17 essential tips for your trip to Chicago

Chicago is a vibrant city with much to explore, attracting visitors every year. However, with so many wonderful options, it can be challenging to decide where to begin.

Having lived here for over 30 years, I advise all my guests to use public transportation, explore the neighborhoods, and be cautious when trying Malört.

You’ll also want to understand the local sports scene, the hefty taxes, and the ketchup debate… and that’s just the beginning. I've compiled the top insider tips to help make your visit to the Windy City smooth and enjoyable.

1. Plan for a stay of 3 to 5 days

You’ll need about two to three days to explore key attractions like the Art Institute, Wrigley Field, Millennium Park, and Willis Tower. Adding a few more days allows you to venture beyond downtown and discover the vibrant neighborhoods that embody Chicago's spirit.

Pilsen and Logan Square invite you with delicious eats and lively street art. Bronzeville features galleries and soul food spots, while Andersonville serves as a vibrant, cafe-filled LGBTIQ+ haven. Don’t miss the culinary treasures in Hyde Park, Wicker Park, and Humboldt Park.

2. Avoid driving, especially in the downtown area

Driving in Chicago can be quite a challenge. Traffic jams are common not only during rush hour but at almost any time of day. Ongoing road construction on the main highway only exacerbates the issue. Finding parking is tough and expensive, especially downtown where garages often charge around $45 per day. To avoid this hassle, it’s best to leave your car behind and utilize public transportation instead.

3. Purchase a Ventra Card for easy public transportation access

Getting around Chicago via public transport is a breeze—primarily using the L trains, which operate on both elevated and underground tracks. They’ll take you to most attractions and neighborhoods well into the night. Buses fill in the gaps where the L doesn’t go.

For convenience and savings, grab a rechargeable Ventra Card for your transit needs and add funds as required. You can find these cards at any L station, including at the airports, and using one saves you about $0.75 per ride compared to single-use tickets. You also have the option to download the Ventra app to purchase a digital card, which offers the added benefit of showing L and bus schedules.

Whether you opt for a physical or digital card, just tap it at the turnstile when entering the L station or at the farebox when boarding the bus. If you plan on riding three times or more in a single day, consider getting an unlimited ride day pass for extra savings.

4. Take the L for airport transfers

The previously mentioned traffic is no joke. Taxis and rideshares can take an eternity to travel between the city and the airports. Instead, hop on the L train—the Blue Line from O’Hare and the Orange Line from Midway take about 30 to 40 minutes and cost between $2.50 and $5. Not only is the L often faster, but it’s also around ten times cheaper than a taxi.

5. Purchase your museum and theater tickets ahead of time

Numerous museums, like the Art Institute, recommend buying tickets online ahead of time through their website. A day or two in advance should suffice, unless there's a major exhibition happening.

It's also smart to secure theater tickets early, whether you're attending a top-notch opera or an improv Shakespeare performance fueled by drinks. Booking a week ahead is generally sufficient. Check out Hot Tix for half-price same-week tickets to drama, comedy, and performing arts—a real boon for budget travelers.

6. Reserve tables at restaurants

Get ready to indulge in Michelin-starred comfort food and dine like royalty. Making reservations is crucial, especially for weekend meals. Use platforms like Tock, Open Table, or Resy. Generally, a week or two in advance will be fine, though popular spots like Alinea and Girl & the Goat require reservations a couple of months ahead. The prime dining hours are between 6 PM and 8 PM.

7. Bring a warm coat, but also a swimsuit

Situated on the shores of expansive Lake Michigan, Chicago's weather can be quite unpredictable. Expect heavy snowfall in winter and windy conditions throughout the year. If you're visiting from November to March, make sure to pack a warm coat, hat, and sturdy footwear. Even during summer, temperatures can drop suddenly, so it’s wise to have a sweater handy for your outings.

However, that doesn't mean you should skip your swimsuit from June to August. The city offers numerous beaches that invite you to enjoy sand and surf.

8. Your accommodations should reflect your activities

Downtown features a variety of stylish architectural hotels close to attractions, but the options for dining and nightlife are quite limited after dark. This makes it less ideal for those looking to party, but a great choice for families traveling with young kids.

Adjacent to downtown, the Near North offers hotels and nightlife, though it tends to be on the expensive side and feels a bit generic. Areas like the West Loop, Lincoln Park, Lake View, and Wicker Park boast vibrant nightlife that keeps the fun going into the early hours. While they are not in close proximity to the main attractions, they are easily reachable via the L train. Aim to book your stay one to two months in advance, if you can.

9. Be ready for significant taxes

Chicago imposes a tax on most goods and services. This includes a 17.4% tax on accommodations, 10.75-11.75% at restaurants and bars (with higher rates nearer downtown), and 10.25% on other purchases. Typically, these taxes are not reflected in the listed price but are added to your bill at checkout.

10. Support the local sports teams

Chicagoans are passionate about their sports – understanding the city’s teams will help you connect with locals wherever you go.

The rivalry between Chicago’s two baseball teams is legendary: the Cubs represent the affluent North Side, while the White Sox embody the working-class spirit of the South Side. Both teams have enjoyed recent success, though they’ve had their fair share of struggles too. Typically, when one team thrives, the other faces challenges.

The Bears, Chicago’s football team, generate a lot of enthusiasm, despite their inconsistent performance. They’re joined by the underperforming Bulls in basketball, the determined Blackhawks in hockey, and the mid-tier Fire in soccer.

11. Keep it casual

In Chicago, the dress code is laid-back. For many men, the peak of style is a pair of khakis paired with a button-down shirt. Women also opt for comfort, favoring easygoing outfits over high fashion. When heading out for dinner or to the theater, it's completely acceptable to don jeans and casual attire—no one will judge!

12. Never add ketchup to a hot dog

Strange but true: the red condiment is a no-go on local hot dogs. The reason remains a mystery, but one theory suggests that the iconic Chicago-style hot dog—topped with mustard, sweet pickle relish, chopped onions, tomato slices, a dill pickle spear, sport peppers, and celery salt—offers a perfect flavor balance. Adding ketchup only disrupts the meaty harmony.

13. Take a seat at the bar

Locals enjoy spending time in bars, likely due to the long winters that drive people to seek warmth together, or the beautiful summer days that make beer gardens and sidewalk patios inviting.

Beer is the beverage of choice here, and it's no surprise since Chicago boasts more breweries than any other city in the U.S. Settle into a neighborhood taproom, and you’ll soon find yourself discussing the Bears or local politics. You might even be offered a shot of Malört, a local spirit notorious for its terrible taste—a true rite of passage for anyone in Chicago.

14. Navigate using the Pedway

When winter arrives and icy sleet hits your face, make your way to the Pedway. Chicago features a 40-block maze of underground walkways that were designed alongside the subway system. While the pathways aren’t fully connected and can be tricky to navigate, they provide a great way to avoid the harsh weather. Look for 'Pedway' signs above ground to find entry points.

15. Practice courtesy on the L

Allow passengers to exit the train before you board; stand by the open door until everyone has alighted. When using escalators in the stations, stand to the right and walk on the left.

16. Avoid smoking marijuana in public

While purchasing recreational cannabis is legal at licensed dispensaries throughout the city (cash only), consuming it is restricted to private property. Backyards and balconies are acceptable, but cars or cafes are not. Always confirm with the property owner whether they permit it.

Regarding cigarettes, smoking is prohibited inside bars, restaurants, and other public venues, as well as within 15 feet of their entrances.

17. Don’t let the news deter you

Chicago has gained a negative reputation as the murder capital of the USA. Although it does have the highest total number of homicides among American cities, its rate is much lower when viewed on a per capita basis.

The majority of violence occurs in the West and South Sides, where a few neighborhoods are responsible for over half of all shootings. These areas suffer from deep-seated segregation and isolation, which have exacerbated inequality, with local gangs being a significant factor in the violence.

According to city statistics, serious crime in Chicago has been declining in recent years. Nonetheless, it's wise to observe standard big-city safety precautions, especially when out alone at night. Many incidents involve cell phone theft, so use yours discreetly. If driving, remain vigilant about your surroundings.