
We use cookies to enhance your browsing experience, serve personalised content, and analyse our traffic. By clicking "Accept All" you accept this and consent that we share this information with third parties and that your data may be processed in the USA. For more information, please read our .
You can adjust your preferences at any time. If you deny, we will use only the essential cookies and unfortunately, you will not receive any personalized content.

Your hotel is packed with Chicago history
From £539 pp
Pirates, with the U.S. reopening for tourists, here's a great deal to visit Chicago this winter!
We've found great rates for a 5-night stay at The Millenium Knickerbocker hotel, which sits right on Magnicent Mile, in the heart of the city. The hotel has plenty of Chicago history and is known for it's 1920s architecture and for Al Capone running a gambling ring there!
The holiday, including flights, starts from £539* per person. If you have more time, make it a week and pay only £56 more!
Travel duration: 5 (longer or shorter stays possible)
Example date: 23 February 2022 (more dates available)
Example flight from London, other airports available at extra cost
Flight + Hotel package from Loveholidays
4* Millennium Knickerbocker Chicago
4/5 stars on Tripadvisor
Board basis – Room Only
Hand luggage included (check airline policy)
Based on 2 sharing
ATOL-protected holiday
Bags and transfers can be added when booking
Five nights from £539* per person
Seven nights from £595* per person
The Millennium Knickerbocker Hotel opened in 1927 and is packed with Chicago history. It's in an area now called Magnificent Mile, Chicago's famous entertainment, shopping and dining district and home to the city's famous Water Tower landmark.
The hotel was known to be a place where Al Capone ran gambling rings and a speakeasy. You can still find a secret backdoor gangsters cut into a wall that helped them escape when police came for raids In the 1970s Playboy Enterprises bought the building, running it as the Playboy Towers Hotel.
Pirates, we love exploring a new city by checking out a new breakfast place every day. Your stay includes room-only rates, as there are plenty of amazing breakfast opportunities around the hotel (you can book your stay with breakfast if you prefer to eat at the hotel). Try the Rosebud on Rush Street, which is only a 10-minute walk from the hotel.
If you rent a car for your city trip, be aware that there's not parking at the hotel. Please check with the hotel as they can give you the cheapest rates for the area.
You can go for a week and pay only £56 more per person!
This holiday package is flexible and you can easily adjust the duration, month, amount of travellers and departure airport of the holiday.
Please note -- *Prices are correct at time of publishing, based on the sample dates provided and are subject to fluctuation, depending on availability. Inventory may be limited. Special T&C’s may apply. *The above prices do not include city / tourist taxes that are / may be payable at the hotel.