Chicago Holiday Packages

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Top Chicago holiday packages

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

Arlo Chicago

4 out of 5
Downtown Chicago
per person
25 July - 30 July
found 24 hours ago
Return direct flight included
Melbourne (MEL) to Chicago (ORD)
9.2/10 Wonderful! (1,757 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
25 July - 30 July
found 24 hours ago
Return direct flight included
Melbourne (MEL) to Chicago (ORD)
9.4/10 Exceptional! (1,602 reviews)
Chicago River Side Suites

Chicago River Side Suites

2 out of 5
Downtown Chicago
per person
25 July - 30 July
found 24 hours ago
Return direct flight included
Melbourne (MEL) to Chicago (ORD)
10/10 Exceptional! (1 review)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
per person
25 July - 30 July
found 24 hours ago
Return direct flight included
Melbourne (MEL) to Chicago (ORD)
9/10 Wonderful! (319 reviews)
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
per person
25 July - 30 July
found 24 hours ago
Return direct flight included
Melbourne (MEL) to Chicago (ORD)
9.4/10 Exceptional! (3,379 reviews)
Wonderful location, beautiful architecture and a magnificent view from the terrace on L22

Reviewed on 7 Dec. 2023

Top Chicago hotels

InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

4.5 out of 5
505 N Michigan Ave, Chicago, IL
Fully refundable
InterContinental Chicago Magnificent Mile by IHG: Luxury hotel with free WiFi and an indoor pool. Located in the city centre.
"Great hotel. Location cost to downtown, the Pier, and a lot of restaurants and night life. Property and rooms are in great shape. Staff is very friendly and helpful."

Reviewed on 8 Jun. 2025

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InterContinental Chicago Magnificent Mile by IHG
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
Hilton Chicago/Magnificent Mile Suites: Pet-friendly hotel with free WiFi and a fitness centre. Located in the city centre.
"Great stay"

Reviewed on 7 Jun. 2025

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Hilton Chicago/Magnificent Mile Suites
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
Embassy Suites by Hilton Chicago Downtown River North: Pet-friendly hotel with free breakfast and an indoor pool. Located near a metro station.
"We enjoyed the place, breakfast was very good."

Reviewed on 7 Jun. 2025

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Embassy Suites by Hilton Chicago Downtown River North
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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.