Boutique Hotels & Resorts in Old Town Chicago from AU$135

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Old Town Chicago Boutique Hotels

Tonight
7 Dec - 8 Dec
Tomorrow
8 Dec - 9 Dec
Next weekend
12 Dec - 14 Dec
In two weeks
19 Dec - 21 Dec

Best 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, (1058)
"Great "
United States
Lillian
The price is AU$216
includes taxes & fees
14 Dec - 15 Dec
Hotel Lincoln
Reception
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3142)
"Amazing and will be staying again!"
United States
Angie
The price is AU$165
includes taxes & fees
5 Jan - 6 Jan 2026
Eurostars Magnificent Mile
Egyptian cotton sheets, premium bedding, pillow-top 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, (3786)
"Great location "
United States
Carlos
The price is AU$135
includes taxes & fees
8 Dec - 9 Dec
The Whitehall Hotel, BW Premier Collection
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, (1107)
"Great hotel for price and location Everything clean and a huge room "
United States
James
The price is AU$168
includes taxes & fees
4 Jan - 5 Jan 2026
Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel
Exterior
L7 Chicago by LOTTE

L7 Chicago by LOTTE

4.5 star property
Downtown Chicago
9.6 out of 10, Exceptional, (3341)
"I loved the location."
United States
Laura
The price is AU$249
includes taxes & fees
1 Jan - 2 Jan 2026
L7 Chicago by LOTTE
Terrace/patio
The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 star property
Downtown Chicago
9.2 out of 10, Wonderful, (2302)
"Great place - stayed with extended family. Lounge areas and amenities met everyone’s needs "
United States
Elizabeth
The price is AU$230
includes taxes & fees
4 Jan - 5 Jan 2026
The Royal Sonesta Chicago River North
Breakfast, lunch, dinner served; American cuisine
Central Loop Hotel

Central Loop Hotel

4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (1923)
"Very clean and well maintained room, comfortable bed, and great location!"
United States
Rebecca
The price is AU$147
includes taxes & fees
11 Dec - 12 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, (2424)
"This hotel was perfect, all the ameneties need for a weekend on Chicago"
United States
Nicole
The price is AU$177
includes taxes & fees
8 Dec - 9 Dec
Hotel Felix River North/Magnificent Mile
Front of property
Ivy Boutique Hotel

Ivy Boutique Hotel

4.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (1032)
"Clean room, nice amenities (especially like the rain shower), very centrally located, and friendly staff. "
United States
Kathleen
The price is AU$180
includes taxes & fees
4 Jan - 5 Jan 2026
Ivy Boutique Hotel
Rooftop terrace
Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1417)
"Excellent hotel the rooms are awesome "
United States
Devita
The price is AU$368
includes taxes & fees
8 Dec - 9 Dec
Virgin Hotels Chicago
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 Old Town Chicago Hotel Reviews

The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

10/10 Excellent
"Clean room. Cozy Chicago stay "
Trevon 1-night trip
Posted 1 day ago
The Whitehall Hotel, BW Premier Collection

Frequently asked questions

What's the best boutique accommodation in Old Town Chicago?
Hotel Lincoln is a favourite hotel with Expedia travellers looking for a stylish stay, and features a rooftop terrace and a 24-hour fitness centre.
What's there to see and do in Old Town Chicago?
Visitors speak positively about this destination's fantastic nightlife, major shopping centres 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 travelling 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 International Airport (ORD) may also be an option. Metro stations nearby include Sedgwick Station and Clark-Division Station.

Explore a world of travel with Expedia