Solo Trip to Chicago: A Local’s Guide to Planning the Best Trip

If you’re planning a solo trip to Chicago, you are in for a treat! This city has beautiful architecture, beautiful parks, a lively entertainment scene, and a top-tier food scene.

Living in Chicago, I might be a bit biased about what makes it so great. But as a frequent solo traveler myself, I can say with confidence that you won’t be disappointed when you visit here.

Safety During a Solo Trip to Chicago 

Safety is always top of mind for us solo female travelers, so let’s start there.

Is Chicago safe to visit? 

There is no denying that Chicago has a reputation for high crime rates that go back to the days of Al Capone. In the last several years, I have also seen more instances of crime in neighborhoods that used to not see as much of it. 

But generally speaking, if you stay within well-populated areas like the ones included in this post you’ll be just fine. 

You should also be mindful not to draw unnecessary attention to yourself with flashy jewelry or striking up arguments with people (but, isn’t this just good practice anywhere?). 

Be respectful of the city, and look like you know where you’re going. 

Is Chicago safe to visit alone? 

There’s no reason you cannot enjoy a safe and fun solo trip in Chicago by following some standard safety precautions:

• don’t over consume alcohol, keep your wits about you 
• don’t walk around alone late at night and in deserted areas 
• keep your valuables close to you, and consider a crossbody purse
• stay aware of your surroundings

These are general safety tips I would offer any fellow solo traveler no matter where in the world they’re traveling.

Where to Stay During a Solo Trip to Chicago 

Especially as a solo traveler, where you stay matters. You’ll want somewhere that’s comfortable, secure and within your budget. Chicago is a major tourist destination, which means there are plenty of great options.

Best Neighborhoods to Stay In

If you are planning on visiting Chicago as a solo traveler, one of the best neighborhoods to stay in is the Loop.

This downtown district gives you a central location to some of the city’s most popular tourist attractions. You’ll also find plenty of places to eat and enough to do at night. 

I have walked around here alone in the evening several times and always feel quite safe, especially as there are lots of tourists around and a decent police presence. 

But, this is not an area where I’d walk around alone too late into the evening. Since downtown is where a lot of people work, it’s not quite as busy late into the night as it is during the daytime.

Other neighborhoods to consider include West Loop, River North, Gold Coast, Old town and Lincoln Park. All will keep you within a reasonable distance to the major tourist sites in Chicago while offering a fun environment. 

Hotel Recommendations 

There are thousands of hotel rooms across Chicago, so you have plenty of options for where to stay. However, it is always worth checking to see if a convention or major event is happening that might affect availability.

🏨 Luxury: The Peninsula Chicago

For a luxe experience, stay at The Peninsula. It is situated in a stunning landmark high rise right around the corner from the Magnificent Mile. The hotel has a rooftop spa, a swimming pool and a sun terrace that provides wonderful views over the city. 

👉 Check prices & availability for your dates

🏨 Mid-Range: The Godfrey Hotel

The Godfrey Hotel in River North is a 6-minute walk to the El station and less than ten minutes on foot to the shops along the Magnificent Mile. The property also has a terrace with a fire pit and a lovely rooftop lounge for guests to enjoy. 

👉 Check prices & availability for your dates

🏨Budget: Kinzie Hotel

Another excellent place to stay in River North is the Kinzie Hotel. It is located a block from the Chicago River and is a 5-minute walk to the nearest El train stop. One of the main perks of staying here is their continental breakfast.

👉 Check prices & availability for your dates

13 Best Things to Do Alone on a Solo Trip to Chicago 

It is absolutely possible to have a great time solo here, and there are some great things to do in Chicago alone: 

Foodie things to do in Chicago

1. Get Pizza

Chicago is known for its outstanding deep-dish pizza and there are several places you can try some in the city.

Pizzeria Uno has been an institution in town since 1942. It’s the original, and where I always recommend first-timers go. My personal favorite is Giordano’s, but there are many great options for where to get Chicago-style pizza. 

Here’s the catch – it’s a lot of food. A lot of very heavy food. If you’re traveling solo, it might be too much food for you alone. If that’s at all a concern for you, I recommend taking a food tour instead. 

Most will include deep dish pizza tasting as part of the experience, of course!

2. Take a Food Tour

Aside from pizza, Chicago is known for being a foodie heaven. 

There are plenty of food tours to choose from, and I recommend the Chicago Favorites Ultimate Food and Walking Tour. Over the span of three hours, you’ll get to eat everything from deep-dish pizza and hot dogs to chocolates and pastries.

It’s part food tour and part walking tour which not only helps with digestion along the way, but allows you to see more of the city. 

Plus, joining a group tour as a solo traveler is a fun way to socialize and meet some new friends.

🍕 Book your spot on the Chicago Favorites Food Tour

3. Eat your way through Chicago’s diverse neighborhoods

If you don’t like the idea of taking an organized tour, I suggest exploring Chicago’s food neighborhoods on your own. 

Devon Ave, Chinatown, Pilsen and Uptown each offer a diverse range of cafes, restaurants and eateries focused on different worldwide cuisines. 

Go to: Devon Avenue for Indian / Pakistani food; Chinatown for Chinese, Korean, Japanese fare and more; Pilsen for Mexican food and in Uptown explore the flavors of Asia on Argyle.

If you’re visiting Chicago in the summer, it’s worth keeping an eye out for any food street festivals going on – we have a lot of them!

Active things to do in Chicago

4. Ride a Bike

Bike riding is a fantastic way to explore the city, whether you brave it out on the streets or stick to riding in the parks. 

You can rent bikes around town or grab one from a Divvy stand, but if you would rather not ride alone you can join a Chicago bike tour with a local guide. 

One of the best ones is Chicago’s Ultimate City Bike Tour. It runs entirely along the city’s bike paths and enables you to take in some of its most sights, including Soldier Field, Millennium Park, Chicago’s Museum campus and the Lakefront Trail.

🚲 Check prices and availability

5. Go for a long walk

One of my favorite things about Chicago is how walkable it is. Last summer, I explored several different walking trails all across the city as I worked my way up to 10k daily steps. 

One of my favorites is the lakefront trail. It’s awe-inspiring to have Lake Michigan stretching out on one side of you, and the skyline ahead of you. 

Plus, the trail is always bustling when the weather is nice so it’s a fun way to be around the energy of fellow walkers, joggers and cyclists all enjoying the beauty of the city together. 

The lakefront trail can also take you to and through Milton Lee Olive Park or Lincoln Park, two of my favorite green spaces in the city.

Alternatively, hit the 606 trail, which is a converted rail line that has been concreted for bikes, walkers and joggers. You can get on and off the trail at various points. I love walking along it until I approach an area with a good coffee shop to stop off at. 

Touristic things to do

6. Take an architecture boat cruise 

Chicago is blessed with incredible and iconic architecture, and a great way to see it is on an architecture boat cruise.

This activity is a favorite of locals and tourists alike, and I strongly recommend building it into your Chicago itinerary.

⛴️ Check prices and availability

7. See a ball game

Chicago has a huge sports culture, so you’ll have plenty of opportunities to see a ball game if you’d like. 

Even as a complete non-sports fan, I’ve been to several baseball and basketball games. The snacks are good, the atmosphere is fun and lively and you’re sure to have a good time. 

Depending on when you’re visiting, see if you can catch a game for whatever sport’s in season at the time. 

8. Climb a skyscraper

Of course, you’ll be surrounded by gorgeous Chicago buildings as you walk around the city and take your architecture river cruise. Level up the experience by actually climbing one. 

You could grab drinks at the signature room on the 95th floor of the John Hancock building (now called 875 N Michigan Ave), or give the TILT ride a whirl on the 94th. 

For an even bigger thrill, check out the skydeck on the 103rd floor of Willis Tower (forever known as Sears Tower to us native Chicagoans). 

9. Shop at the Magnificent Mile

Whether you want to spend money or simply window shop, head to Magnificent Mile. You’ll find plenty of high-end shops, as well as more affordable options. 

Besides, it’s simply a beautiful street to walk along while you’re here. Who knows, maybe you’ll even pick up a Chicago souvenir or two while you’re at it. 

Cultural things to do in Chicago

10. Check out a museum 

Chicago has a good selection of museums you can visit, including the Art Institute of Chicago, the Field Museum, the Museum of Science & Industry and the Chicago History Museum.

Especially if it’s cold or rainy during your visit (not unheard of depending on when you’re coming), a few hours in a museum is a cozy way to get to know the city. 

11. Catch a show

Chicago has a decent theater scene as well as plenty of music or comedy shows going on at any given time. See what’s playing in advance of your trip and consider treating yourself to an evening at the theater. 

If you’re looking for laughs, don’t miss Second City. And if you prefer live music, look into Green Mill or Kingston Mines to see what sparks your interest more. Taking yourself out to a show is the perfect solo date idea in Chicago!

Luxury and wellness things to do in Chicago

12. Dine at Alinea

Gastronomic experiences don’t come much better than the extraordinary culinary delights at Alinea. While this is definitely a foodie experience, it’s also a luxe one. 

Now celebrating its 20th year, the venue has been awarded the title of the ‘Best Restaurant in the World’ by Elite Traveler and the ‘Best Restaurant in North America’ by The World’s 50 Best Restaurants.

Bookings are essential and very hard to come by. But if you can score a table, you can enjoy one of three different dining experiences at the Kitchen Table, The Gallery and The Salon.

I’ll be honest – I haven’t even gone here yet but it is certainly on my list!

13. Get Pampered

After a busy day or a few days of sightseeing, one of the best things you can do in Chicago is to pamper yourself.

We’ve got plenty of options to choose from – saunas, day spas, massage parlors, head spas, the list goes on. Look into Aire Ancient Baths, Perspire Sauna or The CryoBar as a starting point to find what would work best for you. 

FAQ: Planning a Solo Trip to Chicago 

Let’s recap a bit, shall we: 

Is Chicago good for a solo trip? 

Yes! Chicago is a wonderful city to visit on a solo trip. Aside from its many tourist attractions, the city has good public transport that makes it easy to get around on your own.

How to treat yourself in Chicago? 

The best way to treat yourself in Chicago is to stay in a hotel with some excellent amenities, eat at a top-notch restaurant at least once, and do a bit of high-end shopping along the Mag Mile. 

How many days do you need in Chicago? 

For first timers, 4 days in Chicago would give you plenty of breathing room to explore without feeling rundown. But even a couple of days here are worthwhile, in my opinion. 

Final Thoughts on Taking a Solo Trip to Chicago 

Chicago is a fantastic city with so much to offer, and the more I travel around the world the more aware I become of how good we have it here as well. It’s tough to get bored here, because there’s always something to do. 

Yet, the city never feels over-crowded or unkempt as some other tourist hotspots tend to feel. People are generally down-to-earth, the dining options are endless and the stunning architecture is well balanced with nature.

You’ll find plenty of ways to enjoy your own company on a solo trip to Chicago, rest assured.