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Chicago Holidays

Updated on February 13, 2012

Welcome to Chicago

It was Sinatra’s kinda town and dozens of other songs pay homage to it.

At least two musicals have used it as their backdrop (who could forget the British production of Windy City in 1982?) and it’s the name of a rock band (still touring and coming to a town near you soon). Chicago, ‘the City with Big Shoulders’ and the third most populous city in the United States, welcomes some eighteen million visitors every year and hosts 35,000 conventions

While the city may stand in the shadow of more cosmopolitan New York or cutting-edge LA, there’s no shortage of top-rate art and architecture or street-level excitement – with less of the hassle and infrastructure problems of its coastal rivals. Chicago is sport-obsessed, and contains one of America’s best-loved ballparks, Wrigley Field

There’s a strong tradition of live music with a phenomenal array of jazz and blues clubs and ‘Chicago-style’ food will keep your taste-buds (and your wallet) satisfied. Welcome to what one writer called ‘the most typically American place in America.’

Getting to Chicago

By Air

Chicago is a major hub for domestic and international travel and is well served by a number of airlines world-wide. Flying direct into O’Hare International Airport – the country’s second busiest – is your quickest and easiest approach. O’Hare is on the city’s north-west side, about 17 miles out from the centre. It’s served directly by train, taxi, shared-ride van, shuttle and bus. Within the airport, the Airport Transit System provides a quick, convenient, and free service for transfers to and from the terminals. It can also be used to reach the long-term parking facility.

The quickest and most reliable way to travel downtown by public transport is to use the Chicago Transit Authority (CTA) Blue Line train which leaves every eight minutes. Details at Tickets are about $2 one-way.

The shuttle centre is on the ground floor of the elevated parking garage. Continental Airport Express shuttles leave the airport every five to ten minutes; tickets can be purchased at the kiosk outside the international terminal and at the lower levels of terminals 1, 2 and 3.

Alternatively, reserve online at

The shuttle will take you to your hotel for around $25, but bear in mind it’s a shared service and there could be several stops on the way. Taxis are the most expensive option and you’re at the whim of Chicago traffic. A single fare could run anywhere from $40 up, plus tip. Cabs are plentiful and can be found outside any terminal.

Midway Airport, on the city’s southwest side, sees a much smaller flow of mostly domestic commuter flights, but is nonetheless an option for those already in the US who have included Chicago on a multi-city itinerary. The quickest and cheapest way to reach downtown from here is the frequent CTA Orange Line train which makes the ten-mile trip in just under half an hour. Alternatively, you can pick up a taxi just outside the baggage claim area. Fares are metered and a ride into downtown will set you back about $25 plus tip. The Continental Airport Express Shuttle is also available from Midway. The fare’s around $20.

By Train

Travel by train can be a more scenic and leisurely option, though not likely to be much cheaper than air travel. Amtrak rail services ( connect Chicago with most major US cities.

But bear in mind that this is one of the world’s largest countries with vast distances separating the major destinations. A train journey from New York to Chicago, for instance, would be an overnighter taking between 17 and 19 hours.

By Road

The national bus line, Greyhound ( runs frequent buses from major Midwestern cities (Cleveland, Indianapolis, Milwaukee, Minneapolis) – usually around ten a day from each city.

There are also a few buses from farther afield, but again, it’s a long journey from, say, New York or the West Coast. Driving to Chicago will give you some flexibility, but once you reach the city you’re not likely to need a car unless you’re short on time or want to explore outlying areas.

Arranging a car in advance will save you money. At least four major expressways feed into downtown Chicago: I-90/94 from the northwest and north; I-290 from the west; I-55 from the southwest and I-90/94 from the south.

Chicago Travel Tips


George Bernard Shaw once said that England and America were two countries separated by a common language. The language is English but delivered in Chicago-style. Although not as cosmopolitan as New York, there’s a sizeable Hispanic population here too.

Currency And Tipping

The American dollar ($) or greenback, made up of 100 cents. And just in case you need to know, a nickel is 5 cents, a dime is 10 and a quarter 25. Tips are a very important part of some workers’ salaries. In hotels, tip bellhops at least $1 a bag ($2-$3 if you have a lot of luggage) and give the chamber staff $3 a day (more if you’ve left a disaster area for him/her to clear up or if you’re travelling with kids/pets).

Tip the doorman or concierge only if he or she has provided you with a specific service (for example, calling a cab or obtaining difficult-to-get theatre tickets).

Tip the valet parking attendant $1 every time you get your car. In restaurants, bars and nightclubs, tip service staff 15-20% of the check, bartenders 10-15% and coat-check attendants $1 a garment. Cab drivers expect 15% and hairdressers/barbers 15-20%.


For the most part, violent crime in Chicago is concentrated in a few areas, notably pockets of the South Side and West Side.

Tourists, however, have no real business venturing into these areas and therefore shouldn’t expect to encounter problems beyond what they’d expect in any major American city.

The usual precautions and common sense should keep you safe. Stick to well-lit streets at night. Don’t have expensive jewellery on view and don’t carry nice cameras, bags or any other items that might draw attention to you. Men should keep wallets in the front pocket, women should wear purses across the shoulder. When riding the subway at night (not advisable after midnight), have your wits about you and don’t fall asleep.


The public transport system in Chicago is extensive and efficient. Most sights can be reached on the city’s El (elevated) train system, while buses, though slower, fill in the gaps.

The CTA’s El runs on seven colour-coded lines that cover most downtown areas and neighbourhoods. Each line radiates from The Loop, the area that forms the compact heart of Chicago. Fares are $1.75 a ride, but there are lots of options for visitor passes, details on

The CTA also runs Chicago’s buses. There’s not much reason to rent a car in Chicago – congestion and a lack of parking spaces, especially in the Loop, can make for a harrowing experience.

Chicago is, however, a bike-friendly city with miles of bike lanes, plenty of bike racks and some twenty El stations where riders can store their bikes indoors and hop on the train.


“I miss everything about Chicago except January and February,” said American actor, Gary Cole. The city’s climate ranges from the unbearably hot and humid in midsummer to well below freezing from December through February.

The best times to visit are in the early summer (May-July) and early fall (September and October) when the weather is at its most pleasant. Whatever time of year you come, be sure to dress in layers: buildings tend to be overheated during winter and air-conditioned to the extreme in summer. Also bring sturdy, comfortable shoes – you’re going to be doing a lot of walking.


Since 9/11 and, more recently, as a result of a failed plot in Britain to sabotage Transatlantic flights, security has obviously been stepped up to a high level.

The Chicago Airport website, has the latest about what can and can’t be taken into the cabin of the aircraft. It’s important to become acquainted with the restrictions, particularly if you’re travelling with young children because there are instructions about baby milks and medications.

It’s now possible for many travellers, including British citizens, to enter the US without a visa under the Visa Waiver Program. Full details are on the London UK Embassy web-site, or on the site of your city’s embassy or consulate.

Top 10 Attractions

The Sears Tower

Until 1997, the tallest building in the world. The elevator takes about 70 seconds to reach the 103rd floor observatory for a spectacular panorama of the city.

The John Hancock Observatory

Another alternative for skyline viewing.

The Magnificent Mile

The northern part of Michigan Avenue between the Chicago River and Lake Shore Drive is Chicago’s version of Paris’s Champs Elysees. A grand boulevard with exclusive shops, museums, restaurants and ritzy hotels.

Wrigley Field

One of America’s smallest, oldest and best-loved ballparks, home to the Chicago Cubs. Ivy-clad walls, a boisterous crowd, hot dogs and beer.

Navy Pier

50 acres of parks, gardens, shops, restaurants and a 150-foot Ferris Wheel.

Oak Street Beach

A glamorous and unexpected summertime playground, right off the Magnificent Mile.

The Work of Frank Lloyd Wright

The great American architect introduced his ‘Prairie style’ in Chicago and left a collection of eye-catching designs.

Shedd Aquarium

In the Grant Park Museum Complex, with about 70 species, including sharks and stingrays.

Chicago’s Lakefront

Walk, jog or rent a bike and explore the spectacular shores of Lake Michigan.

Marina City

Two cylindrical towers near the Chicago River. Known to locals as ‘the corn cobs’ because of their unique shape.

Boat Tour

The Chicago River, which snakes through the city centre, is best experienced on a boat tour.

Eating and Drinking

If there’s something Chicago does with style, it’s food. Dining out is a big part of the city’s culture. It’s more relaxed and down-to-earth than in other major US cities and that’s reflected in the proliferation of good, reasonably-priced restaurants.

That’s not to say that there aren’t plenty of world-class establishments to give New York a run for its money, where you could easily spend 100 dollars a head. At the other extreme, some of the things that Chicago does best – such as pizza and hot dogs – can be had for a mere $5.

The city built itself around a century ago as the focal point for the distribution and packaging of foodstuffs – possibly the reason why portions locally tend to be not just sizeable but extreme. Servers at many Italian restaurants will make sure to ask you, “Did you want the full portion or just the half?” Steaks are particularly gargantuan and the deep-pan pizzas can easily defeat even the most dedicated trencherman.

Italian beef sandwiches are a speciality in these parts, piled high and slopping out all over the place. It’s a rare Chicago diner who didn’t think he got his money’s worth. Ethnic tastes are well catered for here, too. Close to the city centre, pretty much everything is available.

Most visitors stay in the River North/Magnificent Mile area, where a great number of restaurants are located, such as the Frontera Grill (reckoned by many to have the finest Mexican food in the whole US Gino’s East Pizzeria ( and the Chicago Chop House (

Chicago has been defined by its boisterous drinking scene since at least the early 1900s when Schlitz, a major local brewery, owned more land than anyone else in town bar the Catholic Church.

The city’s hard-drinking reputation was cemented during the Prohibition era of the 1920s and 30s when the need for beer and bathtub gin consumed Chicago in the gangland violence that some still associate with the city eighty years on.

These days, drinking is still a serious business, if usually less dangerous. There are more sports bars here than in New York and LA combined and. beer gardens are popular watering-holes in the summer months. There are also plenty of regular bars, a few English-type pubs and some ritzy cocktail establishments.

Drink prices are fairly reasonable compared with other major US cities, except in the most upscale bars. Local favourites among the beers include Old Style, a mass-produced lager brewed in Milwaukee and the many varieties of Goose Island, a robust Chicago beer from a brewery that runs a few of its own bars in the city.


Chicago ranks right up there near New York for the variety and experience of its shopping. There are classy department stores nestling in historic buildings, especially in the area of the Loop and Near North. You’ll be able to shop even in the dead of winter thanks to the abundance of huge indoor malls. Shopping is concentrated in a few areas of the city:

The Loop

Major department stores such as Marshall Field’s and Carson Pirie Scott are in State Street. All El trains stop in the Loop.

The Magnificent Mile

Chicago’s most famous shopping destination is lined with malls and stores from big-name designers to local establishments. Take the Red Line to Grand.

Gold Coast and the Old Town

Boutique shopping at its priciest happens along Oak Street, close to the north end of Mag Mile. The Gold Coast is reachable on the Red Line (Clark/Division) while the Brown Line stops at Sedgwick in Old Town.

Lincoln Park

The centre of the shopping scene her is the intersection of Armitage Avenue and Halsted Street. Old–established shops make this area a favourite for many Chicagoeans. Take the Brown Line to Armitage.

Night Life

Chicago has one of the best music scenes in the US, often reflecting the changing musical landscape of the country as a whole. Although Louis Armstrong and scores of other top musicians brought jazz from New Orleans more than 75 years ago, Chicago’s modern musical identity is rooted in the blues; indeed, Chicago is considered by many the capital of modern electric blues. Try the Blues bar

There’s also a burgeoning alternative rock scene that came of age in the 1990s, while as far as dance music goes, house and techno are the staple in the clubs. For jazz lovers, a visit to the Green Mill club is a must.

Lincoln Park, Near North and Lakeview have the highest concentration of blues and dance clubs; Bucktown and Wicker Park cater for alternative and indie rockers, while rock ‘n roll can be heard just about anywhere there’s a stage. For current music listings, pick up the excellent free weekly Chicago Reader – copies come out on Thursday afternoon and are usually all gone by Saturday.

Other good sources include the weekly New City and the gay and lesbian Windy City Times. Full listings also appear in the Friday issues of the Chicago Sun-Times and the Chicago Tribune.


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      10 years ago

      Awesome and informative page! what a great way to present Chicago. Good Job.


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