Crestwood Holidays from AU$3,261
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Your Crestwood Holiday
From its highlights to its hidden treasures, this city is best experienced with a Crestwood holiday package. Check out places to stay in Hyde Park, which is good for history, nature and culture. Fill your free time with tours of Trinity Christian College, Chicago Ridge Shopping Mall and Orland Square, some of the attractions you just have to see during your trip to Crestwood. Browse Expedia's wide range of travel options and book your ultimate holiday to Crestwood now.
The Latest Crestwood Holiday Deals
Price found within the past 48 hours. Click for updated prices.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was AU$3,574, price is now AU$3,261 per person
AU$3,261
per person
8 Jan - 15 Jan
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
18.8/10 Exceptional! (2,229 reviews)
Room was super clean. Awesome view and the staff was great!
Reviewed on 16 Nov 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was AU$5,281, price is now AU$4,263 per person
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
Pendry Chicago
Downtown Chicago
Price was AU$3,863, price is now AU$3,404 per person
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
Hilton Chicago O'Hare Airport
O'Hare
Price was AU$4,436, price is now AU$3,975 per person
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
Aloft Chicago Downtown River North
Downtown Chicago
Price was AU$3,611, price is now AU$3,276 per person
AU$3,276
per person
8 Jan - 15 Jan
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
18.8/10 Exceptional! (1,161 reviews)
Staff was nice and helpful. I guess the only thing that I was a bit disappointed was the rooms, you can hear EVERYTHING.
Reviewed on 18 Nov 2025
Crestwood Holiday
Crestwood Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | O'Hare Intl. Airport (ORD) |
Population | 11,000 |
Max Temp Winter | -1.11ºC |
Max Temp Summer | 27ºC |
Top Sights | Galloping Ghost, DuSable Museum of African-American History and Smart Museum of Art |
Our pick of the best Crestwood Hotel Deals
Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
The price is AU$158 per night from 8 Dec to 9 Dec
AU$158
8 Dec - 9 Dec
includes taxes & fees
8.4/10 Very Good! (5,271 reviews)
Great location. Fantastic staff. Breakfast was absolutely amazing. Only issue we had was insufficient bath towels and front desk resolved this quickly. I would gladly stay here again without a doubt
Reviewed on 18 Nov 2025
Palmer House a Hilton Hotel
17 E Monroe St Chicago IL
Fully refundableReserve now, pay when you stay
The price is AU$230 per night from 25 Nov to 26 Nov
AU$230
25 Nov - 26 Nov
includes taxes & fees
8.4/10 Very Good! (2,057 reviews)
Excellent!
Reviewed on 13 Nov 2025
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is AU$162 per night from 14 Dec to 15 Dec
AU$162
14 Dec - 15 Dec
includes taxes & fees
8.8/10 Excellent! (3,284 reviews)
Amazing
Reviewed on 14 Nov 2025
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.
Discover the most popular places to visit in Crestwood
Navy Pier
A waterfront entertainment strip with fun diversions for both young and old, with shops, restaurants and even a Ferris wheel.
Millennium Park
One of Chicago’s main focal points, where locals and visitors flock to see the striking art, architecture and landscape on show.
Chicago Riverwalk
Stroll along the waterfront of the Chicago River to pass some of the city’s most appealing attractions and appreciate how a once grim area has been successfully revamped.
What to do in Crestwood
Skydeck - Willis Tower Admission
AU$67
per adult
98% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
AU$37
per adult
84% of travellers recommend
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
