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Tours and Tailor Made Holidays to

Chicago, IL

UNITED STATES
  • CURRENCY US Dollars
  • LANGUAGE English
  • WEATHER
  • FLYING TIME 8hrs 50 mins
  • TIME ZONE GMT-5
  • AIRLINE British Airways

Steely skyscrapers, top chefs, rocking festivals – the Windy City will blow you away with its low-key cultured awesomeness.

Holiday Offers

Below is a selection of our most popular Chicago, IL Holiday Offers. At Travel Concierge we take pride in not only offering an exceptionally high standard of service, but also the best value for money on Chicago, IL holidays. You will be able to view more Chicago, IL holiday deals on the offers page. If you can't find the Chicago, IL deal you are looking for, please call one of our Chicago, IL reservations consultants on 0161 729 0099

Destination Overview

In Chicago, you will feel like one of the locals. Whether you hang out in one of the 77 vibrant neighbourhoods or simply kick back in Millenium Park, you will always feel welcome during a holiday in Chicago.

So why not grab a seat in one the 200+ theatres. Enjoy miles of shopping. Be amazed by the museum treasures. Soak up the sun on sandy beaches or roof top bars. Dine out at fine Michelin Star restaurants or just take a walk along the 26 miles of lake front which frames the iconic skyline. What ever you choose to do in Chicago, you will feel as comfortable as you do at home.

Take a deep breath before you go on a holiday to Chicago. You are about to be sucked into a whirlwind of action. Chicago is a buzzing, bustling, and vibrant (not to mention windy) city that guzzles anything that smacks of art, high culture, cutting-edge technology, and avant-garde design. Chicago’s architecture is its crowning achievement. Look around you. The city skyline is a medley of stratospheric structures, sweeping lines, and massive stained-glass buildings that leave you gawking and gaping in sheer wonder. And then there are the art installations strewn on the streets. Expect to bump into an abstract Picasso creation during your strolls around the city.

Chicago’s love for innovation and everything edgy also finds expression in its culinary scene. There are about 6,000 eating joints here that craft and serve, besides the Chicago-original deep-dish pizza, an assortment of delicacies from around the world. Where else but on a Chicago holiday can you sample French, Vietnamese, Mexican, Macanese, and American fare, all in the same neighbourhood?

Our Recommended Hotels in
CHICAGO, IL

Viceroy Chicago

VIEW ALL CHICAGO, IL HOTELS

When to visit Chicago, IL

Chicago, IL

Do you need inspiration for when to go on holiday to Chicago, IL? Give the team of experts at Travel Concierge a call and we will help you plan your Chicago, IL holiday at the best time of year for your requirements. Although our Chicago, IL holiday search tool will allow you to search for Chicago, IL holiday prices upto 11 months in advance, we can also price holidays to Chicago, IL for 2025 and 2026. We can advise on the best time to travel on your Chicago, IL holiday based on Chicago, IL weather, special events in Chicago, IL or even when the crowds in Chicago, IL are at their lowest.

Chicago, IL

The diverse topography of Midwest USA means that the climate varies widely across the region. But nowhere will you encounter winters so chilling that they put a dampener on your plans or summers so sultry or scorching that you are compelled to stay indoors during your holidays in Midwest USA.

You can plan a Midwest USA tour anytime during the year. So make sure that you plan a trip around the various festivals of the region and the seasonal shows Mother Nature puts up for your pleasure and enchantment. Plan a Midwest USA holiday, so you can witness the stories of renewed hope, sincerity, and passion unfolding here, both in the wilderness and on the streets and neighbourhoods of the mega cities.

Come summer, and the streets of Chicago transform into a giant musical stage. The air is charged with the pulsating beats emanating from the Chicago Blues Festival, the largest free blues festival in the world; the Chicago Jazz Festival; and the Chicago Summer Dance, a swinging, shaking, and grooving extravaganza that celebrates myriad dance forms. The Custer State Park is a vision of abundant beauty during the summer season. The warm days bring out the animals while the greenery is lush. The trails light up with a thousand blooming flowers as the landscape mesmerises you with a riot of colours. Exploring the park environs is a sensorial experience that will refresh and rejuvenate you.

Winter is also the season when, despite the snow around, Chicago and Detroit come alive with the soulful strains of blues, the pulsating beats of jazz, the heady aroma of food, and the vibrant hues and enticing movements of hordes of dancers parading their way through the streets. Winter sees the Ann Arbor Folk Festival, Anti-Freeze Blues Festival, and Autorama keep Detroit folks on their feet, singing and dancing the nights away.

As the thaw season approaches, Midwest USA sheds off its icy and snowy cover and decks up in a myriad of vibrant hues. The miles of trails in Custer State Park provide enchanting opportunities to lose yourself in the wilderness while feasting your eyes on the towering granite peaks straddling the horizon and the clear mountain lakes and streams glistening in the daylight. The wild animals shrug off their winter lethargy and head out into the open to bask in the warmth. A Midwest USA holiday during spring is a chance to soak in the beauty of Nature and also take part in Detroit’s Electronic Music Festival or chuckle, guffaw, and laugh at one of the many comedy shows that take place across Chicago’s theatres.

Take part in the autumn festivals in Detroit on your holiday to Midwest USA to understand what drives a people to rise up from the ashes and soar up to the heavens like the phoenix.

Excursions

Why not enhance your Chicago, IL holiday experience by adding on an excursion. Our Chicago, IL excursions have been carefully selected by the product team at Travel Concierge. Booking a Chicago, IL excursion in advance can offer much better value for money than booking the excursions whilst you are on holiday in Chicago, IL.

Tours