Westchester Hotels from S$75

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Check prices for these dates

Tonight
11 Mar - 12 Mar
Tomorrow
12 Mar - 13 Mar
This weekend
14 Mar - 16 Mar
Next weekend
21 Mar - 23 Mar

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Top 10 trending Westchester hotels

Four Points by Sheraton Chicago Westchester/Oak Brook
Reception

Four Points by Sheraton Chicago Westchester/Oak Brook

3.0 star property
8.4 out of 10, Very good, (1000)
"Great value "
The price is S$139
includes taxes & fees
23 Mar - 24 Mar
Four Points by Sheraton Chicago Westchester/Oak Brook
Sable at Navy Pier Chicago, Curio Collection by Hilton
Terrace/patio

Sable at Navy Pier Chicago, Curio Collection by Hilton

4.0 star property
9.4 out of 10, Exceptional, (2042)
"The friendliest hotel staff. Everyone was so kind and helpful. The rooms were clean with a beautiful view of the lake and the city. It’s just outside the business of the city so you get a little peace and quiet, but it’s a quick walk in and right on the walking paths. One of the best stays I’ve had in a while. "
The price is S$263
includes taxes & fees
13 Mar - 14 Mar
Sable at Navy Pier Chicago, Curio Collection by Hilton
Swissotel - Chicago
Front of property – evening/night

Swissotel - Chicago

4.5 star property
8.8 out of 10, Excellent, (1950)
"Beautiful hotel with a great fitness facility, and the staff was excellent. The location was also very convenient and was within walking distance from several popular Chicago sites and restaurants. "
The price is S$299
includes taxes & fees
12 Mar - 13 Mar
Swissotel - Chicago
Loews Chicago Hotel
Exterior

Loews Chicago Hotel

4.5 star property
9.4 out of 10, Exceptional, (1421)
"We had an absolutely amazing time! The bed was super comfy, and we just loved the view of the city!"
The price is S$354
includes taxes & fees
23 Mar - 24 Mar
Loews Chicago Hotel
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Exterior

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

4.0 star property
8.2 out of 10, Very good, (2639)
"Beautiful views and building was secure and clean."
The price is S$222
includes taxes & fees
12 Mar - 13 Mar
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
DoubleTree by Hilton Chicago - Magnificent Mile
Lobby

DoubleTree by Hilton Chicago - Magnificent Mile

4.0 star property
8.8 out of 10, Excellent, (1832)
"Wonderful trip to stay there. Very nice place will come back "
The price is S$174
includes taxes & fees
23 Mar - 24 Mar
DoubleTree by Hilton Chicago - Magnificent Mile
Radisson Blu Aqua Hotel Chicago
Indoor pool, seasonal outdoor pool, free pool cabanas, pool loungers

Radisson Blu Aqua Hotel Chicago

4.5 star property
8.6 out of 10, Excellent, (1442)
"The location is convenient for anyone willing to walk- Cloud Gate, Wildberry for breakfast, only a 30 min walk to Chixago 360. Everything is right around you! And the hot tubs and pools will have you never wanting to leave! "
The price is S$287
includes taxes & fees
23 Mar - 24 Mar
Radisson Blu Aqua Hotel Chicago
Fairmont Chicago at Millennium Park
Front of property – evening/night

Fairmont Chicago at Millennium Park

4.5 star property
8.6 out of 10, Excellent, (1645)
"I liked how clean the property is and it’s right across from a cvs so it’s not a hassle to get something quickly if needed. "
The price is S$320
includes taxes & fees
21 Mar - 22 Mar
Fairmont Chicago at Millennium Park
Aloft Chicago Mag Mile
Cocktail bar

Aloft Chicago Mag Mile

3.0 star property
8.6 out of 10, Excellent, (2658)
"Good location"
The price is S$136
includes taxes & fees
23 Mar - 24 Mar
Aloft Chicago Mag Mile
Ivy Boutique Hotel
Front of property

Ivy Boutique Hotel

4.5 star property
8.6 out of 10, Excellent, (1000)
"Everything was good but the floors could have been more clean they were sticky and the bathroom as well. And the wifi didn’t work at alllll so we couldn’t use the tvs."
The price is S$155
includes taxes & fees
12 Mar - 13 Mar
Ivy Boutique Hotel
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
Lobby

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

3.0 star property
8.4 out of 10, Very good, (1682)
"Easy transportation, I love the pillows"
The price is S$178
includes taxes & fees
24 Mar - 25 Mar
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
Hyatt Regency Chicago
2 bars/lounges

Hyatt Regency Chicago

4.0 star property
9.2 out of 10, Wonderful, (3201)
"Staff are very polite and helpful , beautiful environment and real lively. Room is very clean , bed cozy , view is great, bathroom very modern love love love the tub, Tv is huge! I definitely recommend oh and forgot to mention it’s a cozy couch in the room as well."
The price is S$321
includes taxes & fees
24 Mar - 25 Mar
Hyatt Regency Chicago
Hilton Chicago/Magnificent Mile Suites
Exterior

Hilton Chicago/Magnificent Mile Suites

3.5 star property
8.8 out of 10, Excellent, (2040)
"A couple basic items needed attention. I spoke to the staff and they were willing to try to fix the problem. "
The price is S$193
includes taxes & fees
23 Mar - 24 Mar
Hilton Chicago/Magnificent Mile Suites
Millennium Knickerbocker Chicago
View from property

Millennium Knickerbocker Chicago

4.0 star property
8.4 out of 10, Very good, (1797)
"Lovely place. Would stay at again! Thank you!"
The price is S$157
includes taxes & fees
1 Apr - 2 Apr
Millennium Knickerbocker Chicago
Hyatt Centric Chicago Magnificent Mile
Lobby

Hyatt Centric Chicago Magnificent Mile

4.0 star property
9.0 out of 10, Wonderful, (1022)
"We had a great stay! Love the Hyatt!"
The price is S$230
includes taxes & fees
27 Mar - 28 Mar
Hyatt Centric Chicago Magnificent Mile
The Chicago Hotel Collection - Magnificent Mile
Restaurant

The Chicago Hotel Collection - Magnificent Mile

4.0 star property
7.4 out of 10, Good, (1004)
"Rooms and location were great "
The price is S$150
includes taxes & fees
12 Mar - 13 Mar
The Chicago Hotel Collection - Magnificent Mile
Hotel Saint Clair- Magnificent Mile
Restaurant

Hotel Saint Clair- Magnificent Mile

4.0 star property
8.0 out of 10, Very good, (1532)
"Overall, had a nice time here! This room was exactly what I needed for my solo trip in Chicago. I didn't spend a lot of time in the room since I was exploring, but it was spacious and had good amenities. I rated this 4 stars because of three things: when I entered the room for the first time, it had a very musty/dirty laundry type of smell. Maybe through the AC system? Unclear why that was, but linens were inspected well before using anything. The bed was made neatly and linens themselves were...
The price is S$155
includes taxes & fees
24 Mar - 25 Mar
Hotel Saint Clair- Magnificent Mile
Hotel Riu Plaza Chicago
Front of property

Hotel Riu Plaza Chicago

4.0 star property
9.4 out of 10, Exceptional, (1555)
"Very impressed with staff of this hotel. Very friendly yet professional from the first step into the building all the way to the checkout. Room was on a smaller side, but plenty big for my son and me, however if might be tight if it 4 of you and staying for a longer period. Breakfast was amazing as well."
The price is S$202
includes taxes & fees
12 Mar - 13 Mar
Hotel Riu Plaza Chicago
Best Western Grant Park Hotel
Restaurant

Best Western Grant Park Hotel

2.5 star property
8.2 out of 10, Very good, (2500)
"Front desk staff and room cleaning staff were very good; Paris Baguette is a plus."
The price is S$113
includes taxes & fees
8 Apr - 9 Apr
Best Western Grant Park Hotel
Congress Plaza Hotel
Aerial view

Congress Plaza Hotel

3.5 star property
7.8 out of 10, Good, (8578)
"Awesome in overall. "
The price is S$179
includes taxes & fees
23 Mar - 24 Mar
Congress Plaza Hotel
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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Learn more about Westchester

Upscale Westchester is calling! Discover its basketball, dining, golf and more.

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Frequently asked questions

What's the best place to stay in Westchester?

Located 13.3 mi (21.4 km) from the heart of Westchester, Congress Plaza Hotel is a top choice for your stay, based on our traveller data. Two other options for your stay in the area are River Hotel and L7 Chicago by LOTTE. See all available top hotels, or vacation rentals in Westchester.

If I need to cancel my hotel reservation in Westchester, will I receive a refund?

Yes! Most hotel room reservations are refundable if you cancel prior to the accommodation's cancellation deadline, which is often 24 or 48 hours before check in. If you have a reservation that's non-refundable, it may still be possible to cancel it and receive a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Westchester.

What is the favourite LGBTQ-friendly accommodation in Westchester?

Four Points by Sheraton Chicago Westchester/Oak Brook is a top LGBTQ-friendly hotel, and features free Wi-Fi and pillowtop beds. See all available hotels listed as LGBTQ-friendly in Westchester.

What's the best dog-friendly place to stay in Westchester?

Four Points by Sheraton Chicago Westchester/Oak Brook is a top hotel for people travelling with their pets, and offers a restaurant and a fitness centre for its human guests. See more pet-friendly hotel accommodations in Westchester.

What's the best accommodation for a golf trip to Westchester?

Four Points by Sheraton Chicago Westchester/Oak Brook is a hotel featuring free WiFi and pillowtop beds, and it's a top choice for playing a round of golf. See more golf hotels in Westchester.

What are some accommodation options with pools in Westchester?

Hilton Garden Inn Chicago Downtown/Magnificent Mile: Hotel, 4-minute walk from Michigan Avenue. Features complimentary high-speed (wired) Internet access, an indoor pool and LCD televisions. Also, another option that features an on-site pool is Hilton Chicago. View all hotels with pools in Westchester.

What's it like to stay in Westchester?

Visitors to Westchester will definitely enjoy the shopping and restaurants. Tourists can also enjoy so much more including its basketball games. Around the area, top sights include United Center, Wrigley Field and Michigan Avenue. In Westchester, there are 7 hotels and other accommodation options to choose from. Find out more about Westchester.

What should I see while I'm in Westchester?

United Center, Wrigley Field and Michigan Avenue are some of the notable places to visit in the surrounding area. Additionally, you'll find Soldier Field and Navy Pier in the area. Take a look at what more there is to see and do in Expedia's Westchester guide.

What's the seasonal weather in Westchester?

The hottest months are usually July and August, with an average temperature of 22°C, while the coldest months are January and February, with an average of -1°C. The snowiest months in Westchester are January, November, February and December, with each month seeing an average of 13 cm of snowfall.