Chicago Holidays

From iconic landmarks to world-class food, Chicago is a lively city packed with unforgettable experiences for all.

Highlights

• The Magnificent Mile - A shopper's paradise lined with top-tier brands and swanky restaurants.

• Navy Pier - Fun for everyone, this hotspot features rides, attractions, and gorgeous views of Lake Michigan.

• Deep-Dish Pizza - Chicago’s culinary claim to fame – cheesy, thick, and downright delish!

• Architecture Tour - Get your culture fix while cruising down the Chicago River, taking in the city's stunning skyline.

Getting around

Chicago’s got one of the best transport systems in the States, making it super easy to get from A to B. The ‘L’ train system is the city’s public transport superstar, offering a swift and scenic way to explore the area. Plus, with buses running frequently and taxis or rideshare apps on hand, you'll never be stuck. Feeling fancy? Grab a boat tour and explore the city via its waterways. And don’t forget, Chicago’s pretty walkable too, especially around popular spots like Millennium Park and The Loop.

Things to do for families in Chicago

If you’re heading to Chicago with the kiddos in tow, you’re in luck! Start your family day out at Navy Pier, where there’s no shortage of rides, games, and even a children’s museum. The Shedd Aquarium is another family favourite, showcasing aquatic wonders from all corners of the globe – expect to see everything from playful dolphins to glowing jellyfish. Got budding scientists in your crew? The Museum of Science and Industry is perfect for curious little minds. And for some outdoor fun, don’t miss Lincoln Park Zoo, one of the oldest (and free!) zoos in the country.

Things to do for couples in Chicago

Chicago city breaks are fab for a romantic getaway. Start your day with a stroll through Millennium Park, where you can snap a selfie by the famous Cloud Gate sculpture, aka "The Bean". From there, head up to the 360 Chicago Observation Deck at the John Hancock Center for jaw-dropping views of the city and Lake Michigan – perfect for those loved-up moments. Fancy a swanky date night? Chicago’s got a proper good restaurant scene, with Michelin-starred restaurants and cosy jazz bars like The Green Mill where you can enjoy live music in an intimate setting. End the night with a sunset cruise along the Chicago River for a dreamy way to take in the city lights.

Things to do for groups in Chicago

Whether you're heading to Chicago with your mates or looking for a jolly with a larger group, this city knows how to bring the fun. Why not kick things off with a bang by catching a Chicago Cubs game at the legendary Wrigley Field? The atmosphere is always popping off, and it’s a proper good way to experience American sports culture. Fancy some thrills? Head to Six Flags Great America, just outside of the city – it’s perfect for an adrenaline-packed day. And for some group laughs, don’t miss The Second City, Chicago’s famous comedy club where you can catch live improv performances (it’s the birthplace of some of comedy’s biggest names, like Tina Fey!). Round it all off with a night out in River North, where the bars and clubs are always buzzing.

Things to do for foodies in Chicago

Attention all foodies – Chicago is the ultimate destination for anyone who loves to indulge. You simply can’t visit the city without tucking into a deep-dish pizza – it's a whopper of a meal and a unique Chicago experience. But the food scene doesn’t stop there. Head to the West Loop for a sizzling selection of Michelin-starred restaurants, trendy eateries, and hidden gems. Girl & the Goat, for instance, is a must-visit for those looking to treat their taste buds to some seriously creative dishes. Craving street food vibes? The Chicago French Market offers delish options from local vendors, perfect for a snack on the go. And if you’re feeling extra boujee, why not book a spot at Alinea, one of the best restaurants in the world, for a multi-course culinary adventure that’s truly top-tier.