Chicago, located on Lake Michigan, is as cosmopolitan as New York, but with mid-west charm. Many famous and influential people have called Chicago home. Oprah Winfrey and her production company were based here for many years and the Disney creator himself, Walt Disney was born here.

After the Great Chicago Fire of 1871 destroyed a third of the city, including the entire central business district, Chicago experienced rapid rebuilding and growth. Chicago became known as the Second City, since the first city was largely destroyed. During its rebuilding period, Chicago constructed the world's first skyscraper in 1885, using steel-skeleton construction and still boasts some of the tallest skyscrapers in the world – the Willis Tower (formerly Sears), the Aon Center and the John Hancock Center.

Modern day Chicago is awash with performing arts including an array of theatre, opera, ballet, comedy, and of course, jazz and blues clubs. Also a culinary Mecca, Chicago's 9,000 plus restaurants offer everything from Lebanese to Japanese; Cajun to Creole. But don't forget to save room for Chicago's specialty- deep dish pizza - it's truly the best pizza you’ll ever eat and reason enough to visit Chicago on your USA holiday.

From April to October the lakefront and Grant Park come alive with different festivals most weekends. One of the most famous is Taste of Chicago, the largest food festival in the world which runs the final week of June through the 4th of July. Lollapalooza is Chicago's alternative music festival which grows more popular every year and of course - it wouldn't be Chicago without Blues Fest and Jazz Fest. Best advice we can give - book early.

Sports fan? Chicago has professional major league teams in all the popular American sports. Cheer on the Chicago Cubs baseball team at famous Wrigley Field. Located in a residential neighbourhood affectionately known as Wrigleyville - you can't get more American apple-pie than this!

And, if you can bear to drive away, Chicago is also the start of historic Route 66. Only 2,400 miles to Los Angeles!

To include Chicago in your tailor-made holiday to North America contact the experts at Bon Voyage on (0800) 316 3012.

Route 66 - The Mother Road

Route 66, The Mother Road from Chicago to Los Angeles. Take the 2,448 mile holiday of a lifetime and drive the classic Route 66.

Route 66 Guided Motorcycle Tour

There's no better way to experience Main Street USA. Cruise on your favourite motorbike, with like-minded travel companions all the way from Chicago to Santa Monica!

USA Rail Holiday - The Northern Explorer

The Northern Explorer gives you the opportunity to see the rugged Northwest States from the comfort of your train, including Chicago, Seattle and San Francisco.

USA Rail Holiday - Chicago, Memphis and New Orleans

Journey south through the very heart of the USA music scene as you head from Chicago to New Orleans.

USA Rail Holiday -The California Zephyr

Following the wagon tracks of the great pioneers, the Zephyr is the flagship of Amtrak's fleet, a super liner with an all-window panoramic lounge car and a tick list of iconic Americana.

America's Third Coast - The Great Lakes of North America

Discover America's third coast - the Great Lakes of North America. Bordering eight US states and a Canadian province, there's over 4,000 miles of coastline across all five lakes! That includes two time zones and more beaches than you'll...

The Great Lakes, USA

The Great Lakes region is a land of water, woods, hills, lighthouses, ships and wildlife. Experience this beautiful and tranquil part of America on this multi state holiday.

Route 66 - Three Week Extended Road Trip

This three week fly-drive Route 66 holiday packs in all the iconic sights you'd expect from the Mother Road, plus Monument Valley, Grand Canyon, Meteor Crater, Santa Fe and historic Durango.

Get Your Kitsch On Route 66! As featured in The Mail's 'Top Trips Across the Pond'.

Travel across three times zones and eight states, covering 2,448 miles from Chicago to Los Angeles. Crammed with nostalgia, kitsch and tradition at every turn, this is THE holiday itinerary for those wanting to experience the real deal.

USA Coast-to-Coast by Rail

From Seattle to the Big Apple, this 14-day rail holiday showcases the best of the northern half of America.

Route 66 Chicago to New Mexico Guided Motorcycle Tour

Our 8 day guided trip takes in the first half of Route 66 from Chicago to Albuquerque.

Vegas, Voodoo, Elvis & Chi-Town

Four of the USA's most iconic cites, over 14 nights, with no driving - sign us up!

Pre-Planned Motorhome Holiday along Route 66

Experience legendary Route 66 on our 21-day motorhome adventure from Chicago to Los Angeles. Travel through eight states and three time zones and over 2,500 miles!

Chicago's Skyscrapers

In 1885, the first steel-framed high-rise building rose in Chicago ushering in the skyscraper era. Today, Chicago's skyline is among the worlds tallest.

The Shops at North Bridge

On Chicago's Magnificent Mile? CheckNordstrom? Check50 stores? Check20 restaurants? CheckOne amazing stop ticks all the shopping boxes!

Navy Pier

Navy Pier is a 3,300-foot long pier along Chicago's Lake Michigan shoreline.

Chicago Festivals

From May to September, the lakefront, Grant Park and various neighborhoods come alive with festivals nearly every weekend.

Chicago Greeters - A great introduction to the Windy City

Experience Chicago's unique charm, captivating sights and world-class attractions with a local!

Magnificent Mile

The Magnificent Mile is the portion of Michigan Avenue that serves as the main thoroughfare between Chicago's Loop business district and its Gold Coast - the wealthiest neighborhood in Chicago.

"The Ledge" at Skydeck - Chicago

Step outside what’s not only the tallest building in Chicago but the third-tallest building in the Western Hemisphere....

Oakbrook Center

The prestigious Oakbrook Center is always cutting edge and has been voted THE number one shopping center by Illinois shoppers (and trust us – they are some savvy shoppers!).

Destination - Illinois and the history of Route 66....

Route 66 defined a remarkable era in the growth of the USA. As it threaded its way across eight states, it left its indelible mark on the nation's physical, historical and cultural landscape. Illinois is where it starts.....

Water Tower Place

At the pinnacle of Chicago's famed Magnificent Mile, Water Tower Place is Chicago's premier shopping destination.

Tilt at 360 Chicago

The John Hancock Center, 100 stories and 1,127 feet tall, was the tallest building in the world outside New York City when completed in 1969. Now it is the fourth-tallest skyscraper in Chicago and the seventh-tallest in the United States.

Fashion Outlets of Chicago

Fashion Outlets of Chicago is the Midwest’s ONLY two-level indoor outlet experience, offering over 130 stores with savings up to 75% every day!

Where you stay is the heart of your holiday. Location reigns supreme but do you prefer resort facilities or unique and boutique? Historic and old world or modern and shiny?

We aim to present choices across the spectrum but there are many hundreds of places to stay and not room to feature them all. Do speak to your Bon Voyage travel consultant and click the video for our take on this important topic.

Thompson Chicago

Urban, eclectic, hip......we could go on, but why don't you see for yourself!

Viceroy Chicago

Located in the Gold Coast neighbourhood, Chicago's newest hotel is fabulous. Enjoy gorgeously appointed rooms, views of Lake Michigan and the city, plus impeccable service. The location is ideal too with historic Rush Street and the Magnificent Mile a stone's throw away. Oh, and did we mention the rooftop pool?

The James Chicago

The perfect blend of unplug and play. The James invites you to be a part of the scene or just be serene - your choice.

Palmer House Hilton

The story of this downtown gem is one of romance and undeniable charm. Find out for yourself!

The Drake

The pride of Chicago and choice of celebrities and heads of state since opening in 1920.

Kimpton Hotel Monaco Chicago

An ideal Chicago base, right on the river, with everything you need on the doorstep. Kimpton is a favourite of Bon Voyage travellers and will be with you too!

Chicago Holidays