Solo in Chicago: The Perfect Itinerary for a Solo Weekend Trip to the Windy City

Chicago is one of my favorite cities in the Midwest – and indeed one of my favorite cities in all of the United States!

It's a big city (population 2.7 million), but it doesn't feel as daunting or as overwhelming as some other big cities I've visited. (My theory? It's the Midwestern personality that makes it feel different!)

Chicago has all of the things I love in a city: interesting history, cool architecture, plenty of options for eating, sleeping, and sightseeing, and some beautiful natural features, too (in this case, thanks to its location right on Lake Michigan).

For all of these reasons, I love visiting Chicago.

And while I've visited Chicago many times in the past with friends, family, and significant others, I realized I had never written about traveling to the Windy City solo.

Chicago is actually a great destination for solo travel, and so when the opportunity arose earlier this year for me to stop for a few days during a solo road trip, I decided I would finally write that post for you.

Is Chicago dangerous?

Let's just get this one out of the way.

The first question I received when I shared that I was spending a few days on my own in Chicago was the usual “But is that safe?” question that I often get from concerned readers and family members.

Crime rates in Chicago have been all over the news in the last year. And it's true: crime rates in the city HAVE gone up – just like they have in most other large cities in the United States.

But Chicago is a city that covers more than 230 square miles, and the worst crimes are not taking place in the areas you're likely to visit as a tourist. Violent crime in Chicago is often gang- or drug-related, and while I don't want to downplay the tragedy of said violence, I do want to make it clear that it's not really a threat to the majority of visitors to the city.

As a tourist in Chicago, chances are you're going to stick mostly to the neighborhoods along the lakeshore that contain all the must-see sights like museums, parks, and downtown architecture. In neighborhoods like The Loop, River North, the Magnificent Mile, the Gold Coast, and even Lincoln Park, the biggest threats to watch out for are going to be things like pickpocketing and bag snatching.

Petty theft can of course still be scary, especially if you're traveling alone. But as long as you take all the precautions you'd normally take as a solo traveler (keeping an eye on your belongings, not traveling with more cash/valuables than you need, and avoiding dark alleys and empty streets at night), Chicago does not have to be any more “dangerous” than any other city you've visited.

RELATED: How to Keep Your Money and Valuables Safe on Your Travels

Where to stay for a solo weekend in Chicago

When it comes to *feeling* safe in Chicago, a lot of that is going to come down to where you decide to stay. Chicago has a huge number of hotel options, including many in the popular and “touristy” neighborhoods that I mentioned above.

I've been to Chicago many times and have stayed in several different hotels in The Loop, River North, and Gold Coast neighborhoods. Most of these neighborhoods are quite safe for solo travelers.

Things I look for when searching for hotels in a city like Chicago include the following:

1. Hotel amenities – Obviously this is a big one! I look for things like free wifi, parking options, 24-hour front desks, and extras like on-site restaurants or cool spaces for guests.
2. Proximity to public transport – I may opt to walk or take Ubers in big cities, but I prefer to use public transport when I can. Being close to metro stops is always a plus.
3. Surrounding amenities – A good rule of thumb is to look for a hotel that is close to restaurants, shops, and other venues that will be open and busy throughout the day/night. Staying in the middle of a financial district, for example, can sometimes mean empty streets after business hours and would not be my first pick.

Viceroy Chicago

On my most recent solo trip to Chicago, I decided I wanted to treat myself and booked a slightly more luxurious hotel than I normally would. I stayed at the Viceroy Chicago, which is a fancy Gold Coast hotel with mid-century modern vibes and a rooftop pool.

I splurged on a room with views of 875 North Michigan Avenue (formerly the Hancock Building) and Lake Michigan, and think it was absolutely worth it.

The Viceroy is in an excellent neighborhood, less than a block from several restaurants. It's also within walking distance to Oak Street Beach in one direction and the Chicago Riverwalk in another. I felt very safe in this area at all times of day.

Read reviews on TripAdvisor | Book a room here

Other great Chicago hotels

Some other hotels that I would recommend for solo travelers in Chicago include:

• LondonHouse Chicago – A beautiful and modern downtown hotel that's part of Hilton's Curio Collection. It's got one of the best rooftop restaurants/bars in the city.
• Kimpton Hotel Monaco – Near the Riverwalk, this hotel has modern rooms and a complimentary wine hour each night.
• Virgin Hotels Chicago – This has a hip, Millennial feel to it but won't break the bank.

When to visit Chicago solo

You can visit Chicago year-round, but I've written this post with a summer visit in mind (I visited in June). Summer brings long days and warm temperatures to the Windy City, making it the perfect time to enjoy rooftop patios and river cruises.

Things to do in Chicago on your own

I know that planning a solo trip to a big city can sometimes be daunting, so I've done all the hard work for you! Here's my ideal 3-day itinerary for a solo trip to Chicago; feel free to steal it for yourself.

Day 1: Get to know iconic Chicago

Day 1 in Chicago will having you hitting up all the most iconic spots in the city, including the Chicago River, Navy Pier, and one of the city's observation decks.

1. Architecture river cruise

Learn all about Chicago's history (and get a good feel for the city's layout) by starting your trip off with an architecture river cruise on the Chicago River. These narrated boat tours are the top thing to do in Chicago – and they absolutely live up to the hype.

Lasting an average of 90 minutes, these tours take you up and down the Chicago River, where you'll learn about the most famous skyscrapers and the historical figures tied to them.

This is an excellent way to get some great photos of the Chicago skyline from all sorts of different angles.

I booked this 90-minute boat tour with Wendella, and loved it. Several different companies offer these tours (usually ranging from 75-90 minutes), and they all are very similar in price and content.

These boat tours are extremely solo-friendly, as you can either stay put in a seat the whole time, or meander around the boat throughout the cruise.

2. Walk/have lunch along the Riverwalk

No matter which cruise you choose, you'll be starting down at the Chicago Riverwalk, which is arguably one of Chicago's best free attractions.

The Chicago Riverwalk stretches 1.25 miles along both sides of the Chicago River, through the “urban canyon” that is downtown Chicago. The Riverwalk consists of various outdoor areas to sit and recreate, along with public art and plenty of outdoor restaurants and bars.

Take a stroll here this afternoon and grab some lunch. You'll be spoiled for choice, whether you're interested in wine, local craft beer, coffee, or maybe a combination of those.

You can either grab some food to-go and enjoy it at the Floating Garden or the River Theater, or you can grab a table and enjoy some people-watching as you dine. (I ate at Beat Kitchen on the Riverwalk on my most recent trip, and found its small river-facing tables perfect for solo dining.)

3. Wander around Navy Pier

Navy Pier is one of the most recognizable spots in Chicago, and dates all the way back to 1916. But even though it's one of the top tourist attractions in the Midwest now, the pier really wasn't used for entertainment and recreation until the 1990s.

Navy Pier went through another round of redevelopment in the 2010s, when the city added a Ferris wheel, hotel, and more. I last visited Navy Pier back in 2011, before most of this new development had begun. And wow, is it impressive now!

There's no admission fee to walk around at Navy Pier, so I definitely recommend doing that. It's always bustling with people, so it's a good (and safe) spot to be as a solo traveler.

A fun thing to do at Navy Pier is to head up to the new Offshore Rooftop & Bar for a drink or snack. The space is super cool and chilled out, and it gives you excellent views out over Lake Michigan.

You can totally walk from the Riverwalk all the way to Navy Pier, which is what I did. (From Beat Kitchen where I had lunch, it was 1.5 miles to the end of Navy Pier.) Or you can grab an Uber or Lyft to get there.

4. Tower observation deck for sunset

This evening, I recommend booking a ticket for either the Skydeck at the Willis Tower, or the 360 Chicago atop the former John Hancock Building. Both of these observation decks offer sweeping city and lake views, and it's usually pretty easy to snag a ticket around sunset when you only need to purchase one. (You can get your ticket in advance here so you can skip the ticket line.)

I did this on my most recent trip, opting for the 360 Chicago since it usually tends to have shorter lines. You can get excellent Golden Hour photos from up here, and they even have a bar at the top (Bar 94) in case you want to have a sundowner with your views.

(This ticket includes 360 Chicago entry AND a drink at Bar 94.)

RELATED: Willis Skydeck vs. 360 Chicago: Which Is Best?

After a very full day, you can have a relaxing dinner (if you stay at the Viceroy, there are a bunch of restaurants within walking distance) and turn in early tonight.

Day 2: Art and pampering

Today is all about taking things slow and allowing yourself to enjoy some “me time” on your solo trip.

1. Stroll through some parks

Chicago has a lot of green space and public park land, so this morning I recommend hopping on the L (Chicago's metro) and exploring some of it.

Head to Grant Park (take the L to either Jackson or Harrison on the Red Line), and check out the impressive Buckingham Fountain. This iconic fountain is nearly 100 years old, and is one of the largest fountains in the world. You'll also get excellent views of the Chicago skyline here.

From Grant Park, you can head north through the North Rose Garden, into Maggie Daley Park and eventually Millennium Park, where you'll find the famous Cloud Gate sculpture (AKA The Bean).

All of these connected parks are beautiful, and make for a nice morning walk. (Total distance from Buckingham Fountain to The Bean is just over half a mile.)

2. Visit a museum

Museums are ALWAYS a good option for solo travelers, and Chicago has several world-class ones to visit. The most famous museums include the Field Museum of Natural History, the Art Institute of Chicago, the Museum of Science and Industry, and the Museum of Contemporary Art.

If you end your walk at the Cloud Gate, you won't be far from the The Art Institute of Chicago, which is regarded as one of the best art museums in America. (Buy a skip-the-line ticket here.)

I personally enjoy visiting museums on my own, because it means I have the freedom to spend as much (or as little) time in each exhibit as I want! If you've never tried a solo museum visit before, this would be an excellent place to start.

3. Go to a fancy afternoon tea

Something I've become obsessed with doing as a solo traveler in recent years is going to afternoon tea. Now, you might assume that afternoon tea is mostly a British or European thing, but you can actually find afternoon tea offered at many luxury hotels all around the world.

Chicago has no shortage of high-end hotels, and therefore has plenty of fancy afternoon teas to choose from!

Some places in Chicago where you can book a “fancy” afternoon tea include:

• Pavilion at The Langham
• The Lobby at The Peninsula
• Palm Court at The Drake
• The Library Tea Room at Millennium Knickerbocker

The above teas aren't cheap, but sure do feel indulgent. For more wallet-friendly options, check out the Russian Tea Time Restaurant or Vanille Patisserie.

I love going to afternoon teas solo when I travel. Not only does it cover a meal for me, but it's a great way to visit luxury hotels that I can't afford to actually stay in.

(Note: When I was last in Chicago in June 2021, most of these afternoon teas were not running. Instead, I booked myself in for breakfast at The Lobby at the Peninsula hotel, which was almost the same thing!)

4. Pamper yourself at your hotel

Solo travel should be all about your “me time,” so instead of suggesting that you pack your afternoon/evening full with more activities or sightseeing, instead I suggest that you take time today to pamper yourself a bit.

Whether this means booking a spa service at your hotel, hanging out at a rooftop pool, or maybe going shopping along the Magnificent Mile, do something relaxing for yourself today.

The Viceroy Chicago has a nice rooftop pool with comfy lounging areas, so I spent a few hours one afternoon up there with a good book.

5. Rooftop dinner

Chicago has a growing number of rooftop bars and restaurants, and tonight would be the perfect night to treat yourself to a reservation at one.

Popular rooftop spots in central Chicago with great views include:

• LH Rooftop at the LondonHouse hotel
• Cindy's at the Chicago Athletic Association Hotel
• Raised – An Urban Rooftop Bar
• Cerise at Virgin Hotels Chicago
• VU Rooftop Bar
• J Parker at Hotel Lincoln
• Upstairs at The Gwen
• Z Bar at the Peninsula

The Kennedy Rooftop, Aba, Homestead on the Roof, and Whiskey Business are also good rooftop options in other neighborhoods.

Whichever you choose, though, I highly recommend checking to see if you need a reservation first. At most of these spots, you will! (Though as a solo traveler you might be able to snag a spot at the bar last-minute, too; it never hurts to ask if you've forgotten to book ahead.)

Day 3: Food, views, and gangsters

Okay, so today will be kind of a catch-all for all the other cool things I consider to be must-dos on any solo trip to Chicago!

1. Bike or food tour

I LOVE going on food tours as a solo traveler (it ticks off both dining AND sightseeing all in one!), and there are some really unique ones to try in Chicago.

There are pizza tours, donut tours, and regular classic Chicago food tours to choose from. And while all of these are great options (I've done the pizza tour before), the one I'd recommend for today is this Bikes, Bites, and Brews tour with Bobby's Bike Hike.

This 4-hour biking food tour has a little bit of everything, from Chicago dogs to deep-dish pizza to local craft beers. And the best part is that you cover a lot more ground than on a walking tour (this bike tour covers roughly 13 miles through some of the best Chicago neighborhoods).

This biking food tour runs twice per day, with the daytime tour leaving at 11:30 a.m. (My advice? Have a very light breakfast!)

2. Admire Lake Michigan

Sure, you'll have seen this Great Lake plenty of times by now, but take some time to appreciate it up-close this afternoon by visiting a beach, or taking a stroll along the Lakefront Trail.

Beaches you can easily reach from downtown include the Ohio Street Beach and Oak Street Beach near the Gold Coast, the North Avenue Beach in Lincoln Park, and the 12th Street Beach on Museum Campus.

Most people who've never been to the Great Lakes region before are surprised to learn that cities like Chicago have sandy beaches – but they do!

You can also explore part of the Lakefront Trail this afternoon/evening, which is an 18-mile-long shared-use path that follows the lake shore. You can get some truly excellent views of both Lake Michigan and the Chicago skyline from all along this trail.

3. Gangster and ghost tour

You could opt to just chill on your last night in Chicago, but if you're up for one more fun tour, then you can sign up for an evening “Gangsters and Ghosts” tour.

This 2-hour walking tour runs at 4 p.m. and 8 p.m. most evenings. It covers the history and intrigue of The Loop during the Roaring 20s, back when speakeasies and gangsters abounded in Chicago.

You'll visit some purportedly haunted sites and hear some ghost stories, but you'll also learn a good deal of history about Chicago during this time, too. (The gangsters, at least, were very real!)

Walking tours are always fun as a solo traveler, and this one is certainly a unique one. Book a spot here.

And that's it! That's the end to your 3 days in Chicago as a solo traveler!

How to get around Chicago safely

Whenever I mention visiting cities as a solo female traveler to people who don't travel much, they always want to know how I find my way around safely.

In Chicago, there are plenty of options depending on your comfort level and confidence in navigating public transportation.

For this particular itinerary, you can actually reach a lot of places on foot, especially if you opt to stay in the Loop, River North, or Gold Coast neighborhoods.

And otherwise, here are my preferred modes of transport in Chicago:

• The L – Chicago's CTA operates 8 different L train lines. The Red Line (which is the one you're most likely to use) runs 24/7. Rides are fairly affordable, and it's easy to purchase either a single ticket or a Ventra card with a 1-day or 3-day CTA pass on it from vending machines at almost every L station.
• Ride share – Lyft and Uber both operate in Chicago, and both have implemented extra safety features in recent years that make me feel comfortable using them as a solo traveler.
• Water taxi – Two water taxis lines run on the Chicago River and Lake Michigan during the high season, with stops at the most popular tourist areas.
• Bike share – Chicago has a bike share program called Divvy, which has over 580 bike stations all across the metro area. Chicago is an easy place to ride a bike, too, as it's almost all flat and has more than 200 miles of protected bike lanes. You can pay for single rides or day passes.

So there you have it! Everything you need to know in order to plan a memorable solo trip to Chicago.

I hope I've convinced you to give the Windy City a try if you haven't already, or to consider another visit if you've already been before.

Have you ever traveled to Chicago solo before?

Amanda Williams

Amanda Williams is the award-winning blogger behind A Dangerous Business Travel Blog. She has traveled to more than 60 countries on 6 continents from her home base in Ohio, specializing in experiential and thoughtful travel through the US, Europe, and rest of the world. Amanda only shares tips based on her personal experiences and places she's actually traveled!

www.dangerous-business.com