Solo Travel Guide for Chicago


Not only is Chicago a beautiful city to visit, it’s also a perfect city to travel to solo, even if it’s your first time visiting. 

The Basics

When travelling to Chicago there are a few things to keep in mind when planning. Visit during warm weather months, the colder months make it less enjoyable to explore. Plan to stay downtown if you want to be able to walk to most places. Look for places to stay on Michigan Ave. or not far from it. The city is very walkable, but when you need something a little quicker jump on the “L” it’s their train system and it is a quick study. Plus you get some great views of the city when you are elevated. If you do plan to take the “L” while you’re there and want to save a little money, buy the $5 Ventra card and register it to get the $5 back and you will avoid the service fee every time you buy a trip.

Chicago Skyline Riverwalk.JPG

Things to Do 

Okay solo travel is definitely a different experience all together so planning activities will be a little different. Finding activities that don’t require an additional person seems pretty obvious, but really just try to focus on things you’re comfortable doing alone. Here are a few recommendations for exploring the city solo.

The Bean.JPG

Explore Millenium Park - This is where you can find The Bean which is the giant mirrored bean-shaped sculpture. It makes for great selfies. Depending when you are there, they tend to have festivals happening and most of the time it’s free to enter and you can just enjoy the music. There is also a big beautiful amphitheatre that is really cool to see. And just over the bridge there are fun activities available like rock climbing, roller skating and bike tours.

Go on a Chicago Boat Tour - If you want to learn about the history of the city or just enjoy the architecture of Chicago’s buildings, jump on a boat tour and take in the views. They offer different types of boat tours, you can see which ones are available by walking down to the Riverwalk and talking to the guides. The Riverwalk is also an option for a scenic walk along the river if boats aren’t your thing. You won’t be disappointed.

Walk the Magnificent Mile - The Magnificent Mile or “mag mile” is where you can do a lot of your shopping. It’s like the Rodeo Drive of Chicago, so mostly high-end shopping. But if you continue north up Michigan Ave. you will eventually get to the John Hancock building and it has a great view of the city from the top. 

Visit the Art Institute of Chicago - You can’t go to Chicago and not visit a museum. They have several and each one has its own magical experience. Depending on what your interests are will help you narrow down which museum(s) to check out. The Art Institute comes highly recommended, so if you’re undecided you can’t go wrong here. There is something for everyone, if you like art.  

Check out the Neighborhoods - You will need to take the “L” or an Uber to these areas because they aren’t really walkable, but it’s nice to explore the less tourist-y places. Wicker Park is a hip bustling neighborhood and you can walk along North Milwaukee Ave. to find coffee shops, restaurants, bars and boutiques. A couple other neighborhoods to visit depending on time and interests are Lincoln Park, Logan Square and Humboldt Park. 

incredible eats at Dove’s

incredible eats at Dove’s

Where to Eat

Food doesn’t really require a second person, so these recommendations are a mix of solo-friendly eateries and must-try food while you’re in Chicago.

Giordano’s - First things first; deep dish pizza. This is a must! If you love cheese and pie - you will love Giordano’s deep dish pizza. The wait is usually 45 minutes to an hour so grab a seat at the bar and get comfortable. They even have this fun thing they do with your first slice, so get your phones ready!

Protein Bar - This place is great for a quick and healthy bite to eat. They focus on protein for everyone. You can stop in and grab a salad, wrap or sandwich to-go and head down to Millenium Park.  

Portillo’s - Chicago is known for its beef and Portillo’s serves Chicago-style food such as beef hot dogs. Chicago-style hot dogs come with several toppings and none of them are ketchup. It’s definitely something to try while you’re there and you can grab a seat in the restaurant after placing your order, it’s a super casual vibe. 

Dove’s Luncheonette - If you venture into the neighborhoods you will find some really cute places to eat. This southern-inspired Mexican cuisine spot is located in Wicker Park and they have the chillest vibe inside. You can grab a spot at the bar and enjoy the jazz music playing on vinyl records. And the food is ah-mazing! Fun fact: Chicago serves their Bloody Mary’s with a side of beer to sip on.

Garrett’s Popcorn - Ok so Chicago definitely has its own way of doing things and popcorn is another one of  them. Chicago-style popcorn is the mixture of cheddar flavored popcorn and caramel popcorn also known as the Garrett mix. It’s the perfect combination of savory and sweet. The cheddar one alone is SO good. You can always just pop into a Garrett’s and sample their different medlies of popcorn if you are feeling curious.

Traveling Solo with Confidence

There are so many places to visit and food to try in Chicago, so this list is only the beginning, but the ones listed above are all #JUGSapproved. And when traveling alone, safety always comes first. Be sure to let friends or family know what you plan to do on which days. Another added layer of protection when traveling solo would be to wear one of  invisaWear’s discrete pieces of jewelry that can send an alert and contact 911. We love it and you can save 10% off with our referral code INVISAWEAR-PBSHGX. We hope you enjoy your travels to Chi-Town! 

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Colleen Gordon is a content contributor for JUGs. Follow Colleen on Twitter or Instagram at @here.she.stands

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