Crestwood Holidays from AU$2,576
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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.
The Royal Sonesta Chicago River North
Downtown Chicago
Price was AU$5,156, price is now AU$2,576 per person
AU$2,576
per person
17 Oct - 24 Oct
found 1 day ago
Return flight included
Sydney (SYD) to Chicago (ORD)
9.2/10 Wonderful! (2,052 reviews)
Our stay at The Royal Sonesta Chicago River North was truly fantastic. From the moment we arrived, the front desk staff, especially Gabby, greeted us warmly. Our room was spacious and spotless. The hotel's location in the city center with shops and restaurants are well within walking distance. We would highly recommend this hotel and its exceptional staff. We would definitely book this location again on our next visit.
Reviewed on 2 Sep. 2025
The Emily Hotel
Downtown Chicago
Save 100% on your flight
Price was AU$6,594, price is now AU$3,369 per person
AU$3,369
per person
17 Oct - 24 Oct
found 1 day ago
Return flight included
Sydney (SYD) to Chicago (ORD)
9.2/10 Wonderful! (1,192 reviews)
Great hotel, especially for the price, nice area, would go back again if I’m in Chicago.
Reviewed on 2 Sep. 2025
Level Chicago – Old Town
Downtown Chicago
Price was AU$5,603, price is now AU$2,920 per person
AU$2,920
per person
17 Oct - 24 Oct
found 1 day ago
Return flight included
Sydney (SYD) to Chicago (ORD)
9/10 Wonderful! (343 reviews)
Everything was perfect. Be aware of the expensive it is to park in Chicago.
Reviewed on 2 Sep. 2025
Pendry Chicago
Downtown Chicago
Price was AU$5,834, price is now AU$3,123 per person
AU$3,123
per person
17 Oct - 24 Oct
found 1 day ago
Return flight included
Sydney (SYD) to Chicago (ORD)
9.4/10 Exceptional! (1,064 reviews)
Room was very nice and clean. Great location and we were able to walk almost everywhere we wanted to go. Staff was friendly and knowledgeable. Only thing I would say is that it is a little loud at night but you are downtown right off Michigan ave so you should expect some street noise. Would definitely stay here again.
Reviewed on 2 Sep. 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
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$265 per night from 22 Sept to 23 Sept
AU$265
22 Sept - 23 Sept
includes taxes & fees
Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$302 per night from 4 Sept to 5 Sept
AU$302
4 Sept - 5 Sept
includes taxes & fees
The Wade
644 N Lake Shore Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$299 per night from 22 Sept to 23 Sept
AU$299
22 Sept - 23 Sept
includes taxes & fees
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.
Grant Park
Chicago’s front yard is a pretty landscaped park, which is home to public art displays, museums, themed gardens and international music festivals.
What to do in Crestwood
Wendella's 90-min Chicago River Architecture Tour
AU$62
per adult
94% of travellers recommend
Chicago By Night River & Lake Cruise
AU$69
per adult
96% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.