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Chicago Travel Guide

Learn all about the city at your fingertips.
Last Updated
February 17, 2024
Editorial Staff
Cloud Gate, Millennium Park in Chicago, USA
Canva Photos

Chicago. The Windy City. Chi-Town. Second City. Whatever you want to call it, this place rocks. Sure, you’ve heard about the deep-dish pizza that puts you into a food coma, buildings taller than Godzilla, and a lake that looks more like an ocean. But ol’ Chi-Town offers way more than just tourist traps stuffed with screaming kids and selfie sticks.

Want to chomp on Polish sausages? They got ‘em. How about admiring freaky public art while getting drenched in a pop-up rainstorm? Been there, done that. If exploring hidden speakeasies breathing new life into century-old buildings sounds fun, grab a map and comfy shoes because every neighborhood offers an adventure with the best pizza, tacos, bánh mì sandwiches, or whatever your tummy desires.

Yeah, it gets cold here. And windy. Like wind that makes you waddle like a crabby penguin down the sidewalk. But bundles of cozy culture, food, music, and Midwestern warmth await you once you dig deeper. This city rewards intrepid souls yearning to understand what shaped Chicago into the beast it is today.

From Greektown to Little Italy, Pilsen to Chinatown, the Windy City blows hot and cold. But cuddle up with some deep-dish pizza or Italian beef and you’ll warm right up to Chicago’s scrappy yet infectious spirit. Just don’t get blown into Lake Michigan, unless your sea legs can handle these hearty waves! Adventure is on the horizon, my friends. Chi-Town awaits…


About Chicago

Chicago Skyline at Dawn
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If you are planning a vacation to Chicago, it is important to learn a little about the city. Chicago is a big city with a lot to do. It is cosmopolitan and full of diverse ethnicities. The weather can vary a lot from one part of the city to the next. You should dress in layers and wear comfortable shoes. Also, you should bring a water bottle if you plan to spend any time outside.

Chicago is home to 2.7 million people, making it the third-largest city in the U.S. It is also the largest city in the midwest. The city is lined with urban beaches on Lake Michigan and is known for being the birthplace of the modern skyscraper. However, this modern city suffered a devastating fire in 1871 that destroyed much of the city center.

To get the most out of your trip to Chicago, plan a three to four-day vacation. While you will never be able to see everything, you will have the opportunity to experience all the major sights. You should also make sure to leave plenty of time to enjoy the food and culture, as well as to get off the beaten path.


Best Time to Go

Clock tower in Chicago
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The Best Time to go to Chicago is during the cooler fall months, when the weather is pleasant and the crowds are low. Daytime highs are in the low 60s°F, and the humidity is down from the summer. Nighttime temperatures are typically cool, with temperatures dipping into the 40s. This is also the shoulder season, which means lower hotel prices.

If you want to see the sights and avoid the high prices of summer and winter, then the shoulder seasons are the best time to visit. Between April and May, you can find the most affordable hotel rooms. The weather is not as crowded during this time, so you can fill your itinerary with activities that don’t involve a lot of walking. In addition, the temperature is mild, which makes the city great for outdoor activities.

Summer is the busiest time to visit Chicago, but it can also be expensive and offer long waits at restaurants. Summer is also the time when free Navy Pier fireworks are celebrated. But summer can be expensive, so booking your hotel in advance is a great idea.


Things to Know

Chicago Urban Skyscrapers USA
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Before visiting Chicago, you should take some time to learn about the city. The city is a fun, vibrant place to visit and has plenty to offer visitors. While it is not quite as fast-paced as New York, there is a lot to see and do. Here are a few tips to help you make the most of your trip. Also, be aware of the major holidays and citywide events. The city center can get crowded during major events, such as Lollapalooza and the Chicago Blues Festival.

First, dress accordingly. Since Chicago has four distinct seasons, its weather is often unpredictable. Therefore, you should pack layers and winter gear such as down coats, tights, and boots. Also, keep in mind that people in Chicago tend to dress casually. Fortunately, the majority of the city is well-lit and is generally safe.

To get around the city, you can take the CTA or Metra train systems. Chicago is a city of many cultures, and you can visit neighborhoods that reflect that diversity. For example, Pilsen is a great place for tacos, Bronzeville is a cultural destination, and Hyde Park was home to President Obama. The winters in Chicago can be very cold, but the spring and fall are pleasant and temperate. During the summer, it can be humid and hot, but you can still enjoy the outdoors.


How to Get Around

Map of Chicago
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When you visit Chicago, you’ll want to get a sense of how to get around. Since most of the city’s major attractions are located within walking distance, walking is the most convenient way to get around. However, it is important to remember that 8 blocks equal 1 mile, and navigating the city can be challenging. The public transit system is excellent, but parking downtown can be extremely expensive, and traffic is particularly heavy.

There are dozens of ways to get around the Windy City, and one of the best is to use public transportation. The city offers multiple transportation options, from buses to trains to bicycles to boats. The base fare for an “L” train is $2.50, which makes it the most economical option for getting around.

If you are unfamiliar with the city, you should plan your route in advance and stick to well-lit streets. By doing this, the chances of being a victim of a crime are reduced. It is also important to avoid unnecessary contact with strangers and stay in a safe neighborhood.


Best Restaurants

Restaurant view of Gibsons Bar & Steakhouse
Gibsons Bar & Steakhouse

When it comes to choosing the best restaurants in Chicago, there are many factors to consider. While the food is always important, the experience and atmosphere are also important. These factors will vary depending on the type of dining establishment, so be sure to check out the list of restaurants in Chicago before you make your reservations. There are many great options in the Windy City, from high-end establishments to casual hangouts and walk-up windows. Every city has its classics, and there are also some newer places that have earned a lot of positive reviews.

Chicago is home to some of the best steakhouses in the country, so you can expect a great dining experience at one of these restaurants. Chicago’s steakhouses are the result of traditional recipes combined with innovative modern methods. The city is known for its diverse cuisine, but it’s also known for its burger culture. Butcher & the Burger has a reputation as one of the best burger bars in the country, and you can customize your order with a wide range of options. Choose from a classic beef or bison burger, or go for something special like the double patty. This establishment also features a fully-operational butcher shop.

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Things to Do

Downtown Chicago along the Chicago River
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If you are planning a vacation to Chicago, there are a number of things you should do. The city is known for its sports, and you can cheer on the Cubs until your throat is sore and slam your hot dog in a cold beer. There are also many top Chicago hotels to choose from in the Loop and River North neighborhoods. Other popular neighborhoods include Wicker Park, Streeterville, Lincoln Park, and the West Loop.

One of the most popular attractions is Navy Pier. There, you can see the Adler Planetarium, which stands 69 feet tall and is filled with space shuttles and exhibits. Its dome is made of dark granite and features an immersive experience. Another must-see attraction is the Willis Tower, which is 1,729 feet high.

Chicago is a city that is bursting with things to do, from fun to educational. For those who are interested in art and history, there are many museums and cultural attractions that will enrich their visits to the Windy City. If you are a foodie, you’ll love the many restaurants and bars in the area.


Neighborhoods to Know

Chicago rowhouse neighborhood
Adobe Stock

While there are several great neighborhoods to visit in Chicago, a few stand out above the rest. If you’re looking for a cool, cosmopolitan neighborhood, try Wicker Park. This eclectic neighborhood is home to several thrift stores, art galleries, and restaurants. It’s also home to the annual Around the Coyote Fall Arts Festival, which is held in September.

Union Market is a vibrant food market attended by local chefs and foodies. The market is also home to a wide variety of ready-to-eat foods, from bagels to arancini. The Logan Square neighborhood is home to vintage arcades and pinball machines, as well as bars that serve boozy milkshakes.

While many visitors to Chicago visit the tourist-driven areas, there are other areas to visit. Some neighborhoods have a deep history, such as Pilsen, which is home to authentic taquerias. The Swedish neighborhood also has a lively street fair, Midsommarfest.



Chicago Skyline
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Chicago’s weather can be unpredictable, but the city still enjoys mild days in November and December. While winter has not yet fully arrived, the city’s holiday crowds are starting to pick up in late November and December. The city hosts the annual Thanksgiving Day holiday, and the Magnificent Mile Lights Festival kicks off the holiday season.

The weather in Chicago varies throughout the year, but the shoulder seasons are the best times to visit. Typically, Chicago’s weather is more pleasant between April and May. The summer months see heavy rainfall, but July and August are perfect for outdoor activities. The autumn season is another great time to visit Chicago, with cool temperatures in the 40s and 50s F.

The summer tourist season in Chicago starts in June. June’s temperatures are warm, averaging about 70°F during the day. However, the humidity and heat are not as severe as they are during the peak summer months.







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