Plan a trip to see Park West

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Pendry Chicago

Downtown Chicago

AU$3,404

per person

8 Jan - 15 Jan

found 1 day ago

Return direct flight included

Sydney (SYD) to Chicago (ORD)

18.8/10 Exceptional! (1,130 reviews)

The room had no soundproofing. Every night a car was revving loudly across Michigan Ave around midnight, making it impossible to sleep without noise-cancelling AirPods.

Reviewed on 18 Nov 2025

Trump International Hotel & Tower Chicago

Downtown Chicago

AU$4,263

per person

8 Jan - 15 Jan

found 1 day ago

Return direct flight included

Sydney (SYD) to Chicago (ORD)

18.8/10 Exceptional! (1,773 reviews)

Political stigma aside, I must say, this property is stunning across the board. From the moment you enter the building you're met with this amazingly inviting fragrance. The Room was spotless. All the staff was sincere, kind, hospitable, and surprisingly diverse. Also, The front desk was exceptionally accommodating while I (minimally) "stress tested" the room service. 10/10 would and Will return. Mr. & Mrs.S

Reviewed on 17 Nov 2025

Hilton Chicago O'Hare Airport

O'Hare

AU$3,975

per person

8 Jan - 15 Jan

found 1 day ago

Return direct flight included

Sydney (SYD) to Chicago (ORD)

16.4/10 Exceptional! (2,158 reviews)

Not having coffee available until 6 AM (at an airport!) is just so wrong.

Reviewed on 15 Nov 2025

Tours & day trips

See all 153 activities

Wendella's 90-min Chicago River Architecture Tour

Private & custom tours

See all 49 activities

Eastside Chicago The Heist Exploration Game and Tour

Free cancellation available

Food, drink & nightlife

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Chicago Craft Brewery Barrel Bus Tour

Free cancellation available

Attractions

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360 CHICAGO Observation Deck

Free cancellation available

Classes & workshops

See all 12 activities

BYOB Spray Paint 'n' Sip at Studio W.I.P. Chicago

Free cancellation available

Popular places to visit

South Pond

Commune with nature and explore the great outdoors at South Pond during your travels in Chicago. Amble around this vibrant area's lakeside or experience its acclaimed theatre scene.

Lincoln Park Zoo

This small zoo right in the heart of Chicago, Lincoln Park is an ideal family destination, popular with small children eager to see the many different animals.

Lincoln Park Conservatory

This glass structure full of exotic plants is the perfect place to spend a quiet afternoon.

Chicago History Museum

Explore the rich and exciting history of this great, iconic all-American city through an array of artefacts, hands-on exhibits and multi-media presentations.

North Avenue Beach

Why not spend a care-free afternoon at North Avenue Beach during your travels in Chicago? Experience the acclaimed art galleries and fascinating museums in this vibrant area.

Farm-in-the-Zoo

Learn about the local history of Chicago when you spend time at Farm-in-the-Zoo. Stroll along the lakeside or experience the entertainment choices in this vibrant area.