From the reflective Cloud Gate sculpture – aka ‘The Bean’ – to the magnificent Art Institute, to delicious, crusty deep-dish pizza, a visit to Chicago is an unmissable one. Spend your days strolling through Millennium Park, getting some retail therapy along the Magnificent Mile, admiring the city skyline from the Willis Tower or John Hancock Building, or eating, shopping and riding the attractions at Navy Pier. You can even take a Segway tour alongside Lake Michigan, or get out on the water with a boat ride. And, when you’ve exhausted your options in The Windy City, you can explore the rest of the USA; after all, this is where the iconic 2,451-mile Route 66 road trip begins.
Popular Tailor-made Chicago Holidays
Whether you want to discover Chicago’s beaches (yes, it has beaches!), ride the 30-degree TILT! attraction, 313 metres above the Magnificent Mile, or simply discover the city’s thriving foodie scene, our tailor-made Journeys to Chicago can help. Designed by our knowledgeable Travel Experts, these epic itineraries will help you experience the best of the city and beyond, so you can really get under the skin of it all. Most importantly, each holiday can be amended to your requirements and includes flights, accommodation, transfers, car hire and a plethora of amazing travel experiences and tours.
Travel to some of the USA’s most vibrant cities on this self-drive journey, taking in the skyscrapers and deep pan pizzas of Chicago, the musical flavours of both
16 days from£ 2665 pp
Tailor this journey
Drive down America’s most famous highway, Route 66, travelling from Chicago to Los Angeles through incredible natural landscapes, desert towns and spectacular
20 days from£ 2859 pp
Tailor this journey
Choose an Option to Start Tailor-Making Your Holiday
Flight Centre’s Travel Consultants really know their stuff when it comes to creating bespoke holiday itineraries. Get in touch below, and let us tailor-make it easy
More About Chicago
Currency: US Dollar
Vaccinations: Extra vaccinations are not required
Flight time: London to Chicago flight time is around 9 hours
Airport: O’Hare International Airport (Chicago)
Visas: British Citizens require an ESTA, which you can apply for online
Top 3 Things to Do in Chicago
- Eat deep-dish pizza
- See the city skyline from TILT! at 360 Chicago, in the John Hancock Building
- Snap a photo in front of ‘The Bean’
When to Go in Chicago
The nickname ‘The Windy City’ actually has nothing to do with Chicago’s weather or the gusts that blow across Lake Michigan. In fact, it comes from politicians in the late 1800s, who were supposedly full of ‘hot air’. So, in reality, the city is actually a great place to visit year round. The winters can be bitter, but promise plenty of festive cheer for lovers of Christmas – there’s an ice rink, the ‘Christkindlmarket’, inspired by Germany’s seasonal markets, and attractions are adorned with fairy lights. Summer brings the most tourists but also the most festivals – there’s always something to do. For temperate weather and fewer crowds, visit during spring and autumn.
Why Book Your Chicago Holiday with Flight Centre
We know Chicago: Many of our Experts have visited Chicago while our USA specialists work closely with the region’s hotels and tour operators to ensure our holidays feature the latest and greatest it has to offer, and at the best-value prices.
Local knowledge: Flight Centre has stores throughout in Chicago, giving us access to fantastic local knowledge. With a team on the ground, we’ll not only ensure you have a fantastic experience, but also offer you insider information and tips that only locals will know.
Flexibility: We offer flexible deposits, the opportunity to pay the balance of your holiday just 10 weeks before departure and fixed change and cancellation fees.
Flight Centre concierge and 24/7 Emergency Assistance Service: When you book a holiday to the Chicago from our range of tailor-made Journeys, you’ll also enjoy access to our inclusive concierge and 24/7 Emergency Assistance services.