So often we think of travel as a group activity. From family vacations to romantic weekend getaways, when we reminisce on our favorite travel stories, we are often thinking about the people with whom we shared the experience. However, while our travel partners may change, there is one person that is always there; ourselves! Solo travel can be a great way to make lifelong memories while going on an adventure, encouraging self-reliance, and pushing your own boundaries. 

Chicago’s typical tourism season runs from Memorial Day to Labor Day, though there is truly no bad time of year to see Chicago (yes, that even includes visiting Chicago in the winter). What time of year is best to visit depends largely on your interests. A traveler that prefers a packed social calendar may enjoy the warmer months for the nightlife, music festivals, and sporting events, while those looking for a more solitary experience may prefer to travel off-peak to take advantage of the extra elbow room at museums, cafes, and parks. No matter which sounds more like your idea of a good time, part of what makes solo travel so rewarding is the ability to be flexible and learn a little more about yourself, so don’t be afraid to see how the other half lives while you’re exploring – you may surprise yourself.

Tips for Traveling Solo in Chicago and Staying Safe

As the saying goes, “safety first”, which is where to best start your planning. Fortunately for most travelers, the must-see attractions that Chicago is known for are in some of the safest, most populous areas of the city, but that is no reason to not do a little planning to keep yourself out of trouble.

  • Familiarize yourself with a map of your surroundings: Thanks to the ubiquity of smartphones, keeping aware of your surroundings has never been easier. However, smart travelers will spend a little time navigating their destinations before they’ve even arrived. Chicago is well-known for its grid system, so learning how to get around feels simple and intuitive for most. It is also a good idea to look into how to get around, which might mean walking, a rideshare service, or public transit. If you’re a biker, check out our guide to biking in Chicago and biking the Lakefront Trail.
  • Make sure someone knows where you are: Traveling alone doesn’t mean you have to be isolated, so make sure you keep a lifeline with a trusted person so in the event of an emergency you don’t have to worry.
  • Trust your gut: Just because you’re exploring, you don’t have to put yourself in harm’s way. One of the best ways to stay safe is to simply trust your gut. There are a lot of areas of the city that are safe and popular destinations for travelers, but if something doesn’t feel safe to you there is no reason to push forward and find out you were right. 

Getting Around Chicago

It would seem that a city with several million people would always be crowded and tough to navigate, but Chicago is lucky in a way that many coastal cities aren’t. Chicago’s historical focus on planning a city built on a structured and predictable grid makes for simpler navigation than cities like Boston or New York, while avoiding some of the extended sprawl of cities like Los Angeles. Chicago maintains a good balance of convenience and elbow room that few cities can match.

When navigating Chicago, a traveler usually would resort to one of a few options:

  • Public Transit: Chicago’s famous elevated train system cuts across the city, connecting dozens of neighborhoods to each other and moving hundreds of thousands of travelers every day, while filling in the gaps between lines you will find Chicago’s expansive network of buses. Bus stops and L stations are plentiful, especially in the most popular areas of the city for travelers, so figuring out how to get across town is typically no more complicated than finding the closest train. Although buses and trains run almost all day, only select buses (mainly on larger arterial streets) and the Blue and Red line trains run at all hours. Fortunately, these tend to run through many of the most common areas for travelers, but you should still expect to do a little planning to make sure you don’t overspend on a cab or a rideshare service.
  • Uber / Lyft / Taxis: Just like most major cities, Chicago is serviced by a combination of rideshare companies and taxi cab services. The once-ubiquitous yellow cab is now most common in the heart of downtown, while rideshare services can be seen all over — especially around Chicago’s nightlife scenes in Lakeview, Wrigleyville, and Northalsted. The convenience can’t be beaten, but these can get expensive quickly as a solo traveler, especially at peak demand.
  • Biking: As a solo traveler, flexibility will be your greatest asset and among transportation options available to you, a bike is the most flexible of all. Chicago enjoys a great reputation for cycling, with hundreds of miles of biking infrastructure there are very few places in Chicago that aren’t safely accessible by bike. When traveling alone, biking can be a great way to get around as you aren’t dependent on a public transit schedule, and moving by bike is often much faster than by car. In fact, most trips under 5 miles are as fast as, if not faster than the same trip by car. Chicago also boasts more than 10,000 city-installed bike racks, so instead of the hassle and expense of looking for a place to park a car, most blocks have multiple places to safely lock up a bike. When traveling to Chicago, it isn’t a bad idea to bring your own bike, especially the more travel-friendly folding bikes, however it is just as easy to rent a bike for your stay. Learn all about biking in Chicago, where the bike trails are and prepare your bike routes.
  • By Water Transport: Explore the city from the water to experience the unique location of Chicago on Lake Michigan. There are a few ways to see the city from the water, including a water taxi, a river tour, a kayak rental to explore on your own, or the famous Chicago Riverwalk for those who aren’t ready to get on the water but want to be near it.

Popular bike rental options in Chicago include:

  • Bobby’s Bikes: In addition to offering bike tours, Bobby’s Bike Hike also offers bike rentals of all kinds, the most popular being comfort-hybrid bikes, which feature a relaxed and upright riding posture that makes longer biking trips easier on the body. Each bike is individually sized to the renter for optimum fit and includes a helmet, lock, and roadside repair kit so you will be prepared for anything. Bobby’s also offers rentals ranging from just a couple hours to several days so you’ll be able to get around the city with ease no matter how long your stay might be. Located in the Loop-adjacent neighborhood of Streeterville, Bobby’s is also in one of Chicago’s most central locations for the solo traveler that wants to see the city’s most famous sights.
  • Divvy: For short trips, many visitors will take advantage of Chicago’s bikeshare program, Divvy, which has stations in most of the city’s neighborhoods. Based on Dutch utility cycles, Divvy bikes are sturdy and fairly comfortable. As the name suggests, they are designed to be simple and practical for short “A to B” types of trips. Divvy bikes are generally very affordable and convenient for trips under 30 minutes, but travelers exploring Chicago for more than a couple weeks may find a month-long membership to be a better deal.

Lodging Options in Chicago for Solo Travelers

Choosing your lodgings while in Chicago may seem daunting, after all, there are hundreds of hotels, AirBnB’s, hostels, and the like in downtown. When determining where to stay, ask yourself a few questions:

Is there a part of the city I would like to spend most of my time in? Although Chicago is usually easy to get around, the reason for your trip may help you decide where to stay.

If you want to see as much as possible, consider staying in one of the neighborhoods around the Loop. Aside from the amount of sights in the downtown area itself, it is also where most of the trains converge, making it easy to get to any corner of the city from one central location.

If you are traveling for an event like one of Chicago’s many music festivals or pro sports teams, you might consider staying close by. This might mean staying outside of the downtown area, which will make a lot of AirBnB’s an attractive choice. Since there is a long list of possible lodging, it is best to start with the area of the city you most want to enjoy and shorten your list to your favorite options.

How much time will I be spending at the hotel? The amount of sights and entertainment options in Chicago can keep a person busy for years, so just about any visitor should have no trouble filling their itinerary. How busy you like to stay may help inform your choice.

If you are the kind of traveler who wants to pack as many events as possible into your trip, then your hotel may simply be a place to keep your belongings and a comfy bed before getting up early and checking more items off your bucket list. For this person, a simple, no-frills hotel or hostel may be the best choice.

For those that are unafraid to slow down and treat themselves to the finer things, there are a number of luxury hotels along the riverfront or AirBnB’s all around the city that might fit the bill. AirBnB can be an attractive option for many travelers because of the opportunity to stay in some of the more out-of-the-way neighborhoods that will give you a unique take on Chicago that not every traveler will get.

How long would I like to stay? During peak tourism season hotels can fill up quickly, which means booking early is always smart. When this isn’t an option, an alternative is taking advantage of the huge catalog of places to spend the night. Instead of booking a week in a hotel, you may consider booking a couple days at a time in a few different neighborhoods, which makes for an interesting way to add some variety and new perspective to your travels. 

For those coming to Chicago for a short stay via O’Hare Airport, there are dozens of hotels in nearby Rosemont, which is connected to downtown Chicago by the Blue Line train, which runs 24 hours a day, allowing you to come and go as you please and making your arrival and departure as easy as possible.

Places to Eat and Drink in Chicago Solo

Chicago’s restaurants and bars are in a league of their own and trying some of the food Chicago is known for is a vital item in any traveler’s itinerary. One of the best ways to sample Chicago’s famous fare is by taking a tour with Bobby’s Bike Hike. We offer food tours on foot and by bike which cover many of Chicago visitors’ favorite sights and tastes, including deep dish pizza, Italian beef, Chicago-style hot dogs, and much more. Let us take care of deciding where to eat and you’ll be glad you did. If you decide to go it alone, make sure to check out our guide on what food Chicago is famous for, which will give you a great place to start your culinary adventures in the Windy City.

One overlooked aspect of traveling solo is how much easier it is to find a table for one. Chicago has always been a city that loves to eat, but in recent years has also become a haven for hot new restaurants by celebrity chefs including Rick Bayless, Stephanie Izzard, Mindy Segal, and many more. Wait times can be long or reservations hard to come by, but the solo traveler may be lucky enough to slide in for a bite last-second without much of the usual difficulty.

Now that you know where you’re staying and what you should eat, how will you spend your time in Chicago? Perhaps it is best to think of your schedule according to how you normally like to unwind!

How To Spend Your Time in Chicago When Traveling Alone

For the energetic social butterfly: When you’re staying in a city with millions of people, you can always be sure that there will be other like-minded people to find and share an experience with. There is always the tried and true approach of going out for a drink and chatting up your neighbor. Midwesterners and generally a pretty welcoming bunch, so don’t be afraid to find a neighborhood tavern and strike up some conversations.

If you would like an icebreaker, Chicago’s many barcades and rooftop bars can offer a more laid-back and fun alternative to the traditional tavern. Sporting events are another great way to share some time with locals, whether that’s in the bleachers at Wrigley Field or on the 50-yard line at Soldier Field. Ticketed events like this can also be great for the solo traveler, where a single ticket can often be found on the day of the event at a reasonable price.

For those that like their alone time: Sometimes, time spent free from socializing can give us the much-needed reset we want from our time off. If you would describe yourself as a through-and-through introvert, Chicago’s world-class arts scene may be just what you’re hoping for. One can easily spend an entire day at The Art Institute of Chicago taking in the works of Van Gogh, Picasso, Hopper, and more. The same can be said of Chicago’s music scene; with hundreds of venues for live music ranging from stadiums to small rooms, every night of your stay in Chicago can mean a new musical experience, often without leaving the neighborhood. For the movie lover, the Music Box Theater (3733 N Southport Ave) just west of Wrigley Field is an historic movie house that specializes in classics and less-than wide release contemporary films that you just have to see.

For the outdoorsy: Chicago’s official city motto is “Urbs in Orto”, latin for “city in a garden”, and with hundreds of outdoor parks and thousands of acres of dedicated green spaces it is easy to see why. These range from tiny neighborhood pocket parks to huge destinations like Lincoln Park or Humboldt Park. Taking a hike in one of the most developed cities in the world may seem counterintuitive, but Chicago will give you plenty to see. In the heart of the Loop is the newly developed Riverwalk, which perfectly balances the urban and natural worlds of Chicago. The 18.5 miles of Lakefront trail along Lake Michigan have space for all manner of outdoor activities such as biking, hiking, volleyball, swimming, and much more. Chicago’s tree-lined boulevards can also satisfy a need for the great outdoors while showcasing some of the unique and historic architecture scattered all throughout the city.

For the water lovers: A water taxi or kayak rental is a great way to see Chicago. Both the Chicago River and Lake Michigan offer access to various activities to keep you busy and having fun.

For the well-rounded traveler: Taking a tour with Bobby’s Bike Hike is one of the best ways to get a little bit of everything. Bobby’s has city tours designed for all ages and interests, so there is always something for everybody. In addition to meeting a group of travelers like yourself, you will learn all about the city while seeing the sights and experiencing Chicago like few do.

Our expert local guides will show you the most popular attractions as well as many of Chicago’s hidden gems that many travelers don’t know to ask about. A guided tour can also be a great introduction to a new city, providing a necessary overview as well as offering hints of what you might want to further explore on your own. Visiting a city on your own can be overwhelming, especially for a first-timer, but booking a guided tour through Bobby’s Bike Hike is a great way to enjoy your trip without any of the guesswork.

Traveling on your own can be daunting if you let it be, but it can also be liberating, unique, and full of self-discovery. A vacation on your own in Chicago will let you explore the city on your own terms without a need to compromise on your idea of the perfect getaway.