Mon - Fri 9:00am - 5:30pm
Sat 10:00am - 4:30pm
01242 386 474
Call us
Book a new holiday to Chicago with confidence

Flexible booking conditions apply

For all new bookings made up to 31 December 2021 for travel before 31 December 2022, we are offering our guests the flexibility to change or postpone up to 15 days before your travel date. A&K will not charge you should you choose to change to a new destination or move your travel dates and you can rebook to travel any time before 31 December 2022.

Best time to go

May - October

Time difference

GMT -6 hour

Flight duration

8 hours 45 minutes

Fly to

Chicago O'Hare

Get a taste of Chicago’s award-winning fare at one the city’s mouth-watering food festivals

Our Chicago city breaks offer stunning lakefront views, vibrant art scenes, personality-packed neighbourhoods, award-winning dining and no shortage of shopping at Michigan Avenue's 'Magnificent Mile'.

Upon arrival in Chicago, crane your neck skywards to take in the city’s mighty skyscrapers.There’s no shortage to admire, from the famous Willis Tower to the John Hancock Building.

And now you are free to take a look around at ground level. Once you’ve settled in, we’ll help you find the finest cuisine. From famous Chicago deep-dish pizza to food festivals like the Chicago Gourmet and Taste of Chicago, the city is awash with fantastic fare to satisfy every palate. Chicago’s chefs are increasingly considered the best in the US.

Housing some of the best Impressionist and post-Impressionist artworks in the world, be sure to pay a visit to the Chicago Art Institute, located close to the city’s Millennium Park. The Museum of Science and Industry is also nearby. Home to the only German WWII U-Boat in the United States, this offers a great family day out.

If you’re looking for immersion in the city’s jazz and blues scene, there’s no shortage of places to go. But if you’d prefer something a little lower key, our clients often comment on the quality of the countless beaches and the gorgeous 30km stretch of lakeside bike trails at Lake Michigan. There is no place better for a moment’s peace and quiet from the bustle of city life.

North America team

Whether it's an epic road trip, a relaxing escape or a whale-watching expedition, our North America team know how to plan the ultimate holiday
Meet the team

Still looking for inspiration?

We have a huge range of destinations, experiences and hotel options available.

Learn more about our luxury tailor-made holidays and unparalleled escorted tours to USA

Interested in this destination?

Call us on 01242 386 474