Commended Merchant - feefo
0208 290 9751
    Check our contact us page for our Christmas opening hours. Call or email us for great deals.
    Our travel experts are available and ready to take your call or click to email
    Our travel experts are available and ready to take your call or click to email
  • Our experts are available weekdays 9am-6pm and Saturdays 9am-5pm
Children ages
Must select age at time of travel (each child under 18)
Children ages
Must select age at time of travel (each child under 18)
Children ages
Must select age at time of travel (each child under 18)
Children ages
Must select age at time of travel (each child under 18)
Booking an Infant?

Advanced Search Page >>


We are currently searching to find the best Flights and Hotels for your to holiday…



7 nights from £889pp

Price based on 3 night duration in Chicago followed by 4 night duration in Florida Keys. Return flights from London.

Start your trip in Chicago, known as the 'Windy City', where you can take a stroll down Michigan Avenue and visit the Magnificent Mile of shops from designer to boutique stores. Or, why not take a trip 103 floors up the Skydeck where you can see 360 degree breathtaking views of Chicago. Your next destination is Florida Keys, this is where you can get up close with an amazing array of fish while snorkelling or fishing in the warm turquoise waters. Ensure you take the opportunity to go diving as Key Largo is known to be the diving capital of the world!

Remember, we can tailor-make your holiday to suit your needs, contact our travel experts today on 020 8290 9751.


The ‘Windy City’ of Chicago will blow you away with its charm and diversity! This is a very modern kind of metropolis with impressive performing arts, world-class museums and a skyline that bristles with iconic skyscrapers. Yet it's a city that's also big on tradition, and includes an unshifting allegiance not only to its major sports teams the Cubs and the Bears, but to deep-dish pizza and its own style of tasty hot dogs.

Chicago is somewhere that begs to be explored. Sitting pretty on the edge of Lake Michigan, there's a long stretch of coastline to explore, including sandy beaches, Lincoln Park with its famous free zoo, and the stunning public art of Millennium Park. But there are a lot of other interesting neighbourhoods to explore too. Downtown has cutting-edge architecture and all the big city bustle; Wicker Park and Bucktown have a trendy off-beat vibe, and Old Town has historic buildings and a romantic atmosphere.

The View

For a 360 degree view of Chicago, take a ride 103 floors up the Willis Tower (formerly the Sears Tower) and see the stunning views of Lake Michigan and across the city. The second-tallest building in the Western hemisphere even has glass boxes, known as 'The Ledge', which extends out for over a metre from the side of the building. So man up, step out and look straight down - if you dare!

The Shopping

'Magnificent Mile' along Michigan Avenue is the place to shop. You’ll find all of the big names; Bloomingdale's, Neiman Marcus, Nordstrom, Macy's and Sak's Fifth Avenue, as well as three big malls. For independent boutiques, head for Wicker Park/Bucktown and the Lincoln Park area.

The Sights

Chicago is home to some of the world’s best modern architecture so be sure to take a guided tour of the main sights. This is the city that spawned the skyscraper, so there's plenty of interest to discover, as well as Miles van der Rohe's modernist Illinois Institute of Technology buildings, and Frank Lloyd Wright's home and studio.

The Entertainment

Enjoy the bustling nightlife that Chicago has to offer. There's plenty of Broadway hits at the city's string of theatres, and brilliant live comedy at Second City - the venue that kick-started the careers of Mike Myers and Tina Fey. Chicago is the home of Blues music so head to clubs like Kingston Mines or B.L.U.E.S for live entertainment.

The Festivals

If festival are for you, then visit Chicago in the summer. The Blues Festival (June 3-15) is free and attracts big names; the massive Taste of Chicago food festival takes over Grant Park from July 9-13; the Air and Water Show delivers spectacular aerobatics over Lake Michigan from August 16-17; and there are many others.

Sky High Views  
Take an exhilarating ride to the 94th floor of the John Hancock Observatory for the best views of the city. You will get a 360 degree view of what Chicago has to offer - from only £10 per person.

Lake Michigan Cruise  
Take a boat ride along Lake Michigan and see the incredible views of the city's famous sky scrapers from a great vantage on a 30 minute cruise from only £10 per person.

Blues Brothers Coach Tour
Follow the path of blues music history and the famous Blues Brothers on a scenic coach tour through the city, with interesting facts about the Blues Brothers phenomenon as you visit the famous locations - em>from only £20 per person.

Millennium Park
For the family, Millennium Park is a fun attraction to visit. It includes the Crown Fountain, the ‘Bean’ and plenty more to keep everyone entertained.

Chicago Movie Tour
If you’re a film fanatic, you’ll see the best Chicago has to offer on a movie tour of the city. See where Hollywood’s most popular blockbusters were filmed on location from just £20 per person.

You can add tickets for activities to your booking later.

  • Chicago
  • Chicago
  • Chicago
  • Chicago
  • Chicago
  • Chicago


Closer to Havana than to Miami, Key West's intoxicating mix of Caribbean, Latin and US culture never fails to seduce. This is the furthest of the jewel-like islands that lay around Florida's coast, and it's an outpost of off-beat charm. Here the vibe is strictly shorts and flip-flops. In the evening, there's always someone around to share a conversation or a margarita with. No wonder Ernest Hemingway loved Key West so much he made it his home.

If you’re a keen diver then Key Largo is the perfect place to go to. Famously named the 'Dive Capital of the World', divers in the know opt for Key Largo holidays not only for the quality of what lies beneath the water, but for palm trees and sunsets, beach action, excellent sport fishing, and stunningly beautiful State parks.

Celebrate the Sunset

On Key West holidays, sunset is a nightly ritual at the Mallory Square pier. As the sun sinks below the horizon in a purple and orange hue, the Square comes alive with jugglers, fire eaters, buskers and performers of all kinds. You can even catch some cat acrobatics which have to be seen to be believed!

Ernest Hemingway Home

From 1931 to 1942, the infamous author and hell-raiser lived on Key West in a stunning Spanish colonial style house. You can tour Hemingway’s house and see where he wrote classics like To Have and Have Not and take a walk through the lush gardens. Look out for the 40 plus cats that roam the property, they are descendants of Hemingway's own famous six-toed pet.

Dry Tortugas National Park

Take the boat or seaplane out to remote Dry Tortugas National Park to explore its seven islands and Fort Jefferson, a massive 19th-century coastal fortress that are marooned 70 miles off-shore. Wander along brick corridors, learn about its fascinating history and then slip into the glassy waters of the Gulf for superlative snorkelling over coral reefs. Watch out for the amazing birdlife, too.

John Pennekamp Coral Reef State Park

Visit America's first undersea park is a vast natural wonder, with stunning coral reefs, exotic marine life, and a submerged bronze statue of Christ to explore. If you’d prefer not to dive or snorkel, you can glide across the reef in a glass-bottom boat; plus there's canoeing and kayaking and nature trails through the mangrove swamps.

First-Class Fishing

Plenty of boats head out from Key Largo each day, taking anglers to the reef and beyond in search of mahi-mahi, tuna, sailfish, grouper and marlin. In fact it's said that more saltwater fishing world records are broken in the Florida Keys than anywhere else around the globe. There's also excellent backwater fishing for elusive bonefish, and wreck fishing too.

  • Florida Keys
  • Florida Keys
  • Florida Keys
  • Florida Keys
  • Florida Keys
  • Florida Keys

Contact our travel experts who can help put together your dream twin centre holiday, call 020 8290 9751


Travel Experts 

Contact Us

Request a Quote
Request a Callback
Email Us

Why book with
My America Holiday

Fully Protected
  • 100% financial protection.
  • Deposits from £59pp
  • 24 hour in-resort support.

My Caribbean 
​​ ​​​ ​​

©1999 - 2020 My America Holiday 21/10/2020 00:00:26 CST. CST 2009218-20

View Terms & Conditions.

Please see our terms and conditions for more information.

Keyboard Instructions
change date: Ctrl/Command + ///
previous/next month: Page Up/Down
select date: Enter
cancel and close: Esc