A Chicago trip can be exciting, but when you have a big family, it requires some planning to ensure everyone has a fantastic time. From exploring iconic landmarks to indulging in the city’s culinary delights, Chicago offers a number of experiences suitable for all ages. 

However, navigating the Windy City with a large group requires thoughtful preparation to make the most of your time while minimizing stress. In this guide, we’ll provide you with essential tips and tricks to help you plan the perfect Chicago trip for your big family.

Renting a Sprinter Van for Convenience

Opting for a Sprinter van rental in Chicago is an excellent option for families traveling together. These spacious vehicles offer ample seating for passengers and plenty of cargo space for luggage and strollers. 

According to NerdWallet, you can expect to pay around $671 to rent a Sprinter van in Chicago on a weekly basis. 

Eminent Limo notes that with features like air conditioning, entertainment systems, and comfortable seating, Sprinter vans ensure a convenient travel experience for everyone. Additionally, having a dedicated mode of transportation allows you to explore the city’s diverse neighborhoods and attractions at your own pace.

Accommodation Options for Large Families

Finding suitable accommodation for a big family in Chicago is crucial for a comfortable and enjoyable trip. Think about booking accommodations that are suitable for families, such as suites or large rooms with extra mattresses and kitchenettes.

For bigger parties, vacation rentals like homes or apartments provide more privacy and space. When compared to many hotel rooms, this is frequently less expensive. Seek lodging close to key sites or public transit to cut down on travel time and optimize sightseeing possibilities.

Statista notes that in the United States, the vacation rental market is seeing a shift toward urban rentals in major cities. 

Additionally, eco-friendly and sustainable vacation rentals are gaining popularity, aligning with the growing interest in responsible tourism. This trend reflects a broader evolution in the market, providing travelers with diverse options for enhancing their urban getaways while minimizing environmental impact.

Creating a Flexible Itinerary

When planning your Chicago itinerary for a big family, flexibility is key to accommodating everyone’s interests and energy levels. Make a list of the must-see sights and things to do, but also include time for leisure and spontaneity.

To adjust to shifting weather or personal tastes, think about switching between indoor and outdoor events on a regular basis. Be sure to factor in breaks and downtime to prevent fatigue and ensure a more enjoyable experience for everyone in the family.

Dining Out as a Large Group

Dining out with a big family in Chicago can be a fun and memorable experience. Look for restaurants that offer family-style dining or have private dining rooms available for larger groups. According to Time Out, Crosby’s Kitchen, Community Tavern, and Ed Debevic’s are some of the finest spots for families to enjoy a meal together.

Make reservations in advance, especially for popular dining spots or during peak hours, to avoid long wait times. Explore diverse culinary options across the city, from deep-dish pizza joints to international cuisines, to cater to everyone’s tastes and preferences.

Embracing Group Activities and Experiences

Participating in group activities and experiences is a great way to bond and create lasting memories with your family in Chicago. Consider visiting family-friendly attractions like the Shedd Aquarium, where you can explore aquatic exhibits and interactive touch tanks together. 

Embark on a guided river cruise or architectural tour to discover Chicago’s iconic skyline and landmarks from a unique perspective. Don’t forget to check out special events and festivals happening during your visit, offering entertainment and cultural experiences for visitors of all ages.


What part of Chicago is best for families? 

The Lakeview neighborhood in Chicago is often considered one of the best areas for families. With family-friendly attractions like Lincoln Park Zoo and an abundance of parks and playgrounds, it offers a safe and vibrant community environment for children.

How many people can a Sprinter van hold? 

A Sprinter van typically can hold anywhere from 10 to 14 passengers, depending on the specific model and configuration. These vans are spacious and versatile, making them ideal for accommodating large families or groups traveling together comfortably and conveniently.

What is Chicago best known for?

Chicago’s deep-dish pizza, colorful cultural scene, and breathtaking skyline are its most well-known attractions. The city provides a wide range of attractions, from world-class museums and theaters to famous structures like the Willis Tower and Millennium Park.

In conclusion, crafting a memorable Chicago trip for a large family necessitates thoughtful planning and consideration of diverse needs and preferences. From securing spacious accommodations to flexible itinerary planning and embracing group activities, there are myriad ways to ensure a seamless and enjoyable experience. 

By prioritizing comfort, convenience, and shared adventures, families can forge lasting bonds and create cherished memories amidst the backdrop of Chicago’s iconic skyline. With its rich culinary scene and a plethora of family-friendly attractions, the Windy City beckons families to embark on an unforgettable journey of exploration

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