COVID-19 alert: Travel requirements are changing rapidly, including need for pre-travel COVID-19 testing and quarantine on arrival.

Find Boutique Hotels in Downtown Chicago, Chicago from $99

Search over 1 million properties and 550 airlines worldwide.

Members save 10% more on select hotels, cars, activities and vacation rentals. Sign up.

Free cancellation on most hotels. Because flexibility matters.

Top Downtown Chicago Boutique Hotels

Trump International Hotel & Tower Chicago
5 out of 5
401 N Wabash Ave, Chicago, IL
Free CancellationReserve now, pay when you stay
The price is $405 per night from Jun 27 to Jun 27
4.8/5Exceptional! (1,403 reviews)
"Overall excellent service and accommodations."

Reviewed on Jun 22, 2021

Trump International Hotel & Tower Chicago
Waldorf Astoria Chicago
5 out of 5
11 E. Walton Street, Chicago, IL
Free CancellationReserve now, pay when you stay
The price is $435 per night from Jun 27 to Jun 27
4.7/5Exceptional! (994 reviews)
"Beautiful property, helpful staff"

Reviewed on Jun 22, 2021

Waldorf Astoria Chicago
Kimpton Hotel Monaco Chicago, an IHG Hotel
4.5 out of 5
225 N Wabash Ave, Chicago, IL
Free CancellationReserve now, pay when you stay
The price is $240 per night from Jun 27 to Jun 27
4.6/5Exceptional! (980 reviews)
"Great experience"

Reviewed on Jun 15, 2021

Kimpton Hotel Monaco Chicago, an IHG Hotel
You could be seeing lower prices

You could be seeing lower prices

With member prices, you could save 10% or more right now on thousands of properties.
Staypineapple, An Iconic Hotel, The Loop
4 out of 5
1 W Washington St, Chicago, IL
The price is $104 per night from Jul 22 to Jul 22
4.6/5Exceptional! (973 reviews)
"Really enjoyed our stay here (just one night). The $10 credit was a nice touch! Liked the location and the vintage hotel feel. I would recommend staying here to anyone most of all for the more personal touch and very nice staff."

Reviewed on Jun 16, 2021

Staypineapple, An Iconic Hotel, The Loop
Silversmith Hotel Chicago Downtown
4 out of 5
10 S Wabash Ave, Chicago, IL
Free CancellationReserve now, pay when you stay
The price is $169 per night from Jun 27 to Jun 27
4.6/5Exceptional! (1,576 reviews)
"The front desk employees were excellent. Very knowledgeable of restaurants and where to go for the best shopping! Will definitely stay there again when I am in Chicago !"

Reviewed on Jun 22, 2021

Silversmith Hotel Chicago Downtown
Don't see what you're looking for?
We've got more Boutique Hotels. Find the right one for you.
View all properties
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.

Travelers Loved These Boutique Hotels