Chicago Travel Guide

The wonderful city of Chicago goes by many names such as “The Windy City,” “The Second City,” “Chi-town,” and many others. But regardless of what you call the city, it’s a great place to reside. In addition, it remains one of the top tourist destinations in the United States.

A beautiful warm summer, serene parks, incredible architecture, breathtaking museums, and unforgettable cuisines are some of the reasons why Chicago is a world-class destination. There are just so many things to see, places to go, and things to do that you are unlikely to see all of Chicago in a single visit. 

You can begin by exploring Grant and Millennium Park, Tribune Tower, Willis Towers, world-class restaurants, and engaging in other fun activities. No matter what you’re into, Chicago has just the thing for you. It is a wide and versatile city, and with this travel guide, you will be able to plan a trip of a lifetime.

Best Places To Stay In Chicago

Are you in Chicago looking for a place to stay with your friends or family? Thankfully, there are several excellent options for accommodation around the city. However, some of the most important criteria you need to consider before selecting an accommodation include:


Chicago is a big city—getting around could take some time. The best thing to do before making a reservation is to ensure you’re picking a place that isn’t far from all the sites you want to see and activities you want to engage in. That way, you don’t have to worry about rushing from one end of the city to the other.


Chicago is quite expensive. However, the good thing is that you get the value for your money. This means that if you go to an expensive hotel, you’ll get a spacious room with modern facilities and great service. However, if you’re on a budget, there are still great places you can consider.

Cloud Gate – A famous sight for tourists in Chicago


These days, there’s hardly any hotel, hostel, Airbnb, or other kinds of accommodation that don’t offer basic modern amenities such as free Wi-Fi, a gym, a swimming pool, free breakfast, and more. First, however, you need to confirm that the place you’re considering meets your requirements, so you don’t start your holiday off with complaints.

Some of the best places to stay while visiting Chicago include:

The Loop

The Loop is nicknamed after the Chicago Union Elevated Railway, which forms a loop around the city area. It is the main section of downtown Chicago. The area attracts thousands of visitors annually thanks to its breathtaking museums, art, and beautiful park areas.

The iconic Willis Tower (formerly known as Sears Tower) stands majestic in the Downtown skyline. The loop also welcomes its guests with great shops, top-rated restaurants, and architectural wonders all around.

Grant Park is one of the Loop’s main attractions because the Art Institute of Chicago is located within the area. The town also attracts a lot of visitors globally attending Lollapalooza and The Taste of Chicago. 

The Loop has a plethora of hotels you can book a reservation with, depending on your preferences. However, the accommodation price may increase during peak tourist season. Nonetheless, there are usually special discounts and event prices that you could check out online.

Lincoln Park

Lincoln Park is the largest park in Chicago, located on the North Lakeside. It is one of the wealthiest neighborhoods, with beautiful homes and dazzling shops. This area is perfect for beach lovers in the warmer seasons, and nature lovers can explore the Lincoln Park Conservatory.

If you’re traveling with young children, the Lincoln Park zoo is a fun place to visit. Also, you can visit the Chicago History Museum to see the huge climbable Chicago-style hot dog.

Lincoln Park has a rich theatre history you can also explore. For example, it is home to the Steppenwolf Theater Company and the Theatre on the Lake. Both of which are known for unforgettable shows and events.

You can easily find an available Airbnb, a hostel, or some of the finest hotels in Chicago within this area. However, if you’re more interested in getting the homely vibe while on your trip, a hostel will be ideal for you. One of the best in Lincoln Park is the Chicago Getaway Hostel.

Magnificent Mile

The Magnificent Mile stays true to its name in every way. The area boasts of more than a century of Chicago’s history in its architecture and scenery. Here, you’ll find Gilded Age hotels, luxurious mansions, and more.

Walking around the city area, you’ll feel like a speck surrounded by imposing landmarks like the Chicago Water Tower, John Hancock Center, Wrigley Building skyscraper, and Tribune Tower.

If you’re looking for a culturally rich experience, you can visit Richard H. Driehaus Museum. It is a 19th century-themed mansion that houses unique works of art, including Gilded Era art, fashion, and design collections, and the largest Louis Comfort Tiffany collection. In addition, the ballroom on the third floor hosts a regular series of lectures, cocktail series, and cultural soirees.

You can also find the Newberry Library in the Magnificent Mile. It contains letters from some world-renowned authors in excellent condition, first edition classics, historical maps. The great thing is that all of these are available for public viewing.

As expected, accommodation is quite expensive along the Magnificent Mile, but if you can afford it, you’ll get a premium, luxurious experience throughout your stay. The Blackstone Hotel is one of the most popular lodgings in the area, where several politicians, including U.S presidents and the infamous Al Capone.

Old Town

Old Town dates back to 1850, when the first German immigrants settled in the area. The prestigious Victorian architecture makes the town look like it’s frozen in time. People do not crowd the streets even though there’s frequent activity in the area.

If you decide to stay in Old Town, you’ll be within the proximity of the legendary Second City Theater, where comedy stars such as Tina Fey, Stephen Colbert, and John Belushi have performed to sold-out crowds.

For a more upbeat vibe, you can visit the Old Town Pour House nearby to enjoy a variety of beers or explore shops and eateries to keep your taste buds satisfied.

Most of the hotels in Old Town are top standard and are inexpensive. However, you’ll likely need to place a reservation before making your trip to avoid being stranded. Some of the best places to stay in Old Town are Hotel Lincoln and the Sono Chicago.

Best Time To Visit Chicago

For many people visiting Chicago, part of the main attraction is the incredible weather. Spring and fall are perfect times to make the trip. Apart from the comfortable temperatures, the crowd in Chicago thins out during these seasons.

The average daily temperature in fall ranges between 15-21°C (60-70°F). The weather is nice, but you will need to pack a sweater or thick clothes. Only a few tourists visit attractions during this period, and accommodation fees are also lower than they usually are.

However, when summer arrives, tourists return to Chicago. The temperatures are warmer, a little bit above 20°C (mid 80°F). Tourists take advantage of the hot days to explore the city. As a result, there will be more crowds at tourist attractions. Also, the rates for accommodation increase during summer, and there are usually only a few vacancies available.

So, when it comes to the best time to visit Chicago, a lot depends on what you prefer. If you don’t mind extremely cold days and sharp winds, you can spend the winter months in Chicago. It’s a great time to visit museums and art galleries and indulge in some indoor sightseeing. Also, accommodation prices are lower during winter because the tourist crowd in Chicago dwindles.

Top Things to See and Do in Chicago

Chicago is a city bursting with so much energy that you may not have enough time to explore a huge part of the city within one visit. However, here are a couple of things that we suggest you consider while in Chicago:

A Day Out in Grant and Millennium Park

Downtown Chicago has large fun parks. They are excellent for hanging out outdoors in the sun, picnics, or relaxing scenic runs. It is a great place to meet locals or other tourists because it is a popular destination in Chicago. People work out in the park, play chess, and enjoy other fun outdoor activities when the weather is warm. Also, there are usually a lot of free arts and music concerts during the summer.

This is also the location of the world-famous “Chicago Bean” sculpture by Anish Kapoor. The Bean, aka Cloud Gate, is a public work of art unveiled in 2004 which quickly became one of Chicago’s most iconic landmarks. Liquid memory inspired the monument’s design. The body of the sculpture reflects the area surrounding it and people strolling through the park.

The Bean is also one of the largest permanent outdoor installations in the world. If there’s one thing you need to see in Chicago, this breathtaking sculpture is it. It would be a perfect backdrop for selfies or pictures with your family and friends.

See the Tribune Tower

Tribune Tower is a Neo-Gothic skyscraper that has earned a spot in Chicago’s skyline since its completion in 1925. The 36-story skyscraper is an architectural masterpiece. The Chicago Tribune, Tribune Media, and Tribune Publishing have had offices in the building.

Navy Pier

The Navy Pier is Chicago’s dazzling waterfront entertainment zone, complete with a Ferris wheel, thrilling rides, boat tours, beer gardens, mini-golf, a Shakespeare theater, shops, restaurants, and other lively attractions. Navy Pier makes you feel like you’re in a carnival as large as a city.

This location is perfect for some lighthearted fun, especially if you’re visiting Chicago with kids. The bright lights and sounds set the tone for a memorable time out exploring all that Chicago offers.

See the Willis Tower

The Willis Tower is another building in Chicago that has a deep history. It was once known as the Sears Tower, and it was the tallest building in the world for 25 years. Standing tall at 110 stories, it is currently the third-tallest building in the US and the 23rd tallest globally.

For a fee, visitors can experience panoramic views of Chicago from the SkyDeck. The SkyDeck’s Ledge is a glass box that extends 4.3 feet above the city.

Experience St. Patrick’s Day

St. Patrick’s day originated from Ireland, but through the years, Chicago has become one of the best places to be on March 17th. The city focuses on the celebration in honor of Irish-Americans. For example, the city’s river is dyed green, and people organize large colorful parades. Also, they usually organize lively parties in different locations of the city to mark the event.

Suggested Budget

If you’re planning a holiday in Chicago, one of the most important things to do is to ensure that your finances are in a great state. This is why working around a budget is a great idea.

In terms of accommodation, prices increase during the peak seasons. For example, a regular bed in a 4-6-bed dorm may cost up to $50, while standard hotels start at over $100 per night. However, during the off-season, you can find hostel spaces that cost about $28, while the cost of a hotel room can drop to around $80. These options include basic amenities like free Wi-Fi, AC, TV, and a coffee maker.

Food is not expensive in Chicago, but it depends on where you eat. Dinner at a high-class restaurant can cost you up to $50 or more for a single meal. However, you should stick to an inexpensive, casual restaurant if you want to save costs while visiting Chicago. However, if you have the time, you can cook for yourself, friends and family.

How To Stay Safe While Visiting Chicago

Although Chicago has a bad reputation for crime and violence, It is still a safe place for tourists to visit. Reports indicate that violent crimes are usually isolated events common in areas with high rates of drug and gang activities. As a tourist, some of the best places include the Loop, Wicker Park, Bucktown, and Old Town.

Avoid isolated, dark parts of the city because criminals usually lurk around waiting for their next unsuspecting victim.

However, petty crime like theft is more frequent around popular tourist landmarks, so you need to keep an eye out when touring such locations. Be mindful of your belongings wherever you go, especially while in public buses or trains. At particular attractions such as the Field Museum, several con artists go around claiming that they can provide cheaper tours. Avoid people who randomly walk up to tourists with “special offers” because it’s all a ruse to steal from you.

Always remember that you can dial 911 for assistance in case of emergencies.

Another important way to protect yourself is to take out an excellent travel insurance plan. This protects you from illnesses, injuries, theft, and cancellations.


Chicago is a charming cultural and art-rich city with so much to offer to every kind of guest visiting. From magnificent architecture, shops, five-star restaurants to lush green parks, you can fill your days in Chicago with so much wonder. If you plan on visiting soon, we hope this travel guide has been helpful to you.