Crestwood Holidays from AU$666
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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.
Trump International Hotel & Tower Chicago
Downtown Chicago
AU$1,145
per person
22 Sept - 24 Sept
found 1 day ago
Return flight included
New York (NYC) to Chicago (ORD)
9.6/10 Exceptional! (1,960 reviews)
Amazing hotel. We go every year and always have a great time.
We were greeted with a warm hand towel and champagne.
Reviewed on 19 Aug 2026
Hotel Felix River North/Magnificent Mile
Downtown Chicago
AU$743
per person
22 Sept - 24 Sept
found 1 day ago
Return flight included
New York (NYC) to Chicago (ORD)
8.2/10 Very good! (2,899 reviews)
Great staff, very clean property. Enjoyed the café for lattes and cocktails! Breakfast is a fair price for being additional. I loved the location many bars and restaurants just a few minutes walk away.
Reviewed on 19 Aug 2026
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
AU$175
8 Sept - 9 Sept
includes taxes & fees
8/10 Very good! (10,266 reviews)
"The hallways had peeling wallpaper and holes in the walls. The room was updated but not clean."
Reviewed on 19 Aug 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
AU$240
30 Aug - 31 Aug
includes taxes & fees
8/10 Very good! (2,043 reviews)
"Nice hotel, great location. I think that was the fastest check in that I’ve ever experienced. Room was spacious. When I walked in, room was muggy but maintenance came right up and cooled it quickly. Restaurant/bar area is nice!"
Reviewed on 19 Aug 2026
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.
Stay near popular Crestwood attractions
Hollywood Park
This family entertainment centre offers go-karts, mini-golf, bumper cars, and a multi-floor arcade all in one vibrant location. Enjoy chef-crafted meals between activities for a complete day of fun.
What to do in Crestwood
Chicago: Navy Pier Centennial Wheel Ticket
AU$35
per adult
90% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
AU$58
per adult
94% of travellers recommend
Frequently asked questions
How much does a Crestwood holiday package cost?
Offering excellent value package deals from AU$666 on Expedia, you'll be thrilled with how little a holiday to Crestwood costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Crestwood?
If you'd like to book a cheap Crestwood holiday package, consider travelling in January, February and April. You're likely to find better rates on flights and hotels during these quieter months — ideal for a budget-friendly getaway.
How many days is enough for Crestwood?
The ideal length of your Crestwood holiday depends on what you'd like to do. Generally, a few days to a week will give you plenty of time to tick off all the major sights and explore some hidden treasures along the way.
How to find the best Crestwood package deals?
Use Expedia's handy filters to help you find some of the best Crestwood package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your trip for midweek, or browse for Crestwood package deals in the off-season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it's typically best to lock in your holiday package as early as possible.
Is it cheaper to book a Crestwood holiday as a package?
Expedia holiday packages are designed to give you more bang for your buck. Bundle your car rental, hotel and flight into one great-value price and enjoy significant savings. You'll generally score a better deal than booking each component individually. And you'll still have the freedom to create a personalised Crestwood holiday by choosing your preferred airline, accommodation type and car class.
When to book a holiday package to Crestwood?
If you're considering a spur-of-the-moment Crestwood trip, check out our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can score sensational deals on your hotels and flights by booking ahead.
How to plan a trip to Crestwood?
- Choose when to get away: Check your diary and get packing. Your preferred time of year and the activities on offer will also help you decide when to holiday in Crestwood.
- Figure out your budget: Ensure you have enough money to pay for everything from transportation and meals to flights and experiences. Your accommodation will probably be the largest expense during your trip to Crestwood.
- Decide how many days away: Start by compiling a list of the attractions you want to experience in Crestwood. Then, estimate how long you'll need at each, as well as any travel time.
- Bundle your bookings: With your travel dates in order, you can combine your car rental, hotels, flights and more into a customised Crestwood holiday package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
