Experience Chicago with iBestTravel

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, with new things to explore: an Afrobeat band at Millennium Park, a play about a renegade platypus at a storefront theater, or 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 major cities on the coasts. Food and lodging are reasonable, with many top sights and activities in Chicago being entirely free. You won’t pay a dime to enjoy summer concerts at Millennium Park, view exciting art exhibitions at the Chicago Cultural Center, wave to the animals at Lincoln Park Zoo, or be mesmerized by the light show at Art on the Mart. There are plenty of enriching experiences that won’t break the bank.

Where Should I Stay in Chicago?

Your accommodation choice depends on your priorities. The downtown area, known as the Loop, has numerous architectural hotels near key attractions but limited nightlife options after dark. This is ideal for quick museum visits but not for those looking to experience Chicago’s vibrant nightlife.

In contrast, neighborhoods like the West Loop, Lincoln Park, Lake View, and Wicker Park offer an abundance of nightlife options to keep you entertained late into the evening. While these areas may be farther from the main attractions, they are easily accessible via the L train.

If you’re looking to save money, consider staying outside of highly priced neighborhoods like the Loop and Near North, especially if you have access to a vehicle, as parking in the city can be quite costly.

What’s the Best Way to Get Around Chicago?

Utilizing public transit is the most efficient way to navigate the city, especially the L train system, which helps you avoid heavy traffic. The L’s eight color-coded lines connect most attractions and neighborhoods, making it straightforward to plan your outings. An unlimited-ride day pass costs a mere $5, making it a great deal.

The L is particularly beneficial when traveling to and from the airports. The Blue Line from O’Hare and the Orange Line from Midway take about 30 to 40 minutes and cost between $3 to $5. This not only saves time but is also significantly cheaper than a taxi or ride-share.

Moreover, ride-shares offer a convenient alternative when the L isn’t suitable for your travel plans.

Top 5 Experiences for First-Time Visitors

Begin with a 90-minute Chicago Architecture Center river cruise. While it may feel touristy, the insights into Chicago’s historical architecture are remarkable and informative. Next, visit the Art Institute of Chicago, featuring an impressive collection of impressionists and modern art. Don’t miss Millennium Park’s outdoor interactive sculptures.

Another quintessential Chicago experience is indulging in deep-dish pizza, and Giordano’s is a favored choice among locals. Lastly, choose a neighborhood such as Wicker Park, Andersonville, Bronzeville, or Pilsen to explore, where you can soak up local culture while enjoying shopping and drinks.

Dining Recommendations in Chicago

Great neighborhoods teeming with Michelin-starred and Beard-Award winning restaurants include Pilsen, Logan Square, Lincoln Square, and Wicker Park. Each area boasts creative dining options and a vibrant atmosphere. Many restaurants allow reservation-making through their websites; therefore, it’s advisable to plan ahead, especially on weekends.

The popularity of the TV series The Bear has elevated casual spots like Kasama and Loaf Lounge. To avoid long wait times at these busy eateries, you may want to consider ordering takeout and enjoying a picnic in one of Chicago’s many parks.

Seeing a Theater Show in Chicago

For discounted theater tickets, check out Hot Tix for various performances around the city. With venues ranging from major drama houses to improvisational comedy theaters, you’ll discover a wide variety of entertainment options. Many theaters release tickets weekly, with some offering them a month in advance, so you never know what great shows may be available.

Safety in Chicago: What to Know

Yes, Chicago is safe to visit. While you may have heard reports regarding high crime rates, serious crimes are primarily concentrated in specific neighborhoods that are generally off the tourist path. Tourist areas remain safe, though practicing standard city safety precautions is always wise.

Is Winter a Good Time to Visit Chicago?

While May to October is generally the most pleasant time to visit, experiencing Chicago in winter is certainly feasible. Though chilly, with average daytime temperatures around 32°F, bundled up visitors can still enjoy the city’s charm. Another plus is the lower prices and fewer tourists during this season.

Should I Try Malört?

Malört, known as Chicago’s local liqueur, is infamous for its unique and somewhat unpleasant taste. It’s often humorously described by drinkers, and trying a shot of Malört is considered a rite of passage for those engaging with the city’s bar culture.