Crestwood Holidays

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Crestwood Holiday

Our pick of the best Crestwood Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is NZ$270 per night from 25 May to 26 May
NZ$270
25 May - 26 May
includes taxes & fees
8/10 Very Good! (10,171 reviews)
"Good for a sleep and go. Not horrible, certainly not the best hotel i've ever stayed at."

Reviewed on 20 May 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is NZ$350 per night from 25 May to 26 May
NZ$350
25 May - 26 May
includes taxes & fees
9.4/10 Exceptional! (4,201 reviews)
"Breakfast bar was very good just need 0to go cups for coffee.I'm"

Reviewed on 21 May 2026

Hotel Riu Plaza Chicago
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is NZ$246 per night from 25 May to 26 May
NZ$246
25 May - 26 May
includes taxes & fees
7.8/10 Good! (1,449 reviews)
"Great stay"

Reviewed on 21 May 2026

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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.