Chicago, IL

The Best Way to Spend 3 days in Chicago

Quench Your Adventure
Quench Your Adventure

If you know us, follow us on social, or have read our other blog posts, you'd know that we typically favor destinations with fewer people and more nature.

For example, Sedona, AZ, the Jungfrau Region of Switzerland, and the Canadian Rockies. Chicago wasn't really on the radar, but we were feeling spontaneous and the flights were cheap!


Chicago Bean Millennium Park -Did you really go to Chicago if you didn't check out the giant stainless steel "bean"? We aren't going to call it a "Must-Do", but it is an icon of the city and an impressive sculpture. The shape and reflection make it a fun way to capture the skyline with yourself in the photo. People love to touch it for some reason and apparently it gets cleaned multiple times each day! If you're trying to score a photo without mobs of people, go early or learn Photoshop. Free entry

Navy Pier & Fireworks -This pier is full of stuff to do and see. Restaurants, rides, cruises, shopping, art exhibitions, and fireworks. It's 3,300 feet long on the Chicago shoreline of lake Michigan. On Wednesdays and Saturdays from Memorial Day through Labor Day, they put on an excellent display of fireworks that are synchronized to music! Free entry
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Chicago History Museum -A great place to escape the heat and learn more about Chicago. Very nice exhibits that kept Jeremy entertained. Jenna was ready to leave because she was ready for her next meal. $19

Travel tip- Sometimes we do a quick search on our Groupon app to see if there are any enticing deals in the area. That's actually how we ended up in the History Museum. We also look on Facebook events to see whats happening nearby.

Divvy Bikes -Fun to ride around the city for cheap. In a place like Chicago, you can get around just fine without renting a vehicle. We just rode bikes and used our ride sharing apps. $3 and up 

Skydeck Chicago Willis Tower -Are you a fan of big city views and heights? At 1,453 feet, the Willis Tower is the tallest building in Chicago. There are glass box windows that extend out 4.3 feet from the sky deck. Stepping out over the city like this was a fun thrill and the views are great. It's a huge attraction, so there will be lines, but we enjoyed it and took our time. $23
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Food and Drinks

Cindy’s Rooftop Bar Open-Cute restaurant and bar with an open air terrace and panoramic views of the city. 

LondonHouse Rooftop Bar- A great place to get views of the city and enjoy a cocktail and some appetizers. 

Eggsperience Pancakes & Café Local Restaurant- The Nutella Banana Crepes were the bomb! Delicious and indulgent. Super cute cafe and great service.

Lou Malnati’s Pizza- Some of the best deep dish pizza you'll ever have. We also saw basketball player "Big Baby Davis" who played for the Celtics and got a picture with him.  

Chicago Pizza and Oven Grinder Company - This place is known for their pizza pot pies and oven grinders and for good reason! It's cash only, small, first-come-first-served, and in high demand! Get there well before they open and enjoy the curb appeal of the very inconspicuously located pizza joint!


Lincoln Park Zoo - This zoo is gorgeous and has so many animals, exhibits, presentations, and delicious ice cream. We really loved watching the gorillas! Free entry

Swam in Lake Michigan- The water was a bit nipply, but we enjoyed a refreshing swim! There's actually sand and it's a legitimate beach, just quite small. What made us chuckle, as spoiled Floridians, was seeing people sprawled out on beach towels on the concrete slabs that line the water on the city side. I guess there's not enough beach for everyone, but we loved that people were out soaking up summertime and enjoying time outside. 

Tandem Bike Rentals at North Avenue Beach- We loved biking along Lake Michigan and seeing different perspectives of the city. Jeremy, being an avid biker, took the driver seat, while Jenna took some videos and played music. Then we let Jenna try to drive and were cracking up at the struggle to steer and stay straight. Tandem bikes are fun because you're close and there's some teamwork involved. There also just funny and people seemed to enjoy watching us roll by with smiles on our faces. We rode on the nice, paved trail that goes on for miles. The waves from the lake were crashing up against the concrete slabs and it was cool to watch! $18 per hour

To wrap up, Chicago was actually pretty cool! The architecture is impressive with massive skyscrapers and some neat statues. There's tasty food, cool bars, some outside fun, and nice museums. If any of this interests you, maybe you should make the trip! You really only need a long weekend, so open up Google Flights (incognito mode recommended) and get out there! Thank you for reading and we hope this was useful! Any other recommendations?

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Jenna & Jeremy Full Time Travel Travel The World With Us Sold Everything Digital Nomads 46 States & 14 Countries Travel Tips

Jacksonville, FL

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