Chicago holidays

Find and compare the best Chicago holiday deals

United States
Cook County
30 December 2023 | 7 nights | 2 people

4* Chicago Christmas Break – Award Winning Hotel


Flights inc

Join the club...

Be the first to hear about discounted holidays, flash sales and amazing travel competitions to Chicago!

Things to do in Chicago

Books inspired by Chicago

Our hand-picked selection of books to get you in the mood for your Chicago holiday

The House on Mango Street

Sandra Cisneros

A coming of age story about Esperanza, a Hispanic child in Chicago, told through a series of vignettes as she attempts to make sense of life and find her own path in a foreign world. Vividly written with Chicago as an interesting backdrop.

Chicago Blog posts

From the UK's most popular travel bloggers


Weekend in Chicago: Itinerary for 3 days in Chicago + map

27th April 2022 by PommieTravels

I first visited Chicago all the way back in 2010 and my recollection of the city had become somewhat hazy so I decided it was high time I go back. This time I returned to The Windy City with the sole purpose of writing this detailed weekend itinerary so I hope you find it useful! I’ve visited in both summertime and winter now and I’d suggest visiting in summer if you can. Winter is just brutal and with that wind, it makes it difficult to walk around for too long. Summertime brings warmer...


Norwegian launches new services to Chicago and Austin from Gatwick

1st April 2018 by Stuart

It's been a soaring week for Norwegian Air. The third largest low-cost carrier in Europe has expanded their long haul destinations to include American cities Chicago and Austin, bringing their US destinations tally to 14.The London Gatwick to Chicago service began on Sunday 25th March and will be flying four times a week to Chicago O'Hare International: Monday, Wednesday, Friday and Sunday. They'll depart from Gatwick at 10am, arriving in Chicago at 12.25pm (8h25min duration). Return flights...


Triumphs, Travels and Route 66: The inspirational story of Mark & Sarah Pritchard

19th January 2021 by John

As a Brit, it can be difficult to comprehend the enormity of the USA. We see our island as being big, but when you see places on the US map that seem to be close to each other, you may find that it could take a couple of days to drive from one to the other. To drive across America seems, at first, to be a daunting prospect, and how could you possibly put its size into perspective so that you can relate to it? Our Story In fairness, in most people’s eyes, we have travelled our own epic...


Cities with the best street food

1st March 2021 by Andy

Grabbing a bite from street vendors is one of the best ways to discover a new culture. Different flavours, textures, and spices can tell you a lot about a country’s history, its people and their daily lives. And, of course, some cities simply serve the most delicious food ever at incredibly low prices. So, if you are planning your next getaway, consider exploring one of the cities below - your taste buds will thank us!BangkokThailand - It’s hard to find an inch on the streets of Bangkok...

Weather in Chicago

Our month-by-month guide to the weather and climate in Chicago


Chicago weather in


Chicago weather in


Chicago weather in


Chicago weather in


Chicago weather in


Chicago weather in


Chicago weather in


Chicago weather in


Chicago weather in


Chicago weather in


Chicago weather in


Chicago weather in