Crestwood Vacations from ₩1,183,874

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The Latest Crestwood Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
per person
Jun 18 - Jun 22
Roundtrip flight included
San Diego (SAN) to Chicago (ORD)
7.8/10 Good! (1,013 reviews)
The bathroom could have been cleaner, the air conditioning barely worked which made the room incredibly hot. The lobby is nice enough, and the staff is super friendly. The location is wonderful.

Reviewed on May 11, 2024

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun 18 - Jun 22
Roundtrip flight included
San Diego (SAN) to Chicago (ORD)
9.2/10 Wonderful! (1,182 reviews)
The best hotel hands down!

Reviewed on May 13, 2024

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
Jun 18 - Jun 22
Roundtrip flight included
San Diego (SAN) to Chicago (ORD)
9.4/10 Exceptional! (679 reviews)
There is such loud traffic nearby. I could not sleep for one minute.

Reviewed on May 13, 2024

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
per person
Jun 18 - Jun 22
Roundtrip flight included
San Diego (SAN) to Chicago (ORD)
9.2/10 Wonderful! (3,494 reviews)
Property is well kept, location was perfect to walk to restaurants and shops. As far as the room shower and pillows need improvement, shower weak and pillows with zero support. Overall a good experience but expected more from a 4 stars hotel .

Reviewed on May 14, 2024

The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago

The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago

4.5 out of 5
Downtown Chicago
per person
Jun 18 - Jun 22
Roundtrip flight included
San Diego (SAN) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
Good location, nice vibe, amazing staff!

Reviewed on Apr 30, 2024

Crestwood Hotel Deals

Warwick Allerton - Chicago
Warwick Allerton - Chicago
4 out of 5
701 North Michigan Avenue, Chicago, IL
The price is ₩143,750 per night from May 27 to May 28
₩143,750
per night
May 27 - May 28
7.6/10 Good! (2,578 reviews)
"Very clean"

Reviewed on May 14, 2024

Warwick Allerton - Chicago
Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
The price is ₩203,468 per night from May 27 to May 28
₩203,468
per night
May 27 - May 28
7.6/10 Good! (6,728 reviews)
"I really liked how clean the room was."

Reviewed on May 14, 2024

Congress Plaza Hotel
The Westin Michigan Avenue Chicago
The Westin Michigan Avenue Chicago
4.5 out of 5
909 North Michigan Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ₩299,822 per night from May 27 to May 28
₩299,822
per night
May 27 - May 28
8.6/10 Excellent! (1,001 reviews)
"We had a wonderful time in Chicago! This property was located in such a great area and easy walking to all the things we wanted to do...and eat. :)"

Reviewed on May 10, 2024

The Westin Michigan Avenue Chicago
See all 3,373 properties in Crestwood
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.

Frequently asked questions

How much does a Crestwood vacation package cost?
Our Crestwood vacation packages, which begin at just ₩1,183,874, 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

Image for Wrigley Field

Wrigley Field

4.5/5(2,128 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Image for McCormick Place

McCormick Place

4.5/5(1,805 reviews)

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

McCormick Place
Image for Six Flags Great America

Six Flags Great America

4.5/5(347 reviews)

Spend a day at this sprawling theme park to enjoy an array of thrilling roller coaster rides, a water park and entertainment for kids of all ages.

Six Flags Great America

Other vacations you might like

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