Crestwood Holidays

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Your Crestwood Holiday

From its highlights to its hidden treasures, this city is best experienced with a Crestwood holiday package. Check out places to stay in Hyde Park, which is good for history, nature and culture. Fill your free time with tours of Trinity Christian College, Chicago Ridge Shopping Mall and Orland Square, some of the attractions you just have to see during your trip to Crestwood. Browse Expedia's wide range of travel options and book your ultimate holiday to Crestwood now.

Crestwood Holiday

Crestwood Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)
Population
11,000
Max Temp Winter
-1.11ºC
Max Temp Summer
27ºC
Top Sights
Galloping Ghost, DuSable Museum of African-American History and Smart Museum of Art

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 AU$452 per night from 7 Sept to 8 Sept
AU$452
7 Sept - 8 Sept
includes taxes & fees
7.8/10 Good! (8,974 reviews)
"Great location! Rooms are newly renovated and nice."

Reviewed on 5 Aug. 2025

Congress Plaza Hotel
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$350 per night from 22 Aug to 23 Aug
AU$350
22 Aug - 23 Aug
includes taxes & fees
8.2/10 Very Good! (1,831 reviews)
"Great!"

Reviewed on 5 Aug. 2025

Palmer House a Hilton Hotel
Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

3.5 out of 5
25 South Halsted Street, Chicago, IL
Fully refundable
The price is AU$263 per night from 24 Aug to 25 Aug
AU$263
24 Aug - 25 Aug
includes taxes & fees
8.8/10 Excellent! (1,353 reviews)
"Nice hotel and with easy access"

Reviewed on 6 Aug. 2025

Crowne Plaza Chicago West Loop by IHG
See all 3,746 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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Discover the most popular places to visit in Crestwood

Navy Pier

Navy Pier

4.5/5(64 reviews)

A waterfront entertainment strip with fun diversions for both young and old, with shops, restaurants and even a Ferris wheel.

Navy Pier
Millennium Park showing modern architecture, a city and street scenes

Millennium Park

4.5/5(73 reviews)

One of Chicago’s main focal points, where locals and visitors flock to see the striking art, architecture and landscape on show.

Millennium Park
Grant Park

Grant Park

4.5/5(47 reviews)

Chicago’s front yard is a pretty landscaped park, which is home to public art displays, museums, themed gardens and international music festivals.

Grant Park

What to do in Crestwood

River tour boat in Chicago

Architecture River Tour

AU$64
per adult
96% of travellers recommend
Architecture River Tour
Couple on a sightseeing boat in Chicago

Skyline Lake Tour

AU$46
per adult
92% of travellers recommend
Skyline Lake Tour
Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

AU$69
per adult
100% of travellers recommend
Chicago Sightseeing River and Lake Cruise
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.