
Crestwood Vacations from SAR2,151
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The Latest Crestwood Vacation Packages
Price found within the past 48 hours. Click for updated prices.


Level Chicago – Old Town
Downtown Chicago
Price was SAR2,556, price is now SAR2,158 per person
SAR2,158
per person
Feb 19 - Feb 21
found 1 day ago
Roundtrip non-stop flight included
Buffalo (BUF) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
I stayed 5 nights total, 4 nights in a two BR, 1 bath with a balcony and the last night in a one BR. The 2BR was great. It faced East, received a lot of sunlight, was clean, modern and the bed was very comfortable. The gym had what I needed too. actually liked sleeping with the sound of the el nearby because I used to live in the area. I did not give it 5 stars because the walls are super thin. Someone had a party next to me and it was impossible to sleep hearing voices straight through the walls. Being a newer building, I don’t think the best quality appliances or fixtures were chosen. My ice machine wasn’t working and the heat/fan only worked in certain areas in the 2BR. Additional lighting should be added. The 1BR shower fixtures and drain needed some attention. That said, Mihajlo and the front desk staff were very helpful and attentive and helped me with whatever I needed. The 1BR seemed more like a studio to m. I’d prefer to book directly through Level, but it was a better price with Expedia. I still thought it was pricey but I was overall happy with my stay.
Reviewed on 12 January 2026

Hilton Chicago O'Hare Airport
O'Hare
Price was SAR2,814, price is now SAR2,381 per person
SAR2,381
per person
Feb 19 - Feb 21
found 1 day ago
Roundtrip non-stop flight included
Buffalo (BUF) to Chicago (ORD)
8.2/10 Very Good! (2,158 reviews)
Stayed prior to flight, clean, quiet room!
Reviewed on 13 January 2026

The Emily Hotel
Downtown Chicago
Price was SAR2,765, price is now SAR2,347 per person
SAR2,347
per person
Feb 19 - Feb 21
found 1 day ago
Roundtrip non-stop flight included
Buffalo (BUF) to Chicago (ORD)
9.2/10 Wonderful! (1,264 reviews)
room was clean, comfortable, & staff were kind and welcoming
Reviewed on 12 January 2026

Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Price was SAR2,606, price is now SAR2,273 per person
SAR2,273
per person
Feb 19 - Feb 21
found 1 day ago
Roundtrip non-stop flight included
Buffalo (BUF) to Chicago (ORD)
9.2/10 Wonderful! (317 reviews)
Had an amazing stay. Just note, you need to ask for the room cleaning service, and its not for everyday. Overall really loved the place and hope to come back!
Reviewed on 10 January 2026
Find the Best Crestwood Vacation Packages
Crestwood Hotel Deals

Hilton Chicago
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is SAR 489 per night from Feb 1 to Feb 2
SAR 489
SAR 684 total
1 Feb - 2 Feb
includes taxes & fees
8.4/10 Very Good! (2,527 reviews)
THe staff was very efficient and professional and the breakfast was great.
Reviewed on 13 January 2026

Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is SAR 335 per night from Jan 25 to Jan 26
SAR 335
SAR 393 total
25 Jan - 26 Jan
includes taxes & fees
8.8/10 Excellent! (3,708 reviews)
The staff was amazing and helpful. The room was very clean and the view was beautiful. Everything was so relaxing i hardly wanted to leave the room. I had the best sleep ever in the comfortable king size bed. The gym my great , hot towels, water and headphones to use on the equipment. I stayed for ...
Reviewed on 13 January 2026

Club Quarters Hotel Wacker at Michigan, Chicago
75 E Wacker Dr Chicago IL
The price is SAR 306 per night from Jan 27 to Jan 28
SAR 306
SAR 359 total
27 Jan - 28 Jan
includes taxes & fees
8.6/10 Excellent! (2,062 reviews)
Helpful staff! Great view of the river from our room.
Reviewed on 13 January 2026
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.
Discover the most popular places to visit in Crestwood

Wrigley Field
4.5/5(2,128 reviews)
Catch an event at Wrigley Field during your trip to Chicago. Stroll along the lakeside or experience the acclaimed theater scene in this vibrant area.

Michigan Avenue
4.5/5(332 reviews)
You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Navy Pier
4.5/5(4,870 reviews)
With a visit to Navy Pier, a favorite shopping spot in Chicago, you can enjoy some retail therapy. Amble around this vibrant area's lakeside or experience its acclaimed art scene.
