As a travel writer based in Chicago, I've gathered the most common inquiries from visitors.

After 35 years in Chicago, I'm still amazed by the city's vibrant energy, towering architecture, and the vast blue-green lake that stretches to the horizon. There's always something new to discover: an Afrobeat concert at Millennium Park, a quirky play about a renegade platypus at a local theater, or a hearty sandwich made famous by The Bear.

What should you know to fully experience Chicago? Here are answers to the most frequently asked questions I receive.

Is Chicago pricey?

Not at all, especially when you compare it to other major cities and coastal areas. Food and accommodations are quite affordable, and many of Chicago's top attractions and activities are completely free. You can enjoy summer concerts at Millennium Park, explore fantastic art exhibitions at the Chicago Cultural Center, visit animals at Lincoln Park Zoo, take a tour with Chicago Greeter, marvel at the light display at Art on the Mart, and so much more without spending a dime.

Where's the best place to stay in Chicago?

It really depends on what you value most. The downtown area (known as the Loop) features trendy architectural hotels near popular attractions, but has limited nightlife options, making it less ideal for party-goers and better suited for quick museum visits.

Adjacent to the Loop, the Near North offers hotels and nightlife, but it tends to be expensive and somewhat generic with many chain options. In contrast, neighborhoods like the West Loop, Lincoln Park, Lake View, and Wicker Park boast lively nightlife that will keep you entertained late into the night. While they’re a bit farther from the main attractions, they’re easily accessible via the L train.

If you're looking to save money, consider staying outside the Loop, Near North, Gold Coast, and West Loop, especially if you have a car, as parking in the city center can be extremely expensive.

What’s the most efficient way to navigate Chicago?

Public transit is your best bet, particularly the L trains, which help you avoid terrible traffic. The 'L' stands for 'elevated,' since the system operates on both elevated and subway tracks. With eight color-coded lines, the L connects you to most attractions and neighborhoods. Plus, an unlimited-ride day pass is only $5, available at any L station or through the Ventra app.

The L is especially beneficial for trips to and from the airports, where traffic can become a nightmare. The Blue Line from O’Hare and the Orange Line from Midway take about 30 to 40 minutes and cost between $3 to $5. Traveling by L is not only often quicker but also significantly cheaper than taking a taxi or ride-share.

That said, ride-shares are convenient for times when the L isn’t the best option.

What are the must-see attractions for first-time visitors to Chicago?

Begin with a 90-minute Chicago Architecture Center river cruise. It may be touristy, but it's absolutely fantastic, with guides sharing rich Chicago history and stories. The Art Institute of Chicago is a must-see for its stunning collection of impressionists and Picassos, and Millennium Park features engaging interactive sculptures. Don’t miss trying deep-dish pizza for its indulgent appeal; my go-to is Giordano’s. Lastly, pick a neighborhood to explore for shopping, drinks, and local ambiance—Wicker Park, Andersonville, Bronzeville, and Pilsen are all great choices.

Where are the best dining spots, and how can I secure reservations?

Top neighborhoods to explore for Michelin-starred and Beard Award-winning restaurants include Pilsen, Logan Square, Lincoln Square, and Wicker Park, all filled with innovative storefront eateries, as well as the West Loop, home to the trendiest dining spots. Most restaurants accept reservations through their websites using Tock, OpenTable, or Resy, so be sure to book in advance, especially for weekends.

The TV series The Bear has made casual, no-reservation places like Kasama (known for its longanisa sausage breakfast sandwich), Loaf Lounge (famous for chocolate cake), and Mr. Beef (iconic for Italian beef sandwiches) quite popular. To skip long waits, consider ordering for pick-up and enjoy a picnic instead. (Note that Mr. Beef uses various online platforms for orders since it doesn’t have a website.)

What’s the best way to catch a theater show in Chicago?

Check Hot Tix for discounted tickets to performances across the city. Major theaters like Steppenwolf Theatre, improv venues like iO Theater, charming storefronts like Chopin Theatre, and Broadway in Chicago all have available seats. Most venues release tickets for the current week, but some theaters offer tickets a month in advance. You might discover some great options.

Is Chicago a safe place to visit?

Yes. You might have heard that Chicago is labeled the 'murder capital' due to its high homicide and shooting rates. While those statistics are accurate, the violence is primarily confined to a few remote neighborhoods that tourists generally don’t visit. In recent years, serious crime has been decreasing, and the tourist areas are relatively safe. Nevertheless, it’s wise to take typical big-city precautions. Many incidents involve cell phone theft, so be discreet when using yours.

Is Chicago too cold to visit during the winter?

While it’s true that May to October offers the best weather, winter is still a viable time to visit. Temperatures hover around 32°F with a few inches of snow—perfectly manageable with a warm coat, hat, gloves, and boots. Though there are occasional days of subzero temperatures, these cold snaps usually don’t last long. Benefits of visiting in winter include lower prices and smaller crowds.

Should I take a shot of Malört?

Well, how's your pain threshold? Malört, the infamous local liqueur of Chicago, is notorious for its dreadful taste. Drinkers often describe its flavor as akin to pencil shavings, dirty socks, lighter fluid, and burning tires. It’s available at many bars, with the Nisei Lounge being the most famous spot. You might grimace, but taking a shot is considered a rite of passage in Chicago.