. Wrigleyville has a unique culture of it’s own that I am newly obsessed with. If you have a bucket list, add “visiting Wrigley Field” to it. It’s a classic American location that’s fun no matter how much (or how little) into baseball you are.


Day 3. Our most tourist-y day. After breakfast on yet another rooftop (I told you I have a thing for them), we walked down Michigan Avenue and stopped into The Chicago Art Institute. Later, we stopped for chocolate Ghirardelli and stumbled across a Cards Against Humanity exhibit across the street which was hilariously funny and full of fun facts. We finally became true tourists as we entered Millennium Park. Cloud Gate aka “The Bean” was a lot more fun than I imagined and I’m not ashamed to say we took the infamous Bean reflection picture.



Safe to say, weekend getaways to Chicago may have to become a more frequent thing, especially since there is so much more to explore. What must-see places should we visit next time? Tell us your favorite spots in the comments!


Whitney & Andrea


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