Chicago All inclusive Vacations 2025

Explore Chicago's best with our unbeatable all-inclusive vacation deals

Chicago and its surrounding area offer a unique blend of urban charm, architectural wonders, and cultural attractions. The city's iconic skyscrapers, world-class theaters, and stunning art museums make it a must-visit destination for any traveler. With its scenic lakefront and picturesque parks, visitors can enjoy breathtaking views and outdoor activities. The vibrant shopping scene and diverse culinary options add to the city's allure. Whether exploring the historic Navy Pier, admiring the iconic Cloud Gate sculpture, or immersing in the city's lively entertainment scene, Chicago has something for everyone.

Architectural Wonders: Chicago boasts iconic skyscrapers and stunning architecture that are a must-see for any visitor.
Cultural Attractions: The city offers world-class theaters, captivating art museums, and diverse culinary options, making it a cultural hub.
Breathtaking Views: Chicago's scenic lakefront and picturesque parks provide visitors with breathtaking views and outdoor activities.
Endless Shopping: The vibrant shopping scene in Chicago offers endless opportunities for retail therapy.
Vibrant Entertainment Scene: Whether it's exploring Navy Pier, admiring the Cloud Gate sculpture, or immersing in the lively entertainment scene, Chicago has something for everyone.

A travel package combines flights with hotels or car rental, making it convenient to book all your travel needs in one place. It not only saves you time and effort but also offers the opportunity to save money. With various options available, you can customize your package to suit your preferences and budget. Expedia's price and theme filters ensure finding the perfect deal for you.

Booking an all-inclusive package for your vacation in Chicago is the perfect idea because it allows you to experience the city's urban charm, skyscrapers, theaters, architecture, museums, art, monuments, entertainment, scenery, and shopping without worrying about the details. Enjoy everything Chicago has to offer while saving money and having a stress-free vacation.

Take advantage of Expedia's OneKey program to save money on your all-inclusive vacation to Chicago. Collect points and redeem them for discounts on local transport, activities, and sightseeing.
Consider booking your flights and accommodation together to get a better deal. Expedia offers combined packages that can save you money.
Use public transportation, such as the Chicago Transit Authority (CTA), to get around the city. Purchase a Ventra card for unlimited rides on buses and trains at a discounted price.
Save on sightseeing by taking advantage of free attractions in Chicago, such as Millennium Park, Navy Pier, and the Lincoln Park Zoo.
Consider exploring the neighborhoods of Chicago, like Wicker Park or Logan Square, where you can find affordable dining options and unique experiences.
Check for special offers or discounts on Expedia for hotels, restaurants, and tours in the vicinity of Chicago.

Chicago is a vibrant city with diverse neighborhoods that offer something for everyone. Downtown, known as The Loop, is the heart of the city and home to iconic skyscrapers, theaters, and museums. The Magnificent Mile is a shopper's paradise, while Lincoln Park offers beautiful scenery and the Lincoln Park Zoo. Wicker Park and Logan Square are trendy areas with great entertainment and dining options.

Downtown Chicago: Experience the iconic skyscrapers, vibrant urban atmosphere, and world-class architecture. Immerse yourself in the rich cultural scene with museums, theaters, and art galleries. Enjoy scenic views of the river and explore famous monuments. This area is a must-visit for its entertainment and stunning scenery.
The Loop: Discover the urban charm and architectural wonders of The Loop. Explore top-notch museums, admire impressive skyscrapers, and catch a show at one of the renowned theaters. Indulge in shopping and dining experiences while surrounded by iconic monuments. The Loop offers a captivating blend of culture and entertainment.
Near North Side: Embrace the majestic skyscrapers and urban beauty of Near North Side. Marvel at the architectural gems, enjoy scenic views of the river, and immerse yourself in museums and art galleries. Experience the vibrant shopping scene and indulge in lakefront dining. Near North Side offers a perfect mix of culture and relaxation.

Chicago (and vicinity) offers an all-inclusive vacation experience with its urban atmosphere, towering skyscrapers, vibrant theater scene, stunning architecture, world-class museums, captivating art galleries, iconic monuments, exciting entertainment options, breathtaking scenery, and endless shopping opportunities. Whether you're exploring Millennium Park, admiring the views from Willis Tower, or indulging in deep-dish pizza, Chicago offers a diverse range of experiences for every tourist.

Wrigley Field: Experience the excitement of a live sports event at Wrigley Field. This iconic stadium is a must-visit for sports enthusiasts, offering a unique blend of urban charm and thrilling entertainment. Marvel at the towering skyscrapers surrounding the stadium, soak in the stunning lake views, and appreciate the architectural beauty of the venue. Immerse yourself in the vibrant atmosphere and witness the passion of friendly fans. Whether it's a baseball game or an opera performance, Wrigley Field guarantees an unforgettable experience.
Navy Pier: Discover the best of Chicago's urban landscape at Navy Pier. This bustling jetty offers a variety of attractions, from awe-inspiring skyscrapers to stunning architecture. Take a leisurely stroll along the pier, enjoy theatrical performances, and admire the scenic views of the lake. Dive into the world of art and culture at the nearby museums or simply relax and soak up the friendly atmosphere. With its vibrant energy and picturesque river backdrop, Navy Pier is a must-see destination for tourists.
McCormick Place: Immerse yourself in the vibrant atmosphere of McCormick Place, a premier event and conference venue in Chicago. Marvel at the towering skyscrapers and admire the stunning architectural design. Take in the scenic views of the lake and explore the nearby museums. Engage with friendly locals and learn about the city's rich history and culture. With its impressive monuments and artistic allure, McCormick Place offers a unique experience for visitors seeking to delve into the urban charm of Chicago.

Chicago boasts a year-around average temperature of 51.3°F, peaking at 75.9°F in July, its warmest month, and dipping to an average low of 24.8°F in January, the coolest. Rainfall averages at 82.8mm annually, with May seeing the heaviest showers and February being the driest month.

Month	Temperature (Fahrenheit)	Rainfall (mm)
January	24.8	52.3
February	28.8	49.3
March	38.8	69.1
April	50.5	92.5
May	61.0	104.9
June	71.1	103.1
July	75.9	101.9
August	74.1	101.3
September	66.4	84.1
October	54.3	82.3
November	41.5	86.9
December	28.9	65.3

Can I book a Chicago vacation with airfare and meals?

On an all-inclusive vacation, your mind and body can wander far from your wallet. Pay one simple price when you bundle your accommodation and airfare, and you avoid all those yucky bills after conversation-starting cocktails or decadent dinners.

How can I find Chicago all-inclusive vacations that are adults only?

All the best all-inclusive, all-adult vacations are a click of a filter or two away. Choose from great grown-up features. Say, a spa for a couple’s massage, a hot tub to soak away the stresses of the day, or a swim-up bar to get the party started.

How much is an all-inclusive trip to Chicago?

Affordable all-inclusive is yours, whatever your budget. Packages start tempting you from just . Prices and availability are subject to change. Additional terms may apply.

How can I book cheap all-inclusive trips to Chicago?

Whenever you book your travel, sorting by price and filtering by budget shows you what’s out there in your price range.

What are the benefits of all-inclusive Chicago vacations with airfare?

Create your dream getaway by bundling your flight and hotel and you get delightful deals and discounts. Add your car rental, too, and you save on all three.

What should I think about when I book an all-inclusive Chicago family vacation package?

With little tummies taken care of, you just need to put smiles on their faces. Easy! Book an all-inclusive vacation with a full-on water park or epic pools—or book your stay near the world’s biggest theme parks and attractions.

Why should I book an all-inclusive honeymoon package in Chicago?

You can start your married life how you mean to go on with an all-inclusive honeymoon package. Eat and drink to your heart’s content, waltz around in happy harmony, and have your fill of delights. Together, you can book up adventure excursions and return to a pool-side cabana for cocktails at sunset.

Can I book an all-inclusive Chicago package with free cancellation and/or flexible dates?

When you’re searching for your all-inclusive getaway, filter your results by payment option to find free cancellation and buy now, pay later options. That way, you can rebook without worry, should your plans change.

Why should I book an all-inclusive Chicago package vacation with Expedia?

Book amazing all-inclusive adventures, all in one place. Choose from a vast inventory of deals, adding every little extra to build your brilliant break in minutes.