Crestwood Holidays

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    Save up to NZ$545 when you book a flight and hotel together*
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Our pick of the best Crestwood Hotel Deals

River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NZ$219 per night from 27 Oct to 28 Oct
NZ$219
per night
27 Oct - 28 Oct
8.6/10 Excellent! (3,415 reviews)
"Great Walkability. Close to shoping, river walk, restaurants, museums, theaters, etc. The rooms are small and good enough. Nothing special. But I would recommend to buy snacks and drinks for your room, there is no hotel shop."

Reviewed on 24 Sep. 2024

River Hotel
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 NZ$252 per night from 1 Oct to 2 Oct
NZ$252
per night
1 Oct - 2 Oct
7.6/10 Good! (7,860 reviews)
"I loved the lake view from the room, the classic feel of the property, and the super helpful and friendly staff!"

Reviewed on 24 Sep. 2024

Congress Plaza Hotel
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 NZ$334 per night from 27 Oct to 28 Oct
NZ$334
per night
27 Oct - 28 Oct
8.6/10 Excellent! (2,577 reviews)
"It was very clean and nice. The gym was very underwhelming but that's really it."

Reviewed on 24 Sep. 2024

Eurostars Magnificent Mile
See all 3,172 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 holiday package cost?
Our Crestwood holiday packages, which begin at just , are the best way to save precious money. Select your favourite 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 holiday 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 holiday 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 Centre 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 holiday?
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 travellers 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 holiday package?
With a holiday 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 holiday package?
Whether it’s your flight or hotel, you can cancel and rebook it. Locked in your Crestwood holiday 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 McCormick Place

McCormick Place

4.5/5(21 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
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Michigan Avenue

5/5(5 reviews)

You can find the perfect gifts to bring home when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue
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Navy Pier

4.5/5(64 reviews)

One of Chicago’s most popular attractions, especially on a hot day, with its fun fair, boats, circus and theatre.

Navy Pier

What to do in Crestwood

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Flyover in Chicago

NZ$45
Per adult
96% of travellers recommend
Flyover in Chicago
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Architecture River Tour from Navy Pier

NZ$87
Per adult
94% of travellers recommend
Architecture River Tour from Navy Pier
Image for Chicago by Night: 90 Minute River and Lakefront Cruise

Chicago by Night: 90 Minute River and Lakefront Cruise

NZ$68
Per adult
86% of travellers recommend
Chicago by Night: 90 Minute River and Lakefront Cruise
See all activities in Crestwood
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.