^ Book your 2025/26 holiday with Netflights and secure your holiday with a deposit from £49 per person. Call us on 0330 029 3995 to find out more (calls charged at a local rate). Deposit amounts may vary. The exact deposit required will be advised at the time of booking. This offer only applies to flight and hotel bookings made in one transaction over the telephone with an agent. This promotion is not applicable to bookings made online. The balance of the cost of your travel arrangements must be paid 8 weeks prior to the departure date. If your booking is made within 8 weeks of your departure date, the total cost of your travel arrangements must be paid at the time of booking. PLEASE NOTE FAILURE TO PAY ON TIME WILL RESULT IN CANCELLATION. The above prices are guidelines only and are correct at the time of publishing. Subject to availability. Family prices are based on 2 adults and 2 children under 12 sharing a room. Other travel dates are available, supplements may apply. Please use the search box or call for details. For more information please read our Pricing Terms and Conditions.
Holidays to Chicago – £49pp deposits^
from as little as £714
3 nights in Four Points By Sheraton Chicago O'hare Airport, Chicago, departing London Gatwick on 15 / Aug / 2025 with Icelandair
Subject to availability, prices correct of the last 24 hours
Find the perfect Chicago holiday package
Chicago holidays are perfect for those looking to venture to the United States and experience a city break like no other.
Nicknamed the Windy City, tourists can experience a captivating mix of history and culture. Dominated by stunning skyscrapers, the Chicago skyline is recognised across the world and contains some of the finest architecture you’ll ever see. From fascinating museums to lush green parks, and trendy restaurants to vibrant nightlife, there's plenty of activities to fill your time in Chicago!
Featured holidays in Chicago
Book now, pay later with low deposit holidays from £49pp^ - call 0203 139 7579 today!from £853 per person 3 nights, Room Only Includes return flights and hotel
View holidayfrom £800 per person 3 nights, Room Only Includes return flights and hotel
View holidayfrom £789 per person 3 nights, Room Only Includes return flights and hotel
View holidayfrom £770 per person 3 nights, Room Only Includes return flights and hotel
View holidayfrom £756 per person 3 nights, Room Only Includes return flights and hotel
View holidayfrom £1,251 per person 3 nights, Room Only Includes return flights and hotel
View holiday5★ Holidays in Chicago
from £944 per person 3 nights, Room Only Includes return flights and hotel
View holidayfrom £1,277 per person 3 nights, Room Only Includes return flights and hotel
View holidayfrom £1,569 per person 3 nights, Room Only Includes return flights and hotel
View holiday4★ Holidays in Chicago
from £843 per person 3 nights, Room Only Includes return flights and hotel
View holidayfrom £833 per person 3 nights, Room Only Includes return flights and hotel
View holidayfrom £826 per person 3 nights, Room Only Includes return flights and hotel
View holidayfrom £878 per person 3 nights, Room Only Includes return flights and hotel
View holidayfrom £867 per person 3 nights, Room Only Includes return flights and hotel
View holidayfrom £872 per person 3 nights, Bed And Breakfast Includes return flights and hotel
View holidaySofitel Chicago Magnificent Mile
5 ★ Sofitel Chicago Magnificent Mile
Subject to availability, prices correct of the last 24 hours
The Langham Chicago
5 ★ The Langham Chicago
Subject to availability, prices correct of the last 24 hours
Waldorf Astoria Chicago
5 ★ Waldorf Astoria Chicago
Subject to availability, prices correct of the last 24 hours
River Hotel Chicago
4 ★ River Hotel Chicago
Subject to availability, prices correct of the last 24 hours
Hilton Chicago O'Hare
4 ★ Hilton Chicago O'Hare
Subject to availability, prices correct of the last 24 hours
Sheraton Grand Chicago Riverwalk
4 ★ Sheraton Grand Chicago Riverwalk
Subject to availability, prices correct of the last 24 hours
Chicago Marriott Downtown Magnificent Mile
4 ★ Chicago Marriott Downtown Magnificent Mile
Subject to availability, prices correct of the last 24 hours
Palmer House
4 ★ Palmer House
Subject to availability, prices correct of the last 24 hours
The Whitehall Hotel
4 ★ The Whitehall Hotel
Subject to availability, prices correct of the last 24 hours

Key facts about Chicago
Timezone
6 hrs behind GMT
Currency
United States dollar
Language
English
Great value holidays to cities near Chicago





