Chicago Solo Travel Guide

solo travel guide Chicago

New York City



Chicago is a vibrant city that’s often recognized for its fascinating architecture, deep-dish pizza, and blues music.

The city center is separated by the Chicago River, which runs along the downtown Chicago Loop area. Following the river system, are 18 bascule bridges, giving the city a unique backdrop.

With an abundance of sights to see and activities to do, Chicago is an exciting choice for solo travel. Visit popular landmarks such as Cloud Gate, catch an amazing 360-degree view from the tower observation deck, or indulge in the various mouthwatering eateries. Chicago is also home to a variety of energetic live music bars that are worth checking out.

With everything conveniently concentrated right in the heart of the city, Chicago is a superb choice for a solo weekend getaway. If you’re thinking of taking a trip alone to this dynamic city, keep reading below for our solo travel guide to Chicago.

Top Solo Things to Do in Chicago

When it comes to attractions, solo travelers visiting Chicago have a diverse range of activities and sights to consider. From cultural sights, to live music, to eclectic eateries, the energetic city has a lot to offer people traveling alone. 


Cloud Gate 

sightseeing alone in Chicago

Also referred to as “The Bean”, this massive modern art sculpture is the centerpiece in Millennium Park. On the surface of the sculpture, you’ll see the reflections of the surrounding skyscrapers. Walk directly underneath the curved chamber to get an up-close look, as well as catch a glimpse of your own reflection off the ceiling.


The Art Institute of Chicago

Founded in 1879, the Art Institute of Chicago is home to a large permanent collection consisting of almost 300,000 works of art. Discover an extensive Impressionist collection as well as captivating contemporary pieces. Discover pieces from local artists and remarkable selections from around the globe.


Chicago Riverwalk

solo travel for women to Chicago

Take a leisurely stroll on the 1.25-mile pedestrian walkway along the river’s south bank. A walk along the river is a great way to appreciate the city’s spectacular architecture and explore the many tasty eateries along the way. Watch the riverboats go by, or book an architecture boat tour, where you can uncover notable city buildings and key highlights on a guided journey down the river.


Millennium Park 

This lovely green space is located in the heart of downtown Chicago. While it is home to the iconic Cloud Gate sculpture, it also has a beautiful garden, live music pavilion, skating rink, and various works of art. The park is a wonderful spot for solo travelers to relax and take a leisurely walk away from the buzzing streets and sidewalks of the city.


Sky Deck at Willis Tower

view from Chicago observation deck

At one of the tallest buildings in North America, catch a soaring 360-degree panorama from the 103rd floor of the impressive observation deck. For solo travelers interested in an exhilarating view, step out onto The Ledge, a glass box that jets out beyond the building’s edge. From here, you can get a glimpse of the view that’s directly 1,353 feet below.


Magnificent Mile

Magnificent Mile is a commercial district that stretches over 13 blocks of Michigan Avenue. This lively strip is home to over 450 retailers, with a variety of upscale shops, boutiques, and dining. Along with fabulous views of the architecture, you’ll also come across historic landmarks such as the Chicago Water Tower and the Wrigley Building. Magnificent Mile is fantastic spot for solo travelers to wander through and take-in the fun atmosphere, grab a coffee, browse the storefront displays, or do a bit of shopping.


What to Do at Night in Chicago

Enjoy a Nighttime Panoramic View of the City

solo female travel nightlife in Chicago

There are two incredible observation decks in Chicago, both of which are open late into the night. Take your pick between the Skydeck which is on the 103rd floor of Willis Tower, or 360 Chicago which is on the 94th floor of the former John Hancock Center. Whether you stop by as the sun sets, or when the skies are fully dark, you’ll be able to take-in this spectacular outlook of the city and twinkling lights below.


Experience a Live Music Performance 

Catch a live jazz or blues performance at one of the various live music venues or bars. There’s plenty of spots where you can grab a meal and enjoy an energetic performance, such as House of Blues Chicago, and Blue Chicago, which are top-rated spots located right downtown.


See a Broadway Show

singles weekend getaway to Chicago theater

While the selection is not as extensive as that of New York’s City’s, the city of Chicago does feature a solid offering of Broadway shows at various theaters. You never know what musicals or shows might be playing during your solo trip. Check out the theater listings for an up-to-date list of upcoming shows. The performances are usually in the late evening, and are a great after-dinner activity for those traveling alone.


What to Eat in Chicago

where to eat alone in Chicago

Chicago offers a wonderful selection of restaurants and eateries in a variety of different cuisines. You’ll also find popular classics specific to the city, such as deep-dish pizza, a Chicago-style hot dog, or an Italian beef sandwich. When traveling by yourself, there’s no shortage of tasty eateries to choose from.


Chicago-Style Pizza (Deep-Dish Pizza)

A solo trip to Chicago is not quite complete without a taste of one of their most popular dishes, which is pizza! Chicago-style deep-dish pizza is filled with layers of toppings and has a chunky crust that is at least 1-inch deep. The flavors of the toppings —which can include a combination of cheese, tomato sauce, vegetables and meat—come together as they are baked in a round pan. Lou Malnati’s and Giordano’s are two of the top spots to try this dish. Both are long-standing favorites with multiple locations in the city.

Italian Beef Sandwich

Another beloved Chicago food is the Italian beef sandwich, which dates back to the early 1900’s and consists of seasoned thinly-sliced roast beef, hot giardiniera, and sweet peppers on a delicate roll. Al’s #1 Italian Beef and Luke’s Italian Beef are top rated joints to grab a sandwich.

Chicago Mix Popcorn

Head over to Garrett Popcorn Shops for a tasty treat of handmade gourmet popcorn. Established in 1949, there are multiple locations across the city. While there’s plenty of flavors to choose from, a popular choice is the Chicago Mix. This blend consists of two types of contrasting popcorn flavors, combining the sweetness of caramel with the savory taste of cheddar cheese.

Chicago-Style Hot Dog

Another classic item to try is the Chicago-style hot dog, consisting of an all-beef hot dog (frankfurter) on a poppy seed bun, topped with onions, tomatoes, relish, mustard, a pickle spear, and sport peppers. Stop by the famous Portillo’s, a fast-casual restaurant chain whose specialty is their Chicago-style hot dogs.

Where to Stay in Chicago

Chicago hotel for single traveler

Chicago Loop is the energetic central district of the city. Along with the adjacent neighborhoods of West Loop and River North, are where a large selection of hotels are located. Within these three neighborhoods, solo female travelers will be in close proximity to a diverse variety of the city’s top attractions, restaurants, entertainment, and shops.

Chicago Loop

In the heart of downtown Chicago, this vibrant area is a fantastic neighborhood for solo women that want to be close to the action. You’ll be surrounded by remarkable skyscrapers, a mix of eateries, and lovely parks. This area is a great base for exploring, providing easy access to the city’s top sights such as Cloud Gate, Buckingham Fountain, and Art Institute of Chicago.

West Loop

This hip neighborhood is a great choice for solo travelers interested in the culinary scene as well as bars. A diverse mix of awesome eateries are available, along with live music venues and bars. West Loop is formerly an industrial area, where plenty of warehouses have been transformed into trendy restaurants. 

River North

This vivid neighborhood offers a sizable selection of extravagant shops and amazing dining spots. Situated across the river from the downtown Loop, the River North is easy to walk around and well-located for exploring the sights. It’s also home to a variety of chic bars, upscale art galleries and nightlife.


Getting Around Chicago as a Solo Traveler

singles getaway to Chicago

Chicago’s public transportation system consists of a multitude of train lines and bus routes throughout the city. Specifically in the center of the city, you’ll conveniently find plenty of bus stops and train stations within a short distance of each other. The train lines mostly run on elevated railways.

For public transit, single travelers can choose between single-use fares, or day passes which offer unlimited rides for a specific period of time. Passes are available for 1-day, 3-day, and 7-day periods.

Chicago’s downtown area is also quite walkable. Many of the city’s top attractions, restaurants, and shops are centrally-located. Some of these sights include Willis Tower, Millennium Park, Cloud Gate, and Magnificent Mile. Take a nice stroll along the Riverwalk, and admire the soaring skyscrapers and energetic streets as you explore the city by foot.


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