Luxury Hotels & Resorts in Old Town Chicago from AU$125

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Check availability on Old Town Chicago Luxury Hotels

Tonight
6 Dec - 7 Dec
Tomorrow
7 Dec - 8 Dec
Next weekend
12 Dec - 14 Dec
In two weeks
19 Dec - 21 Dec

Best Old Town Chicago Luxury Hotels

City view from property
Hotel Lincoln

Hotel Lincoln

4.0 star property
Lincoln Park
7.8 out of 10, Good, (1057)
"Great "
United States
Lillian
The price is AU$216
includes taxes & fees
14 Dec - 15 Dec
Hotel Lincoln
Cocktail bar
Freehand Chicago

Freehand Chicago

4.0 star property
Downtown Chicago
8.0 out of 10, Very good, (2621)
"Great location "
United States
Stacy
The price is AU$125
includes taxes & fees
4 Jan - 5 Jan 2026
Freehand Chicago
Lobby
Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (2100)
"Would stay again. "
United States
Montroy
Silversmith Hotel Chicago Downtown
Reception
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3136)
"Amazing and will be staying again!"
United States
Angie
The price is AU$154
includes taxes & fees
4 Jan - 5 Jan 2026
Eurostars Magnificent Mile
Ballroom
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4.0 star property
Downtown Chicago
8.4 out of 10, Very good, (2117)
"Loved and enjoyed our stay"
United States
Luis
The price is AU$220
includes taxes & fees
28 Dec - 29 Dec
Palmer House a Hilton Hotel
Snack bar
Cambria Hotel Chicago Loop - Theatre District

Cambria Hotel Chicago Loop - Theatre District

4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (1454)
"Clean, modern, friendly/helpful staff, the perfect spot for staying for a show at The Chicago Theatre. Parking was close and easy too. "
United States
Megan
The price is AU$155
includes taxes & fees
4 Jan - 5 Jan 2026
Cambria Hotel Chicago Loop - Theatre District
Exterior
Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile

4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1045)
"Great Hotel!"
United States
Wendy
The price is AU$217
includes taxes & fees
3 Jan - 4 Jan 2026
Hyatt Centric Chicago Magnificent Mile
Reception
Swissotel - Chicago

Swissotel - Chicago

4.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (2992)
"Great stay"
Canada
Lorrington Ashford
The price is AU$247
includes taxes & fees
2 Jan - 3 Jan 2026
Swissotel - Chicago
Lobby
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 star property
Downtown Chicago
9.4 out of 10, Exceptional, (3421)
"Great Hotel!"
United States
Siranush
The price is AU$232
includes taxes & fees
4 Jan - 5 Jan 2026
LondonHouse Chicago, Curio Collection by Hilton
Terrace/patio
DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile

4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (2176)
"Nice Hotel"
United States
Alan
The price is AU$158
includes taxes & fees
17 Dec - 18 Dec
DoubleTree by Hilton 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.
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Top Old Town Chicago Hotel Reviews

Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

10/10 Excellent
"Very nice rooms and happy hour!"
Rachel Ann 3-night trip
Posted 4 hours ago
Embassy Suites by Hilton Chicago Downtown River North

Frequently asked questions

Are you searching for the perfect hotel for your luxury getaway to Old Town Chicago?
Use Expedia to arrange your flight to Chicago Midway Airport (MDW) airport or Chicago O'Hare International Airport (ORD) airport, and then select from a variety of places to stay that will deliver the luxury you want. Amenities are important when you plan a trip, so we make it easy to find what you'd like to make your stay relaxing and comfortable. If you want an upscale hotel with a spa, an indoor pool or luxury bedding, Expedia can help you find the best luxury hotel experience that Old Town Chicago offers. During your visit, you might want to enjoy the lake views and shopping which Old Town Chicago is known for.
What's there to see and do in Old Town Chicago?
Take in some sights and attractions while you're in Old Town Chicago by visiting Second City, Armitage Avenue and Henry Gerber House. If you have some spare time during your trip, you might want to check out Hudson Chess Park and Lighthouse ArtSpace Chicago.
How can I get around Old Town Chicago?
It's easier to get around town comfortably when you know your options. Metro stations nearby include Sedgwick Station and Clark-Division Station.

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