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Our top choices for Crestwood hotels

Holiday Inn Express Crestwood by IHG

Holiday Inn Express Crestwood by IHG
2.5 star property
Crestwood
7.8 out of 10, Good, (1,000 reviews)
"Honestly the staff were some friendly people, made you feel comfortable. It’s my third time staying there. "
United States
Lino
The price is CA $155
CA $174 total
includes taxes & fees
Apr 5 - Apr 6
Holiday Inn Express Crestwood by IHG

River Hotel

River Hotel
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (5,029 reviews)
"very beautiful hotel and great location "
United States
Ciandra
The price is CA $130
CA $152 total
includes taxes & fees
Mar 23 - Mar 24
River Hotel

Freehand Chicago

Freehand Chicago
4.0 star property
Downtown Chicago
8.0 out of 10, Very good, (2,812 reviews)
"Great location, clean and decent sized room, staff was helpful and amenities are very convenient!"
United States
MaryJane
The price is CA $100
CA $141 total
includes taxes & fees
Mar 25 - Mar 26
Freehand Chicago

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2,334 reviews)
"We had a great stay and the staff are very friendly and accommodating. "
United States
Krista
The price is CA $185
CA $251 total
includes taxes & fees
Apr 5 - Apr 6
Palmer House a Hilton Hotel

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (3,589 reviews)
"Great location ans staff was amazing!!"
United States
Bianca
The price is CA $181
CA $251 total
includes taxes & fees
Apr 6 - Apr 7
Hotel Riu Plaza Chicago

FOUND Hotel Chicago River North

FOUND Hotel Chicago River North
2.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (506 reviews)
"Lots of stuff close by , cool vibe inside and very nice staff"
United States
Abel
The price is CA $120
CA $141 total
includes taxes & fees
Mar 23 - Mar 24
FOUND Hotel Chicago River North

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (3,147 reviews)
"Nice location and good hotel"
United States
Taneshia
The price is CA $148
CA $174 total
includes taxes & fees
Mar 29 - Mar 30
Aloft Chicago Mag Mile

Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (3,403 reviews)
"Clean room | Nice location | Discounted parking garage."
United States
Conrad
The price is CA $129
CA $152 total
includes taxes & fees
Mar 23 - Mar 24
Club Quarters Hotel, Central Loop, Chicago

Ivy Boutique Hotel

Ivy Boutique Hotel
4.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (1,175 reviews)
"Clean friendly staff love the decor "
United States
Kiasha
The price is CA $175
CA $205 total
includes taxes & fees
Apr 15 - Apr 16
Ivy Boutique Hotel

L7 Chicago by LOTTE

L7 Chicago by LOTTE
4.5 star property
Downtown Chicago
9.6 out of 10, Exceptional, (3,794 reviews)
"Amazing hotel-- Loved staying here."
United States
Maureen
The price is CA $210
CA $247 total
includes taxes & fees
Mar 31 - Apr 1
L7 Chicago by LOTTE

The Godfrey Hotel Chicago

The Godfrey Hotel Chicago
4.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (2,105 reviews)
"Nice place to stay. "
United States
Akanksha
The price is CA $136
CA $192 total
includes taxes & fees
Mar 23 - Mar 24
The Godfrey Hotel Chicago

Club Quarters Hotel Wacker at Michigan, Chicago

Club Quarters Hotel Wacker at Michigan, Chicago
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (2,125 reviews)
"Great stay!"
United States
Hannah
The price is CA $125
CA $147 total
includes taxes & fees
Mar 24 - Mar 25
Club Quarters Hotel Wacker at Michigan, Chicago

Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (1,021 reviews)
"Lots of places to eat and shop nearby"
United States
Analicia
The price is CA $184
CA $256 total
includes taxes & fees
Apr 5 - Apr 6
Staypineapple, An Iconic Hotel, The Loop

Hilton Chicago

Hilton Chicago
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2,697 reviews)
"Amazing place to stay!"
United States
Nia
The price is CA $179
CA $250 total
includes taxes & fees
Apr 1 - Apr 2
Hilton Chicago

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (2,404 reviews)
"Great spot and view, would stay again!"
United States
Kimberly
The price is CA $206
CA $289 total
includes taxes & fees
Mar 30 - Mar 31
Sable at Navy Pier Chicago, Curio Collection by Hilton

Hyatt Centric The Loop Chicago

Hyatt Centric The Loop Chicago
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (2,418 reviews)
"this location is safe and convenient-would book here again."
United States
eduardo
The price is CA $192
CA $260 total
includes taxes & fees
Mar 27 - Mar 28
Hyatt Centric The Loop Chicago

Moxy Chicago Downtown

Moxy Chicago Downtown
3.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (916 reviews)
"Very nice place to stay!"
United States
Daniel
The price is CA $152
CA $178 total
includes taxes & fees
Apr 5 - Apr 6
Moxy Chicago Downtown

Central Loop Hotel

Central Loop Hotel
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2,034 reviews)
"Staff was friendly and location was central to walk to many of the big sights "
United States
Jensen
The price is CA $129
CA $152 total
includes taxes & fees
Mar 24 - Mar 25
Central Loop Hotel

Hotel 55 Chicago Downtown

Hotel 55 Chicago Downtown
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (1,576 reviews)
"How clean everything was and great staff "
United States
Darius
The price is CA $145
CA $211 total
includes taxes & fees
Mar 29 - Mar 30
Hotel 55 Chicago Downtown

The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile
4.0 star property
Downtown Chicago
7.6 out of 10, Good, (1,244 reviews)
"Amazing stay "
United States
Napoleon
The price is CA $165
CA $194 total
includes taxes & fees
Mar 23 - Mar 24
The Chicago Hotel Collection - Magnificent Mile
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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Stay near popular Crestwood attractions

Learn more about Crestwood

Explore the sprawling Playfield Park where locals gather for weekend softball tournaments and picnics under shady oak trees. Visit Caesar Park's splash pad in summer, then grab a slice at the family-owned Aurelio's Pizza that's been serving locals since 1959.

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

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Frequently asked questions

What is the best area to stay in Crestwood?
The best area to stay in Crestwood is near the intersection of Cicero Avenue and Cal Sag Road, as this offers the most convenient access to amenities and attractions.

This area is the commercial heart of Crestwood. Along Cicero Avenue, you'll find a variety of shops, restaurants, and essential services. It's also very accessible, being close to major roadways, which is ideal for getting around.

For travellers attending events or visiting the entertainment venues, staying near Cicero Avenue and Cal Sag Road is particularly convenient. Many hotels in this vicinity are within easy reach of the local sports and concert arena, making it simple to get to and from events without much fuss.

Families will appreciate this area for its practicality. There are numerous family-friendly dining options, and the proximity to the arena means less travel time for activities suitable for all ages.
What are the best hotels in Crestwood that travellers recommend?
For hotels in Crestwood that travellers recommend, the Holiday Inn Express Crestwood by IHG is a superb option.

This hotel, with a 7.8 rating, is frequently praised for its friendly and amazing staff. Guests appreciate the clean, big rooms and comfortable beds, ensuring a relaxing stay. A great and delicious complimentary buffet breakfast is available, and the hotel features an indoor pool and fitness facilities. Off-street parking and self-parking are also provided free of charge. It is conveniently located near Hollywood Park, just 0.9 kilometres away.
What are the best family hotels in Crestwood?
For families visiting Crestwood, the Holiday Inn Express Crestwood by IHG is a much-loved option.

This hotel, with a 7.8 rating, offers excellent amenities for families, including sofa beds and connecting rooms, which are very convenient. Guests frequently mention the clean and spacious rooms, as well as the comfortable beds. A complimentary buffet breakfast is provided, and guests often praise it as delicious and great. You will also find free wired internet and complimentary self-parking. The hotel staff, particularly the front desk team, are consistently described as friendly and amazing. For a bit of family fun, Hollywood Park is less than a kilometre away. Find more child-friendly accommodations in Crestwood
What hotels in Crestwood offer free breakfast?
For hotels in Crestwood offering complimentary breakfast, the Holiday Inn Express Crestwood by IHG is a great option.

The Holiday Inn Express Crestwood by IHG, with a 7.8 rating, provides a free buffet breakfast to all guests, which many describe as both great and delicious. Guests frequently praise the friendly and amazing staff, the clean and big rooms, and comfortable beds. Additionally, the hotel offers free wired internet and free self-parking for added convenience. Find more hotels with free breakfast in Crestwood
What are the top pet-friendly hotels in Crestwood?
For a top pet-friendly hotel in Crestwood, the Holiday Inn Express Crestwood by IHG is an excellent choice.

This hotel, with a 7.8 rating, offers convenient amenities such as free wired and wireless internet, and a complimentary breakfast buffet. Guests frequently praise the friendly and amazing staff, the clean and big rooms, and the delicious breakfast. The comfortable beds also receive high marks. It is also well-located, being just 0.9 kilometres from Hollywood Park. See more pet-friendly hotels in Crestwood
What are the best budget hotels in Crestwood?
For budget-friendly accommodation in Crestwood, the Holiday Inn Express Crestwood by IHG is a top choice.

This hotel, with a 7.8 rating, offers guests a comfortable stay with several convenient amenities. Travellers frequently mention the friendly and amazing staff, along with the clean and spacious rooms. A great complimentary breakfast buffet is served daily, and guests appreciate the comfortable beds. Free wired and wireless internet access is available, as is free self-parking. View all budget hotels in Crestwood
When is the best time to go to Crestwood?
The best time to visit Crestwood is during the warmer months, from late spring to early autumn, specifically between May and October.

During this period, the weather is generally pleasant, with comfortable temperatures great for exploring the local area. You'll find that most local attractions and outdoor activities are fully operational, and the longer daylight hours allow for more extensive sightseeing.

For those looking to enjoy local events, the summer months often feature community gatherings and outdoor markets. The weather is typically sunny, making it ideal for families who want to spend time outdoors without the chill of winter.

If you prefer slightly cooler temperatures and fewer crowds, early autumn, particularly September and October, offers a lovely experience.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Crestwood.
How can I save on a Crestwood hotel booking with Expedia?
Members always get our best prices. Find our best Crestwood hotel deals by joining Expedia's free travel rewards program today. As a member, you can unlock instant savings and member perks when you're logged in to your account. Another tip is to book your hotel and flights together on Expedia, where bundling can result in significant savings.
How much is the nightly rate at a Crestwood hotel?
Prices for hotels in Crestwood often vary, but you can find a great deal from CA $83 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

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