Chicago Holidays
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Cosmopolitan Chicago enjoys a picturesque setting on the shores of Lake Michigan and even has lakeside beaches. It also boasts a scenic river plus there’s plenty of green spaces including wonderful Millennium Park, home to the Cloud Gate sculpture.
A Chicago holiday has plenty to keep you busy. Explore the superb museums, indulge in shopping along Magnificent Mile, admire the famed architecture on a river cruise, have fun on the Ferris wheel at Navy Pier and ascend to the ‘360 Chicago’ observation deck for spellbinding views across the city. By night head to the Theatre District for dining and theatre shows, or tuck into a slice of deep-dish pizza before catching some live music in one of Chicago's many cool blues bars.
Trailfinders offers a range of Chicago holidays and our expert travel consultants are a mine of information about what to do here, often with first-hand travel experience. Whether you want a city break or hope to combine Chicago with an iconic road trip like Route 66 or a memorable rail holiday – they are the perfect people to ask.
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TF's Bulletin
OUR HOLIDAYS TO CHICAGO
Here's a snapshot of some of our most popular Chicago holidays. If you don’t see what you’re looking for, click on the link below them to see our complete range of holidays and tours in the destination.
The Rhythm Road - Chicago to New Orleans
USA
12 days / 11 nights
Route 66 - The Mother Road
USA
16 days / 15 nights
Chicago City Break
USA
5 days / 4 nights
Chicago & The Great Lakes Loop
USA
15 days / 14 nights
Iconic Cities of America
USA
15 days / 14 nights
Chicago To Nashville - Blues, Bourbon & Honky Tonks
USA
12 days / 11 nights
OUR RECOMMENDED HOTELS IN CHICAGO
What you won’t find here are thousands of Chicago hotels to wade through. We have done the hard work for you and selected the best places to stay and our travel consultants are on hand to help you plan your Chicago holiday, often with first-hand experience.
The Gwen
Chicago
21c Museum Hotel Chicago
Chicago
Palmer House Hilton
Chicago
WHAT TO DO IN CHICAGO
One day you might be visiting Chicago’s top attractions with the CityPASS, the next learning about the city’s unique architecture on a walking tour. Our collection of unmissable experiences will really help bring your Chicago holiday to life.
Chicago CityPASS
- Pre-book admission to top attractions
- Save time & money
- Skip most ticket lines
Chicago 2 Day Hop-On Hop-Off Bus Tour
- Hop-on hop-off bus tour
- See Chicago’s top sites
- Great way to see the city
Chicago & the Great Lakes Top Tips From Our Travel Experts
Ally Haviland
Chicago is a must for anyone who loves bustling cities but has already experienced the bright lights of New York and waterfront views of San Francisco. Home to some of the tallest and most unique skyscrapers, how about jumping on a river cruise to admire them from below, getting your culture fix at the Art Institute and finishing off the day relaxing in one of the beautiful parks or on the beach that meets Lake Michigan. As evening descends get your teeth into perhaps what Chicago is most famous for, deep dish pizza, and dance the night away in one of the many renowned jazz clubs that are dotted around this eclectic city.
Jane Poyser
Chicago is one of my favourite cities in the USA and it's so easy to explore on foot. The newly renovated River Walk has some brilliant bar options and is perfect for a morning run. I'd also recommend taking an Architecture River Cruise for a great orientation of the city.
Chicago Fast Facts
Tales from the Trail
Top tips and travel inspiration from the Trailfinders team
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