Crestwood Vacations from $455

Book a Hotel + Flight or Car together to unlock savings

Choose one or more items to build your trip:
    Plan, book, travel with confidence
  • payments icon
    Better together
    Save up to $580 when you book a flight and hotel together*
  • lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

Your Crestwood Vacation

Say farewell to planning hassles and hello to a Crestwood vacation package. With your travel details organized before you leave, you can focus on discovering every inch of this city, starting with Hyde Park, which is great for history, nature and culture. Make your trip to Crestwood even more fun and exciting by including some sightseeing. Chicago Ridge Shopping Mall, Trinity Christian College and Lake Katherine Nature Center are some of the top attractions worth exploring. Whoever you're taking a break with and whatever the size of your budget, your ultimate Crestwood vacation is just a few clicks away with Expedia.

The Latest Crestwood Vacation Packages

Fairmont Chicago at Millennium Park Gold Experience
Waldorf Astoria Chicago
Sheraton Grand Chicago Riverwalk
Trump International Hotel & Tower Chicago
Park Hyatt Chicago
Prices and availability subject to change. Additional terms may apply.

Crestwood Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)
Population
11,000
Max Temp Winter
30ºF
Max Temp Summer
80ºF
Top Sights
Calumet Beach, Galloping Ghost and Midwest Carvers Museum

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 $125 per night from Apr 1 to Apr 2
$125
$147 total
includes taxes & fees
Apr 1 - Apr 2
7.6/10 Good! (6,459 reviews)
"As others have mentioned, this place is daaaaated. It was probably a fancy hotel back in its time but it definitely older now. That being said, it's a great place location wise particularly given the price. The rooms are old but clean. The service is good. The heating is centralized and it was cold ..."

Reviewed on Mar 28, 2024

Congress Plaza Hotel
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is $109 per night from Mar 31 to Apr 1
$109
$128 total
includes taxes & fees
Mar 31 - Apr 1
8.6/10 Excellent! (2,720 reviews)
"ㆍ"

Reviewed on Mar 28, 2024

River Hotel
Club Quarters Hotel, Central Loop, Chicago
Club Quarters Hotel, Central Loop, Chicago
4 out of 5
111 West Adams Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is $99 per night from Mar 31 to Apr 1
$99
$116 total
includes taxes & fees
Mar 31 - Apr 1
8.4/10 Very Good! (2,928 reviews)
"Good deal. Small room. Pretty small lobby. Comfortable bed and pillows. Staff was great. Location was amazing. Easy walk to any of the downtown theaters. Lots of restaurants close by. Would stay again!"

Reviewed on Mar 28, 2024

Club Quarters Hotel, Central Loop, Chicago
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.

Explore other types of vacation packages

Frequently asked questions

How much does a Crestwood vacation package cost?
Our Crestwood vacation packages, which begin at just $455, are the best way to save precious money. Select your favorite hotels, flights and rental car to create your dream getaway.
How do I get a cheap travel package to Crestwood?
Bundle your hotel and flight bookings, toss in extras such as a rental car or activities, and save with a Crestwood vacation package. You won’t just walk away with exciting discounts on your trip — you’ll have plenty of choice within your reach too. When you book with Expedia, you’ll have your pick of over 550 air carriers and 1,000,000 properties globally. Your unforgettable vacation starts right here, right now!
Where should I stay in Crestwood?
With so much to discover in Crestwood, it’s a good idea to stay close to its attractions. Gaelic Park, Trinity Christian College and Lake Katherine Nature Center are some fascinating ones to add to your must-see list.
What are the top hotels in Crestwood?
When it comes to comfy and convenient places to stay in Crestwood, you can’t go past Holiday Inn Express Crestwood, an IHG Hotel. Take a look at our offers and pick up a bargain.
How far in advance should I book my Crestwood vacation?
It depends on the air carrier, but you can generally browse through international airfares on Expedia up to a year in advance. While it’s a good idea to book ahead of time, lucky travelers will occasionally find a cheaper ticket just weeks prior to their intended journey.
What does an Expedia Crestwood travel package include?
From airfares and hotels to rental cars, Expedia can help you create a Crestwood package that works for you. Heading away for a week or longer? Consider a rental car, hotel and flight bundle. If you can only manage a quick getaway, a flight and hotel deal could be more your style. Activities can also be added after you’ve booked. Our travel packages make it easy to save and plan.
What should I know before booking a Crestwood travel package?
We already have low prices. However, you’ll enjoy even more bargains when you book your flights, hotels and car rentals together. With an Expedia package, you’ll get transparent pricing and loads of choice.
Can I choose my airline with a Crestwood Expedia vacation package?
With a vacation package, you’re the one in charge. Whether you’re hoping to fly to Crestwood in economy or business class, simply choose from the available airline options. Expedia has access to over 550 airline partners throughout the world.
If I'm not able to travel, can I cancel my Crestwood vacation package?
Whether it’s your flight or hotel, you can cancel and rebook it. Locked in your Crestwood vacation package in the last 24 hours? You may be able to make changes at no cost. If it’s been longer than that, you may incur a charge from your hotel, airline or car rental company. For more information, visit our Customer Service Portal. We’re here to help you each step of the way.

Discover the most popular places to visit in Crestwood

What to do in Crestwood

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.