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If you're looking for a specific style of holiday, we've got you covered. Our range of travel types includes honeymoons, family breaks and solo travel, as well as specialist trips focused on wellness, wildlife-watching and lots more.
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Call us on - 0800 294 9710
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Chicago & Route 66 Holidays
Upscale eateries, endless shopping opportunities all in the iconic Windy City
Whether your eyes are drawn upwards to downtown’s skyscrapers, your feet are pounding their way to Magnificent Mile’s luxury shops, or you take a different turn and end up in Andersonville’s resplendently retro neighborhood, Chicago is worth exploring.
Victorian mansions and beautiful brownstones mix well with modern apothecaries and hygge style boutiques in a brilliant blend of historic neighbourhoods and hipster enclaves. Head up to the bleachers at Wrigley Field for a fun-loving Chicago Cubs baseball game or, for a completely different view of the city, take a peaceful eveing kayak down the only backwards flowing river in the USA. You can hit the Beaux Arts beauty of the Art Institute for a splash of culture, the speakeasy bars for a dash of decadence and Lincoln Park for a big dose of gourmet greats. Make like a Windy City local and cycle the Bloomingdale 606 Trail and end the day on a high with sunset views of an epic skyline from the top deck at 360 Chicago.
Want the inside scoop on Chicago? We bring you carefully curated Chicago holidays designed to suit city lovers looking to soak up the atmosphere. We’ve sorted out all the details, kept everything simple and stress-free and made choosing your holidays easy and with online booking in just a few clicks.
Chicago & Route 66 Hotels
Our recommendations for the best places to stay in Chicago & Route 66
Moxy Chicago Downtown
Offering small but comfy rooms in hip, designer digs, the Moxy Chicago Downtown couples a funky u...
AC Hotel by Marriott Chicago Downtown
Keen to base yourself at the heart of the action without breaking the bank? The AC Hotel by Marri...
LondonHouse Chicago, Curio Collection by Hilton
Set in a classic 1920s Chicago tower and designated ‘historic landmark,’ LondonHouse Chicago is a...
Hotel Zachary, A Tribute Portfolio Hotel
You don’t have to be into baseball to appreciate the chic décor and unstuffy ambiance of this bou...
Staypineapple, An Iconic Hotel, Chicago
Who needs run of the mill? With its whimsical approach to design and warm welcome Staypineapple p...
Omni Hotel Chicago
Along with fabulous city views the Omni Chicago offers a supremely comfortable base at the heart...
The Gwen, A Luxury Collection Hotel, Chicago
In a landmark building just off the Magnificent Mile, close to the city’s best shopping and top a...
Holidays in Chicago & Route 66
- Chicago & Route 66
- 3 Star
Offering small but comfy rooms in hip, designer digs, the Moxy Chicago Downtown couples a funky urban vibe with affordable prices.
- Chicago & Route 66
- 3 Star
Keen to base yourself at the heart of the action without breaking the bank? The AC Hotel by Marriott could be just what you’re looking for.
- Chicago & Route 66
- 4 Star
Set in a classic 1920s Chicago tower and designated ‘historic landmark,’ LondonHouse Chicago is a stylish riverside address affording some of the city’s best rooftop views.
- Chicago & Route 66
- 4 Star
You don’t have to be into baseball to appreciate the chic décor and unstuffy ambiance of this boutique hotel. It does overlook the legendary Wrigley Field however, so if you are a fan of the sport, you’ve hit a home run already by making it your pick.
- Chicago & Route 66
- 4 Star
Who needs run of the mill? With its whimsical approach to design and warm welcome Staypineapple promises guests a relaxed stay in a plum location – minus the high price tag. Who needs run of the mill? With its whimsical approach to design and warm welcome Staypineapple promises guests a relaxed stay in a plum location – minus the high price tag.
- Chicago & Route 66
- 4 Star
Along with fabulous city views the Omni Chicago offers a supremely comfortable base at the heart of the action. The Magnificent Mile is right there outside.
- Chicago & Route 66
- 4.5 Star
In a landmark building just off the Magnificent Mile, close to the city’s best shopping and top attractions, the glamorous Gwen is an excellent choice for a city-break splurge, or a celebration with girlfriends.
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Wind down those windows, tune the radio and enjoy the open road as you make your way through the USA’s legendary highway
Route 66 is a bucket-list favourite and in a land of self-drives our itineraries are the best way to enjoy Chicago and Route 66’s legendary highlights. Start your epic cross-country journey in the ‘Windy City’, but not before you’ve made time to learn about some of its striking buildings on a Chicago Architectural River Cruise or teetered on the glass ledge that extends from the Skydeck on the 103rd floor of Willis Tower (the tallest building in the Western Hemisphere). Affectionately dubbed 'The Mother Road', you can enjoy this classic highway as you tour through Missouri, Oklahoma, Texas, New Mexico, Arizona and Nevada, finally stopping in Los Angeles as you complete your 2,400+ mile trip. Destinations, durations and accommodation are all completely flexible and easily adapted to suit your own needs.
Our recommened Chicago and Route 66 tours
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Chicago Culture & Architecture
This walking tour starts under the dazzling marquee of the Chicago Theater. The first stop is inside one of Chicago's shopping hubs with a striking atrium. Next, you'll walk the Chicago Pedway, a network of underground tunnels used by locals and commuters to move about the city. Back above-ground, City Hall is next. Most weekday tours mean you can head inside to see the classic interior design and architecture. Peckish? You'll stop for a sweet treat and local tradition: Chicago-style popcorn. With boosted energy, stroll along the Chicago Riverwalk to see Marina Towers, the Britannica Building, and the Sears Tower (now known as the Willis Tower). From there, depending on the weather, you'll hop on the train or a water taxi. You'll feel like a local as you zip past buildings. If your guide takes you on a water taxi, you'll be seeing the Chicago skyline from a different perspective. On the way to your next destinatng and the incredible Chicago Tribune building. Your second snack is locally made chocolate. Finally, you'll take a stroll through the lakefront parks along Michigan Avenue, finishing up in Millennium Park, home to the iconic Bean sculpture.
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