Crestwood Holidays from NZ$2,542

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The Latest Crestwood Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
Downtown Chicago
per person
15 Aug - 18 Aug
found 17 hours ago
Return flight included
Auckland (AKL) to Chicago (ORD)
8.4/10 Very Good! (3,410 reviews)
It was a convenient location and very clean. Would be nice if they offered a small breakfast for free.

Reviewed on 21 Jun. 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
15 Aug - 18 Aug
found 17 hours ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9.4/10 Exceptional! (1,613 reviews)
Great hotel with great staff.

Reviewed on 20 Jun. 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
per person
15 Aug - 18 Aug
found 17 hours ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9.4/10 Exceptional! (2,039 reviews)
Very nice hotel and clean. Perfect breakfast and wonderful location. Staff was very nice as well; attentive.

Reviewed on 21 Jun. 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
per person
15 Aug - 18 Aug
found 17 hours ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9/10 Wonderful! (319 reviews)
I had no idea how nice this property would be! I had a full one-bedroom apartment and amazing view and amenities. 10/10, would stay again!

Reviewed on 1 Jun. 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
per person
15 Aug - 18 Aug
found 17 hours ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9.2/10 Wonderful! (1,087 reviews)
Great setup, location

Reviewed on 21 Jun. 2025

Crestwood Holiday

Our pick of the best Crestwood Hotel Deals

Embassy Suites by Hilton Chicago Downtown River North
Embassy Suites by Hilton Chicago Downtown River North
4 out of 5
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NZ$301 per night from 30 June to 1 July
NZ$301
30 June - 1 July
includes taxes & fees
8.4/10 Very Good! (4,234 reviews)
"I love everything about this hotel, especially the breakfast plus you have a happy hour. The only thing that I can say is that the bathroom needs to have a vent because if you shut the door for a long time, it smells like mildew, so I had to keep making sure the door stays open but other than that, ..."

Reviewed on 18 Jun. 2025

Embassy Suites by Hilton Chicago Downtown River North
InterContinental Chicago Magnificent Mile by IHG
InterContinental Chicago Magnificent Mile by IHG
4.5 out of 5
505 N Michigan Ave, Chicago, IL
Fully refundable
The price is NZ$362 per night from 1 July to 2 July
NZ$362
1 July - 2 July
includes taxes & fees
9/10 Wonderful! (1,903 reviews)
"Over all, a very pleasant stay."

Reviewed on 20 Jun. 2025

InterContinental Chicago Magnificent Mile by IHG
Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile Suites
3.5 out of 5
198 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NZ$272 per night from 6 July to 7 July
NZ$272
6 July - 7 July
includes taxes & fees
8.8/10 Excellent! (2,313 reviews)
"Valet parking too expensive."

Reviewed on 18 Jun. 2025

Hilton Chicago/Magnificent Mile Suites
See all 3,551 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?
Offering excellent value package deals from NZ$2,542 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.

Discover the most popular places to visit in Crestwood

Wrigley Field which includes a city, central business district and a sporting event

Wrigley Field

A big piece of Chicago's soul, an ancient stadium that keeps alive the quirky, edgy madness of baseball.

Wrigley Field
Navy Pier

Navy Pier

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

Navy Pier
McCormick Place

McCormick Place

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

River tour boat in Chicago

Architecture River Tour

NZ$81
per adult
94% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

NZ$75
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

NZ$74
per adult
92% of travellers recommend
Chicago By Night River & Lake 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.