Crestwood Holidays

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Crestwood Holiday

Our pick of the best 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 NZ$245 per night from 10 Nov to 11 Nov
NZ$245
10 Nov - 11 Nov
includes taxes & fees
8/10 Very good! (10,085 reviews)
"it needs a lot of work. our bathroom had several cracks in the floor. , a huge gaping hole in the ceiling , dried dirt and hair on bathroom doors, the showered were stained and rusty, i couldn’t even shower in there because of how disgusting it was. the hotel was 14 floor and only one working elevator. ..."

Reviewed on 1 Nov 2026

Congress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is NZ$262 per night from 2 Dec to 3 Dec
NZ$262
2 Dec - 3 Dec
includes taxes & fees
8/10 Very good! (2,636 reviews)
"Great location and staff were kind! Would stay here again"

Reviewed on 1 Nov 2026

The Chicago Hotel Collection Ambassador Gold Coast
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$251 per night from 23 Nov to 24 Nov
NZ$251
23 Nov - 24 Nov
includes taxes & fees
8.8/10 Excellent! (5,584 reviews)
"Amazing staff and view! Highly recommend"

Reviewed on 1 Nov 2026

River Hotel
See all 3,687 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.

Stay near popular Crestwood attractions

Hollywood Park

This family entertainment centre offers go-karts, mini-golf, bumper cars, and a multi-floor arcade all in one vibrant location. Enjoy chef-crafted meals between activities for a complete day of fun.
See properties

What to do in Crestwood

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

NZ$43
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

NZ$71
per adult
92% of travellers recommend
Art Institute of Chicago
Chicago's Navy Pier Centennial Wheel Ticket

Chicago's Navy Pier Centennial Wheel Ticket

NZ$43
per adult
100% of travellers recommend
Chicago's Navy Pier Centennial Wheel Ticket
See all activities in Crestwood

Frequently asked questions

How much does a Crestwood holiday package cost?
Offering excellent value package deals 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.

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