Chicago and New York, with rich histories and vibrant atmospheres, attract global visitors seeking dynamic urban adventures.
CHICAGO HOLIDAYS
Expect to find
Striking Skylines & Lakefront Views
Walk among iconic skyscrapers, take in sweeping views from observation decks and unwind along Lake Michigan’s scenic shoreline.
Deep Dish Done Right
Indulge in Chicago’s iconic deep dish pizza at legendary spots like Giordano’s or discover hidden local favourites.
Music That Moves You
Experience live blues and jazz in intimate clubs where local talent shares the stage with world-renowned artists.
Overview
Welcome to Chicago
Chicago is one of America’s most exciting cities, offering everything you need for a memorable city break. From bold architecture and legendary blues bars to deep dish pizza and lakefront strolls, Chicago is packed with culture, history and plenty of things to do.
Set on the shores of Lake Michigan, the city is made for exploring, with world-class museums, lively neighbourhoods and iconic sights all within easy reach. Walk along the Chicago River, catch views from the Skydeck or relax in one of the many parks and cafés.
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Discover Chicago’s exciting culture, history and food in your next USA holiday.
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Chicago Holidays
Explore iconic architecture, lakefront parks and vibrant neighbourhoods with our handpicked Chicago city break offers.
Centennial Historic Route 66 Escorted Tour
Centennial Historic Route 66 Escorted Tour
14 Nights From €4699 per person
Get your kicks along America’s mother road and most historic highway, Route 66!
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Eagle Rider Route 66 Self Guided Motorcycle Tour
Eagle Rider Route 66 Self Guided Motorcycle Tour
14 Nights From €4999 per person
A 15-day journey riding along the world famous “Mother Road” highway from Chicago to Los Angeles by motorcycle.
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Things To Do In Chicago
Lakefront & Landmarks
Stretching along Lake Michigan, Chicago’s shoreline is made for exploring. Walk or cycle the boardwalk, relax on city beaches or hop on a lake cruise for views of the skyline from the water. Back on land, stroll along the Chicago Riverwalk or head to Millennium Park to see the famous Cloud Gate sculpture, known as ‘The Bean’. For unbeatable views, go sky high at the Willis Tower’s Skydeck or 360 Chicago in the John Hancock Center.
Music, Sport & Nightlife
Whether it is blues, baseball or buzzing bars, Chicago delivers. Catch live music at the legendary House of Blues or enjoy a late night set at Kingston Mines, where the music plays into the early hours. Sports fans should make time for Wrigley Field Baseball Stadium, where tickets are often available on the day. After dark, head to a rooftop bar, comedy club or local brewery for a taste of the city’s nightlife.
Food, Pizza & Neighbourhood Eats
Chicago is famous for its deep-dish pizza, a thick-crust pie with layers of cheese topped with tangy tomato sauce. Giordano’s is one of the city’s most renowned places to try this iconic dish, offering a true taste of the Chicago pizza experience. Chicago’s food scene offers plenty of variety, from traditional steakhouses to taquerias and bakeries. Each neighbourhood has its own flavour, so it is worth exploring areas like West Loop or Pilsen for something truly local.
Museums and Tours
Chicago’s museums offer something for everyone, from the stunning Impressionist collection at the Art Institute to the immersive exhibits at the Field Museum. If you’re after something different, take a stroll along the Chicago Riverwalk or join a boat tour to explore the city from the water. Walking tours reveal fascinating stories of Chicago’s past, including the lives of famous mobsters and the city’s rich history.
Best Times To Travel To Chicago
Spring in Chicago sees average temperatures rising from around 4°C in March to 18°C by May. It’s a lovely time to explore parks, riverside paths and outdoor attractions before summer crowds arrive. March brings the famous St. Patrick’s Day celebrations, including the iconic dyeing of the Chicago River and a lively parade through Grant Park. Expect the weather to be changeable, so layers and a light raincoat are wise.
Summer is Chicago at its liveliest, with long sunny days and average highs between 24°C and 29°C. This is festival season, with headline events like Lollapalooza and Chicago Blues and Jazz Festivals drawing big crowds. The Navy Pier hosts twice-weekly firework displays over the lakefront, and the city’s beaches, rooftop bars and riverside cafés are in full swing. It’s a popular time to visit, so booking ahead is advised.
Autumn is a fantastic time for a city break, with mild temperatures around 22°C in early September, cooling to 7°C by November. Crisp days and autumn foliage make city walks especially scenic, and cultural events continue throughout the season. Crowds thin out after summer, making it easier to enjoy top attractions at a relaxed pace. It’s also a great time to catch local sports, theatre shows or explore neighbourhood food spots without the heat.
Chicago winters are cold and often snowy, with temperatures ranging from -6°C to 2°C. While not for everyone, winter brings a magical atmosphere with festive lights, ice rinks and cosy cafés. Holiday markets and Christmas displays create a buzz in December, and the city’s museums, jazz clubs and restaurants offer plenty to enjoy indoors. If you’re prepared for the weather, this quieter period can offer excellent value and fewer crowds.
Chicago, IL, USA
Location
Chicago is the United States’ third largest city, yet it is surprisingly easy to navigate. Situated on the western shore of Lake Michigan, one of the Great Lakes, it combines an urban feel with natural beauty. The city is famous for its striking architecture that spans from historic Art Deco buildings to modern skyscrapers. Visitors can enjoy waterfront parks, lively neighbourhoods, and a rich cultural scene that includes world-class museums, music venues, and sports stadiums.
Guides
Staff Tips
Chicago's annual summer dance festival is held for 11 weeks each year. Get a free one-hour dance lesson and follow that by indulging in two hours of live music and dancing.
Emer ThomasOperations Manager
Chicago- Head to the underwater viewing area to catch a glimpse of swimming sea lions or take a guided tour of the hundreds of species on view at the Lincoln Park Zoo. Admission to the zoo is free seven days a week.
Fiona KellyPersonal Travel Planner
Chicago - You can't go wrong with the Wiener Circle or Byron's, both by Wrigley Field, for a genuine Chicago dog & fries experience. For deep dish pizza, Uno/Due are owned by the same place so you'll get an equally wonderful meal at either. Be prepared to wait though, the lines can be 2 hours long in summer. Giordano's is an acceptable alternative.
Claire SomersPersonal Travel Planner
Chicago - See a free water display every hour at the Buckingham Fountain from mid-April to mid-October. The best time to go is between dusk and 10 p.m. when the fountain's 134 spouting jets are accompanied by a music and light display.
Denise WalshPersonal Travel Planner
Chicago - Definitely check out Wrigley Field, home of the Chicago Cubs baseball team. Catch a game and enjoy the experience of attending an American baseball game or enjoy a stadium tour. With over 100 years of history there's lots to see and learn!
Emer ThomasOperations Manager
Chicago FAQs
What are typical opening hours for shops, cafés, and attractions in Chicago?
Most shops and cafés open around 9 or 10am and close by 6 or 7pm. Tourist attractions often stay open later, especially in summer.
Are Sunday hours or public holidays likely to impact travel plans or availability?
Some shops and attractions may close early or not open at all on Sundays and major public holidays like Thanksgiving or Christmas, so it’s best to check ahead of time.
What should I expect from Chicago’s weather—especially if I’m visiting in spring or winter?
Spring can be changeable with chilly, rainy days, while winters are cold with frequent snow and temperatures often below freezing. Layers and windproof clothing are essential.
Is Chicago a good base for exploring other parts of the Midwest or for starting a longer trip across the U.S.?
Yes. Chicago’s major airports and transport links make it a convenient hub for exploring the Midwest or travelling further across the U.S.
How easy is it to get around Chicago without a car?
Very easy. The city centre is walkable and well connected by public transport including the ‘L’ trains and buses, making it simple to reach most attractions.
How does the public transport system work—can I use contactless cards or do I need a special transit pass?
Contactless payment cards and mobile apps are accepted on Chicago’s buses and trains.
What are the best ways to get to and from major attractions like Wrigley Field or Navy Pier?
The Red Line train is a cheap and quick option to reach Wrigley Field, while Navy Pier is easily accessible by bus, bike or a scenic walk along the lakefront.
Are taxis or ride shares recommended?
Ride shares like Uber and Lyft are widely used and convenient. Licensed taxis are also available but can be more expensive. Public transport is usually quicker and cheaper.
Which neighbourhoods are best for a local, authentic Chicago experience beyond the tourist areas?
Pilsen, West Loop and Logan Square offer rich cultural experiences, local markets, street art and independent eateries.
What are some common local customs or etiquette travellers should be aware of?
It is polite to greet people when entering shops or eateries. For dining, tipping around 15-20% is expected.
How accessible is Chicago for travellers with mobility needs or pushchairs?
The city is generally accessible, with many transit stations equipped with elevators and ramps. Most major attractions and shops also accommodate mobility needs, but it’s advisable to check ahead of time.
Are there any safety tips visitors should keep in mind while in Chicago?
Like any large city, it’s best to stay aware of your surroundings, especially at night. Stick to well-known areas and use licensed transport options.
What should I pack for a trip to Chicago?
Pack layers and waterproof clothing for variable weather. Comfortable walking shoes are essential. If visiting in winter, warm coats, hats, scarves and gloves are a must.
