Title: Book the Best BOUTIQUE Hotels in Near South Side in 2026 | Expedia.ca

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# Find Boutique Hotels in Near South Side, IL from CA $115

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## Check availability on Near South Side Boutique Hotels

Tonight

[Dec 27 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=6132399&startDate=2025-12-27&endDate=2025-12-28&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Dec 28 - Dec 29](https://www.expedia.ca/Hotel-Search?regionId=6132399&startDate=2025-12-28&endDate=2025-12-29&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=6132399&startDate=2026-01-02&endDate=2026-01-04&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=6132399&startDate=2026-01-09&endDate=2026-01-11&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Near South Side boutique hotels

![Signature Suite, 1 Bedroom](https://images.trvl-media.com/lodging/8000000/7820000/7818200/7818107/896f58e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Sports facility](https://images.trvl-media.com/lodging/8000000/7820000/7818200/7818107/09b5ecfb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/8000000/7820000/7818200/7818107/c6aa1dd1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/8000000/7820000/7818200/7818107/w3908h6229x0y7-cf0011db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Wheeler Mansion

[](https://www.expedia.ca/Chicago-Hotels-The-Wheeler-Mansion.h7818107.Hotel-Information)

Near South Side

9.0/10

Wonderful

(4)

"A unique place to stay near the convention centre. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Leonardo

[](https://www.expedia.ca/Chicago-Hotels-The-Wheeler-Mansion.h7818107.Hotel-Information)

![Reception](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/08bbf982.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/06b28362.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception hall](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/8076f539.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite (Magnificent)](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/53a89031.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Eurostars Magnificent Mile

[](https://www.expedia.ca/Chicago-Hotels-Eurostars-Magnificent-Mile.h1880320.Hotel-Information)

Downtown Chicago

9.0/10

Wonderful

(3169)

"Amazing stay very clean and beautiful views "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Deigo

CA $128

CA $150 total

includes taxes & fees

Jan 26 - Jan 27, 2026

[](https://www.expedia.ca/Chicago-Hotels-Eurostars-Magnificent-Mile.h1880320.Hotel-Information)

![Egyptian cotton sheets, premium bedding, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/1000000/20000/18000/17903/daaf5f2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bar (on property)](https://images.trvl-media.com/lodging/1000000/20000/18000/17903/8750140b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Meeting facility](https://images.trvl-media.com/lodging/1000000/20000/18000/17903/a23482f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bar (on property)](https://images.trvl-media.com/lodging/1000000/20000/18000/17903/c8177aa6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Whitehall Hotel, BW Premier Collection

[](https://www.expedia.ca/Chicago-Hotels-The-Whitehall-Hotel.h17903.Hotel-Information)

Downtown Chicago

8.2/10

Very good

(3812)

"Hotel stay was excellent, great dining options walkable, easy parking "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jason

CA $105

CA $123 total

includes taxes & fees

Jan 5 - Jan 6, 2026

[](https://www.expedia.ca/Chicago-Hotels-The-Whitehall-Hotel.h17903.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/1000000/10000/4200/4200/6dfbfa42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/10000/4200/4200/12c82a23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from room](https://images.trvl-media.com/lodging/1000000/10000/4200/4200/4d5fc313.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/10000/4200/4200/bf403e2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### L7 Chicago by LOTTE

[](https://www.expedia.ca/Chicago-Hotels-L7-Chicago-By-LOTTE.h4200.Hotel-Information)

Downtown Chicago

9.6/10

Exceptional

(3444)

"Amazing place to stay and super accommodating "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Carson

CA $171

CA $200 total

includes taxes & fees

Dec 30 - Dec 31

[](https://www.expedia.ca/Chicago-Hotels-L7-Chicago-By-LOTTE.h4200.Hotel-Information)

![Interior detail](https://images.trvl-media.com/lodging/1000000/290000/284800/284792/eac2e31f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/1000000/290000/284800/284792/bfc1b4b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from property](https://images.trvl-media.com/lodging/1000000/290000/284800/284792/48e8b586.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bar (on property)](https://images.trvl-media.com/lodging/1000000/290000/284800/284792/d7b084d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Staypineapple, An Iconic Hotel, The Loop

[](https://www.expedia.ca/Chicago-Hotels-Staypineapple.h284792.Hotel-Information)

Downtown Chicago

9.4/10

Exceptional

(1012)

"Location was great, staff was very friendly, and the rooms were clean. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Lori

CA $133

CA $197 total

includes taxes & fees

Jan 12 - Jan 13, 2026

[](https://www.expedia.ca/Chicago-Hotels-Staypineapple.h284792.Hotel-Information)

![Lobby sitting area](https://images.trvl-media.com/lodging/3000000/2230000/2222400/2222364/d46a8a4d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/3000000/2230000/2222400/2222364/d2b26aad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![City view from property](https://images.trvl-media.com/lodging/3000000/2230000/2222400/2222364/2b1c0fd0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior entrance](https://images.trvl-media.com/lodging/3000000/2230000/2222400/2222364/9097f753.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hotel Felix River North/Magnificent Mile

[](https://www.expedia.ca/Chicago-Hotels-Hotel-Felix-Chicago.h2222364.Hotel-Information)

Downtown Chicago

8.2/10

Very good

(2480)

"Decent hotel in a great location with extremely helpful staff. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Aaron

[](https://www.expedia.ca/Chicago-Hotels-Hotel-Felix-Chicago.h2222364.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/4000000/3030000/3023900/3023837/20c3f16a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool](https://images.trvl-media.com/lodging/4000000/3030000/3023900/3023837/fa7d1870.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/4000000/3030000/3023900/3023837/e1eb307d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite (The Artist Suite)](https://images.trvl-media.com/lodging/4000000/3030000/3023900/3023837/0144d6ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Royal Sonesta Chicago River North

[](https://www.expedia.ca/Chicago-Hotels-Royal-Sonesta-Chicago-River-North.h3023837.Hotel-Information)

Downtown Chicago

9.2/10

Wonderful

(2336)

"Great property and room"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Steven

CA $136

CA $204 total

includes taxes & fees

Jan 4 - Jan 5, 2026

[](https://www.expedia.ca/Chicago-Hotels-Royal-Sonesta-Chicago-River-North.h3023837.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/1000000/30000/21200/21142/886bf093.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast, lunch, dinner served; Regional cuisine ](https://images.trvl-media.com/lodging/1000000/30000/21200/21142/b2a072ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/30000/21200/21142/c5557162.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/1000000/30000/21200/21142/3f21eaa8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel

[](https://www.expedia.ca/Chicago-Hotels-Hotel-Blake.h21142.Hotel-Information)

Downtown Chicago

9.6/10

Exceptional

(1129)

"Amazing hotel "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Alondra

CA $130

CA $153 total

includes taxes & fees

Jan 18 - Jan 19, 2026

[](https://www.expedia.ca/Chicago-Hotels-Hotel-Blake.h21142.Hotel-Information)

![Breakfast, lunch, dinner served; American cuisine ](https://images.trvl-media.com/lodging/3000000/2160000/2151900/2151878/43ee742c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Room, 2 Single Beds](https://images.trvl-media.com/lodging/3000000/2160000/2151900/2151878/cf9be100.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Nightclub](https://images.trvl-media.com/lodging/3000000/2160000/2151900/2151878/0a805224.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 1 Bedroom, Kitchenette (One Room)](https://images.trvl-media.com/lodging/3000000/2160000/2151900/2151878/d1710471.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Central Loop Hotel

[](https://www.expedia.ca/Chicago-Hotels-Central-Loop-Hotel.h2151878.Hotel-Information)

Downtown Chicago

8.6/10

Excellent

(1956)

"Good value and location worked well for our trip"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Todd

CA $98

CA $115 total

includes taxes & fees

Jan 28 - Jan 29, 2026

[](https://www.expedia.ca/Chicago-Hotels-Central-Loop-Hotel.h2151878.Hotel-Information)

![Front of property](https://images.trvl-media.com/lodging/6000000/5210000/5204900/5204897/9833019f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/6000000/5210000/5204900/5204897/a7f85665.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bar (on property)](https://images.trvl-media.com/lodging/6000000/5210000/5204900/5204897/3f6518d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/6000000/5210000/5204900/5204897/325381ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Ivy Boutique Hotel

[](https://www.expedia.ca/Chicago-Hotels-Ivy-Boutique-Hotel.h5204897.Hotel-Information)

Downtown Chicago

8.8/10

Excellent

(1048)

"I love this hotel "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Tiara

CA $106

CA $124 total

includes taxes & fees

Jan 19 - Jan 20, 2026

[](https://www.expedia.ca/Chicago-Hotels-Ivy-Boutique-Hotel.h5204897.Hotel-Information)

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](https://expedia.ca/Hotel-Search?startDate=2026-01-11&endDate=2026-01-12&regionId=6132399&adults=2&specialized_stays_group_explore=boutique_property&sort=RECOMMENDED&openPlayBack=true)

## Top Near South Side Hotel Reviews

![Hilton Chicago](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/274f52b9_y.jpg)

### Hilton Chicago

10/10 Excellent

" Check in staff were great and room was clean. Worst part was house cleaner knocking at door at 1030am, after being up till 2am night before have a good time at football game. Hot tub amazing and our view!"

[](https://expedia.ca/Chicago-Hotels-Hilton-Chicago.h12570.Hotel-Information)

![Palmer House a Hilton Hotel](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/7f542141_y.jpg)

### Palmer House a Hilton Hotel

10/10 Excellent

"Great place "

[](https://expedia.ca/Chicago-Hotels-Palmer-House-A-Hilton-Hotel.h8079.Hotel-Information)

![River Hotel](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/9a897fc5_y.jpg)

### River Hotel

10/10 Excellent

"Everything was great"

[](https://expedia.ca/Chicago-Hotels-River-Hotel.h2675313.Hotel-Information)

![Eurostars Magnificent Mile](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/08bbf982_y.jpg)

### Eurostars Magnificent Mile

10/10 Excellent

"10 out of 10 will definitely be back! "

[](https://expedia.ca/Chicago-Hotels-Eurostars-Magnificent-Mile.h1880320.Hotel-Information)

![Club Quarters Hotel Wacker at Michigan, Chicago](https://images.trvl-media.com/lodging/1000000/890000/889800/889753/f3eb640d_y.jpg)

### Club Quarters Hotel Wacker at Michigan, Chicago

10/10 Excellent

"Clean room...friendly staff"

[](https://expedia.ca/Chicago-Hotels-Club-Quarters-Hotel.h889753.Hotel-Information)

![Warwick Allerton - Chicago](https://images.trvl-media.com/lodging/1000000/30000/25500/25452/w1261h711x0y1-96bd53d1_y.jpg)

### Warwick Allerton - Chicago

10/10 Excellent

"Clean room"

[](https://expedia.ca/Chicago-Hotels-Warwick-Allerton-Chicago.h25452.Hotel-Information)

![Hyatt Regency Chicago](https://images.trvl-media.com/lodging/1000000/10000/5000/4903/w3837h2157x3y3-c3ed4c01_y.jpg)

### Hyatt Regency Chicago

10/10 Excellent

"."

[](https://expedia.ca/Chicago-Hotels-Hyatt-Regency-Chicago.h4903.Hotel-Information)

![Hilton Chicago/Magnificent Mile Suites](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/f21f6764_y.jpg)

### Hilton Chicago/Magnificent Mile Suites

10/10 Excellent

"Staff was incredibly welcoming upon arrival and was fantastic throughout the stay! Perfect location for walking as well as catching the train, can’t recommend enough"

[](https://expedia.ca/Chicago-Hotels-Hilton-ChicagoMagnificent-Mile-Suites.h18514.Hotel-Information)

![Silversmith Hotel Chicago Downtown](https://images.trvl-media.com/lodging/1000000/120000/116700/116674/da03d6b4_y.jpg)

### Silversmith Hotel Chicago Downtown

10/10 Excellent

"Very friendly and helpful staff"

[](https://expedia.ca/Chicago-Hotels-Silversmith-Hotel-Chicago-Downtown.h116674.Hotel-Information)

## Frequently asked questions

### What's the best boutique accommodation in Near South Side?

### What's there to see and do in Near South Side?

### What's the best way to get to my boutique hotel in Near South Side?

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- [The Loop Hotels ](https://www.expedia.ca/The-Loop-Chicago-Hotels.0-n800024-0.Travel-Guide-Filter-Hotels)
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- [Flights to Chicago ](https://www.expedia.ca/Cheap-Flights-To-Chicago.d178248.Travel-Guide-Flights)
- [Flights from Toronto (YYZ) to Chicago (ORD) ](https://www.expedia.ca/lp/flights/yyz/ord/toronto-to-chicago)

- [Visit Downtown Chicago ](https://www.expedia.ca/Chicago-Downtown-Chicago.dx6350699)
- [Visit Prairie District ](https://www.expedia.ca/Chicago-Prairie-District.dx553248635976473159)
- [Visit South Loop ](https://www.expedia.ca/Chicago-South-Loop.dx6130108)
- [Visit The Loop ](https://www.expedia.ca/Chicago-The-Loop.dx800024)
- [Chicago Vacations ](https://www.expedia.ca/Chicago.d178248.Destination-Travel-Guides)
- [South Loop Vacations ](https://www.expedia.ca/South-Loop.d6130108.Destination-Travel-Guides)

- [Advantage Rent-A-Car Rental Cars in South Loop ](https://www.expedia.ca/Advantage-Rent-A-Car-Car-Rentals-In-South-Loop.d6130108-c3.Car-Rental-Guide-Suppliers)
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- [Things to do in Chicago ](https://www.expedia.ca/Things-To-Do-In-Chicago.d178248.Travel-Guide-Activities)

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