Crestwood Vacations from ￥111,956

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The Latest Crestwood Vacation Packages

Price found within the past 48 hours. Click for updated prices.
JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Downtown Chicago
per person
Jul 4 - Jul 7
found 23 hours ago
Roundtrip flight included
San Francisco (SFO) to Chicago (ORD)
9.2/10 Wonderful! (1,002 reviews)
Good price, good service.

Reviewed on May 29, 2024

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
Jul 4 - Jul 7
found 23 hours ago
Roundtrip flight included
San Francisco (SFO) to Chicago (ORD)
9.2/10 Wonderful! (1,190 reviews)
It was a nice place to stay, but I don’t feel it was worth the price at all. Especially when you had to pay $68 to park your vehicle when you were already paying an exorbitant amount for the room. I don’t see how parking is not included in the price of the room for guests. Will not be staying there again for that reason aside from I don’t think the rooms are much nicer than anywhere else I have stayed.

Reviewed on May 31, 2024

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
per person
Jul 4 - Jul 7
found 23 hours ago
Roundtrip flight included
San Francisco (SFO) to Chicago (ORD)
9.8/10 Exceptional! (1,012 reviews)
Very nice property with good room size, pool, and amazing service.

Reviewed on May 29, 2024

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
Jul 4 - Jul 7
found 23 hours ago
Roundtrip flight included
San Francisco (SFO) to Chicago (ORD)
9.4/10 Exceptional! (687 reviews)
The Art Deco architectural beauty of this hotel is stunning! Every time I was in the elevator area, I was wowed. We had a corner room on the 22nd floor and it was great. Lots of space and great art deco inspired furniture and lights. We had a view of the bridge and the lake. The breakfast at the French cafe was so so. Overall I highly recommend this hotel.

Reviewed on May 30, 2024

The Langham, Chicago

The Langham, Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 4 - Jul 7
found 1 day ago
Roundtrip flight included
San Francisco (SFO) to Chicago (ORD)
9.8/10 Exceptional! (1,000 reviews)
Stile, breakfast, location

Reviewed on May 27, 2024

Crestwood Hotel Deals

Eurostars Magnificent Mile
Eurostars Magnificent Mile
4 out of 5
660 North State Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ￥26,656 per night from Jun 30 to Jul 1
￥26,656
per night
Jun 30 - Jul 1
8.4/10 Very Good! (1,988 reviews)
"Very nice hotel"

Reviewed on May 30, 2024

Eurostars Magnificent Mile
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 ￥27,763 per night from Jun 5 to Jun 6
￥27,763
per night
Jun 5 - Jun 6
7.6/10 Good! (6,816 reviews)
"Be aware there is only Analog TV in the room"

Reviewed on May 29, 2024

Congress Plaza Hotel
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
The price is ￥26,664 per night from Jun 30 to Jul 1
￥26,664
per night
Jun 30 - Jul 1
8.6/10 Excellent! (2,912 reviews)
"The facility was beautiful. The staff was extremely friendly and helpful. The views of the city were phenomenal."

Reviewed on May 28, 2024

River Hotel
See all 3,327 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 ￥111,956, 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 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
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

What to do in Crestwood

Image for Odyssey Lake Michigan Premier Dinner Cruise

Odyssey Lake Michigan Premier Dinner Cruise

￥27,764
Per adult
76% of travellers recommend
Odyssey Lake Michigan Premier Dinner Cruise
Image for Chicago Pizza Tour

Chicago Pizza Tour

￥13,111
Per adult
100% of travellers recommend
Chicago Pizza Tour
Image for Chicago Museum of Contemporary Art: General Admission Ticket

Chicago Museum of Contemporary Art: General Admission Ticket

￥3,241
Per adult
90% of travellers recommend
Chicago Museum of Contemporary Art: General Admission Ticket
See all activities in Crestwood

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