Chicago Walking Tour | Always A Foreigner

Chicago Walking Tour

Chicago Walking Tour | Always A Foreigner

Caren and Cazzie

Hi, We're Caren and Cazzie and we're Always A Foreigner. Welcome to our travel blog! We hope you find it useful. We love waterfalls, street eats, and anything to do with travel and adventure. We met while volunteering in India, and since then have made it our goal to travel to as many places as we can. Join us on our journey!

Enter your email address to receive updates and newsletters from the blog directly to your email!

Chicago Walking Tour

Last weekend, we headed back to my old stomping grounds to celebrate our engagement with my family. For those of you who don’t know, I’m originally from outside the magnificent city of Chicago. While I will always treasure my time there, ultimately the winters were too harsh and I was forced to flee to warmer weather.

Chicago in the summer is truly magical. After the long, freezing cold winter, the people of Chicago come out of hibernation and celebrate the three good months of the year…and they know how to celebrate.

While the actual city of Chicago is huge, their public transportation system is one of the best in the world. Fondly called the “El,” or Elevated train, the system will take you essentially everywhere around the city you need to go. And it’s generally clean!

Most of the favorite tourist attractions are located in the Loop, or the centrally located grouping of skyscrapers that the El  makes a loop around. Get it? Clever, huh.

I recently was asked create walking city maps on This website is a great way to see how other people toured a city by walking, and different routes are uploaded by different users. It’s pretty cool! If you’re more interested on the route we took to tour downtown Chicago, click here to their website to see it!

We started near the Willis Tower, or what was once formally known as the Sears Tower. Growing up, this was the tallest building in the world for a little while. For some odd reason, I still harbor a little bit of pride for that fact.

Next up on the list of “must-sees” for Chicago is Millennium Park and the famous “Bean” art piece. Quite literally a giant metallic bean, the park is in the forefront of the Chicago skyline. It creates quite the scene, and draws quite the crowd.

Millennium Park
Millennium Park and The Bean


A nice stroll around Millennium Park on the path will take you further from downtown into Maggie Daley Park if you wish. Most of the time the grass is closed around the music pavilion, but if you’re in town for a night that they’re holding a concert or movie, definitely bring a blanket and picnic!

From Millenium Park, it’s an easy walk down the glitzy Michigan Avenue to the Chicago Riverfront walk. The river walk is truly one of my favorite parts about the city.

chicago walking tourchicago walking tour

There are tons of super cute restaurants along the River Walk. City Winery is a great place to stop and cool off from the sun! They also have live music if you check their event schedule.

Part of the fun of the River Walk is to gawk at the giant yachts that pull in and out of the harbors. Seriously….how can I get one? If you’re into boats and want to take one out on the lake for the day, you can rent one from various rental places around downtown. Half the fun of having a city on a lake should be being on the lake, so take advantage!

Trump Tower is also visible from the River Walk. The City of Chicago currently has an art installment that “is not a political statement in any form,” but you can judge for yourself. I personally love it.

Be sure to walk out on one of the bridges. Dearborn is one of my personal favorites. The view of the river and the buildings towering over you is gorgeous. The Dark Knight was filmed in Chicago, and the bridges give Chicago that eerie feeling of Gotham City.

Don’t miss the iconic Chicago Theater. Built in 1921, this grand theater has a dazzling marquis and is host to many live events. If there’s a show there that you would like to see, I would recommend snagging tickets. The interior is marvelous.

That about sums it up for the downtown portion of Chicago must-sees. Of course, there is always something to see in Chicago, so don’t stop your tour of the city there. Head out to one of the many “neighborhoods” that make up so much of the charm of the city.

Written by


Tell Us What You Think!