Chicago Holiday Packages

Save when you book Chicago package deals

Choose two or more items and save on your trip:

Top Chicago holiday packages

Price found within the past 48 hours. Click for updated prices.
Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
Downtown Chicago
Price was AU$820, price is now AU$574 per person
AU$574
per person
22 Sept - 24 Sept
found 11 hours ago
Return flight included
Los Angeles (LAX) to Chicago (ORD)
8.4/10 Very good! (2,089 reviews)

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was AU$1,156, price is now AU$766 per person
AU$766
per person
22 Sept - 24 Sept
found 11 hours ago
Return flight included
Los Angeles (LAX) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
The property waa clean and spacious Staff were very nice and helpful. The location was perfect a short walk or drive to alot of places ans the best of all was that A Garrett's popcorn shop waa right across the street!

Reviewed on 11 Aug 2026

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was AU$924, price is now AU$670 per person
AU$670
per person
22 Sept - 24 Sept
found 11 hours ago
Return flight included
Los Angeles (LAX) to Chicago (ORD)
8.2/10 Very good! (2,879 reviews)
This was such a great hotel. It’s in a wonderful neighborhood, and walking distance from the Riverwalk and Michigan Ave. I’m a solo female traveler, and I felt safe and comfortable here. The room was great and the bed was cozy. I would definitely stay here again.

Reviewed on 11 Aug 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was AU$1,464, price is now AU$1,068 per person
AU$1,068
per person
22 Sept - 24 Sept
found 11 hours ago
Return flight included
Los Angeles (LAX) to Chicago (ORD)
9.6/10 Exceptional! (1,960 reviews)

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Price was AU$1,055, price is now AU$779 per person
AU$779
per person
22 Sept - 24 Sept
found 11 hours ago
Return flight included
Los Angeles (LAX) to Chicago (ORD)
8.8/10 Excellent! (2,293 reviews)
Good location, room was spacious, big bathroom.

Reviewed on 11 Aug 2026

Top Chicago hotels

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 AU$193 per night from 8 Sept to 9 Sept
AU$193
8 Sept - 9 Sept
includes taxes & fees
Congress Plaza Hotel: Business-friendly hotel with free WiFi and 2 restaurants. Located in the city centre.
Opens in a new windowCongress Plaza 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 AU$241 per night from 30 Aug to 31 Aug
AU$241
30 Aug - 31 Aug
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast: Pet-friendly hotel with free WiFi and a bar/lounge. Located near a metro station.
Opens in a new windowThe Chicago Hotel Collection Ambassador Gold Coast
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
The price is AU$360 per night from 11 Sept to 12 Sept
AU$360
11 Sept - 12 Sept
includes taxes & fees
Hilton Chicago O'Hare Airport: Pet-friendly hotel with free WiFi and 2 restaurants. Located adjacent to the airport.
Opens in a new windowHilton Chicago O'Hare Airport
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