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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, (1,004 reviews)
"Staff was incredible, room felt nice and clean, the only way I knew the building was older was because of the elevators. Overall wonderful experience."
United States
Xavier
The price is CA $160
CA $179 total
includes taxes & fees
May 28 - May 29
Holiday Inn Express Crestwood by IHG

River Hotel

River Hotel
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (5,190 reviews)
"excellent stay"
United States
Jaeyoung
The price is CA $163
CA $194 total
includes taxes & fees
May 26 - May 27
River Hotel

Freehand Chicago

Freehand Chicago
4.0 star property
Downtown Chicago
8.0 out of 10, Very good, (3,016 reviews)
"Great central location, lots to do nearby."
United States
Michael
The price is CA $115
CA $161 total
includes taxes & fees
May 25 - May 26
Freehand Chicago

Aloft by Marriott Chicago Mag Mile

Aloft by Marriott Chicago Mag Mile
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (3,239 reviews)
"Nice place to stay"
United States
Jimmie
The price is CA $206
CA $245 total
includes taxes & fees
May 26 - May 27
Aloft by Marriott Chicago Mag Mile

The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile
4.0 star property
Downtown Chicago
7.8 out of 10, Good, (1,456 reviews)
"Great stay"
United States
Ontario
The price is CA $168
CA $199 total
includes taxes & fees
May 25 - May 26
The Chicago Hotel Collection - Magnificent Mile

Congress Plaza Hotel

Congress Plaza Hotel
3.5 star property
Downtown Chicago
8.0 out of 10, Very good, (10,131 reviews)
"Excellent stay"
United States
Jennifer
The price is CA $185
CA $219 total
includes taxes & fees
May 25 - May 26
Congress Plaza Hotel

Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

Fairfield Inn & Suites Chicago Downtown / Magnificent Mile
3.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,002 reviews)
"All around great stay. "
United States
Nicholas
The price is CA $178
CA $212 total
includes taxes & fees
May 25 - May 26
Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (4,214 reviews)
"Great location & breakfast was amazing."
United States
sierra
The price is CA $220
CA $301 total
includes taxes & fees
May 27 - May 28
Hotel Riu Plaza Chicago

Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (2,246 reviews)
"Close to many attractions and shopping and nice unique hotel"
United States
Brittany
The price is CA $165
CA $238 total
includes taxes & fees
May 25 - May 26
Silversmith Hotel Chicago Downtown

Eurostars Magnificent Mile

Eurostars Magnificent Mile
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3,564 reviews)
"Great location, large rooms, we loved our stay and would definitely recommend "
Australia
Belinda
The price is CA $221
CA $263 total
includes taxes & fees
May 25 - May 26
Eurostars Magnificent Mile

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, (2,506 reviews)
"I loved it here and will definitely stay again."
United States
Gina
The price is CA $265
CA $363 total
includes taxes & fees
May 26 - May 27
Sable at Navy Pier Chicago, Curio Collection by Hilton

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, (2,283 reviews)
"Excellent location and friendly staff."
United States
Radhika
The price is CA $163
CA $194 total
includes taxes & fees
May 26 - May 27
Club Quarters Hotel Wacker at Michigan, Chicago

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2,446 reviews)
"My favorite place to stay!"
United States
Teresa
The price is CA $254
CA $343 total
includes taxes & fees
May 25 - May 26
Palmer House a Hilton Hotel

Central Loop Hotel

Central Loop Hotel
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2,149 reviews)
"Great place! Would stay again!"
United States
Tasha
The price is CA $152
CA $180 total
includes taxes & fees
May 26 - May 27
Central Loop Hotel

Hyatt Centric The Loop Chicago

Hyatt Centric The Loop Chicago
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (2,545 reviews)
"Excellent location, great staff, clean rooms "
Canada
Brigita
The price is CA $205
CA $279 total
includes taxes & fees
May 25 - May 26
Hyatt Centric The Loop Chicago

La Quinta Inn & Suites by Wyndham Chicago Downtown

La Quinta Inn & Suites by Wyndham Chicago Downtown
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2,786 reviews)
"Very clean room, nice breakfast and really nice hotel restaurant"
United States
Hugo
The price is CA $192
CA $253 total
includes taxes & fees
May 25 - May 26
La Quinta Inn & Suites by Wyndham Chicago Downtown

Arlo Chicago

Arlo Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (2,103 reviews)
"Very beautiful hotel!"
United States
Ingrid
The price is CA $185
CA $262 total
includes taxes & fees
May 26 - May 27
Arlo Chicago

Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago
3.5 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,393 reviews)
"Nice location nestled I'm the middle of it all. Great stay the staff was communicative."
United States
Erik
The price is CA $241
CA $325 total
includes taxes & fees
May 26 - May 27
Sports Illustrated Resorts Chicago

FOUND Hotel Chicago River North

FOUND Hotel Chicago River North
2.0 star property
Downtown Chicago
8.4 out of 10, Very good, (618 reviews)
"Excellent stay in good location"
United States
Nicholas
The price is CA $147
CA $172 total
includes taxes & fees
May 25 - May 26
FOUND Hotel Chicago River North

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile
4.0 star property
Downtown Chicago
8.2 out of 10, Very good, (2,715 reviews)
"Amazing place"
United States
Rodolfo
The price is CA $120
CA $185 total
includes taxes & fees
May 25 - May 26
Hotel Felix River North/Magnificent Mile
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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)

Top Crestwood Hotel Reviews

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Hotels in Crestwood with star rating

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 $101 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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