Chicago City Guide

Chicago is a city that wears its architectural legacy on its sleeve, blending soaring skyscrapers with lush lakefront spaces. Begin at Millennium Park, where the reflective surface of Cloud Gate offers a classic photo opportunity before heading next door to the Art Institute of Chicago, one of the oldest and largest art museums in the United States. For a different perspective, a stroll along the Chicago Riverwalk provides a front-row seat to the city's unique skyline, especially when paired with an architectural boat tour that explains the engineering marvels rising from the water.

Beyond the Loop, the city's diverse neighborhoods offer endless exploration. From the trendy eateries of the West Loop to the historic jazz clubs of Uptown, there is a distinct rhythm to every corner. For panoramic views, head to the Skydeck at Willis Tower to stand on the glass Ledge over 1,300 feet above the street. Wrap up the day by exploring the scenic Lakefront Trail or catching a game at Wrigley Field, soaking in the Midwestern hospitality that makes this metropolis feel like home.

While the Loop offers iconic skyscrapers, locals often escape to the neighborhoods for a more authentic pulse. The 606, an elevated rail line transformed into a multi-use trail, connects vibrant districts like Wicker Park and Logan Square. It provides a scenic, urban canopy walk away from the heavy traffic of the Lakefront Trail.

For a dose of history and rhythm, the Green Mill Cocktail Lounge in Uptown is an essential stop. This former Al Capone haunt remains a premier jazz destination, retaining its original Art Deco charm and a no-nonsense atmosphere that celebrates the city's musical roots.

Farther west, the Garfield Park Conservatory offers a "landscape under glass." This massive botanical sanctuary is one of the largest in the world, providing a lush, tropical reprieve from the city's bustle within its stunning historic glass structures.

Chicago’s grid system and robust public transit network make navigating the city straightforward and efficient. The Chicago Transit Authority (CTA) operates the iconic "L" train system and an extensive bus network that connects the Loop to diverse neighborhoods. The Blue Line provides 24/7 service from O'Hare International Airport, while the Orange Line offers a quick link to Midway. For those preferring to travel on foot or by pedal, the city’s flat terrain and scenic lakefront path are ideal for walking or using Divvy, Chicago’s bike-share program.

Taxis and rideshare services like Uber and Lyft are ubiquitous, offering convenient door-to-door service across the city. Within the downtown core, walking is often the most pleasant way to explore landmarks like Millennium Park and the Magnificent Mile. For longer distances or during inclement weather, the CTA remains the most cost-effective choice for both residents and visitors.

Expect to pay $2.50 for a standard CTA train or bus fare, though a trip from O’Hare starts at $5.00. A taxi or rideshare from O’Hare to the Loop generally costs between $40 and $60, while the trip from Midway to downtown ranges from $30 to $45. Short rides within the central business district typically cost between $10 and $20, depending on time of day and demand.

Chicago is a premier shopping destination, anchored by the iconic Magnificent Mile on North Michigan Avenue. This world-famous stretch offers high-end luxury, featuring flagship stores, designer boutiques, and upscale malls like Water Tower Place. Whether seeking haute couture or the latest tech, the refined atmosphere and stunning architecture make it a must-visit for any serious shopper.

For those seeking value or historic charm, head to the Loop’s State Street. Home to the legendary Macy’s in the former Marshall Field’s building, this area blends modern retail with architectural history. Don't forget to pick up a box of Frango Mints, a local chocolate staple, or grab a bag of Chicago-style Garrett Popcorn—a savory-sweet mix of caramel and cheese corn that remains the city's most famous edible export.

For a more eclectic, local experience, explore the boutiques of Wicker Park and Bucktown. These neighborhoods are perfect for finding unique vintage clothing, independent bookstores, and locally made goods. From the high-rises of the downtown core to the trendy sidewalks of the West Side, Chicago provides a diverse retail landscape that caters to every budget and style.

In Chicago, tipping is a standard practice and an essential part of the local service economy. When dining out at sit-down restaurants, a gratuity of 18% to 22% of the total bill before tax is expected for good service; for exceptional experiences, many locals lean toward the higher end. At bars, it is customary to tip at least $1 to $2 per drink or 20% of the total tab. Since the currency used is the US Dollar (USD), ensure you have small bills on hand, as many service professionals rely on these gratuities as a significant portion of their income.

For other services around the Windy City, tipping remains the norm to show appreciation. When using taxis or rideshare apps like Uber and Lyft, a tip of 15% to 20% is standard. If staying at a hotel, plan to offer $2 to $5 per bag to bellhops and leave $3 to $5 per night for housekeeping staff. While not mandatory for quick counter service at cafes, rounding up or leaving a small amount in the tip jar is a friendly gesture widely appreciated by Chicagoans.

Chicago is at its most inviting during late spring (May and June) and early autumn (September and October). These shoulder seasons strike a perfect balance, offering pleasant temperatures for exploring the Magnificent Mile or the lakefront without the extreme humidity of summer or the biting chill of winter. While crowds are thinner than in the peak summer months, the city remains vibrant with outdoor markets and cultural events, and hotel rates are often more competitive.

For those who thrive on energy, summer is the undisputed peak season. From June through August, the city pulses with street festivals, rooftop bars, and lakeside activities, though visitors should expect higher prices and significant crowds at major attractions. Conversely, winter travelers can secure the best bargains and enjoy a quieter experience, provided they are prepared for freezing temperatures and Lake Michigan’s legendary winds.