Find Luxury Hotels in Uptown, IL

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Check availability on Uptown Luxury Hotels

Tonight
Dec 26 - Dec 27
Tomorrow
Dec 27 - Dec 28
This weekend
Dec 26 - Dec 28
Next weekend
Jan 2 - Jan 4

Our top choices for Uptown luxury hotels

Rooftop terrace
The Guesthouse Hotel

The Guesthouse Hotel

The Guesthouse Hotel
4.0 star property
Uptown
9.8 out of 10, Exceptional, (367)
"Beautiful well kept rooms, accessible friendly staff, quiet, clean, comfortable."
United States
Susan F
The price is NT$5,673
NT$6,660 total
includes taxes & fees
Jan 4 - 2026/1/5
The Guesthouse Hotel
Cocktail bar
Freehand Chicago

Freehand Chicago

Freehand Chicago
4.0 star property
Downtown Chicago
8.0 out of 10, Very Good, (2661)
"It's an excellent place."
United States
Jose
The price is NT$1,839
NT$2,713 total
includes taxes & fees
Jan 4 - 2026/1/5
Freehand Chicago
Front of property
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (3050)
"Great rooms, love the bar and amazing breakfast!"
United States
Michelle
The price is NT$3,134
NT$4,565 total
includes taxes & fees
Jan 4 - 2026/1/5
Hotel Riu Plaza Chicago
Lobby sitting area
Club Quarters Hotel Wacker at Michigan, Chicago

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, (2013)
"Great stay"
United States
Kramer
The price is NT$2,566
NT$3,012 total
includes taxes & fees
Jan 8 - 2026/1/9
Club Quarters Hotel Wacker at Michigan, Chicago
Terrace/patio
Sable at Navy Pier Chicago, Curio Collection by Hilton

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, (2276)
"Great staff and restaurants!!"
United States
Abigale
The price is NT$2,688
NT$4,226 total
includes taxes & fees
Jan 20 - 2026/1/21
Sable at Navy Pier Chicago, Curio Collection by Hilton
Premium bedding, down comforters, pillowtop beds, in-room safe
The Wade

The Wade

The Wade
4.5 star property
Downtown Chicago
8.4 out of 10, Very Good, (1536)
"Great staff and great location. "
United States
Joe
The price is NT$2,924
NT$3,433 total
includes taxes & fees
Jan 4 - 2026/1/5
The Wade
Terrace/patio
DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (2206)
"Great location, easy parking. "
United States
Maria
The price is NT$2,681
NT$3,148 total
includes taxes & fees
Jan 4 - 2026/1/5
DoubleTree by Hilton Chicago - Magnificent Mile
Exterior
Arlo Chicago

Arlo Chicago

Arlo Chicago
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1904)
"Great location, friendly staff rooms were great and clean."
United States
Derrick
The price is NT$2,530
NT$3,908 total
includes taxes & fees
Dec 30 - Dec 31
Arlo Chicago
Cocktail bar
Claridge House Chicago, Tapestry Collection by Hilton

Claridge House Chicago, Tapestry Collection by Hilton

Claridge House Chicago, Tapestry Collection by Hilton
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1493)
"Nice stay"
United States
Michelle
The price is NT$2,037
NT$3,314 total
includes taxes & fees
Jan 18 - 2026/1/19
Claridge House Chicago, Tapestry Collection by Hilton
Exterior
Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1052)
"Clean room, clean hotel, wonderful restaurant/bar. AMAZING location! "
United States
Rebecca
The price is NT$3,081
NT$4,540 total
includes taxes & fees
Jan 2 - 2026/1/3
Hyatt Centric Chicago 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.
View all properties

Top Uptown Hotel Reviews

Hyatt Regency Chicago

Hyatt Regency Chicago

10/10 Excellent
"Great hotel on the riverwalk with great amenities. "
Morgan 1-night trip
Posted 6 hours ago
Hyatt Regency Chicago

Frequently asked questions

Are you searching for a great accommodation for your luxury trip to Uptown?
Expedia can help you arrange a flight to Chicago O'Hare Intl. Airport (ORD) airport or Chicago Midway Airport (MDW) airport, and then you can select from various places to stay that will deliver the luxury you'd like to find. Amenities are important when you plan a trip, so we make it easy to get what you need to make your stay special. If you want an upscale hotel with fine dining, a spa, or several swimming pools, Expedia can help you find the best luxury hotel experience that Uptown offers. Uptown has some interesting things to see and do including Lake Michigan and Aragon Ballroom, so you might want to take in the local sights during your visit.
What's there to see and do in Uptown?
Take in the sights and attractions that Uptown offers with a visit to Lake Michigan, Aragon Ballroom, and Riviera Theatre. If you have a bit of extra time while you're in the area, you might want to check out Montrose Beach and Montrose Harbor.
How can I get around Uptown?
It's easier to get around town in style when you know your options. You can take advantage of metro transit at Wilson Station, Lawrence Station, and Argyle Station.

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