Find Boutique Hotels in Old Town Chicago, IL

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Check availability on Old Town Chicago Boutique Hotels

Tonight
Dec 29 - Dec 30
Tomorrow
Dec 30 - Dec 31
This weekend
Jan 2 - Jan 4
Next weekend
Jan 9 - Jan 11

Our top choices for Old Town Chicago boutique hotels

City view from property
Hotel Lincoln

Hotel Lincoln

Hotel Lincoln
4.0 star property
Lincoln Park
7.8 out of 10, Good, (1066)
"Front desk and valet were excellent. Quick check in. "
United States
Sean
The price is NT$2,923
NT$3,985 total
includes taxes & fees
Jan 12 - 2026/1/13
Hotel Lincoln
Reception
Eurostars Magnificent Mile

Eurostars Magnificent Mile

Eurostars Magnificent Mile
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3174)
"stunning hotel"
Canada
Yiwei
The price is NT$2,942
NT$3,454 total
includes taxes & fees
Jan 27 - 2026/1/28
Eurostars Magnificent Mile
Egyptian cotton sheets, premium bedding, pillowtop beds, in-room safe
The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection
3.5 star property
Downtown Chicago
8.2 out of 10, Very Good, (3819)
"Hotel stay was excellent, great dining options walkable, easy parking "
United States
Jason
The price is NT$2,406
NT$2,825 total
includes taxes & fees
Jan 5 - 2026/1/6
The Whitehall Hotel, BW Premier Collection
Lobby sitting area
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile
4.0 star property
Downtown Chicago
8.2 out of 10, Very Good, (2484)
"The room was amazing and the customer service was great!"
United States
Chelsi
The price is NT$2,791
NT$4,236 total
includes taxes & fees
Jan 2 - 2026/1/3
Hotel Felix River North/Magnificent Mile
Exterior
L7 Chicago by LOTTE

L7 Chicago by LOTTE

L7 Chicago by LOTTE
4.5 star property
Downtown Chicago
9.6 out of 10, Exceptional, (3452)
"Amazing place to stay and super accommodating "
United States
Carson
The price is NT$4,430
NT$5,201 total
includes taxes & fees
Jan 11 - 2026/1/12
L7 Chicago by LOTTE
Terrace/patio
The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North
4.5 star property
Downtown Chicago
9.2 out of 10, Wonderful, (2343)
"Great property and room"
United States
Steven
The price is NT$3,485
NT$5,097 total
includes taxes & fees
Jan 4 - 2026/1/5
The Royal Sonesta Chicago River North
Interior detail
Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (1012)
"Location was great, staff was very friendly, and the rooms were clean. "
United States
Lori
The price is NT$3,363
NT$4,869 total
includes taxes & fees
Jan 14 - 2026/1/15
Staypineapple, An Iconic Hotel, The Loop
Exterior
Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel

Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel

Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel
4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (1133)
"Amazing hotel "
United States
Alondra
The price is NT$2,993
NT$3,513 total
includes taxes & fees
Jan 18 - 2026/1/19
Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel
Breakfast, lunch, dinner served; American cuisine
Central Loop Hotel

Central Loop Hotel

Central Loop Hotel
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (1957)
"Good value and location worked well for our trip"
United States
Todd
The price is NT$2,563
NT$3,009 total
includes taxes & fees
Jan 11 - 2026/1/12
Central Loop Hotel
Front of property
Ivy Boutique Hotel

Ivy Boutique Hotel

Ivy Boutique Hotel
4.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (1051)
"I love this hotel "
United States
Tiara
The price is NT$2,621
NT$3,077 total
includes taxes & fees
Jan 12 - 2026/1/13
Ivy Boutique Hotel
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

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

10/10 Excellent
"Easy check in and check out, staff were very friendly, room was great, bed was very comfortable. The hotel was also very clean. We loved the location. It was so close to Michigan Avenue, but it was quiet. "
Cindy 1-night trip
Posted 17 hours ago
Hilton Chicago/Magnificent Mile Suites

Frequently asked questions

What's the best boutique accommodation in Old Town Chicago?
Hotel Lincoln is a favorite hotel with Expedia travelers looking for a stylish stay, and features a rooftop terrace and a 24-hour fitness center.
What's there to see and do in Old Town Chicago?
Visitors speak positively about this destination's fantastic nightlife, major shopping centers, and panoramic lake views. While you're out and about in Old Town Chicago, popular attractions like Michigan Avenue, Wrigley Field, and Navy Pier are worth a visit. You might also want to see spots like United Center, Second City, and Armitage Avenue during your trip.
What's the best way to get to my boutique hotel in Old Town Chicago?
You have a few options for traveling to and around Old Town Chicago. The nearest major airport is Chicago Midway Airport (MDW), which is located 10 mi (16 km) away, but Chicago O'Hare Intl. Airport (ORD) may also be an option. Metro stations nearby include Sedgwick Station and Clark-Division Station.

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