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Chicago Destination Guide

Exclusively Elegant Travel Since 1988

For more information, please call our Luxury Travel Specialists on:01244 897 221

Your guide from the Luxury Travel Specialists

Welcome to the Elegant Resorts Destination Guide for Chicago, created to help make your choice of luxury holiday as easy as possible. Here, you will find more detailed factual information about the destination you have selected.

If you require further information, not featured on this page, please call one of our Luxury Travel Specialists.


Capital State: Illinois. Capital: Springfield. Largest City: Chicago.
Language English
Time Difference -5 hours
Currency US Dollar
Voltage 120V

The ‘Windy City’ will blow you away! Chicago stands on the western shore of Lake Michigan, in the state of Illinois, and its been said that no other city has influenced the rest of the world, in terms of modern architecture, quite as much as Chicago - films such as 'Ferris Bueller's Day Off 'and 'The Fugitive' will give you an idea of the spectacular diversity that this magnificent city offers. Chicago is a superb multicultural melting pot; here, you can visit Greek Town, Little Italy, Chinatown, Little Saigon and the Ukrainian Village, amongst others, to experience fantastic speciality bars, award-winning restaurants and eateries. You’ll also find world-class department stores and shopping malls; the beautiful parks and beaches of Lakeshore Drive; a famous symphony hall, ballet and opera hall, plus a host of vibrant venues serving up the classic jazz and blues that the city is famous for. If that wasn’t enough, Chicago is also the starting point of the legendary Route 66.

Sports Mad Chicago

Chicago is sports crazy! Offering a pro team for every season, visitors will not miss out on the amazing sporting atmosphere in this amazing city! Head over to Wrigley Field to watch the famous Chicago Cub’s (Baseball) or partake in a tour around the ground (available from April to September) – built in 1914, it is the second-oldest baseball park in the major leagues. You can also visit the historic Soldier Field to watch the mighty Bears (American Football) take on a rival. If basketball is your sport, visit United Center arena, home to the world-famous Chicago Bulls.

City Views

Enjoy the best views of Chicago during a visit to Willis Tower or 360° Chicago. Willis Tower is Chicago’s tallest building and the 103rd-floor Skydeck places you high above the city. The 70-second lift takes you to the top, where you will step onto one of the glass-floored ledges, providing astonishing, knee-buckling views of the streets below. 360° Chicago also offers stunning views from the 94th floor, where visitors can stand on a floor-to-ceiling window that leans out over the ground below, or visit the 96th floor at the Signature Lounge, where the view is free and you can enjoy a well-deserved drink.

Fascinating Museums

Chicago boasts an array of extraordinary museums that offer mind-blowing artefacts and exhibitions. The Field Museum of Natural History, for example, holds almost 30-million artefacts, along with the main highlight, Sue, the largest Tyrannosaurus Rex yet discovered. For art-lovers, the Art Institute of Chicago (the second-largest art museum in the country) has an Impressionist and Post-Impressionist collection rivalling museums in France, while the Museum of Science & Industry will allow your inner geek to come out as you search for a WWII German U-boat or spectate a mock tornado or tsunami.

Awesome Parks

Amidst the glistening skyscrapers, Chicago is home to many beautiful open green spaces, perfect for long, lazy afternoons in the glorious sunshine. Visit the superb Millennium Park, with its magnificent Pritzker Pavilion, hosting free summer concerts where you can you sit and enjoy your picnic and a bottle of wine. Chicago’s largest park, Lincoln Park, stretches 1,200 acres for six miles, taking advantage of the paths and playing fields, along with a zoo. Northerly Island, meanwhile, is a popular destination for bike-riding, bird-watching, fishing and outdoor concerts.

Starting Point for Route 66

For Route 66 fanatics, Chicago is the starting point for one of the greatest adventures you could possibly do. Search for the original ‘Historic 66 Begin’ sign that marks the starting point on Adams Street’s southern side, as you travel west towards Wabash Avenue. From here, you will leave Chicago and navigate 2,400 miles to Los Angeles, past motels, neon lights and popular diners. This is a once-in-a-lifetime adventure.

Travel Gems+

Chicago River
Take a sightseeing boat ride along the Chicago River and marvel at the scale of the state-of-the-art, high-rise design that the city encapsulates, as well as the outstanding architecture that the city is known for, with points of interest including Tribune Tower, the Wrigley Building, Marina City, Trump Tower and Willis Tower. Alternatively, you could head up to The Peninsula Chicago's  Spa which boasts views of Lake Michigan and the Gold Coast.

Sightseeing Tours
A great way to acquaint yourself with the city and take in the sights without doing too much walking is to hop on and off one of the city's classic Green or Red Trolleys or double-decker buses.

Jazz/Blues Festivals
If you love jazz and/or the blues, time your visit to coincide with one of the hundreds of festivals and parades that take place each year - feel free to ask your Travel Consultant for the most up-to-date details.


Whilst largely undeserving of its nickname, the `Windy City', Chicago is nevertheless rather brisk during the winter months and the gales, snow and low temperatures keep most sensible people indoors. In the summer months, Chicago gets extremely hot, whilst spring can be unpredictable, making autumn (September to November), when it’s sunny and mild, probably the best time to visit.

Temperature Guide

These figures show monthly average maximum temperatures and monthly average rainfall for Chicago.

  Temp °C Rain mm

Getting There+

Flight Information
British Airways, Virgin Atlantic and United Airlines direct from London Heathrow. American Airlines direct from London Heathrow and Manchester.

Flight Time
From London Heathrow to O'Hare International, Chicago: 8 hours, 35 minutes.

Travel Documentation+

Travelling With Children or Without an Adult

Children travelling without both parents should be aware that some countries require documentary evidence of parental responsibility before allowing lone parents to enter the country or, in some cases, before permitting the children to leave the country. Please contact the relevant Embassy for the county you are travelling to for further information.

Visa and Advance Passenger Information

All passengers must ensure they have a valid, acceptable passport, any required visa and any other documentation for both the final destination and any stop-off points en route. Please make sure that Advance Passenger Information is submitted in advance to travel for all destinations. Failure to hold correct documentation or submitting incorrect details with Advance Passenger Information or Visa applications may result in refusal of carriage or entry into a country. Please check with the relevant Embassy regarding visa requirements well in advance of your travel date. Charges may apply for some visas.

Travel Advice Update
The FCO travel advice for the USA has been updated with an amendment to the Entry requirements section - on 18 December 2015, the US Congress passed a Bill updating the requirements for the Visa Waiver Programme (VWP); under the new rules, with effect from 1 April 2016 all travellers wishing to enter the US under the VWP will need to hold a passport with an integrated chip.

The web-based Electronic System for Travel Authorisation (ESTA) requires all passengers (including infants) travelling via or to the USA to apply for authority to travel a minimum of 72 hours prior to travel. You may be denied boarding or refused entry to the US if you have not registered and obtained authorisation. To apply visit the official website: A charge of UD$14 per person (subject to change) will apply and must be paid by either credit or debit card. For up-to-date resort information, visit

Customs and Border Protection programme Global Entry gets pre-approved travellers through border control faster at some US airports. If you’re a British citizen and a frequent visitor to the USA you can now register to get a UK background check on If you pass the background checks, you’ll be invited to apply for Global Entry.

Passengers not travelling on a British Passport are advised to contact their relevant Foreign & Commonwealth office for individual Visa requirements.

For up-to-date resort information, visit


Health facilities, hygiene and disease risks vary worldwide and you should take health advice about your specific needs from your general practitioner or a specialist clinic as early as possible before travel. Those planning to become pregnant should discuss their travel plans with their healthcare provider to assess their risk of infection with Zika. For information about Zika, other mosquito-borne diseases (such as Dengue fever and Chikungunya), Lyme Disease (caused by tick bites), and to receive advice on mosquito bite avoidance measures, please visit Insect and tick bite avoidance. In addition, we highly recommend that you seek specialist advice from your doctor and, where recommended, obtain vaccinations or tablets for protection against, for example: Malaria, Hepatitis A, Polio and Typhoid. In some cases, treatments for Malaria should begin well in advance of travel. Travellers may also be required to show Yellow Fever Certificates on arrival in certain destinations i.e, some African countries. Please note that you are strongly advised against scuba-diving for 24 hours before travelling by air. We would also like to draw your attention to the risk of DVT (Deep Vein Thrombosis) and recommend that you consult with your doctor before travelling. Visit the FCDO website and select your destination country for the very latest travel advice: Foreign Travel Advice. Additional sources of information include: Public Health England, The National Travel Health And Network Centre, Foreign And Commonwealth Office and your General Practitioner or a specialised clinic.

Talk to our Americas experts

Our dedicated Americas experts are ready to help you design your luxury holiday to Chicago. Furthermore, we have many Luxury Travel Specialists who've personally visited Chicago and can offer you their first-hand knowledge and experience.

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