Planning a trip to Chicago may be an exciting journey. With countless entertainment, culture, & history, the Windy City is a real treasure of attractions. Chicago is a beautiful blend of opposites, a bustling big city with Midwestern charm, towering skyscrapers surrounded by miles of quiet beaches, & a city in a garden. In simple terms, everyone feels at home in Chicago. You can customize your trip to Chicago to your own desires by choosing appropriate Chicago vacation packages, regardless of whether you’ve been to the city before or not.  

Well, there is a lot of opportunity for customization, from famous sites like Millennium Park to the lively neighborhoods and cultural attractions. We’ll guide you on how to set up a vacation package in this guide that ensures a relaxing and unforgettable trip to Chicago. 

Determine Your Trip Preferences 

Knowing your travel desires is the first step in choosing the ideal vacation package. Think about the kind of experience you want to have first.  

• Guided tours of famous sites & museums are usually included in sightseeing and cultural packages for people who want to learn about Chicago’s rich history and culture.  

• Activities for all ages are included in family-friendly packages, ensuring an exciting time for all.  

• If you want a more lavish experience, luxury and VIP packages offer superb amenities, plus luxurious lodging that will make your vacation one to remember.  

• Romantic honeymoon packages cater to couples who are celebrating a particular event by highlighting exclusive dinners or beautiful views. 

Best Time to Visit Chicago 

Well, because of the pleasant weather plus the abundance of festivals April to May and September to October are the best times to visit Chicago.  

• Chicago experiences its busiest tourist and festival season in the summer when visitors from all over the nation come to enjoy the pleasant weather and plethora of activities.  

• While housing costs will be higher during certain times of the year, you will also be able to avoid Chicago’s notoriously harsh winters.  

• From November through March, Chicago has extremely cold temperatures; but if you are resourceful, you can easily find cheap hotels. 

Chicago Itinerary Planning Around Must-See Attractions 

You’ll find countless attractions that are must-see, entertainment options, plus cultural attractions in Chicago. Customize your itinerary to make it completely memorable: 

1. Explore Downtown Chicago 

Millennium Park 

A journey to Millennium Park is a must for anybody visiting Chicago for the first time. To begin your exploration of the downtown area, Visit Millennium Park, which is home to some of Chicago’s finest landmarks. The 25-acre site acts as a backdrop for festivals and concerts in accumulation to showcasing creative landscaping, architecture, and art. The Crown Fountain and Cloud Gate, also referred to as “The Bean,” are the main attractions for most visitors to Millennium Park.   

Art Institute of Chicago 

The massive Art Institute of Chicago is home to one of the nation’s finest collections of impressionist and post-impressionist art (plus works from many other genres). Its permanent collection includes around 300,000 works from throughout the world. A Sunday on La Grande Jatte by Georges Seurat and American Gothic by Grant Wood are two classic works that you should not ignore.  

Navy Pier 

Navy Pier, one of Chicago’s most visited spots, extends into Lake Michigan and provides plentiful culinary options, entertainment, plus outdoor pursuits. The 196 feet tall Ferris wheel is the first thing you’ll see when you step onto the pier; you’ll also find a carousel & a drop tower. Once the kids have had their fill of exhilarating rides, you may take a sightseeing or speedboat cruise along the Chicago River. 

2. Cultural and Historical Chicago 

The Field Museum 

An essential attraction for children (and any lover of the “Indiana Jones” movies), this big natural history museum takes almost half an acre of Grant Park’s Museum Campus and features exhibits that highlight objects from many eras & locations. The “Inside Ancient Egypt” exhibit is one of the museum’s most visited attractions. But without spending some time with SUE, the Field Museum’s T. rex, who also happens to be the biggest and most complete T. rex ever found, a visit wouldn’t be complete.  

Shedd Aquarium 

With almost 32,000 animals, Shedd Aquarium is one of the biggest indoor aquariums in the world. You can learn about a variety of turtles, see sea lions bark, and feel stingrays float beneath your fingers while you’re here. Plus animals such as penguins, piranhas, sharks, and beluga whales can be found in the Shedd Aquarium’s plethora of habitats.  

Skydeck Chicago at the Willis Tower 

At the peak of the Willis Tower (previously Sears Tower), Skydeck Chicago offers stunning city vistas. The Ledge is the main attraction for the majority of visitors. The entire platform, including the floor, is composed of glass. The visual screens that show what it would be like to be 103 floors above famous Chicago landmarks, such as Millennium Park and Wrigley Field, were also beloved by visitors.  

Chicago Cultural Center 

A hidden gem for people looking for calm as well as a relaxed, art-filled experience is the Chicago Cultural Center. With free entry to this incredible building and continuous art, film and concert events taking place throughout the year it is open to all. Also, remember to check out the stunning Tiffany Dome which is one of its kind in the whole world. 

3. Nature and Adventure in Chicago 

Chicago Riverwalk 

The Chicago Riverwalk is one of the most suitable places to relish the outdoors when the weather in Chicago warms up. The best area to walk and take in the city skyline is the 1.25-mile pedestrian walkway on the south bank of the Chicago River. Also, you can find lots of aquatic pursuits to enjoy, like boat or kayak tours. Visit the public gardens and art exhibits, or stop by a famous restaurant with a view of the Chicago River if you prefer to go on foot. 

Lincoln Park Zoo 

The Lincoln Park Zoo, founded in 1868 and located just two miles north of the Loop within its namesake neighborhood on Chicago’s North Side, is home to about 200 species. And luckily for you, it’s fully free to enter! As such, it houses all manner of creatures like lions, penguins and gorillas, making it a remarkable destination for families. 

Lakefront Trail 

The Lakefront Trail is a beautiful way to get your steps in and sneak views of Lake Michigan. Popular among walkers, joggers, plus bikers, this 18-mile path wraps the shoreline. The entire way, you can take advantage of the beaches, harbors and parks to visit; however, if you choose not to stop by any locations a simple lake view with a city skyline is mesmerizing. In summer you can chill out by the water at one of Chicago’s beaches like North Avenue Beach or Oak Street Beach. 

Chicago Botanic Garden 

A little further out from downtown, the Chicago Botanic Garden is a huge garden with more than 27 display gardens. To get away from the city for a few hours it is an amazing location for nature lovers. More than 2.8 million plants from around the globe that grow in the Chicago region and are suited to the climate and soils of the Midwest can be found in the Garden’s living collections within its gates.  

Add Unique Experiences to Your Package 

Add other experiences to your package to make your trip to Chicago genuinely unforgettable. Some tips to make the trip more enjoyable: 

• Helicopter Tour: Try to reserve a helicopter tour that provides top views of Lake Michigan plus the Chicago skyline for a unique experience. 

• Architectural River Cruise: Accepting an architectural boat trip down the Chicago River is one of the most incredible ways to discover the city’s famous architecture. 

• Chicago Theater Performance: The theater culture in Chicago is thriving. Chicago has a vibrant theatre scene. Consider including tickets to a Broadway musical or improv comedy night at The Second City in your Chicago package deals. 

Conclusion 

Your Chicago vacation package can be customized to fit your interests, travel preferences, & budget range. Chicago is perfect for the culture, adventure seekers and if you just want to relax.  

Q1 How much does a Chicago holiday package cost?

Starting from an affordable price, you can customize Chicago trips to fit your preferences exactly the way you want. 

Q2 What are the top hotels in Chicago?

Top hotels in Chicago vary based on preferences, offering luxury, trendy atmospheres, or historic charm to suit different tastes. 

Q3 Where should I stay in Chicago?

Among the best places to stay in Chicago is in Central Chicago. The Willis Tower and Millennium Park are both nearby, so you won’t have to worry about running out of exciting things to do here.  

Q4 Can I customize the Chicago holiday packages?

Yes, you can customize the Chicago vacation packages by choosing your sightseeing options, activities, hotels and attractions.