Chicago Holiday Packages

Save when you book Chicago package deals

Choose two or more items and save on your trip:

Top Chicago hotels

River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
The price is NZ$358 per night from 27 Sept to 28 Sept
NZ$358
27 Sept - 28 Sept
includes taxes & fees
Stay at this business-friendly hotel in Chicago. Enjoy free Wi-Fi, room service and a fitness centre. Our guests praise the helpful staff and the clean rooms ...
"Great place to travel!"

Reviewed on 25 Sept 2026

Opens in a new windowRiver Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is NZ$338 per night from 25 Oct to 26 Oct
NZ$338
25 Oct - 26 Oct
includes taxes & fees
Stay at this business-friendly hotel in Chicago. Enjoy free Wi-Fi, a 24-hour fitness centre and valet parking (surcharge). Our guests praise the helpful staff ...
"Clean room"

Reviewed on 25 Sept 2026

Opens in a new windowThe Chicago Hotel Collection Ambassador Gold Coast
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is NZ$337 per night from 26 Oct to 27 Oct
NZ$337
26 Oct - 27 Oct
includes taxes & fees
Stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, 2 bars/lounges and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
Opens in a new windowCongress Plaza Hotel
Don't see what you're looking for?
See all available properties in Chicago
View all properties
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.

More Destinations