Chicago holidays

America’s second city is anything but when it comes to top attractions. Beneath its glittering skyline lies a bustling metropolis packed with cutting-edge museums, lakefront beaches, and enough blues bars and ball games to keep you busy around the clock. Spend your holiday to Chicago trying to do a little bit of everything, but know that you’ll be back for seconds.

Chicago holiday highlights

World-class museums

Every holiday to Chicago should include at least one museum visit. The choices are superb, particularly the Art Institute of Chicago, with its 300,000-piece collection. See ancient Egyptian artefacts and dinosaur fossils at the Field Museum and climb through a real submarine at the Museum of Science and Industry. Get an insider's view of Chicago's rich architectural history at Frank Lloyd Wright's Robie House.

Lakeshore

Spend time on the Lake Michigan Shoreline. Rent a bike and pedal the Lakefront Bicycle Trail, stopping for a picnic and skyline views in Grant or Millennium Parks. Or visit the free zoo in Lincoln Park. Catch the L, Chicago’s transit system, to Grand Station and stroll to Navy Pier for more views from the Centennial Wheel.

Chicago sounds

Chicago has fostered some of the world’s best musical talent. Discover the sounds for yourself at places like the Green Mill, where world-famous jazz acts have played since 1907. For blues music greats, visit Blue Chicago in the River North area. Book your flights and hotels to Chicago when your favourite touring acts are playing the Vic Theatre or the Riviera Theatre.

Chicago: Know before you go

Language

English

Currency

United States dollar ($)

Time zone

UTC-6 (CST) and UTC-5 (CDT)

High season

June – August

Low season

January – February

Find the best time to go to Chicago

Weather in Chicago

March – May: The season welcomes the return of sunshine and spring flowers in city parks and along Lake Michigan. But the weather can change quickly, so don’t forget an umbrella.

June – August: Though June is Chicago’s rainiest month, summer crowds still flock to patios and rooftop bars. July and August can be hot and humid, but breezes off the lake help cool things down at night.

September – November: Autumn is cool and dry. The city experiences its first frosts around October and snowfall in November.

December – February: Cold and cloudy, Chicago usually sees around 94 centimetres of snow each winter. Heavy storms can make for slow going around the city.

Events in Chicago

St Patrick’s Day (March): Thousands head downtown for this day of festivities celebrating Irish heritage. Join the crowds lining the parade route through Grant Park and watch the Chicago River flow green.

Lollapalooza (August): Dance and sing along to some of the world’s biggest musical acts at this sprawling, multi-day outdoor festival.

Chicago Air and Water Show (August): Civilian and military pilots perform synchronised stunts over Lake Michigan during this free, two-day event. Grab a spot on the beach to watch acrobatic displays of aviation.

Bank of America Chicago Marathon (October): Cheer on top athletes as they run through the streets of downtown Chicago in one of the most popular marathons in the US.

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The best neighbourhoods in Chicago

The Loop

The Loop

The Loop is where to stay in Chicago if you want to be near the action. Stroll to city highlights like Millennium Park and the Riverwalk, and shop at the huge Merchandise Market. Join locals at the Blues Festival and Jazz Festival here in summer and sing along to your favourite musicals on Broadway in Chicago at the Cadillac Palace and the Auditorium.

Good for: Shopping, convenience, theatres

Lincoln Park

Lincoln Park

This lakeside neighbourhood is the best area to stay in Chicago if you love nature. Explore the district's namesake greenspace, stopping at the conservatory and free zoo. At night, hear blues at the legendary Kingston Mines club or dip into some fondue at Geja's Cafe. For culture, head to the Chicago History Museum.

Good for: Outdoor activities, dining, live music

Hyde Park

Hyde Park

Hyde Park is the best neighbourhood to stay in Chicago for culture. Start your day at Valois Restaurant, a favourite of the neighbourhood's most famous resident, former US President Barack Obama. Check out the exhibits at the Hyde Park Art Center and the Smart Museum of Art, which has free admission. See authentic Japanese landscaping at Osaka Garden or hike to Promontory Point to enjoy the best skyline views.

Good for: Gardens, skyline views, art

Things to do in Chicago

Shedd Aquarium

Family friendly things to do

The Shedd Aquarium tops the list of things to do with family in Chicago. Encounter sharks and beluga whales in this historic building next to the Field Museum. Spark the kids' imaginations at the Maggie Daley Park Play Garden. Head to the top of Willis Tower for the Skydeck Chicago where you can look through the see-through floor at the street below. 

Shopping

Window-shop or splurge at the boutiques on the Magnificent Mile and State Street. Then, go beyond Downtown to see the diverse options for shopping in Chicago. Browse the independent clothing shops in Andersonville and books and handmade crafts in Hyde Park. Find a unique souvenir in Chinatown or Chicago's largest shopping centre, the 300-store Woodfield Mall.

Beaches

More than 20 beaches in Chicago cover the vast lakefront, so there’s plenty to do if you feel like being outdoors. Try volleyball on North Avenue Beach or combine shopping on the Magnificent Mile with sunbathing at the nearby Oak Street Beach. Paddle onto Lake Michigan with a rental kayak at 31st Street Beach. Or spend a summer afternoon with the kids at family-friendly Montrose Beach.

Nightlife

Explore nightlife in Chicago beyond its live music highlights. Laugh at comedy improv acts at the legendary Second City or stargaze at the weekly late-night sky shows at the Adler Planetarium. Sip creative cocktails at the Chicago Magic Lounge, set in a converted 1940s laundromat. And you’ll always find frothy pints at Double Clutch Brewing in Millennium Park, where there’s outdoor seating in the summer.

Places to eat

Try hearty headliners like deep-dish pizza, Chicago-style hot dogs and Italian beef sandwiches. There’s a wide diversity of restaurants in Chicago. Munch on tacos at Xoco or sample modern Mediterranean at Aba. Ride the L to Argyle Street for Southeast Asian fare or let your taste buds guide you on a visit to Fulton Market.

Free things to do

Check out public installations like Millennium Park's Cloud Gate without paying admission. Other free things to do in Chicago range from taking in a performance at the Chicago Cultural Center to spending a summer evening on the Chicago Riverwalk. You can also meet rhinos, giraffes and more at one of the country's last free zoos in Lincoln Park.

Plan your holiday to Chicago

Budget

As one of the most affordable big cities in the US, cheap holidays to Chicago are a breeze. Enjoy free attractions like Millennium Park, and hunt down cheap eats in neighbourhoods like Pilsen and Chinatown. A meal at an inexpensive restaurant will cost you about 25 US dollars ($). A short taxi trip will be around $7, but you can save even more by using public transport.

Day trips from Chicago

Explore the historic mansions and buildings of downtown Joliet, a little more than an hour away by train. Visit nearby Midewin National Tallgrass Prairie to experience what the Great Plains looked like before human habitation. East along the lake shore, the dramatic landscape of Indiana Dunes National Park is the perfect retreat from city skyscrapers.

Getting around Chicago

The Chicago Transit Authority (CTA) operates eight L-train lines and more than 100 bus routes. Buy single fares at train stations and on buses. Or purchase a reloadable Ventra Card at convenience stores in the city. The card also works on regional Metra trains. Use the Ventra App to reload your card and plan trips.

FAQs about Chicago holidays

The United States dollar (USD) is the currency you'll use for day-to-day purchases and activities during your trip to Chicago.
Organise your Chicago trip for January and you'll be there when conditions are at their coolest. -12ºC (10ºF) is as cold as it gets.
The wettest month is June, which has an average rainfall of 14 cm. But don't let that take the shine off your Chicago trip — there's still loads to do indoors like shopping, visiting galleries, or checking out cosy cafes.
While on your city break in Chicago, you'll hear the locals speaking mostly in English.
You can easily hit the Magnificent Mile, Navy Pier and the Field Museum during a weekend break in Chicago. Set aside at least four days if you plan to explore the neighbourhoods and sample the restaurant scene.
May is the cheapest month to travel to Chicago based on airfares. Cash in on the savings on Chicago flights and hotels and reward yourself with an extended break.
With temperatures reaching a high of 29ºC (84ºF), July is the hottest month in Chicago.
Chicago's crime rates are similar to other major US cities. Risks vary from neighbourhood to neighbourhood. Exercise caution, know where you are going and remain in crowded areas instead of wandering alone, especially at night.
Whether you're an explore-every-inch traveller or a more relaxed explorer, the cost of your city break in Chicago will largely depend on how you want to experience it. Be sure to factor in everything from meals to entry fees, on top of your Chicago flights and hotels.
Whether it's your first visit or your tenth, this city always has something new to offer. If seeing the sights is on your list of things to do in Chicago, don't forget to include Millennium Park and Art Institute of Chicago.
Daily high temperatures are between 27°C and 30°C from June through August. Nightly lows dip below 0°C from December through March, with Lake Michigan winds making it feel even colder. Winter clothing is a must for a city break in Chicago during these four months.

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