Crestwood Holidays from AU$2,249

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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.
Holiday Inn Chicago O'Hare – Rosemont by IHG
Hilton Chicago O'Hare Airport
Sonesta Chicago O'Hare Airport Rosemont
DoubleTree by Hilton Chicago Schaumburg
Staybridge Suites Chicago O'Hare - Rosemont by IHG

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

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$242 per night from 1 Sept to 2 Sept
AU$242
1 Sept - 2 Sept
includes taxes & fees
7.8/10 Good! (8,921 reviews)
"Took water awhile to get hot for shower, and parking is ridiculously expensive. Other than that enjoyed staying at hotel"

Reviewed on 8 Aug. 2025

Congress Plaza Hotel
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$350 per night from 21 Aug to 22 Aug
AU$350
21 Aug - 22 Aug
includes taxes & fees
8.2/10 Very Good! (1,835 reviews)
"The property if beautiful and historic. The main room is incredible. The rooms are well taken care of, you can just tell they are a little dated with a slight smell. I would definitely stay here again."

Reviewed on 8 Aug. 2025

Palmer House a Hilton Hotel
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
10 E Grand Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$276 per night from 24 Aug to 25 Aug
AU$276
24 Aug - 25 Aug
includes taxes & fees
8.4/10 Very Good! (3,635 reviews)
"I liked the security and safeness. I did not like that there was no valet/door person to help with bags, when spending thousands of dollars I would expect a door person to be there to assist with bags out of car and up to room and would also appreciate complimentary water each day not 2 bottles in ..."

Reviewed on 8 Aug. 2025

Hilton Garden Inn Chicago Downtown/Magnificent Mile
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

What to do in Crestwood

Frequently asked questions

How much does a Crestwood holiday package cost?
Offering excellent value package deals from AU$2,249 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.