An Awesome Chicago & New Orleans Multi centre holiday

Chicago & New Orleans – 6 nights

Take in 2 fabulously cultural cities with completely different vibes. Fly from London to Chicago and spend 3 days exploring everything the city has to offer, before taking the 2 ½ hour flight down to New Orleans for another 3 nights

Chicago doesn’t just welcome you, it sweeps you up in its energy, its skyline, its flavours, and its unmistakable Midwestern charm. If you’re dreaming of a city break that blends world‑class culture with neighbourhood warmth, Chicago delivers an experience that feels both iconic and personal. This is a city that invites you to explore, taste, wander, and wonder. And it rewards you at every turn.

Chicago’s architecture is more than a back-drop, it’s a character in its own right. Start your adventure with an architectural river cruise, where glass towers and historic stone facades rise dramatically above the water. It’s the perfect way to understand how Chicago became the birthplace of the modern skyscraper. For a different perspective, head up to the Skydeck at Willis Tower or 360 Chicago at the John Hancock Centre. Whether you’re stepping onto the glass ledge or leaning out over the city in the TILT experience, the views are unforgettable.

Art lovers will feel instantly at home. The Art Institute of Chicago, crowned by its iconic bronze lions, houses masterpieces from Monet to Warhol. Wander through its vast galleries and you’ll find yourself immersed in centuries of creativity. For something more contemporary, explore the Museum of Contemporary Art or stroll through Millennium Park to see the beloved Cloud Gate sculpture, affectionately known as “The Bean.” It’s impossible not to smile when you see the skyline reflected in its gleaming surface.

Chicago’s food scene is a journey in itself. Yes, you should absolutely try a deep‑dish pizza, thick, cheesy, and unapologetically indulgent. But don’t stop there. The city is a playground for food lovers, from Michelin‑starred restaurants to family‑run neighbourhood gems. Savour smoky barbecue in Pilsen, sample global street food at Time Out Market, or treat yourself to a classic Chicago‑style hot dog (just don’t ask for ketchup). Every meal feels like a celebration.

Despite its urban buzz, Chicago offers peaceful pockets of nature. Stroll along the Lakefront Trail, where the city meets the sparkling waters of Lake Michigan. Relax on sandy beaches, cycle through parks, or wander the lush gardens of Lincoln Park. The Garfield Park Conservatory, one of the largest in the world, feels like stepping into a tropical paradise, no matter the season.

Chicagoans are passionate about their teams, and catching a game is a rite of passage. Feel the history at Wrigley Field, home of the Chicago Cubs, or experience the electric atmosphere of a Bulls or Blackhawks game. Even if you’re not a sports fan, the energy is contagious.

New Orleans

New Orleans isn’t just a destination, it’s a feeling. A rhythm. A flavour. A city that wraps you in music, history, and irresistible charm from the moment you arrive. If you’re searching for a getaway that blends culture, cuisine, and pure joy, the Big Easy delivers an experience unlike anywhere else.

Music is the heartbeat of New Orleans, and you’ll feel it everywhere. Wander through the French Quarter and you’ll hear jazz drifting from balconies and blues rolling out of intimate clubs. Legendary Bourbon Street buzzes with energy, while hidden gems across the city offer unforgettable live performances every night. Whether you’re a jazz devotee or simply love a good groove, the city’s musical soul is impossible to resist.

New Orleans is a living museum of French, Spanish, Creole, and African influences. Stroll through the French Quarter’s historic streets, explore elegant architecture, or dive into the city’s past with a guided walking tour. For a deeper look at American history, the National WWII Museum is one of the most acclaimed in the country and a must‑visit for travellers seeking powerful storytelling.

Like Chicago, this city is a paradise for food lovers. From classic Cajun and Creole dishes to innovative modern cuisine, every meal feels like a celebration. Treat yourself to beignets dusted with powdered sugar, savour a hearty bowl of gumbo, or indulge in a Po’ Boy that locals swear by. With New Orleans ranked among the top food cities in the U.S., your taste buds are in for an unforgettable adventure.

While Mardi Gras is world‑famous, New Orleans celebrates all year long. Street performers, art markets, parades, and cultural festivals fill the calendar. Even on an ordinary day, the city feels like it’s throwing a party just for you. Whether you’re exploring vibrant neighbourhoods or joining a spontaneous second‑line parade, joy is always just around the corner.

Looking for something different? New Orleans offers ghost tours, river cruises, jazz shows, culinary adventures, and more. From historic mansions to atmospheric cemeteries, from bustling markets to serene parks, the city is full of surprises waiting to be uncovered.

As an Independent Travel Agent with years of experience visiting the USA, we would tailor your 2 centre trip to your personal needs, increasing or reducing the number of days as you see necessary, give you tips and ideas for the places you want to visit, before pulling it all together in your own personalised itinerary! 

It’s so easy to get started, simply give us a call, click on the enquiry button or book a consultation to design your dream trip!