Ultimate Guide to a Trip to Chicago
Chicago, the "Second City," is a vibrant and dynamic metropolis that offers an unforgettable experience for every type of traveler. From its world-class architecture to its mouthwatering food scene, this city on the shores of Lake Michigan is a destination that truly has it all. If you're wondering why you should visit Chicago, here’s a look at what makes this city so special.
Architectural Marvels and City Views
Chicago's skyline is an art form in itself. The city is a living museum of modern architecture, home to groundbreaking designs by legends like Frank Lloyd Wright and Mies van der Rohe. A great way to appreciate this is to take a river cruise, which offers stunning views and fascinating commentary on the city's iconic buildings. Don't miss the Willis Tower Skydeck for a breathtaking panoramic view of the city, or a stroll through Millennium Park to see the famous "Bean" (Cloud Gate), an iconic piece of public art that reflects the city's magnificent skyline.
A Food Lover's Paradise
Prepare your taste buds for an incredible journey. While Chicago is famous for its deep-dish pizza—a must-try for any visitor—the city's culinary scene goes far beyond that. From Michelin-starred restaurants to cozy neighborhood eateries, you can find a diverse range of cuisines. Explore the West Loop for some of the city’s trendiest spots, or head to neighborhoods like Pilsen and Little Italy for authentic, local flavors. Don't forget to try a Chicago-style hot dog, piled high with a unique combination of toppings on a poppy seed bun.
World-Class Museums and Culture
Chicago is a hub for art, history, and science. The city's museums are among the best in the world. The Art Institute of Chicago houses a stunning collection of Impressionist and Post-Impressionist art, including masterpieces by Monet, Renoir, and Van Gogh. At the Field Museum, you can come face-to-face with Sue, the largest and most complete T-Rex skeleton ever discovered. And for a truly unique experience, visit the Museum of Science and Industry, which is located in the former Palace of Fine Arts from the 1893 World's Columbian Exposition.
Endless Entertainment and Nightlife
When the sun goes down, Chicago comes alive. The city has a legendary live music scene, with blues clubs in Lincoln Park and jazz bars in neighborhoods across the city. Catch a show at a historic theater in the Loop, or grab tickets to a comedy show at The Second City, where some of the biggest names in comedy got their start. For sports fans, Chicago offers no shortage of excitement, whether it's a Cubs game at Wrigley Field or a Bulls game at the United Center.
A City for All Seasons
Chicago is beautiful year-round. In the spring and summer, the city is filled with festivals, outdoor concerts, and bustling patios. In the fall, the changing leaves make for a picturesque landscape, perfect for walking along the lakefront. And in the winter, the city transforms into a magical wonderland with ice skating rinks and holiday markets.
No matter when you visit or what your interests are, Chicago promises a trip full of exploration, flavor, and unforgettable memories.
Flying Into Chicago?
Chicago O'Hare International Airport (ORD)
O'Hare is one of the busiest airports in the world, so it's best to be prepared for a large and bustling environment.
Terminal Connections: Terminals 1, 2, and 3 are connected by secure pedestrian walkways, which makes it easy to walk between them if you have a domestic connection. Terminal 5, however, is a separate building. To get there, you'll need to use the Airport Transit System (ATS) or a shuttle bus. Always factor in extra time if you're transferring to or from Terminal 5.
Security: Security lines can be long, especially during peak hours. A good rule of thumb is to arrive at least two hours early for domestic flights and three hours for international flights. If you have TSA PreCheck or CLEAR, check which security checkpoints have dedicated lanes, as they are not all open 24/7. Visit our Travel Info page >> goinginstyle.com/collections/travel-information-center
Transportation to the City: The most cost-effective way to get downtown is the CTA Blue Line. The train runs 24/7 and takes about 45 minutes to get to the Loop. The station is located on the lower level of the main parking garage, with easy access from all terminals. Rideshares and taxis are also available, but fares can be high and traffic can be heavy.
Layovers: If you have a long layover, there are things to do. A four-hour layover is enough time to grab a taxi or shuttle to the Fashion Outlets of Chicago, which are a short drive away. With a six-hour layover, you could take the Blue Line downtown for a quick meal and to see a landmark like the Bean at Millennium Park.
Amenities: O'Hare has plenty of dining and shopping options, free Wi-Fi, and even a yoga room. If you're looking for a quiet place, try the pedestrian walkways between terminals, as they are often less crowded.
Chicago Midway International Airport (MDW)
Midway is a much smaller, single-terminal airport that is generally easier to navigate than O'Hare. It's the primary hub for Southwest Airlines.
Simple Layout: Midway has one main terminal and three interconnected concourses (A, B, and C). All passengers go through one large, centralized security checkpoint to access the gates. This makes navigating the airport very straightforward.
Connecting Flights: Since all concourses are linked past security, you can easily walk between them without having to re-clear security, which is a major time-saver for domestic connections.
Transportation to the City: The CTA Orange Line is your best bet for getting downtown. It takes about 25-30 minutes and the station is directly connected to the terminal. Taxis and rideshares are also available from a designated area on the lower level outside baggage claim.
TSA Wait Times: While Midway is generally efficient, it can still get busy, especially during peak travel times. It's wise to arrive at least two hours early for domestic flights and three hours for international flights, particularly if you're flying Southwest during a busy season.
Amenities: Midway offers a variety of amenities, including a USO Lounge for military members, a yoga room, and family-friendly areas for kids. You can find plenty of dining options, and the airport has free Wi-Fi and charging stations throughout the concourses.
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