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Chicago Holiday Packages 2025/2026

Welcome to Chicago, the magnificent heart of America's Midwest, where a breath-taking skyline meets the shimmering waters of Lake Michigan. This vibrant metropolis offers endless adventures, from strolling along the Chicago Riverwalk – a social hub buzzing with energy and spectacular city views – to losing yourself in masterpieces at the world famous Art Institute of Chicago.

Experience the magic of live entertainment at The Chicago Theatre, or create lasting memories aboard the iconic Ferris Wheel at Navy Pier's lively boardwalk. When summer arrives, pristine beaches beckon with golden sands and cooling lake breezes. Whether you're a passionate shopper, devoted sports fan, adventure seeker, or culinary enthusiast, Chicago's dynamic spirit promises unforgettable experiences for every type of traveller.

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chicago Package Holidays

10 holiday deals Found
Fairmont Chicago Millennium Park
Top Pick

Fairmont Chicago Millennium Park

Illinois

Overlooking the legendary skyline, downtown parks and Lake Michigan, Fairmont Chicago, Millennium Park offers a sophisticated escape in the heart of the Windy City. Enjoy elevated brewpub fare in The Lobby Bar and indulge in deeply restorative botanical treatments at full-service Leaf Spa. When you reserve your stay at one of the very best hotels in Chicago, downtown highlights such as Millennium Park, the Magnificent Mile, and the Museum Campus are practically at your doorstep.

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Loews Chicago O Hare Hotel
Top Pick

Loews Chicago O Hare Hotel

O hare Airport

Loews Chicago O'Hare Hotel formerly known as (InterContinental Chicago O'Hare) offers a bar/lounge. Wireless Internet access is in public areas. This smoke-free property include a 24-hour business center and meeting rooms, additional amenities include a nightclub, a fitness center, and gift shops/newsstands. The 556 air-conditioned guestrooms provide desks, newspapers, and phones. Bathrooms offer shower/tub combinations with rainfall showerheads, bathrobes, designer toiletries, and hair dryers. All units feature minibars and coffee/tea makers.

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The Palmer House Hilton
Top Pick

The Palmer House Hilton

Downtown

The Palmer House Hilton offers 1639 Rooms & suites. All 1,639 guestrooms at the Palmer House Hilton feature antique-style decor, pillowtop mattresses, marble bathrooms, premium channels, and high-speed Internet access. Amenities include flat-screen TVs and WiFi. Stylish suites feature abundant space with comfortable seating and wet bar areas, creating an ideal setting for entertaining.

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The Langham Chicago
Recommended

The Langham Chicago

CHICAGO

Discover the perfect blend of convenience and stylish comfort only at The Langham, Chicago. Legendary service and timeless British style in an iconic Chicago landmark. The perfect blend of convenience and luxurious comfort only at The Langham, Chicago. Majestic views of the cityscape, the Chicago River, and Lake Michigan. All housed in a skyscraper designed by renowned architect Mies van der Rohe. Situated in downtown Chicago, hotel is mere minutes from the Loop, Grant Park, Magnificent Mile, Millennium Park and Navy Pier. 268 guest rooms and 48 suites designed for the discerning traveller. Warm colour tones accented with rich textiles and dark woods create open and inviting spaces. Floor-to-ceiling windows provide sweeping vistas of the Chicago skyline and river. Modern conveniences and signature amenities make every room a comforting place to unwind.

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Thompson Chicago
Recommended

Thompson Chicago

CHICAGO

Chicago luxury boutique hotel. British design icon Tara Bernerd turns her worldly, eclectic sensibility to eleven on the Gold Coast, with the luxurious loft-like, urban industrial bones of the lobby and lounge accented with warm American woods and clean, mid-century lines throughout Thompson Chicago. Imagine your own luxury studio in the skies overlooking the hip Gold Coast neighborhood’s leafy streets and the Magnificent Mile, with sweeping floor-to-ceiling vistas of the downtown Chicago skyline and Lake Michigan waterscape daring you to look away.

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21c Museum Hotel Chicago

21c Museum Hotel Chicago

E Ontario St

21c Museum Hotel Chicago is the intersection of comfort, culture and curation. A hotel where inspiration is around every corner - dine, entertain and recharge while surrounded by world-class art. Come experience the extraordinary.

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Jw Marriott Chicago

Jw Marriott Chicago

CHICAGO

Experience an extravagant escape from everyday reality at our luxurious, landmark hotel with a historic past at JW Marriott Chicago. Our premier downtown hotel is located inside the Chicago Loop making it easy for travellers to visit Columbia College, the University of Illinois, the Art Institute of Chicago, Millennium Park and Sky deck Chicago. After a busy day in the city, explore our hotel's incredible array of luxury amenities, including an onsite spa, an indoor lap pool and a delicious restaurant and lounge with upscale Italian cuisine and specialty cocktails. Retreat to elegantly-designed rooms with high ceilings, marble bathrooms, featherbeds and Wi-Fi. Upgrade to our Executive Level rooms or suites for expansive space and exclusive lounge access. If visiting for business or social gatherings, succeed like never before in our iconic hotel's 44,000 square feet of event space, including our stunning Burnham Ballroom. Whatever the reason for your visit, we look forward to welcoming at JW Marriott Chicago.

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The Westin Chicago River North

The Westin Chicago River North

CHICAGO

Located in the heart of downtown Chicago, IL, in the prestigious River North district, our iconic hotel in the Chicago River North area is an ideal home base for work or rest. Connect with our historic and energetic Windy City using The Westin Chicago River North, which is within walking distance from Millennium Park, the Chicago Riverwalk, the Magnificent Mile and the Chicago Theatre District. Refreshed in early 2020, our flexible event spaces provide a perfect setting for executive retreats and conferences. Recharge in your choice of pet-friendly hotel accommodations ranging from traditional rooms to spacious suites with views of the Chicago River or downtown Chicago skyline. Maintain your health and exercise goals at our WestinWORKOUT® Fitness Studio, offering free classes with a personal trainer. Fuel your day with delicious and healthy on-site dining at 320 RiverBar. If you have to spend time away from home, do it effectively and fully rested.

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The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

Illinois

Hotel near Lake Michigan in Chicago, Illinois is located within walking distance of Oak Street Beach, luxury fashion at 900 North Michigan Shops, the breathtaking 360 Chicago Observation Deck, and all of Chicago's most famous attractions. The Westin Michigan Avenue Chicago hotel offers pet-friendly hotel rooms and spacious suites featuring sweeping lake views, a renowned Heavenly® Bed and relaxing bath amenities. Maintain your routine with \WestinWORKOUT® Fitness Studio, featuring Peloton bikes, or Run Concierge. Rise and rejuvenate your body and mind at \Body Rituals Boutique Spa.

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Virgin Hotels Chicago

Virgin Hotels Chicago

Wabash Avenue

When it comes to unrivalled comfort, spectacular events and ‘to die for’ dishes, the skyline is the limit. Ease into your stay with a rooftop cocktail, work up a hunger in our expansive gym or head straight to your spacious chamber and enjoy room service from your unbelievably comfy bed. This is your stay, your way.

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Top 3 Luxury Hotels in Chicago

The Langham Chicago
  • Stunning river and city views from floor to ceiling windows
  • Award-winning Asian inspired spa with tranquillity pool
  • Luxurious rooms featuring modern amenities and marble bathrooms
  • Multiple acclaimed restaurants and sophisticated dining options
  • Exceptional concierge service and prime downtown location
Fairmont Chicago Millennium Park
  • Sophisticated rooms with contemporary design and city views
  • Full-service spa offering signature treatments and wellness services
  • Multiple dining options including acclaimed gastropub and wine bar
  • State of the art fitness centre with personal training available
  • Prime location near Millennium Park and Chicago's cultural attractions
<21C Museum Hotel Chicago
  • Contemporary art museum integrated throughout the property
  • Stylish rooms featuring original artwork and modern amenities
  • Signature restaurant offering innovative seasonal cuisine
  • Curated cultural programming and rotating art exhibitions
  • Central location in River North's vibrant arts district
Chicago's Culinary Scene

Chicago stands as one of America's premier culinary destinations, offering an extraordinary dining landscape that rivals its famous architecture. The city's diverse food scene caters to every palate and budget, featuring:

Fine Dining Excellence
  • Michelin-starred restaurants
  • Chef-driven innovative establishments
  • Contemporary fusion cuisines
  • Sophisticated tasting menus
Local Favourites
  • Traditional deep-dish pizzerias
  • Family-owned sandwich shops
  • Authentic international eateries
  • Trendy food halls
Must-Try Restaurants
  • Aloha Poke Co. - Fresh Hawaiian-inspired bowls
  • Sweetgreen - Seasonal salads and grain bowls
  • Beatrix - Modern American comfort food
  • Native Foods Cafe - Creative plant-based cuisine
Signature Dishes
  • Kalbi Barba Korea Tacos - Korean-Mexican fusion
  • Mykono's Combination Plate - Mediterranean classics
  • Wang Mandu - Korean dumplings
  • Artisanal Gelato Sandwiches
Shopping in Chicago

Chicago ranks among the world's premier shopping destinations, offering an incredible variety of retail experiences for every style and budget. Here's where to find the best shopping in the city:

Michigan Avenue - The Magnificent Mile
  • World-class architectural design
  • Tree-lined streets
  • High-rise luxury malls
  • Designer boutiques
  • Department stores
Notable Shopping Districts
  • Oak Street - Home to exclusive designer boutiques and luxury brands
  • Bucktown & Wicker Park - Trendy boutiques and independent retailers
  • Lincoln Park - Mix of popular brands and local shops
Must-Visit Shopping Malls
  • Water Tower Place - Iconic shopping centre with over 100 stores
  • 900 North Michigan Shops - Luxury shopping across seven levels
  • The Shops at North Bridge - Premium retail experience in the heart of Michigan Avenue
  • Westfield Old Orchard - Expansive outdoor shopping destination
FAQ's
  • Is Chicago a good holiday destination?

    Chicago holidays offer an exceptional experience in one of the United States' most vibrant cities. Known as the Windy City, Chicago combines world-class attractions, stunning architecture and diverse cultural experiences. With pristine beaches along Lake Michigan, renowned museums like the Art Institute of Chicago and iconic landmarks like the Magnificent Mile, Chicago provides endless entertainment options for all types of travellers.

  • What is the best month to go to Chicago?

    The best time to visit Chicago is during late spring (April-May) or early fall (September-October) when average temperatures are mild and comfortable. Summer (June-August) offers warm weather perfect for beaches and outdoor festivals but tends to be more crowded and humid. Winter months can be quite cold but offer unique experiences like ice skating and holiday markets.

  • What part of Chicago is best to stay in?

    The best areas to stay depend on your interests:

    • River North: Perfect for dining and nightlife
    • Magnificent Mile: Ideal for shopping and luxury hotels
    • The Loop: Central location near major attractions
    • Gold Coast: Upscale neighbourhood with historic charm
    • Water Tower area: Combines shopping, dining, and attractions

  • What UK airports fly to Chicago?

    Direct flights to O'Hare International Airport operate from several UK airports:

    • London Heathrow (British Airways, United Airlines, American Airlines)
    • London Gatwick (seasonal flights)
    • Manchester (seasonal service)
    • Edinburgh (seasonal service)
    Most flights take approximately 8-9 hours from the UK to Chicago.

 
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