The Ultimate Chicago Travel Guide
Everything you need to know before visiting the Windy City
Are you planning a trip to the Windy City? Look no further than our Ultimate Chicago Travel Guide! Whether you’re a first-time visitor or a lifelong resident, you’ll find all the essential tips and tricks to make the most of your trip to Chicago. From iconic landmarks and must-see attractions to the best restaurants and hidden gems, we’ll guide you through the city like a local. So buckle up and get ready to explore Chicago!
This article may contains links to our affiliate partners.
About Chicago
Chicago is the largest city in the state of Illinois, and the third-largest in the United States. Located on Lake Michigan, Chicago is home to iconic sights like the Willis Tower and Wrigley Field, as well as a vibrant food and art scene. Nicknamed the Windy City, Chicago is known for its impressive architecture, diverse neighborhoods, and vast cultural offerings.
Chicago’s nightlife is world-renowned, with plenty of bars and clubs that cater to a variety of tastes. The city also hosts dozens of music festivals, outdoor art fairs, and other special events throughout the year. Additionally, Chicago is home to numerous professional sports teams and venues, making it a great destination for sports fans.
No matter what brings you to Chicago, you’ll find something to love about this amazing city. From the vibrant cultural scene to the iconic skyline, Chicago has something to offer everyone. Whether you’re visiting for a day or planning an extended stay, make sure to take some time to explore the city’s unique attractions and experiences.
Chicago Highlights
Chicago is a unique city filled with world-famous attractions, incredible architecture, and amazing cuisine. From the skyline of the Windy City to its vibrant nightlife, Chicago has something to offer every traveler. Here are some of the highlights that make this iconic city so special:
The Magnificent Mile
This prestigious shopping district boasts luxury boutiques, restaurants, and cafes along one of the most well-known streets in the world. It’s an ideal place to wander, shop, and people watch.
The Skyline
Chicago has an impressive skyline of tall buildings, which can be best viewed from the lakefront. The famous Hancock Building provides a stunning view from the observation deck.
Millennium Park
Home to the iconic “Bean” sculpture, Millennium Park is a great spot for a stroll and also hosts many outdoor concerts and events throughout the year.
Deep Dish Pizza
Chicago is famous for its delicious deep dish pizza! If you’re looking for a true Chicago experience, be sure to grab a slice of one of the city’s famous pies.
Buckingham Fountain
Located in Grant Park, Buckingham Fountain is a beautiful piece of art and an iconic symbol of the city. It’s worth stopping by to admire the fountain, particularly at night when it’s lit up with vibrant colors.
Sports
Chicago is home to two Major League Baseball teams (the Cubs and the White Sox), as well as professional football, basketball, hockey and soccer teams. Don’t miss the chance to catch a game while in town.
Getting There
Getting to Chicago is easy and convenient, no matter what mode of transportation you prefer.
Chicago’s O’Hare International Airport (ORD) is one of the busiest airports in the world and a major hub for domestic and international flights. Midway Airport (MDW) is another option for flying into the city, though it is primarily served by domestic flights. From either airport, travelers can take public transportation or a taxi to their destination in the city.
Chicago is served by Amtrak, with two stations located in the city: Union Station and Ogilvie Transportation Center. Amtrak also provides connections from many cities across the US, making it easy to get to Chicago from many locations.
Greyhound serves Chicago with multiple stops throughout the city. The company also provides connections from other cities across the US and Canada, making it a convenient way to travel to Chicago.
Chicago is located at the intersection of several major highways and is easily accessible by car. Major roads like I-90, I-94, and I-290 make it easy to reach the city from all directions.
Parking in Chicago can be difficult and expensive, so consider using public transportation or other forms of transportation while in the city.
Getting Around
Getting around Chicago is fairly easy with its comprehensive public transit system. The CTA (Chicago Transit Authority) operates an extensive bus and train network that serves the entire city and surrounding suburbs.
Chicago’s iconic L train, an elevated rail network, is a great way to not only get around the city, but take in the skyscrapers and views of downtown.
You can purchase fares for single trips or get an unlimited ride pass for a day, 3-day, 7-day, or 30-day period. If you’d rather not use public transportation, there are plenty of other options for getting around town. Taxis and rideshare services like Uber and Lyft are widely available. Bicycling is also popular, with bike share programs and dedicated bike lanes making it easier to get around the city on two wheels.
You can also explore the city in style with Divvy, Chicago’s official bike share program. If you want to get up close and personal with the city, walking is an excellent way to explore Chicago. Just make sure you know the streets before you go as navigating Chicago can be tricky with its large grid-style layout.
Where to Stay
Chicago is full of unique lodging options to suit any budget or preference. Whether you’re looking for luxury, budget, family-friendly, or something unique, there’s something for everyone.
For those looking for a luxurious stay in the city, there are plenty of upscale hotels located right in downtown. The Ritz Carlton and the Peninsula Chicago both offer excellent service and amenities, while the Palmer House Hilton is a historic Chicago institution that offers classic elegance.
If you’re on a budget, there are plenty of budget-friendly hotels available as well. The Fairfield Inn & Suites Downtown is a great option for those looking for an affordable stay close to downtown, while the Hyatt Place Chicago River North is another great option for those looking for a comfortable stay at a reasonable price.
For families, there are plenty of family-friendly hotels throughout the city, such as the Residence Inn by Marriott Chicago Magnificent Mile and the Hilton Garden Inn Chicago Downtown/Magnificent Mile. Both of these properties provide spacious rooms and family-friendly amenities.
Finally, if you’re looking for something truly unique and special, there are plenty of unique lodging options throughout the city, such as Airbnbs and hostels. Airbnbs offer a chance to stay in a unique home setting, while hostels can be a great way to meet fellow travelers and enjoy a low-cost stay.
No matter what kind of lodging you’re looking for, Chicago has something for everyone. From luxury hotels to budget-friendly stays and everything in between, the city has something for every traveler.
The best things to do
Visit Millennium Park
From interactive public art and beautiful gardens to live music and a stunning reflective pool, Millennium Park is one of the most popular attractions in Chicago. This is a great place to get the full Chicago experience while you’re here.
Take an architectural tour
You won’t want to miss out on Chicago’s amazing architecture! Taking a guided boat or walking tour is a great way to get up close and personal with some of the city’s most iconic buildings.
Shop on The Magnificent Mile
For some of the best shopping around, The Magnificent Mile is your destination. Here you’ll find upscale department stores, designer boutiques, and more. Don’t forget to check out Navy Pier too!
Enjoy a night out in Wicker Park
Wicker Park is an eclectic neighborhood that has something for everyone. From craft cocktail bars and live music venues to hidden speakeasies and dive bars, you can find whatever kind of nightlife you’re looking for.
Catch a game at Wrigley Field
Home of the Chicago Cubs, Wrigley Field has been hosting baseball games since 1914. Going to a game here is a great way to experience the local sports culture. Even if you’re not a baseball fan, you’ll still have a great time!
Where to Eat
Chicago has some of the best restaurants in the world. From classic deep dish pizza to Michelin star restaurants, the options for food lovers are endless. For the seafood-lover, be sure to check out Devon Seafood Grill or Oyster Bah. If you’re feeling adventurous, try the unique fusion dishes at Fat Rice, while gastro-pubs such as The Publican provide a great atmosphere and delicious pub grub.
Italian favorites can be found in Little Italy and Chinatown, while more upscale restaurants like Spiaggia and Everest offer high-end fare. For a truly Chicago experience, take a bite of famous deep-dish pizza at Pequod’s. No matter your food preference, Chicago has something delicious to offer.
Tips for Visiting
Plan your itinerary ahead of time. Consider using the Chicago CityPASS to save money on attractions
Try to stay near downtown and public transportation options, as this makes it easier to get around the city
Pack an umbrella or raincoat in case of inclement weather
Dress in layers in case the weather changes quickly
Wear comfortable shoes—there's a lot of walking to be done in Chicago
Don’t forget your camera—there are lots of great places for photos!
Be sure to get a Chicago-style deep dish pizza and try some of the local foods like a Chicago hot dog.
If you’re visiting during the winter, bundle up and be prepared for some snow
Visit the neighborhood festivals that occur throughout the year to experience the unique culture of each area
Take advantage of the many museums and theaters in Chicago
Take a walk along the lakefront and take in the sights and sounds of the city
Chicago FAQs
Q: What is the best time of year to visit Chicago?
A: The best time to visit Chicago depends on what you plan to do while there. Generally, summer is the most popular season to visit due to the warm weather and variety of festivals, but winter and spring can also be great times to explore the city.
Q: What is the best way to get around Chicago?
A: The easiest and most efficient way to get around Chicago is by taking public transportation. The CTA (Chicago Transit Authority) offers both buses and trains that can take you around the city with ease. Additionally, biking, walking, and ride-sharing services such as Uber and Lyft are popular options for getting around.
Q: Is there anything free to do in Chicago?
A: There are plenty of free things to do in Chicago! Some popular free attractions include the Lincoln Park Zoo, Millennium Park, and Navy Pier. Additionally, the city offers several free outdoor activities including walking tours, yoga classes, outdoor movies, and more.
Q: Is Chicago a safe city?
A: Yes, Chicago is generally considered a safe city. However, like any major city, it is important to be aware of your surroundings and take extra precautions at night.
Share with a friend
Read next
