Best Things to Do in Chicago in One Day 3

Big Cities can be very daunting, especially if you’ve never been there before. Especially, if you only have ONE day to see it! With this guide you can be time-efficient and discover all the best things to do in Chicago in one day!

Chicago Bean with the City Skyline Best Things to Do in Chicago in One Day

1. The Chicago Bean

The Chicago Bean Plaza

 Landon Standing Under the Bean in Chicago Kissing Picture at the Chicago Bean in the Reflection 

Such a random, but amazing design right in the heart of downtown area. Make sure you get your “reflection” pictures and walk under it. It’s really neat! Take your time here – sit in the shade, share an ice cream and watch the crazy selfie action going on all around you. It’s entertaining! Even though it can get crowded, don’t be steered away, it’s really cool and worth seeing. After all, it’s one of the top things to see in Chicago!

2. Downtown Walking Tour (2-3 hours)

From the Chicago Bean, you will see big signs that give you a route for a guided walking tour.

Walking Tour Path Route in Downtown Chicago

We followed the route and saw lots of neat statues, fountains, buildings, and gardens! Don’t forget to do a little geocaching along the way! There are SO many! There are lots of great cafe’s along the way to find lunch at too! If you leave some time, you can even go rock climbing at the park

 Splash Pad in the Middle of Chicago Silver Horse in the Quiet Gardens in Downtown Chicago 

If it’s a hot day out, be sure to check out the splash pad where you can get your feet wet and cool off with the stream of water coming out of the person’s mouth on the huge screen.

Exploring Downtown Chicago in the Summer

This HUGE fountain was just beautiful! It’s definitely a work of art.

Fountain in Chicago on the Walking View Path Panorama

3. Sunset Kayaking Along the Chicago River

Kayaking at Sunset on the Chicago River

Kayaking on the river was a perfect way to end our day in Chicago, not to mention a fun way to get some exercise! We had a beautiful sunset tour, kayaking along and watching the city come to life at dusk. Absolutely gorgeous! The riverwalk is one of the most beautiful areas in Chicago.

4. Explore the City Lights at Night

Skyscrapers of Chicago City Lights at Night

Chicago lights up beautifully at night. It was so stunning to just sit and watch the twinkling lights and the moon rising up over the skyscrapers!

Theater in Chicago at Night

Tips for Getting Around:

Great Budget Option for Traveling Using the Subway Train in Chicago

Use the subway, it is very easy to get around and pretty cheap too! If in doubt, ask someone about where you want to go. People are very helpful! Also download the Pocket Earth Map that I use, it’s invaluable, and works offline when you’re 20 feet underground in the subway tunnels!

The best Chicago travel hack we found: The subway goes directly to the airport! No need to flag a bus or pay a $50 taxi; the subway only costs $2.50 and is very easy to use.

Great Budget Option for Sleeping:

Wrigley’s Hostel is right by the Cubs Stadium, on the North side of Chicago. It was a cheap option for the area, had new furnishings, and also a great breakfast! It’s only a 1 minute walk to the subway – very convenient! If you plan it right, maybe you could even see a Cubs game at the Wrigley Stadium! (Be sure to book your room early because this place fills up on game nights.)

Chicago Aerial Picture of Skyline and Downtown

Check Out Our Aerial Footage of the Cubs Stadium!


Chicago is a beautiful city, and there’s plenty of things to do in one day! We were very impressed with the buildings, the brickwork, and overall style! Have you been to Chicago? What’s your favorite part?

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3 thoughts on “Best Things to Do in Chicago in One Day

  • Trinity

    We’ve been wanting to get back to Chicago for awhile. I agree it’s an incredible city with a lot to see and do. I went on the architecture tour and loved it. It’s a great way to see a lot of the city. Oh and the hotdogs! Yum.

    • Landon Post author

      Hey Trinity! Now that we got a taste of it, we are excited to go back and spend some more time there! It would be a fun city to live in too! Maybe someday haha! The architecture tour sounds fun! There is a lot to learn I’m sure because walking around it sure is hard to take it all in! Thanks for stopping by!