Hotels in Crestwood

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Check prices for these dates

Tonight
Dec 24 - Dec 25
Tomorrow
Dec 25 - Dec 26
This weekend
Dec 26 - Dec 28
Next weekend
Jan 2 - Jan 4

Where to stay in Crestwood?

Exterior
Holiday Inn Express Crestwood by IHG
Holiday Inn Express Crestwood by IHG
2.5 star property
7.8 out of 10, Good, (1001)
The price is $79
$88 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Holiday Inn Express Crestwood by IHG
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.
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Budget hotels in Crestwood and vicinity

Cocktail bar
Freehand Chicago

Freehand Chicago

Freehand Chicago
4.0 star property
Downtown Chicago
8.0 out of 10, Very Good, (2658)
The price is $59
$86 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Freehand Chicago
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.
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When is the best time to visit Crestwood?

Our prices for hotels in Crestwood are cheapest in January
Price trends for hotels in Crestwood
Pricing is based on two traveler single night rates
View properties in December
Currently viewing crowd sizes and weather for December.
Typical weather for Crestwood
December
Low crowds
High 3°C / low -3°C. Cloudy most days.
View properties in December
3°
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December, Low crowds, average high temperature 3 degrees Celsius, average low temperature -3 degrees Celsius. Cloudy most days.
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January, Low crowds, average high temperature -1 degrees Celsius, average low temperature -7 degrees Celsius. Snow likely.
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February, Low crowds, average high temperature 1 degrees Celsius, average low temperature -6 degrees Celsius. Snow likely.
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March, Moderate crowds, average high temperature 8 degrees Celsius, average low temperature 0 degrees Celsius. Cloudy most days.
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April, Low crowds, average high temperature 14 degrees Celsius, average low temperature 5 degrees Celsius. Partly sunny.
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20°
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May, High crowds, average high temperature 20 degrees Celsius, average low temperature 11 degrees Celsius. Sunny most days.
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25°
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June, High crowds, average high temperature 25 degrees Celsius, average low temperature 17 degrees Celsius. Sunny most days.
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28°
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July, High crowds, average high temperature 28 degrees Celsius, average low temperature 19 degrees Celsius. Sunny most days.
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27°
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August, Moderate crowds, average high temperature 27 degrees Celsius, average low temperature 19 degrees Celsius. Sunny most days.
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24°
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September, Moderate crowds, average high temperature 24 degrees Celsius, average low temperature 16 degrees Celsius. Sunny most days.
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October, High crowds, average high temperature 17 degrees Celsius, average low temperature 9 degrees Celsius. Sunny most days.
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9°
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November, Moderate crowds, average high temperature 9 degrees Celsius, average low temperature 2 degrees Celsius. Partly sunny.
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Monthly weather averages (˚C)

Top landmarks in Crestwood

Hollywood Park

If thrills are what you're after, head to Hollywood Park, located 0.5 mi (0.8 km) from central Crestwood. If you have fun at Hollywood Park, you'll love Childrens Museum of Oak Lawn and Lake Katherine Nature Center, both located nearby.
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Learn more about Crestwood

The region around Crestwood is home to attractions such as Hollywood Park and McCormick Place.

See all hotels in Crestwood
Reflection on Lake at Dusk at Turtlehead Lake Nature Preserve in Orland Park, IL (Suburban Chicago)

Check out reviews of Crestwood hotels guests love

Holiday Inn Chicago Dwtn - The Mart by IHG

Holiday Inn Chicago Dwtn - The Mart by IHG

10/10 Excellent
"Room was clean, staff amazing and just an overall great place to stay. "
Jerome 2-night trip
Posted 1 day ago
Holiday Inn Chicago Dwtn - The Mart by IHG

Frequently asked questions

What accommodations do travelers like in Crestwood?
Holiday Inn Express Crestwood by IHG is an accommodation that is popular with guests.
Can I book a refundable hotel in Crestwood?
If you need the flexibility to change your plans to Crestwood, most accommodations offer refundable* bookable rates. You can find these properties by searching our site and using the "fully refundable" filter to narrow the results down.
What will the weather in Crestwood be like during my visit?
July and August are typically the warmest months in Crestwood when the average temp is 71°F. January and February are the coldest months when the average temperature is 31°F. June and May are the months with the most rain.
Why should I book my Crestwood hotel through Hotels.com?
There are lots of reasons to book your Crestwood trip with us: our free cancellations on selected hotels gives you flexibility, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.