2020 Holidays in Chicago

United States
Chicago's blend of office-laden skyscrapers and rail and steel industries lend it a cosmopolitan feel with blue-collar sensibility. Tourists are drawn to The Loop with its high-rise hotels and iconic attractions like the Willis (formerly Sears) Tower , the world-renowned Art Institute of Chicago , the Museum of Contemporary Photography …

Photos from other travellers

Flying to Chicago

Book cheapest flight tickets to Chicago. You can see the cheapest month to fly and a snapshot of flight prices for the following month. Also, don't forget to factor in your travelling time - the typical flight from London Heathrow to Chicago takes 7 hours, 25 minutes

When to go to Chicago

$1799 per person

The average price of hotels and apartments in Chicago varies according to the time of year. To help you plan when to go, we've looked at the hotels available on our site, then worked out the average price per night for the quietest and the busiest months.

Cheapest Month to visit

January

Based on a typical 1 week holiday - adding together the cost of flights and accommodation - January is the cheapest month to go to Chicago.

Where to stay in Chicago

Whatever your preference, we can help you find the perfect place to stay. From luxurious hotels to practical accommodation, these are our most popular hotels in Chicago, according to travellers like you

Nearby destinations

Milwaukee