Find Boutique Hotels in Old Town Chicago, IL

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Check availability on Old Town Chicago Boutique Hotels

Our top choices for Old Town Chicago boutique hotels

City view from property
Hotel Lincoln

Hotel Lincoln

4.0 star property
Lincoln Park
7.8 out of 10, Good, (1061)
"Great "
United States
Lillian
The price is AED 393
AED 526 total
includes taxes & fees
17 Dec - 18 Dec
Hotel Lincoln
Reception
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3135)
"Amazing and will be staying again!"
United States
Angie
The price is AED 344
AED 404 total
includes taxes & fees
7 Jan - 8 January 2026
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

3.5 star property
Downtown Chicago
8.2 out of 10, Very Good, (3782)
"Spacious room, cute boutique hotel in great location!"
United States
Julie
The price is AED 281
AED 330 total
includes taxes & fees
10 Dec - 11 Dec
The Whitehall Hotel, BW Premier Collection
Exterior
L7 Chicago by LOTTE

L7 Chicago by LOTTE

4.5 star property
Downtown Chicago
9.6 out of 10, Exceptional, (3347)
"I loved the location."
United States
Laura
The price is AED 518
AED 608 total
includes taxes & fees
1 Jan - 2 January 2026
L7 Chicago by LOTTE
Exterior
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, (1109)
"Great hotel for price and location Everything clean and a huge room "
United States
James
The price is AED 350
AED 410 total
includes taxes & fees
4 Jan - 5 January 2026
Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel
Breakfast, lunch, dinner served; American cuisine
Central Loop Hotel

Central Loop Hotel

4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (1922)
"Very clean and well maintained room, comfortable bed, and great location!"
United States
Rebecca
The price is AED 299
AED 352 total
includes taxes & fees
22 Dec - 23 Dec
Central Loop Hotel
Lobby sitting area
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, (2430)
"Staff was amazing! "
United States
Erica
Hotel Felix River North/Magnificent Mile
Interior detail
Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop

4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (1005)
"Great hotel location and friendly staff! "
United States
Kathleen
The price is AED 331
AED 496 total
includes taxes & fees
29 Dec - 30 Dec
Staypineapple, An Iconic Hotel, The Loop
Rooftop terrace
Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1418)
"Excellent hotel the rooms are awesome "
United States
Devita
The price is AED 645
AED 882 total
includes taxes & fees
11 Dec - 12 Dec
Virgin Hotels Chicago
Cocktail bar
ACME Hotel Company

ACME Hotel Company

3.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1911)
"Lived up to expectations. Bathroom was really nice. Would stay here again."
United States
Nolan
The price is AED 393
AED 462 total
includes taxes & fees
10 Dec - 11 Dec
ACME Hotel Company
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
"Dpacious,clean,comfortable"
Elizabeth 1-night trip
Posted 11 hours ago
Hilton Chicago/Magnificent Mile Suites

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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.