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The famous ‘Bean’ sculpture reflects the sunshine across the Chicago Business District on a bright summers’ day in Illinois, USA

Chicago Holidays


usa
Chicago holidays offer a fantastic mix of attractions ranging from iconic skyscrapers with awe-inducing views to world-renowned museums and fabulous nightlife.

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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OUR HOLIDAYS TO CHICAGO

Nobody offers more ways to explore Chicago than Trailfinders.

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
Fly Drive Holiday
12 days / 11 nights

Take in the Mother Road, the River Road and the Blues Highway on this soulful trip through the musical heart of America.

Guide Price: €1,425 pp

Guide Price: £1,215 pp

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Route 66 - The Mother Road
USA
Fly Drive Holiday
16 days / 15 nights

Regarded by many as the ultimate road trip, the Mother Road combines vibrant cities, natural wonders and the nostalgia of bygone America.

Guide Price: €1,869 pp

Guide Price: £1,595 pp

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Chicago City Break
USA
City Break
5 days / 4 nights

Chicago blends beautiful architecture with gleaming glass towers, lakeside beaches with multicultural neighbourhoods, intriguing museums with its Magnificent Mile shopping and all this within an easily navigable city.

Guide Price: €915 pp

Guide Price: £749 pp

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Chicago & The Great Lakes Loop
USA
Fly Drive Holiday
15 days / 14 nights

Combine vibrant Chicago with Wisconsin’s welcoming cities and Michigan’s characterful towns on this relaxed journey along the shores of the magnificent Great Lakes.

Guide Price: €2,045 pp

Guide Price: £1,634 pp

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Iconic Cities of America
USA
Multi Centre Holiday
15 days / 14 nights

Combine five of the USA’s most legendary cities on one incredible cross country trip.

Guide Price: €1,989 pp

Guide Price: £1,679 pp

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Chicago To Nashville - Blues, Bourbon & Honky Tonks
USA
Fly Drive Holiday
12 days / 11 nights

Journey from sensational Chicago down to Kentucky’s bluegrass hills and bourbon trails, then onwards to Tennessee’s music, mountains and moonshine.

Guide Price: €1,979 pp

Guide Price: £1,635 pp

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OUR RECOMMENDED HOTELS IN CHICAGO

We feature a great range of accommodation in Chicago, with something to suit all budgets. Maybe you’re looking for a sleek 5 star with a superb location in the heart of Chicago or perhaps it’s a simple, good value option that you’re after?

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
5 star

Chicago

Located near Chicago’s famous Magnificent Mile, this luxurious hotel combines chic elegance with a vintage charm which dates back to the city’s golden Art Deco era.
21c Museum Hotel Chicago
4 star

Chicago

Immerse yourself in a world of art at this hotel that blends comfortable amenities with thought-provoking contemporary exhibitions to explore throughout the property.
Palmer House Hilton
4 star

Chicago

This historic hotel has a great location in the heart of Chicago, ideal for exploring the city sights.

WHAT TO DO IN CHICAGO

As well as some great sightseeing opportunities, Chicago is also home to some unforgettable experiences.

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 Culture & Architecture
2.5 hours
  • Amazing architecture
  • Tasty food
  • Iconic sights
Chicago CityPASS
Attraction Ticket
  • Pre-book admission to top attractions
  • Save time & money
  • Skip most ticket lines
Chicago 2 Day Hop-On Hop-Off Bus Tour
Attraction Ticket
  • 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 & the Great Lakes expert
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 & the Great Lakes expert
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

Time Zone: Chicago is 6 hours behind GMT

Flight Time to Chicago: Flights to Chicago take approximately 8 hours

Currency: US Dollar (USD). ATM's are available across the country and most restaurants, shops and hotels will accept credit/debit cards

Tipping: Tipping in Chicago is expected. A tip of 15-20% for all service staff is usually sufficient

Language: The official language of the USA is English

Visa: A USA ESTA visa is required for travel. Visit our visa pages for more information.


Tales from the Trail

Top tips and travel inspiration from the Trailfinders team

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