Chicago Holidays

Choose Chicago!

All for the Love of Chicago

There are endless things to see, do, and experience in Chicago — one of the many reasons why the city has been named the Best Big City in the U.S. for the past eight years in a row.

Chicago with Tour America

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Ready to start planning your next holiday? Speak with a member of our team today! We’ll take care of the details and help you create a holiday that’s tailored to you.

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Ready to start planning your next holiday? Our offices are currently closed but get in touch and someone from our team with reach out to you as soon as possible! We’ll take care of the details and help you create a holiday that’s tailored to you.

Chicago has the perfect combination of towering city views and natural beauty.

From outdoor movies in the park and a mile of world-class shopping to thrilling roller coasters and iconic attractions, you’ll never run out of things to do in the vibrant ‘Windy City!’

Explore the heart of the city and the surrounding neighbourhoods. Everywhere you go there is plenty of places to explore and attractions to see, making Chicago a vibrant destination for visitors. Whether you’re wandering through Millennium Park, enjoying the architecture along the Chicago River, or checking out local shops in neighborhoods like Wicker Park and Logan Square, there’s something for everyone.

The city’s public transportation system is one of its standout features. The CTA offers a reliable network of buses and trains that make it easy to get around. You’ll find that the “L” train system can take you to almost any area of the city, and with frequent service, you won’t have to wait long. If you prefer walking, Chicago is very pedestrian-friendly, with wide sidewalks and well-marked paths throughout the city. Because of this, there’s really no need to rent a car. Whether you’re hopping on the “L” or enjoying a leisurely stroll, getting around Chicago is simple and convenient.

City Pass

Explore the best of New York City with one easy pass. With CityPASS®, you’ll enjoy access to iconic attractions like the Empire State Building, Statue of Liberty, Top of the Rock, 9/11 Memorial & Museum, and more — all while saving up to 40% on regular admission prices. Skip the hassle of buying multiple tickets and spend more time soaking in the sights, sounds, and energy of the city that never sleeps.

Citypass New York | Attraction Pass | Tour America

Information

Average Flight Time:
8 Hours
Average Temperature:
17°C
/ 63°F
Best Time to Visit:
May
Best Suited To:
Singles
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13 Nights
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Route 66 by Train

Board Amtrak® and ride the rails along historic Route 66! Take in the iconic architecture of Chicago “The Windy City”, enjoy a walking tour around historic Albuquerque, ride the Grand Canyon Railway to the Canyon’s South Rim, and tour Beverly Hills to see the homes of the stars and starlets of Los Angeles. Journey along the famous Route 66 highway system as you make your way south towards the Grand Canyon and marvel at the immense beauty at one of the 7 natural Wonders of the World. A magical trip across the country awaits on the Route 66 by Rail journey!
Your Gateway to a Perfect Stay

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