American Holidays to Chicago

Chicago is a melting pot of culture, cuisine, music, and modern innovation, offering something for every traveller. From soaring skyscrapers to tranquil lakefront trails, Chicago embodies the best of urban sophistication and natural charm. With Cassidy Travel, your trip is crafted with care and attention, tailored to your style and budget.

A Perfect Holiday Destination

Chicago combines all the elements of a dream getaway – awe-inspiring landmarks, interactive museums, high-end shopping, delicious food, and welcoming locals. Whether you're travelling solo, as a couple, or with family, there's no better place for a complete USA holiday experience.

Must-Visit Attractions in Chicago

Architectural Marvels

Chicago’s skyline is one of the most recognisable in the world. You can't miss:

• Willis Tower Skydeck – Enjoy jaw-dropping views from 1,353 feet above the city.
• Chicago River Architecture Tour – Cruise along the river to learn the stories behind the city’s famous structures like the Tribune Tower and Wrigley Building.
• The Magnificent Mile – A paradise for shoppers and architecture lovers alike.

Cultural and Historical Highlights

• Art Institute of Chicago – Admire world-famous works from Monet, Van Gogh, and more.
• Millennium Park – Take a selfie with Cloud Gate (aka “The Bean”) and enjoy open-air concerts.
• Museum Campus – A trifecta of learning: Field Museum, Shedd Aquarium, and Adler Planetarium.

Shopping in Chicago

From designer labels to unique local finds, Chicago is a shopper’s haven.

• Magnificent Mile – High-end retailers, flagship stores, and boutique brands await you here.
• State Street – Home to iconic department stores and historic shopping experiences.
• Chicago Premium Outlets – For those looking for luxury brands at discounted prices.

Dining and Entertainment

Culinary Experiences

Food lovers, prepare your taste buds!

• Deep-Dish Pizza – A must-try Chicago staple with a buttery crust and cheesy, saucy centre.
• Chicago-Style Hot Dog – No ketchup, all flavour – loaded with local toppings.
• Michelin-Star Dining – Chicago boasts a growing number of award-winning restaurants and international cuisine.

Nightlife & Music

The Windy City’s nightlife is just as exciting as its daytime adventures:

• Live Jazz & Blues Clubs – Enjoy world-class performances at legendary venues like Buddy Guy’s Legends or the Green Mill Cocktail Lounge.
• Rooftop Bars – Sip cocktails with a view of the glittering skyline.
• Theatre District – Catch Broadway-calibre shows and local productions in the historic Loop.

Getting to Chicago

Getting to Chicago has never been easier. With daily flights to Chicago from major UK and European airports, your holiday to Chicago can begin sooner than you think. Cassidy Travel works with top airlines to bring you Chicago travel packages that suit all travel styles and budgets.

Our flexible booking options include return flights, hand-picked Chicago hotels, and bespoke experiences designed for you.

Best Destinations Nearby

Extend your adventure beyond Chicago with exciting nearby getaways:

• Milwaukee – A short drive north, known for its breweries and lakefront festivals.
• Indianapolis – A sports fan’s dream with major stadiums and racing heritage.
• Michigan Wine Country – Just a couple of hours away, offering scenic vineyards and charming small towns.

Best Time to Visit

• Spring (April–June): Blooming gardens and comfortable temperatures – perfect for sightseeing.
• Summer (July–September): Festival season with lakefront fun, beach time, and outdoor concerts.
• Autumn (October–November): Fall foliage, crisp air, and fewer crowds.
• Winter (December–March): Cozy Christmas markets, ice skating at Millennium Park, and a magical snowy skyline.

No matter the season, Chicago offers an unforgettable holiday experience.

Book Your Chicago Holiday with Cassidy Travel

At Cassidy Travel, we take the hassle out of planning so you can focus on the excitement. Whether you're booking in advance for Chicago holidays 2025/2026 or looking for last-minute Chicago vacation deals, our team is here to help. Explore tailored Chicago travel packages that include return flights, accommodation, tours, and more.

Want a quote today? Click here to get a customised itinerary and start your journey to the Windy City. Don’t miss out on our unbeatable deals on flights to Chicago and handpicked Chicago hotels that suit all budgets.

Why Choose Cassidy Travel?

• Trusted Irish travel experts since 1985
• Customised USA holiday packages
• Flexible payment options and low deposits
• Unmatched support from planning to takeoff

With Cassidy Travel, every detail of your holiday to Chicago is in good hands.

Final Word

There’s no place quite like Chicago – a city where the past and future meet in breathtaking harmony. Whether you're drawn by the historic architecture, legendary music, or the buzz of its diverse neighbourhoods, Chicago holidays 2025/2026 with Cassidy Travel promise memories to last a lifetime.

So what are you waiting for? Discover the energy, charm, and heart of the Windy City with Cassidy Travel – your gateway to unforgettable USA holidays.

Book your Chicago adventure now!