I’ve lived in Chicago for 35 years and I’m still wonderstruck by the big-city buzz, sky-high architecture and the expansive, blue-green lake spilling over the horizon. There’s always tons to do here, new things to explore: an Afrobeat band at Millennium Park, a play about a renegade platypus at a storefront theater, a meaty sandwich made famous by The Bear.
What do you need to know to experience Chicago yourself? Here are answers to the questions I get asked most often.
Is Chicago expensive?
No, especially when compared to other big cities and those on the coasts. Food and lodging are reasonable, and many top sights and activities in Chicago are 100% free. You won’t pay a dime to hear summer concerts at Millennium Park, view terrific art exhibitions at the Chicago Cultural Center, wave to the animals at Lincoln Park Zoo, tour the city with Chicago Greeter, gawp at the light show at Art on the Mart, and much more.
Where should I stay in Chicago?
That depends on your priorities. Downtown (aka the Loop) has loads of cool architectural hotels near the sights, but limited eating and drinking options after dark. Not ideal if you’re looking to party, but a good option if you’re focused on quick and easy museum-hopping.
Next door the Near North has hotels and evening action, but it’s pricey and a bit generic, with more chain lodgings. The West Loop, Lincoln Park, Lake View and Wicker Park all have abundant nightlife to keep you entertained into the wee hours. They’re farther from the main sights but are easy enough to access via the L.
If keeping the price down is a concern, look beyond the Loop, Near North, Gold Coast and West Loop, especially if you have a vehicle, as parking costs in the city’s core are exorbitant.
What’s the best way to get around Chicago?
Public transit is the way to go, especially the L trains, which help you bypass dreadful traffic. “L” stands for “elevated,” as the system runs on raised tracks in addition to subway tracks. The L’s eight color-coded lines get you to most sights and neighborhoods. Bonus: an unlimited-ride day pass costs just $5. Buy it at any L station or via the Ventra app.
The L is particularly useful when going to or from the airports, where traffic can snarl beyond your wildest dreams. The Blue Line from O’Hare and Orange Line from Midway take 30 to 40 minutes and cost $3 to $5. Not only are travel times often quicker on the L, but it’s about 10 times cheaper than a taxi or ride-share.
That said, ride-shares are handy to pick up the slack when the L isn’t convenient.
What are the top 5 things first-time visitors should experience in Chicago?
Start with a 90-minute Chicago Architecture Center river cruise. Yes, it’s touristy, but it’s also marvelous, with guides providing classic Chicago history and lore. I also love the Art Institute of Chicago with its rock-star impressionists and Picassos, and Millennium Park’s interactive sculptures. Deep-dish pizza is fun for the sheer excessiveness of it; Giordano’s is my doughy favorite. Finally, choose a neighborhood to ramble around for shopping, drinks and soaking up the local vibe. Wicker Park, Andersonville, Bronzeville and Pilsen are well-stocked options.
Where should I eat and how do I get reservations?
Great neighborhoods to scope for Michelin-star and Beard-Award winners include Pilsen, Logan Square, Lincoln Square and Wicker Park – all jam-packed with inventive storefront restaurants – and the West Loop, where the buzziest eateries huddle. Most places take reservations via their websites using Tock, Open Table or Resy. Book ahead, especially for weekends.
The Bear TV series has brought stardom to casual, no-reservations spots like Kasama (for the longanisa sausage breakfast sandwich), Loaf Lounge (the chocolate cake) and Mr Beef (the Italian beef sandwich). To avoid waiting in a lengthy line, order the goods for pick-up and then make a picnic out of it. (Note Mr Beef uses various online ordering platforms, since it has no website.)
What is the best way to see a theater show in Chicago?
Check Hot Tix for discounted tickets to shows around the city. Major drama houses like Steppenwolf Theatre, improv favorites like iO Theater, storefront gems like Chopin Theatre and Broadway in Chicago showplace theaters all have seats on offer. Most venues release tickets for the current week, but some theaters make tickets available a month or so in advance. You never know what you’ll find.
Is Chicago safe to visit?
Yes. You may have heard about Chicago being the “murder capital,” thanks to its high rate of homicides and shootings. While those numbers are true, the violence is mostly concentrated in a handful of far west and far south neighborhoods that are off the beaten path for visitors. Serious crime in Chicago has been dropping in recent years, and the tourist areas are reasonably safe. Still, it’s wise to take normal, big-city precautions. Many crimes involve cell phone theft, so be subtle when using yours.
Is Chicago too cold to visit in winter?
No doubt May to October is the best time to visit weather-wise, but being here in winter is doable. It’s chilly (average daytime temperature around 32°F) with a few inches of snow on the ground – all manageable with a warm coat, hat, gloves and boots. To be fair, days of below-zero weather do occur, but deep freezes typically don’t linger. Wintertime perks include lower prices and fewer crowds.
Should I drink a shot of Malört?
Hmm, how’s your pain tolerance? Malört, Chicago’s local liqueur, is renowned for tasting awful. Drinkers compare its flavor to pencil shavings, dirty socks, lighter fluid and burning tires. Many bars sell it, the Nisei Lounge most famously. You’ll likely grimace, but downing a shot is a Chicago rite of passage.
