The 2 Best Day Trips in Chicago

Chicago is a city full of wonders that never ceases to amaze. Its bustling streets, diverse neighborhoods, stunning architecture and rich history make it one of the most exciting destinations in the world. But what about taking a break from the buzz of the city and exploring the surroundings? Chicago’s surroundings are rich in natural beauty, fascinating history and unique attractions waiting to be discovered. In this post, we’ll take a closer look at some of the best day trips you can take from Chicago that will take your breath away and enrich your travel experience!

The 2 Best Day Trips in Chicago

  1. Private Day Sailing on Lake Michigan
  2. 1 Day Chicago City Tour Chicago Departure Ch1

The 2 Best Day Trips in Chicago

1. Private Day Sailing on Lake Michigan

Looking for a unique and memorable way to spend a day in Chicago? Consider a private day sailing tour on Lake Michigan. You and your invited guests will have exclusive use of a sailboat for the entire tour, complete with a licensed captain and crew. Enjoy stunning views of Chicago’s skyline as you sail on the lake, and feel free to take a turn at the helm if you wish. You can choose from morning, afternoon, or evening departures, and the itinerary is fully customizable to suit your group’s interests. You’re welcome to bring your own food and drinks, but please note that glass containers are not allowed. The tour includes ice and a fridge to keep your beverages cool, as well as Bluetooth speakers so you can enjoy your favorite tunes on the water. The meeting point is located at East Monroe Street & South Lake Shore Drive, and parking is included. All applicable taxes and gratuities are also included, making this an all-inclusive and hassle-free way to enjoy a day out on the water.

2. 1 Day Chicago City Tour Chicago Departure Ch1

Leave all the planning to your guide and discover the best of Chicago in one day on this introductory coach tour. Departing from Chinatown in the morning, you’ll see local landmarks like Millennium Park, Grant Park, Michigan Avenue, and more. Customize your experience by upgrading to visit the Art Institute of Chicago, going for a river cruise, or even visiting the 360 Chicago observation deck. This tour is perfect for first-time Chicago visitors who want to see the highlights of the city in one day. Transportation is provided via a 7-seat SUV, minivan, or motorcoach, depending on the number of guests on the day. Your professional driver and guide (or driver-guide) will ensure you have a seamless experience. Food and beverage are included, but optional admission fees (if applicable) should be purchased from the tour guide. Personal expenses and other expenses not listed in the Cost Includes are not included in the tour price. Customize your schedule and visit the sights that interest you most on this comprehensive City Tour of Chicago.

The Most Frequently Asked Questions About Chicago

Chicago, often called the “Windy City,” is one of the most popular tourist destinations in the United States. With its rich history, stunning architecture, and vibrant culture, Chicago offers visitors an unforgettable experience. However, for those who have never been to Chicago before, planning a trip can be daunting. In this post, we will answer some of the most frequently asked questions about Chicago to help make your trip planning easier.

1. What is the best time to visit Chicago?

Chicago is a year-round destination, but the best time to visit depends on what you are looking for. The summer months (June-August) are the most popular amongst visitors because of the warmer weather and numerous festivals such as the Taste of Chicago and Lollapalooza. However, it can also be crowded and expensive during this time. The winter months (December-February) can be cold and snowy, but the city transforms into a winter wonderland with ice skating rinks, festive holiday lights, and the famous Christkindlmarket.

2. What are the must-visit tourist attractions?

Chicago has some of the most iconic tourist attractions in the United States. Here are some of the must-visit places when in Chicago:

Millennium Park (including “The Bean”)

Millennium Park is a 25-acre park located in the heart of downtown Chicago. Highly recommended is a visit to “The Bean,” otherwise known as the Cloud Gate Sculpture. This massive metallic sculpture reflects both the skyline of the city and visitors, creating a unique photo opportunity.

Art Institute of Chicago

The Art Institute of Chicago is one of the largest and oldest art museums in the country housing more than 300,000 works of art, including iconic pieces such as “American Gothic.” The museum is open every day except for Thanksgiving and Christmas Day.

Chicago Riverwalk

The Chicago Riverwalk is a 1.25-mile walkway along the Chicago River. A stroll along this path will provide astonishing views of the city’s skyline, with opportunities to stop in cafés and bars along the way.

Grant Park & Buckingham Fountain

Grant Park is a large public park that is home to some of the city’s most famous landmarks, including Buckingham Fountain. Built-in 1927, the fountain is one of the largest in the world and features a water show every hour.

3. How do I get around Chicago?

Chicago has a robust public transportation system known as the “L” or elevated train, which is both cheap and efficient. The trains run 24 hours a day, providing access to all of the popular tourist destinations in the city. The city also has an extensive bike-sharing system, Divvy Bikes, which provides affordable bike rentals for visitors.

4. What is Chicago-style pizza?

Chicago-style pizza is a deep-dish pizza that originated in Chicago in the 1940s. The crust is thick, made of cornmeal, and baked in a deep-dish pan with cheese and toppings on the bottom, topped with tomato sauce. Notable restaurants in Chicago for this style of pizza include Lou Malnati’s and Giordano’s.

5. Is Chicago a safe city?

Chicago has a reputation for being a dangerous city, but the reality is that most visits are trouble-free. As with any major city, it is essential to be aware of your surroundings and stay alert at all times. Always lock your doors and windows in your hotel room, and avoid walking alone at night in unfamiliar areas.

How to Spend Your Time as a Tourist in Chicago

If you’re planning a vacation to the Windy City, you’re in for a treat! Chicago is a vibrant city with a rich culture, stunning architecture, and amazing food. To make the most of your time in Chicago, here’s a guide on how to spend your time as a tourist in the city.

Explore the Magnificent Mile

The Magnificent Mile is a shopper’s paradise. It’s located on Michigan Avenue and stretches from the Chicago River to Oak Street. The best time to visit is during the holiday season when the whole street is lit up with festive lights.If you’re looking for high-end shopping, you’ll find stores like Saks Fifth Avenue, Neiman Marcus, and Bloomingdale’s. For more affordable options, check out stores like H&M, Zara, and Topshop.Once you’re done shopping, take a stroll along the Chicago Riverwalk. You’ll get stunning views of the city skyline and can grab a bite to eat at one of the many restaurants along the way.

Visit the Art Institute of Chicago

The Art Institute of Chicago is one of the top art museums in the world. It’s home to over 300,000 works of art, including pieces by Monet, Picasso, and Van Gogh.If you’re short on time, be sure to check out the Thorne Miniature Rooms. These tiny, meticulously detailed rooms are filled with miniature furniture and decorations that will transport you to different eras and cultures.

Take in the Views from the Willis Tower

The Willis Tower, formerly known as the Sears Tower, is the tallest building in Chicago. Head to the top to experience the Skydeck. Here, you’ll get stunning views of the city skyline and can step out onto The Ledge, a glass balcony that juts out from the building.Be prepared for long lines, especially during peak tourist season. To save time, purchase tickets online in advance.

Try Chicago-Style Pizza

When in Chicago, you have to try the city’s famous deep-dish pizza. It’s known for its thick crust, tons of toppings, and hearty sauce.There are many places to try deep-dish pizza in Chicago, but two of the most famous are Lou Malnati’s and Giordano’s. Expect a long wait, but trust us, it’s worth it.

Visit Millennium Park

Millennium Park is a 24-acre park in downtown Chicago. It’s home to several iconic landmarks, including the Cloud Gate sculpture (also known as “The Bean”).Take a stroll through the park and be sure to check out the Crown Fountain, which features faces of Chicagoans spouting water, and the Jay Pritzker Pavilion, an outdoor concert venue that hosts free concerts during the summer.

Take a River Architecture Tour

Chicago is known for its stunning architecture, and one of the best ways to see it is on a river architecture tour. These tours are led by knowledgeable docents who will point out different architectural styles and landmarks along the river.There are several companies that offer river architecture tours, but the Chicago Architecture Foundation is the most well-known. Be sure to book in advance, especially during peak tourist season.

Explore the Historic Neighborhoods

Chicago is made up of several unique neighborhoods, each with its own distinct personality. To get a taste of Chicago’s history and culture, take a stroll through some of the city’s historic neighborhoods.Some of the must-visit neighborhoods include:

  • Lincoln Park: home to the Lincoln Park Zoo and DePaul University
  • The Loop: Chicago’s central business district
  • Wicker Park: known for its hipster vibe and street art
  • Old Town: filled with Victorian-era homes and cobblestone streets

Take a Day Trip to Oak Park

If you have some extra time in Chicago, consider taking a day trip to Oak Park. This historic suburb is just a short train ride away and is home to several landmarks designed by legendary architect Frank Lloyd Wright.Be sure to check out Wright’s home and studio, as well as the Unity Temple, a stunning example of Wright’s Prairie-style architecture.


Chicago is a city that has something for everyone. Shopaholics will love the Magnificent Mile, foodies will enjoy the deep-dish pizza, and culture enthusiasts will appreciate the Art Institute of Chicago. By following this guide, you’re sure to have a memorable and enjoyable trip to the Windy City.

The 2 Best Day Trips in Chicago