Solo Travel Chicago: Top Tips

Looking for solo travel Chicago tips?  This is the guide for you!

I regularly visit Downtown Chicago and have tons of tips for taking a solo trip.  Chicago is an amazing Metropolitan city with so many things to do!

Solo travel in Chicago is an amazing way to experience the windy city on your schedule and prioritize your preferred activities like museums, architecture, events, or simply walking around. 

My top solo travel tips in Chicago are to join a free walking tour, stay in a hostel, enjoy city views, join a social group, do seasonal planning, share your location, not rent a car, and use public transportation or ride-share apps.

Let’s begin planning your solo Chicago trip!

Top Solo Travel Chicago Tips

1. Free Walking Tour

Free walking tours are one of my favorite ways to get my bearings set in a new city- especially when I am traveling solo. 

I like the social opportunity to meet a local and learn about some of their favorite spots in the city at the start of my trip.

This is also a great way to form connections with other solo travelers. 

2. Choose a Hostel

Staying in a hostel is a great way to make friends on a solo trip anywhere. 

It’s popular for solo travelers and budget travelers to stay in hostels.  Because of this, socialization is just kind of an element built into hostels!  You can meet new friends in the lobby or through a weekly scheduled hostel event.

3. Stay in a Walkable Neighborhood

I recommend staying in a walkable neighborhood of the city.  Lakeview, The Loop, West Loop, River North, Streeterville, and West Town are all very walkable neighborhoods in the city.

Each of these neighborhoods is in a central location allowing you to walk to many of the best things to do in Chicago or get there quickly through Uber or bus.

4. Enjoy Skyline Views

My top tip to anyone visiting Chicago for the first time is to enjoy the incredible Chicago skyline views!

One of my favorite places to do this is at the Signature Lounge at the top of the John Hancock building. 

Bring a book, order a pop, and take in the views from the floor-to-ceiling windows all around you.

Other options for skyline views include:

• Godfrey Rooftop
• LH Rooftop
• Skydeck Chicago

5. Get Outside: Chicago Riverwalk, Millennium Park, Lakeshore Trail

My favorite ways to experience Chicago are outdoors. 

The Chicago Riverwalk is by far one of my favorite things to do, and it’s free.  You can also take one of Chicago’s most famous tours here, the Chicago Architecture Cruise. 

Millennium Park is one of the largest and most famous parks in the city.  I recommend bringing a book or journal to Lurie’s Garden within the park and kicking back to relax. 

Lakeshore Trail is an 18-mile path along Lake Michigan that goes through tons of neighborhoods like Lakeview. 

Exploring outdoors in Chicago allows you to find hidden gems and new surprises as you explore. 

6. Join a Social Group

There are tons of social groups that meet in Chicago on the weekends. 

This is a great opportunity to meet new friends, socialize, and learn what locals in Chicago like to do over the weekend!

7. Plan For The Season

Chicago experiences all 4 seasons, so it is essential to pack accordingly for the season. 

For example, winter in Chicago is freezing and I would recommend following a winter packing list to make sure the cold weather doesn’t tamper with your plans. 

Spring is relatively mild and rainy, so I recommend packing an umbrella this time of year.  Checking the local weather when planning a solo trip to Chicago is crucial. 

4 seasons in Chicago also means there are seasonal activities year-round, and experiencing these events is a great non-touristy thing to do in the city!  I love any opportunity to get local experiences. 

8. Share your Location

I would say that the touristy parts of Chicago are relatively safe to travel, even if crime has been increasing in recent years.

In any case, I always recommend sharing both your itinerary and location with loved ones before leaving on a solo trip. 

In case of emergency, it’s important that someone knows your whereabouts. 

A couple of phone applications that you can easily share your location on include Life 360 and Glympse.

9. Don’t Rent A Car

If you are not a fan of parallel parking, parking in Chicago can be difficult.  It can also be expensive. 

Most hotels in Chicago do not have their own parking lots.  It’s common for Chicago hotels to partner with local parking garages and offer hotel guests a discount. 

You’ll save more money and have less stress by taking public transportation, Uber, or walking in Chicago.

I only recommend renting a car if you are planning to take a day trip to a location that does not have a direct public transportation route, like Starved Rock.

10. Uber or Public Transportation

Public Transportation is widely available throughout Chicago and is a great alternative to renting a car.

Uber and Lyft are also widely available throughout Chicago, so you have your pick of transportation options. 

Tip: You can tap your credit card to pay on buses in Chicago, so you don’t need to purchase a transportation card unless you want to! 

Conclusion

Solo travel in Chicago is an amazing way to experience the windy city!

If you are interested in meeting new friends or socializing while you travel, I recommend staying in a hostel or joining a walking tour.  There’s no need to rent a car because Chicago has plentiful public transportation options and Uber/Lyft access. 

Now that you’re equipped with these tips, get ready to explore Chicago solo and create unforgettable memories.

Happy planning!