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Boutique Hotels & Resorts in Old Town Chicago from AU$208

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Check availability on Old Town Chicago Boutique Hotels

Best Old Town Chicago Boutique Hotels

Hotel Felix River North/Magnificent Mile
Lobby sitting area

Hotel Felix River North/Magnificent Mile

4.0 star property
8.2 out of 10, Very good, (2059)
"Great place and excellent options to eat "
The price is AU$827
includes taxes & fees
30 Aug - 31 Aug
Hotel Felix River North/Magnificent Mile
Ivy Boutique Hotel
Front of property

Ivy Boutique Hotel

4.5 star property
8.8 out of 10, Excellent, (1008)
"Great location and hotel "
The price is AU$260
includes taxes & fees
24 Aug - 25 Aug
Ivy Boutique Hotel
Eurostars Magnificent Mile
Reception

Eurostars Magnificent Mile

4.0 star property
8.8 out of 10, Excellent, (3080)
"Great stay!"
The price is AU$260
includes taxes & fees
25 Aug - 26 Aug
Eurostars Magnificent Mile
Hotel Lincoln
City view from property

Hotel Lincoln

4.0 star property
7.8 out of 10, Good, (1010)
"Fantastic historic hotel. "
The price is AU$272
includes taxes & fees
25 Aug - 26 Aug
Hotel Lincoln
The Chicago Hotel Collection - Magnificent Mile
Rooftop terrace

The Chicago Hotel Collection - Magnificent Mile

4.0 star property
7.4 out of 10, Good, (1174)
"Very enjoyable stay"
The Chicago Hotel Collection - Magnificent Mile
Bluegreen Vacations Hotel Blake, Ascend Resort Collection
Exterior

Bluegreen Vacations Hotel Blake, Ascend Resort Collection

4.0 star property
9.6 out of 10, Exceptional, (1012)
"Great hotel To stay at :)"
The price is AU$305
includes taxes & fees
3 Sept - 4 Sept
Bluegreen Vacations Hotel Blake, Ascend Resort Collection
Staypineapple, An Iconic Hotel, The Loop
Interior detail

Staypineapple, An Iconic Hotel, The Loop

4.0 star property
9.4 out of 10, Exceptional, (1014)
"The staff were really friendly, beds super comfy, the hotel was beautiful "
The price is AU$419
includes taxes & fees
1 Sept - 2 Sept
Staypineapple, An Iconic Hotel, The Loop
The Royal Sonesta Chicago River North
Terrace/patio

The Royal Sonesta Chicago River North

4.5 star property
9.2 out of 10, Wonderful, (2025)
"Great location awesome staff..."
The price is AU$355
includes taxes & fees
1 Sept - 2 Sept
The Royal Sonesta Chicago River North
The Whitehall Hotel, BW Premier Collection
1 bedroom, Egyptian cotton sheets, premium bedding, pillow-top beds

The Whitehall Hotel, BW Premier Collection

3.5 star property
8.2 out of 10, Very good, (3549)
"Overall an amazing hotel that is reasonably priced!"
The price is AU$208
includes taxes & fees
2 Sept - 3 Sept
The Whitehall Hotel, BW Premier Collection
Central Loop Hotel
Breakfast, lunch, dinner served; American cuisine

Central Loop Hotel

4.0 star property
8.6 out of 10, Excellent, (1816)
"Enjoyed our stay"
The price is AU$209
includes taxes & fees
1 Sept - 2 Sept
Central Loop 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.

Top Old Town Chicago Hotel Reviews

The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

10/10 Excellent
"Loved this Hotel, it was in a great area the staff was nice and friendly and the room was beautiful, up to date and clean. And the price was good. "
James 3-night trip
Posted 4 hours ago
The Royal Sonesta Chicago Downtown

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, Navy Pier and Wrigley Field are worth a visit. You might also want to see spots like United Center, Second City and Armitage Avenue during your trip.
#### When Should I Plan a Trip to Old Town Chicago?\n
If you're wondering about the local weather, you can use this info to plan when to get away to Old Town Chicago:
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.