Chicago Holiday Packages

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Top Chicago holiday packages

Price found within the past 48 hours. Click for updated prices.
Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
Downtown Chicago
Price was AU$3,925, price is now AU$3,585 per person
AU$3,585
per person
1 Aug - 3 Aug
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.2/10 Wonderful! (1,799 reviews)
Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

4.5 out of 5
Downtown Chicago
Price was AU$4,362, price is now AU$3,896 per person
AU$3,896
per person
1 Aug - 3 Aug
found 1 day ago
Return flight included
Sydney (SYD) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was AU$4,089, price is now AU$3,701 per person
AU$3,701
per person
1 Aug - 3 Aug
found 1 day ago
Return flight included
Sydney (SYD) to Chicago (ORD)
9.6/10 Exceptional! (1,888 reviews)
Nobu Hotel Chicago

Nobu Hotel Chicago

5 out of 5
Downtown Chicago
Price was AU$4,099, price is now AU$3,733 per person
AU$3,733
per person
1 Aug - 3 Aug
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.4/10 Exceptional! (864 reviews)
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
Downtown Chicago
Price was AU$3,992, price is now AU$3,683 per person
AU$3,683
per person
1 Aug - 3 Aug
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
8.2/10 Very Good! (1,569 reviews)

Top Chicago hotels

Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
The price is AU$219 per night from 28 June to 29 June
AU$219
28 June - 29 June
includes taxes & fees
Hyatt Regency O'Hare Chicago: Pet-friendly hotel with free WiFi and a bar/lounge. Located next to the convention centre.
"Great experience with clean rooms and very good breakfast"

Reviewed on 15 June 2026

Opens in a new windowHyatt Regency O'Hare Chicago
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$230 per night from 29 June to 30 June
AU$230
29 June - 30 June
includes taxes & fees
Congress Plaza Hotel: Business-friendly hotel with free WiFi and 2 restaurants. Located in the business district.
"The gentleman that checked me in was not friendly. Barely spoke to me at all. Did not really give me any info on where things were located or how to get to my room. Thankfully a kind staff member realized I was walking in circles and helped me out. I get to my room and the tv does not work unless ..."

Reviewed on 15 June 2026

Opens in a new windowCongress Plaza Hotel
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Fully refundable
The price is AU$244 per night from 30 June to 1 July
AU$244
30 June - 1 July
includes taxes & fees
The Chicago Hotel Collection - Magnificent Mile: Pet-friendly hotel with free WiFi and 2 restaurants. Located in the entertainment district.
"Huge clean well-appointed room. Gym was good. Shower water pressure was weak. Bed was comfy. Location awesome! Would stay again."

Reviewed on 15 June 2026

Opens in a new windowThe Chicago Hotel Collection - Magnificent Mile
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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.

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