Chicago Solo Travel Guide

Planning a solo trip to Chicago? Here’s everything you need to know for your visit:


  • The third most populous city in the United States, Chicago has around 2.75 million residents.
  • A financial powerhouse, Chicago has the 4th largest GDP of any city in the world.
  • Over a million people in the Chicago metro area claim Polish ancestry.
  • Nicknames: Chi-Town, Windy City, Second City, Chi-City. The city and suburbs are collectively known as “Chicagoland.” The locals are known as “Chicagoans.”


  • Currency: US Dollar (USD).
  • Spoken languages: predominantly English (Polish and Spanish widely spoken).
  • Best time to visit: from May to October. Gets very hot in the summer months.
  • Arriving via airport: The Chicago Transit Authority operates the Blue Line from to O’Hare, and the Orange Line from Midway. The cost from O’Hare to downtown is about $5, and from Midway to downtown is $2.25. Taxi from O’Hare airport is about $36.


  • Best hostel for solo travelers: Freehand Chicago. Very comfy beds, clean rooms/bathrooms, and a great location with a view (close to the Loop). Friendly and welcoming staff, and a very cool interior design (just check out the pics). Book ahead, as room prices in Chi-Town can spike during busy times of year!
  • Downtown hotel rooms average $160 a night, while in North Chicago hotel rooms average between $50 and $130. Downtown hotels are more upscale, and in higher demand.
  • South Chicago hotel rooms average $70 to $250 a night.
  • Accommodation is more expensive the closer you are to the museums and sport stadiums.
Aerial shot of Chicago from Willis Tower skydeck
The best views of the city are from the Skydeck on the 103rd floor of the Willis Tower


  • The Chicago Transit Authority serves 1.6 million riders daily on their extensive public transit system. The system is composed of subways, elevated trains, and buses. Fares are $2.50 for a single ride, with reduced fares for seniors, military, and grade school students. All fares must be paid with exact change or with a Chicago Card.
  • Taxis are relatively expensive in Chicago – fares start at $3.25 for the first 1/9th of a mile, and $0.20 per each additional 1/9th of a mile. Yellow Cab: (312) 829-4222.
  • To save time and money, call an Uber or Lyft instead (through their respective mobile apps).
  • The ZipCar car rental is immensely popular as it’s expensive and cumbersome to own a car in Chicago. There are hundreds of Zip Car pick-up locations in the city.


  • Drinking age is 21, last call is 2 AM (3 AM on Saturday nights).
  • Trendy scene: some of the most popular clubs are right in Chicago’s downtown.
  • Hip/local scene: the neighborhood between Milwaukee Avenue, Division, and Damen in Wicker Park has dozens of bars. Check out the the intersection of Milwaukee, Damen, and North.
  • Great bars in Chicago: The Green Mill (live jazz), The Whistler (live music or DJs), Chef’s Special Cocktail Bar, The Charleston (relaxed setting), The Corner Bar (fun dive bar), and O’s Tap (hidden gem).


  • The Bean. While the proper name for this monument is “Cloud Gate,” the nickname stuck as it resembles a kidney bean. This highly-polished statue is located near the Art Institute (in Millennium Park), and gives off a distorted reflection of its surroundings.
  • Chicago is famous for its diverse and unique architecture. While you’re in town, hop on a guided boat tour and learn all about the city’s skyscrapers (there are numerous tour operators along the Chicago River Esplanade and Riverbank). Don’t forget to bring a camera!
  • The Art Institute of Chicago is the second largest art museum in the United States, taking up over 1 million square feet. Its encyclopedic collection spans centuries, and includes treasures from all around the world.
  • The Adams House. Designed by Frank Lloyd Wright, the Adams House is a Prairie school style house built in 1901.
  • A popular tourist destination, the historic Navy Pier features rides, attractions, events, and food spanning 50 acres.
  • Illinois-Michigan Canal: this canal spanned 96 miles, and allowed boat transit through the Great Lakes to the Mississippi River (then down to the Gulf of Mexico). While no longer in service, portions have been preserved and maintained. To see where the canal originated, go to the 2800 block of S. Ashland Avenue (directions).


  • Go for a stroll through historic Old Town, near Lincoln Park. You’ll find the Chicago History Museum, the Midwest Buddhist Temple, and a delicious mix of restaurants and pubs.
  • Walk down North Michigan Avenue, and you’ll be in the heart of downtown. Known as the Magnificant Mile, there is always something here to feast your eyes on.
  • In the afternoon, take the Red Line to Bryn Mawr Avenue. Walk a few blocks to the east and marvel at the fabulous Living 2007 mural underneath Lake Shore Drive.
  • Enjoy a walk along the shore of the city’s gorgeous lake. The Lakefront Trail is well-maintained, and gets crowded. Go south of the museum campus to avoid the crowds.


  • Chicagoans love their festivals – over 400 are thrown annually. Two festivals not to miss: the Chicago Blues Festival and Chicago Jazz Festival.
  • Chicago is home to sixteen-inch softball. It’s still played locally (without gloves), and you can join in a game at city parks all summer long. There are over 500 public parks in the city!
  • Great restaurants in Chicago (that locals l0ve): Demera Restaurant ($$ – Ethiopian), Little Bad Wolf (burgers – sometimes very busy), Bavette’s Bar & Boeuf ($$$$ – steakhouse), Community Tavern ($$$), HaiSous Vietnamese Kitchen ($$), Tango Sur ($$ – Argentinian), Monteverde ($$$ – reserve in advance).
  • Where to find good cheap eats: the city’s food scene is extensive, and you can find any style of food at any price. Don’t miss the chance to try some authentic Chicago style pizza. You can also buy up a Chicago Dog at any number of vendors. A Chicago Dog is an all-beef frankfurter in a poppy seed bun. Pop by the Joong Boo Market for delicious Korean food, or visit Red Hot Ranch for excellent burgers.
  • Tip: use the Yelp website (or app) for the latest restaurant listings and reviews.
  • Dangerous areas: avoid the Southside, especially the neighborhood of Burnside (which has the highest murder rate in the city). “West Wicker Park” is a nice way of saying “Humboldt Park,” where the lines between safe and seedy blur. The Howard Red Line Stop is not somewhere you want to be alone, especially at night, as this area is known for it’s gang-related violence.

Recommended trip duration: 3-4 days


Leave a Reply

Your email address will not be published.