Title: Book the Best BOUTIQUE Hotels in Old Town Chicago in 2025 | Expedia.ca [Vacation Rentals in Chicago](https://expedia.ca/Chicago-Vacation-Rentals.d178248.Travel-Guide-VacationRentals)[Flights to Chicago](https://expedia.ca/Cheap-Flights-To-Chicago.d178248.Travel-Guide-Flights)[Things to do in Chicago](https://expedia.ca/Things-To-Do-In-Chicago.d178248.Travel-Guide-Activities)[Old Town Chicago Car Rentals](https://expedia.ca/Car-Rentals-In-Old-Town-Chicago.d6351828.Car-Rental-Guide)[Old Town Chicago Vacations](https://expedia.ca/Old-Town-Chicago.d6351828.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/11fd6e63e168e646892c8441abd32c9c.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by trenton.badillo # Find Boutique Hotels in Old Town Chicago, IL ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![bed illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Old Town Chicago Boutique Hotels Tonight [Oct 3 - Oct 4](https://www.expedia.ca/Hotel-Search?regionId=6351828&startDate=2025-10-03&endDate=2025-10-04&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 4 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=6351828&startDate=2025-10-04&endDate=2025-10-05&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=6351828&startDate=2025-10-03&endDate=2025-10-05&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=6351828&startDate=2025-10-10&endDate=2025-10-12&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Old Town Chicago Boutique Hotels ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/21200/21142/886bf093.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/21200/21142/0b4236d8.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) ### Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel Downtown Chicago 9.6/10 Exceptional (1026) "Great stay" CA $244 CA $287 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Chicago-Hotels-Hotel-Blake.h21142.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) ![Egyptian cotton sheets, premium bedding, down comforters, in-room safe](https://images.trvl-media.com/lodging/3000000/2230000/2222400/2222364/279c3768.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) ![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) ### Hotel Felix River North/Magnificent Mile Downtown Chicago 8.2/10 Very good (2238) "Hotel was nice, staff were friendly, and near attractions and restaurants " CA $131 CA $196 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Chicago-Hotels-Hotel-Felix-Chicago.h2222364.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) ![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) ![Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds](https://images.trvl-media.com/lodging/6000000/5210000/5204900/5204897/661195c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ivy Boutique Hotel Downtown Chicago 8.8/10 Excellent (1003) "The hotel was nice and super close to a lot of shopping and dining options " CA $212 CA $249 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Chicago-Hotels-Ivy-Boutique-Hotel.h5204897.Hotel-Information) ![City view from property](https://images.trvl-media.com/lodging/1000000/30000/23400/23314/48b7272b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, hypo-allergenic bedding, in-room safe, desk](https://images.trvl-media.com/lodging/1000000/30000/23400/23314/f253ae17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, hypo-allergenic bedding, in-room safe, desk](https://images.trvl-media.com/lodging/1000000/30000/23400/23314/8d1e22e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/23400/23314/6a77d719.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Lincoln Lincoln Park 7.8/10 Good (1033) "Great location and friendly staff!" CA $116 CA $161 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Chicago-Hotels-Hotel-Lincoln.h23314.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/1000000/30000/24000/23963/0ae99f9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/1000000/30000/24000/23963/e00a5f2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/24000/23963/36bc94a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; Mediterranean cuisine, alfresco dining ](https://images.trvl-media.com/lodging/1000000/30000/24000/23963/1145f7d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Talbott, Autograph Collection Downtown Chicago 9.4/10 Exceptional (37) "Fantastic location and hotel! " CA $296 CA $382 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Chicago-Hotels-The-Talbott-Hotel.h23963.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/21700/21619/ca00b143.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor wedding area](https://images.trvl-media.com/lodging/1000000/30000/21700/21619/e3571b7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/21700/21619/67428c96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/1000000/30000/21700/21619/d91ad5fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Chicago Hotel Collection - Magnificent Mile Downtown Chicago 7.2/10 Good (1372) "Location was great!" CA $192 CA $226 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Chicago-Hotels-Hotel-Audrey.h21619.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) ![Snack bar](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/7697ff8c.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) ![Exterior](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/edcb7f57.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Eurostars Magnificent Mile Downtown Chicago 8.8/10 Excellent (3056) "Perfect location, walkable to many restaurants and shops" CA $181 CA $212 total includes taxes & fees Nov 3 - Nov 4 [](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) ![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) ![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) ### The Whitehall Hotel, BW Premier Collection Downtown Chicago 8.2/10 Very good (3610) "Great location , good breakfast" CA $143 CA $168 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Chicago-Hotels-The-Whitehall-Hotel.h17903.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) ![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) ![Exterior detail](https://images.trvl-media.com/lodging/1000000/290000/284800/284792/bfc1b4b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![50-inch LCD TV with cable channels, iPod dock, streaming services](https://images.trvl-media.com/lodging/1000000/290000/284800/284792/17d930ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Staypineapple, An Iconic Hotel, The Loop Downtown Chicago 9.4/10 Exceptional (1002) "Staff was excellent , a great central spot to stay in Chicago. " CA $281 CA $371 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Chicago-Hotels-Staypineapple.h284792.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 Downtown Chicago 8.6/10 Excellent (1859) "Amazing place to stay" CA $168 CA $198 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Chicago-Hotels-Central-Loop-Hotel.h2151878.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=2025-10-17&endDate=2025-10-18®ionId=6351828&adults=2&specialized_stays_group_explore=boutique_property&sort=RECOMMENDED&openPlayBack=true) ## Top Old Town Chicago Hotel Reviews ![The Allegro Royal Sonesta Hotel Chicago Loop](//images.trvl-media.com/lodging/1000000/40000/34500/34496/69c2e798_y.jpg) ### The Allegro Royal Sonesta Hotel Chicago Loop 10/10 Excellent "Staff was excellent. Decor was very elegant and classy. Enjoyed my two nights here." [](https://expedia.ca/Chicago-Hotels-The-Allegro-Royal-Sonesta-Hotel.h34496.Hotel-Information) ![Hilton Garden Inn Chicago Downtown/Magnificent Mile](//images.trvl-media.com/lodging/1000000/430000/424200/424187/d51caee8_y.jpg) ### Hilton Garden Inn Chicago Downtown/Magnificent Mile 10/10 Excellent "Great location to and walking to riverwalk, millennium park. Metro is right outside the front door. " [](https://expedia.ca/Chicago-Hotels-Hilton-Garden-Inn-Chicago-DowntownMagnificent-Mile.h424187.Hotel-Information) ![Hilton Chicago/Magnificent Mile Suites](//images.trvl-media.com/lodging/1000000/20000/18600/18514/f21f6764_y.jpg) ### Hilton Chicago/Magnificent Mile Suites 10/10 Excellent "Clean rooms, great staff, everything in walking distance from hotel. Would stay here again. " [](https://expedia.ca/Chicago-Hotels-Hilton-ChicagoMagnificent-Mile-Suites.h18514.Hotel-Information) ![Warwick Allerton - Chicago](//images.trvl-media.com/lodging/1000000/30000/25500/25452/w1261h711x0y1-96bd53d1_y.jpg) ### Warwick Allerton - Chicago 10/10 Excellent "someone smoked as the mattress smelled of smoke. luggage rack is broken" [](https://expedia.ca/Chicago-Hotels-Warwick-Allerton-Chicago.h25452.Hotel-Information) ![Freehand Chicago](//images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/3b3ade3c_y.jpg) ### Freehand Chicago 10/10 Excellent "Rooms were clean and staff were always happy to help " [](https://expedia.ca/Chicago-Hotels-Freehand-Chicago.h9418281.Hotel-Information) ![Palmer House a Hilton Hotel](//images.trvl-media.com/lodging/1000000/10000/8100/8079/7f542141_y.jpg) ### Palmer House a Hilton Hotel 10/10 Excellent "Great property with great staff and amenities. " [](https://expedia.ca/Chicago-Hotels-Palmer-House-A-Hilton-Hotel.h8079.Hotel-Information) ![The Chicago Hotel Collection - Magnificent Mile](//images.trvl-media.com/lodging/1000000/30000/21700/21619/ca00b143_y.jpg) ### The Chicago Hotel Collection - Magnificent Mile 10/10 Excellent "Room was a little run down, but everything was amazing!" [](https://expedia.ca/Chicago-Hotels-Hotel-Audrey.h21619.Hotel-Information) ![The Whitehall Hotel, BW Premier Collection](//images.trvl-media.com/lodging/1000000/20000/18000/17903/daaf5f2e_y.jpg) ### The Whitehall Hotel, BW Premier Collection 10/10 Excellent "It was great. Juat wish there was a fridge and microwave in the room." [](https://expedia.ca/Chicago-Hotels-The-Whitehall-Hotel.h17903.Hotel-Information) ![Hyatt Regency Chicago](//images.trvl-media.com/lodging/1000000/10000/5000/4903/w3837h2157x3y3-c3ed4c01_y.jpg) ### Hyatt Regency Chicago 10/10 Excellent "Everything was on point" [](https://expedia.ca/Chicago-Hotels-Hyatt-Regency-Chicago.h4903.Hotel-Information) ## Frequently asked questions ### What's the best boutique accommodation in Old Town Chicago? > [Hotel Lincoln](https://www.expedia.ca/Chicago-Hotels-Hotel-Lincoln.h23314.Hotel-Information) 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, 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. ### 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. 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[Cheap Hotels in Lincoln Park](https://www.expedia.ca/Lincoln-Park-Chicago-Hotels-Cheap-Hotels.0-n6059328-0-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels & Resorts for Couples in Lincoln Park](https://www.expedia.ca/Lincoln-Park-Chicago-Hotels-Couples-Resorts-Hotels.0-n6059328-0-tCouplesResortsHotels.Travel-Guide-Filter-Hotels) - [Family Hotels in Lincoln Park](https://www.expedia.ca/Lincoln-Park-Chicago-Hotels-Family-Hotel.0-n6059328-0-tFamilyHotel.Travel-Guide-Filter-Hotels) - [Historic Hotels in Lincoln Park](https://www.expedia.ca/Lincoln-Park-Chicago-Hotels-Historic-Hotel.0-n6059328-0-tHistoricHotel.Travel-Guide-Filter-Hotels) - [Hotels with Early Check-in in Lincoln Park](https://www.expedia.ca/Lincoln-Park-Chicago-Hotels-Hotel-With-Early-Check-In.0-n6059328-0-thotelwithearlycheckin.Travel-Guide-Filter-Hotels) - [Hotels with Wifi in Lincoln Park](https://www.expedia.ca/Lincoln-Park-Chicago-Hotels-Hotel-With-Wifi.0-n6059328-0-tHotelwithwifi.Travel-Guide-Filter-Hotels) - [Hotels with Bar in Lincoln Park](https://www.expedia.ca/Lincoln-Park-Chicago-Hotels-Hotels-With-Bar.0-n6059328-0-tHotelswithBar.Travel-Guide-Filter-Hotels) - 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[Hotels & Resorts for Couples in Magnificent Mile](https://www.expedia.ca/Magnificent-Mile-Chicago-Hotels-Couples-Resorts-Hotels.0-n800025-0-tCouplesResortsHotels.Travel-Guide-Filter-Hotels) - [Romantic Hotels in Magnificent Mile](https://www.expedia.ca/Magnificent-Mile-Chicago-Hotels-Romantic-Hotel.0-n800025-0-tRomanticHotel.Travel-Guide-Filter-Hotels) - [Waterpark Hotels in Magnificent Mile](https://www.expedia.ca/Magnificent-Mile-Chicago-Hotels-Waterpark-Hotels.0-n800025-0-tWaterparkHotels.Travel-Guide-Filter-Hotels) - [Winery Hotels in Magnificent Mile](https://www.expedia.ca/Magnificent-Mile-Chicago-Hotels-Winery-Hotel.0-n800025-0-tWineryHotel.Travel-Guide-Filter-Hotels) - [Magnificent Mile Hotels](https://www.expedia.ca/Magnificent-Mile-Chicago-Hotels.0-n800025-0.Travel-Guide-Filter-Hotels) - [Apartments in North-Clybourn Station](https://www.expedia.ca/North-Clybourn-Station-Apartments.d6189355-aaApartments.Travel-Guide-Accommodation) - [Old Town Triangle Hotels](https://www.expedia.ca/Old-Town-Triangle-Chicago-Hotels.0-n553248635976809331-0.Travel-Guide-Filter-Hotels) - 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[Chicago History Museum](https://www.expedia.ca/Chicago-History-Museum-Lincoln-Park.d6064041.Vacation-Attraction) - [Visit Lincoln Park](https://www.expedia.ca/Chicago-Lincoln-Park.dx6059328) - [Visit The Loop](https://www.expedia.ca/Chicago-The-Loop.dx800024) - [Chicago Vacations](https://www.expedia.ca/Chicago.d178248.Destination-Travel-Guides) - [International Museum of Surgical Science](https://www.expedia.ca/International-Museum-Of-Surgical-Science-Downtown-Chicago.d6065139.Vacation-Attraction) - [Lincoln Park Zoo](https://www.expedia.ca/Lincoln-Park-Zoo-Lincoln-Park.d6065147.Vacation-Attraction) - [Lincoln Park Vacations](https://www.expedia.ca/Lincoln-Park.d6059328.Destination-Travel-Guides) - [Alamo Rent A Car Rental Cars in Lincoln Park](https://www.expedia.ca/Alamo-Rent-A-Car-Car-Rentals-In-Lincoln-Park.d6059328-c6.Car-Rental-Guide-Suppliers) - [Avis Rental Cars in Lincoln Park](https://www.expedia.ca/Avis-Car-Rentals-In-Lincoln-Park.d6059328-c41.Car-Rental-Guide-Suppliers) - 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