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Chicago Holidays

Choose two or more items and save on your trip:

Your next trip to Chicago with ebookers

  • Browse our 2021 holiday package deals today! They feature hotels and flights or cars at discounted bundled rates. Book your perfect trip all in one place!
  • You're in luck! We have amazing deals on wonderful properties in Chicago. Start browsing our accommodations simply by using the wizard above.
  • We offer free cancellation on most hotels in case you need to change your plans*

For more information, visit our COVID-19 information page
Find the trip that is just right for you now!

*Some hotels require you to cancel at least 24-48 hours before check-in. Details on site.

Chicago Holidays

Can't stop daydreaming about Chicago? From flights to room nights, car hire to tours, the committed team at ebookers are the ultimate travel whisperers.

With over 500 partner airlines and more than 500,000 worldwide properties, it's never been easier to escape.

Remember, if you book a Flight + Hotel package with ebookers and see a better deal elsewhere within 48 hours pre check in, we'll match it and repay the difference. That's our Price Guarantee.

Now is the time to start ticking off your lifetime travel dreams. Whether it's a freezing mountain peak or a scorching desert, we'll help you satisfy each and every last wanderlust. Terms and Conditions apply.

More Chicago hotels

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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Cheap flights to Chicago

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Sun, 20 Jun
LAX
Los Angeles
ORD
Chicago
€223
Alaska Airlines
Sun, 20 Jun
LAX
Los Angeles
ORD
Chicago
€252
Alaska Airlines
Sun, 20 Jun
LAX
Los Angeles
ORD
Chicago
€290
Alaska Airlines
Sun, 20 Jun - Fri, 2 Jul
LAX
Los Angeles
ORD
Chicago
€524
Alaska Airlines
Sun, 20 Jun - Fri, 2 Jul
LAX
Los Angeles
ORD
Chicago
€553
Alaska Airlines
Sun, 20 Jun - Fri, 2 Jul
LAX
Los Angeles
ORD
Chicago
€578
Alaska Airlines

Top things to do in Chicago

^Savings based on all package bookings with Flight + Hotel made on ebookers.ie from as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.