Chicago solo travel guide. Here is your ultimate guide to planning a visit to one of the most dynamic cities in the United States.
As you will see throughout this book, Chicago is a lively, walkable city. It really mixes world-class architecture, unique history, diverse neighborhoods, and unforgettable food.
From gorgeous lakefront views to incredible museums and buzzing music scenes, it has big-city energy with Midwestern warmth.
In other words, it’s the perfect destination to travel alone. Expect friendly, inspiring, and full of moments that stick with you.
So, if you’re planning a trip, keep reading.
Chicago Solo Travel
As one of the unique places to visit in the USA, this city is awesome. So, your Chicago solo travel is going to be perfect.
For example, if you want lively city energy, amazing architecture, and cultural uniqueness, then Chicago is the spot for you.
After all, Chicago is the third largest city in the United States. As a result, you will get to explore world-class museums, stroll scenic lakefront trails, and dive into the music, food, and art scenes.
That is all without needing company to have fun.
As you will see throughout the guide, the city is walkable, full of friendly locals, and truly has something for every mood. For instance, there is everything from peaceful parks to colorful nightlife.
With a solid public transit system, it’s easy to navigate solo in Chicago. For example, there are trains, buses, and lots of rideshare options.
Plus, Chicago’s mix of urban grit and Midwestern warmth gives it an unforgettable charm. You’ll leave feeling like you’ve truly experienced something special.
Meanwhile, this is a big city and I can’t stress enough the importance of a travel insurance. Make sure it includes medical!
Also, they don’t call it “Windy City” for no reason. If you’re here in winter, spring, or fall, be ready for a breezy experience.
Chicago is on the shores of Lake Michigan, which is one of the largest lakes in the world. Yet, it’s in the Midwest, meaning temperatures get trapped all over the place, leading to a crazy experience.
So, be ready for that!
Best Time to Visit
The best time for Chicago solo travel is late spring (May–June) or early fall (September–October). In my opinion, these months come with most comfortable temperatures.
Plus, you will see fewer crowds at popular places, and these months are also packed calendar of events. For example, there are outdoor concerts and food festivals.
Summer is fun but busy and hot, while winter—though magical with holiday lights—is brutally cold. Winter is also less solo-travel-friendly, in my opinion.
In spring and fall, you’ll enjoy lake breezes, fall foliage or blooming parks. And, of course, all the good vibes without sweltering heat or deep snow.
So, yeah, these seasons give you the perfect balance of things to do, walkability, and that “I could live here” feeling.
Chicago Solo Travel Arrival
Chicago has two major airports: O’Hare (ORD) and Midway (MDW). O’Hare is a global hub with tons of flights, especially international ones.
Midway is smaller and usually easier to navigate, mainly serving domestic routes.
Both are accessible via public transportation. For example, O’Hare is on the Blue Line and Midway on the Orange Line.
For those of you who prefer taxis, there are a ton of them. And you will also have access to rideshare, if that’s your preference.
If you’re flying solo, go for whichever airport gives you the best deal and arrival time.
O’Hare is huge, so give yourself extra time for security and getting to your gate.
Either way, you’ll be just 30–45 minutes from downtown.
Neighborhoods to Stay
Wanna ditch the hotels and live like a local? You will absolutely love Chicago neighborhoods.
For your Chicago solo travel, you have options like the Loop, River North, and Lincoln Park. And each of them has its own thing going on.
The Loop is great for first-timers. For instance, it’s close to museums, parks, and landmarks.
On the other hand, River North is for the chic returner. This neighborhood is trendy with art galleries, restaurants, and nightlife.
Of course, Lincoln Park is world-famous. This neighborhood has a laid-back, residential vibe. For instance, it has a zoo, nature boardwalk, and easy lake access.
Meanwhile, Wicker Park and Logan Square are perfect if you want to be super local. For instance, they are perfect for exploring hip cafés, boutiques, and local flavor.
Stay near an “L” train station for easy movement. This is what the elevated rapid transit system trains are called here.
So, each neighborhood gives you a slightly different slice of the city, all worth exploring solo.
Last but not least, grab our vacation rentals survival guide to help you get the most out of your stays.
Food to Try in Chicago
American summer foods are plentiful in Chicago. This is definitely a food city, no question.
For your Chicago solo travel, you must try deep-dish pizza. Giordano’s or Lou Malnati’s are classics for sampling this.
Although Giordano’s has over 50 locations worldwide today, it’s still a Chicago icon. And Lou Malnati’s pizzas are favorite across Chicagoland. The company has some 60+ locations in the area.
In another day, grab a Chicago-style hot dog—no ketchup!—from Portillo’s or a local stand. Nothing beats a Portillo’s hot dog in hand to a Cub’s game.
Of course, you don’t miss Italian beef sandwiches (Al’s Beef or Johnnie’s). These are especially great when dipped and with peppers.
If you’re into finer dining, try a tasting menu at places like Girl & the Goat or Avec. And there are about 20 Michelin starred restaurants here.
For dessert, grab a Garrett Popcorn mix. The cheddar + caramel is a great combination, especially for movies.
And if you’re here for brunch, go for chicken and waffles or a hearty skillet. So many places to get this, by the way.
Meanwhile, Chicago is also home to global cuisines. For example, there are a ton of spots serving Mexican, Indian, Chinese, and more.
I absolutely love the Ethiopian restaurants in Chicago. For instance, they are so diverse!
And, last but not least, eating solo here is easy. Bars, counters, and food halls welcome everyone.
What to Do & See in Chicago
Vacation trip ideas for this city are plentiful, and your Chicago solo travel will definitely make you a happy visitor.
Start with Millennium Park and the incredible Bean (Cloud Gate). Perfect for grabbing a selfie, so get your vacation poses done right.
Then, walk the Lakefront Trail or hop on a boat tour for unbeatable skyline views. For example, doing both is a great option!
If you’re here in the summer, don’t miss the beaches. The city has a few good beaches, where you will like you’re at the sea.
Of course, you definitely want to plan a visit to the Art Institute of Chicago. It’s a massive, gorgeous, and easy to explore solo.
Also, check out the Museum Campus. Expect the Field Museum, Shedd Aquarium, Adler Planetarium.
Meanwhile, the Skydeck at Willis Tower or 360 CHICAGO at the Hancock are great. They give you sky-high views of the entire city.
And architecture lovers will adore the Chicago Riverwalk and a river architecture cruise. Be ready to click, click, and click!
You definitely don’t want to miss the other popular attractions. For example, there is the Lincoln Park Zoo (free!), Navy Pier, or you might even catch some live music or comedy in the evening.
So, yeah, a lot to do!
Chicago Solo Travel Day Trip
Travel life is a thing, and that’s exactly why we love day trips. And as luck would have it, there are great day trip here.
For your Chicago solo travel, start by taking the train or drive to Oak Park. You will get to see Frank Lloyd Wright homes and Hemingway’s birthplace.
Then, head to Evanston. I love this place as it’s perfect for a relaxed beach vibe and Northwestern’s scenic campus.
Of course, add Indiana Dunes National Park to your trip. This is only an hour away—perfect for hiking, beaches, and nature.
Meanwhile, I highly recommend Milwaukee. This is doable in a day, and has breweries, lakefront views, and a cool art scene.
Or, escape into small-town charm with Galena or Geneva. Honestly, so many options.
Basically, the good thing is that Amtrak, Metra trains, and buses make it easy to get out of the city for a breather.
Where to Shop
For your Chicago solo travel shopping, start on the Magnificent Mile. This is Michigan Avenue, lined with flagship stores.
Expect to see brands like Nike, Apple, Nordstrom, and Zara. Plus, a bunch of other boutique stuff.
Then, head to State Street for Macy’s in the historic Marshall Field’s building. I absolutely love this as it doubles as an attraction.
If you love boutiques, I highly recommend Wicker Park. For example, you will find indie fashion, records, and books.
For artsy finds and home goods, try Andersonville or Logan Square. Andersonville has a Swedish vibe.
Meanwhile, Lincoln Park has great mid-range shops. For example, they have brands like Anthropologie and Warby Parker.
Of course, you should not miss Water Tower Place. This is a great place for a classic mall experience.
Looking for something unique? Visit the Chicago French Market or Randolph Street Market (if you’re in town during its weekend events).
So, yeah, so much to check out!
7-Day Chicago Solo Travel Itinerary
A 7-day Chicago solo travel itinerary gives you enough to really feel like you have seen and felt the city.
For your first day, arrive in town and check into a hotel in River North or the Loop. They are both great areas to stay for central feel.
Ease into your trip with a relaxing stroll along the Riverwalk. And then grab deep-dish pizza at Lou Malnati’s.
On day two, head over to Millennium Park, snap a photo at the Bean, wander Maggie Daley Park, and dive into the Art Institute.
Then, walk the Magnificent Mile for shops and city vibes. I think this is a great area to window shop!
Day three should be perfect for an architecture boat tour. And then follow that with Navy Pier—ride the Centennial Wheel at sunset.
On day four, spend time at Museum Campus. You will get to visit the Shedd Aquarium, Field Museum, and Adler Planetarium.
Day five may take you to Lincoln Park Zoo and Nature Boardwalk. Feel like a local with brunch at Summer House or Café Ba-Ba-Reeba.
Use day six for a day trip to Oak Park or Evanston. And then return for dinner in Wicker Park or a comedy show at Second City.
On your final day, enjoy coffee, city views, and some relaxed shopping. Grab as many pictures and videos to remember the Windy City!
What to Avoid
Your Chicago solo travel is generally fine, but you should know that there are a couple of things to avoid.
First and foremost, avoid being too flashy with valuables. This is especially at night or on public transit.
Of course, you want to stay aware in less-touristy areas. These would include South and West sides, as they can be hit or miss depending on the neighborhood.
I highly recommend that you don’t wander into parks alone at night. Honestly, you would only ask for trouble.
Meanwhile, I recommend that you skip trying to “wing it” with transportation. Download the CTA app or use Google Maps for train/bus directions.
Also, avoid tourist traps. For example, the overly pricey Navy Pier restaurants—explore local gems instead.
Oh, and don’t call it “Chi-Town” (locals don’t). Stick with “Chicago” or “the Chi” if you must.
Stay smart, alert, and friendly—you’ll have an awesome solo trip.
Final Thoughts
Of course, this guide has shown you how a Chicago solo travel is an awesome experience.
Yet, although the guide is super helpful, Chicago is just one of those places that speaks to you personally.
There really isn’t “one” Chicago, as everyone experiences it differently.
So, take the guide with you, but be prepared to encounter unique experiences.
AJ Paris is a travel photographer based in New York. He is the editor of Caravanzers.
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