Exploring Chicago: Travel Tips And Insights

Chicago is a bustling city steeped in Midwestern charm, with towering skyscrapers and tranquil beaches. It's a harmonious blend of opposites, making everyone feel right at home. When travelling to Chicago, there are a few things to keep in mind.

First, Chicago has a vast public transportation system, including the L trains and buses, which are a convenient and affordable way to get around. It is also a highly walkable city, but be prepared for delays and give yourself plenty of time to get to your destination.

Second, Chicago is known for its sports culture, with several professional teams to cheer for, such as the Cubs, the White Sox, and the Bears. It is also a foodie paradise, with deep-dish pizza, Italian beef sandwiches, and Chicago-style hot dogs (but never ask for ketchup!) being local favourites.

Third, the city has a rich artistic and cultural scene, with world-class museums, architectural gems, and live music venues. The Art Institute of Chicago and the Museum of Contemporary Art are must-visits, as well as the Chicago Riverwalk and the Navy Pier for stunning views of the city.

Finally, Chicago has distinct seasons, with freezing winters and warm, sunny summers. Pack accordingly and be prepared for unpredictable weather, especially in the summer when storms can roll in unexpectedly.

With its friendly atmosphere, vibrant neighbourhoods, and abundance of attractions, Chicago is a city that has something for everyone.

How to get around

There are five main ways to get around Chicago: public transportation, driving, ridesharing (Uber, Lyft, and taxis), walking, and biking.

Public Transportation

Chicago has the third-largest public transportation system in the country. All the train lines meet downtown to form a loop (hence the name "downtown loop"), so it's easy to navigate and access different places around Chicago. Train and bus lines are laid out like a grid, with eight train lines and 129 bus routes in total.

If you're coming from Chicago O'Hare International Airport, the Blue Line will connect you to downtown Chicago. If you're arriving from Midway Airport, the Orange Line will bring you into downtown Chicago as well.

To pay your fare, you'll need a Ventra card. You can purchase or load more funds onto a Ventra card at the vending machines located at the front of every station. Then, touch your Ventra Card to the reader located at the top of every turnstile.

Public transportation is the cheapest transportation option, but trains and buses can be delayed. It's also a good idea to practice extra caution when travelling at night.

Driving

If you're visiting Chicago on a road trip or plan to take day trips during your visit, renting a car may be worth considering. However, finding parking spaces and dealing with heavy traffic can be a hassle. Parking garages can also be expensive.

Ridesharing

Ridesharing services like Uber, Lyft, and Chicago-based taxi services like "Curb" are largely available throughout the city at any time of day. Fares fluctuate depending on location, distance, and time of day, and ridesharing can be pricier for larger groups.

Walking

Chicago is quite walkable, with tons of wide, designated walking areas. If you plan on staying in the main neighbourhood areas of Chicago, you should be able to walk between different neighbourhoods. Chicago also has scenic walking trails like the Lakefront Trail along Lake Michigan and the Riverwalk on the Chicago River, as well as sprawling parks like Grant Park, Millennium Park, and Lincoln Park, which are great for walking.

Biking

If you visit during the warmer months, biking is a great way to explore different parts of the city. The main form of bike rental in Chicago is Divvy Bikes (by Lyft). Download the Divvy Bikes app to locate nearby bikes, and then you can unlock them from your phone.

What to eat and drink

Chicago is a foodie's paradise, with a diverse range of culinary delights to offer. Here's a guide to what to eat and drink when visiting the Windy City:

Chicago-Style Hot Dogs

The famous "Chicago Dog" is a must-try when visiting the city. This savoury treat consists of an all-beef frank in a poppy seed bun, topped with yellow mustard, chopped onions, sweet pickle relish, a dill pickle spear, tomato, sport peppers, and a dash of celery salt. Remember, no ketchup is allowed on a true Chicago-style dog! Try it at classic spots like Portillo's, The Wieners Circle, or Dave's Red Hot for a taste of history.

Deep-Dish Pizza

Deep-dish pizza is another iconic Chicago dish. This hearty pie features tall walls of buttery crust filled with layers of mozzarella and topped with tangy tomato sauce. It's a cheesy, gooey delight that you can find at places like Uno Pizzeria & Grill, Lou Malnati's, Gino's East, and Giordano's.

Jibarito

The jibarito is a unique Puerto Rican sandwich that has become a Chicago staple. It consists of sliced and fried plantains instead of bread, filled with your choice of protein, lettuce, mayo, and cheese. Head to La Bomba, Papa's Cache Sabroso, or Marina's Bistro for an authentic taste.

Italian Beef Sandwich

The Italian beef sandwich is a Chicago original, created by the city's Italian immigrant community in the early 1900s. Thinly sliced beef, stewed in its juices, is piled into a bun and often topped with giardiniera (pickled vegetables). Try it at Al's Italian Beef, Mr. Beef, or Johnnie's Beef for a true taste of Chicago history.

Steak

Chicago was once considered America's top source for beef, so it's no surprise that the city boasts some excellent steakhouses. Gene & Georgetti is a famously old-school option, while Gibsons Bar & Steakhouse and Rosebud Prime offer modern takes on classic cuts.

Desserts

For something sweet, try the famous Eli's Cheesecake, which comes in 40 unique flavours. Or, head to Margie's Candies, a vintage ice cream parlour that's been around since 1921, for a rich hot fudge sundae.

Drinks

When it comes to drinks, Chicago has something for everyone. Beer lovers will want to check out the craft brewery scene, with places like Three Dots and a Dash offering unique cocktails. For a more relaxed vibe, explore the city's many beer gardens and outdoor bars.

Chicago is also known for its classic cocktails, like the Martini at the Green Mill Cocktail Lounge, a former hangout of Al Capone. And don't forget to try the local favourite, Malört, a bitter Scandinavian-style liquor.

What to pack

When packing for Chicago, it's important to be prepared for unpredictable weather. Even in summer, temperatures can drop, so it's advisable to bring a sweater or light jacket. For visits between November and March, a warm coat, hat, and sturdy shoes are essential. However, don't be surprised if you encounter warm weather too; Chicago has several beaches, so a bathing suit is recommended for the summer months.

Chicago is a walkable city, so comfortable walking shoes are a must. The city is also known for its excellent public transportation system, so you may want to bring a reusable water bottle to stay hydrated while on the go.

If you plan to visit museums, theatres, or other attractions, check their websites in advance. Booking tickets online can save you time, and some venues offer discounted tickets for advance purchases. Additionally, carrying a small bag or purse can make it easier to navigate crowded spaces and speed up security checks at large venues.

Chicago has a vibrant food scene, so you may want to bring attire suitable for dining out. The city also has a thriving craft beer and cocktail culture, so if you plan to indulge, don't forget your ID!

Lastly, if you take any prescription medications, remember to carry them in their original containers, along with a copy of your prescription.

Where to stay

When it comes to where to stay in Chicago, it's best to consider your priorities and preferences. Here's a list of some of the best neighbourhoods to stay in, depending on your interests:

• The Loop: The Loop is the downtown district and the heart of the city. It's perfect for first-time travellers as it's where most of the attractions are, including major theatres, world-class public art, and the Art Institute of Chicago. It's also close to other tourist-oriented neighbourhoods. However, there are few restaurants in the area.
• Magnificent Mile: North of the Loop, the Magnificent Mile is Chicago's main shopping street, lined with restaurants, luxury shops, and night spots. It's very central and one of the best districts for tourists looking for entertainment.
• River North: River North is the Party District, where people go to have fun and be seen. It's close to the Loop and the Magnificent Mile, and is home to numerous art galleries, bars, nightclubs, and fine-dining restaurants.
• Gold Coast: The Gold Coast is an upmarket residential area away from downtown Chicago, offering a quieter and more relaxed atmosphere. While you'll likely need to travel to see most sights, the coastal setting and numerous eateries offer a different feel from downtown neighbourhoods.
• Lincoln Park: Lincoln Park is a great option for families, with affordable accommodations. It's home to attractions like DePaul University, Lincoln Park Zoo, and St. Michael's Church.
• Streeterville: Located between the Magnificent Mile and Lake Michigan, Streeterville is a good option for travellers on a budget. Its major attraction is Navy Pier, a vibrant entertainment hub with parks, shops, games, rides, and restaurants.
• West Loop: The West Loop is ideal for foodies, with culinary streets like Greektown and Little Italy, a flourishing gallery scene, elite restaurants, and museums.
• Wicker Park: Wicker Park is the city's hipster haven, with upscale taco stands and doughnut shops, innovative restaurants, local boutiques, and famous live music venues.
• South Loop: The South Loop is perfect for families, offering plenty of sightseeing opportunities while maintaining a residential vibe. It's home to attractions like the Field Museum of Natural History, Shedd Aquarium, and Buckingham Fountain.
• Boystown/Lakeview: Lakeview is a good option for return visitors who want to explore beyond downtown Chicago. It's pedestrian-friendly and home to attractions like the Music Box Theatre and the Mercury Theatre.
• Oak Park: Oak Park is a charming village close to downtown Chicago, known as the birthplace of Ernest Hemingway and Frank Lloyd Wright. It's ideal for a romantic getaway, with quaint restaurants and a small-town feel.

When choosing accommodation in Chicago, it's recommended to book well in advance to secure your preferred options, especially if you're visiting during peak seasons or popular events.

What to see

Chicago is a city with a lot to offer, from museums and architecture to sports and comedy. Here are some must-see attractions and experiences to add to your itinerary:

Millennium Park Campus

Visit one of the city's most famous public artworks, Cloud Gate, also known as "The Bean". Splash around in Crown Fountain, a shallow pool with two 50-foot towers where the faces of Chicago locals spout water. In the summer, you can dine on the outdoor patio or go ice skating on the plaza in the winter. Hear free live music, attend summer festivals, and watch films under the stars at the Jay Pritzker Pavilion. Wander through Lurie Garden and meet birds, bees, and butterflies. Don't miss the Art Institute of Chicago, ranked as one of the top museums in the world.

Navy Pier

This family-friendly attraction offers scenic boat rides, summer fireworks displays, food, the largest rooftop bar in the county, free outdoor music, indoor gardens, carnival rides, and more. The Centennial Wheel, inspired by the world's first Ferris wheel, offers a unique view of the city.

Chicago Riverwalk

The Chicago Riverwalk is a great place to sip wine on a riverside patio or go island-style under a canopy of light-strewn trees. You can kayak through the skyscraper canyon, take an architectural boat tour, or party on a tiki boat. Visit a working bridgehouse and see the largest video-projected artwork in the world at Art on theMART.

Museum Campus

Set in lush parks and gardens on the shores of Lake Michigan, the Field Museum, Shedd Aquarium, and Adler Planetarium (the oldest in the Western Hemisphere) form a beautiful trio of attractions. Getting there by Shoreline Sightseeing Water Taxi from Navy Pier or Willis Tower is a great option on a summer day.

Observation Decks

For a bird's-eye view of the city, check out the Skydeck at Willis Tower (formerly Sears Tower) or TILT at 360 CHICAGO, where you can step out onto a glass box or tip out over The Magnificent Mile for breathtaking views.

Boat Cruises

Chicago offers a variety of boat cruises to suit your interests. Learn about the city's history, admire the architecture, watch fireworks over the lake, or simply enjoy the sights.

Theatre

Chicago is known for its vibrant theatre scene, including Broadway shows, improv at The Second City, and over 200 storefront theatres. Plan your trip during Chicago Theatre Week in February for discounted tickets.

Food and Drink

Taste classic Chicago foods like deep-dish pizza, Italian beef sandwiches, and Chicago-style hot dogs (hold the ketchup!). Experience award-winning fine dining at Michelin-starred restaurants or sample the city's craft breweries and distilleries. Plan your trip around food and drink festivals like Chicago Restaurant Week, the James Beard Awards, Taste of Chicago, or Chicago Gourmet.

Frequently asked questions