Title: 5 Stars Hotels in Old Town Triangle, Chicago from CA $166 - Find Cheap Old Town Triangle Hotels With 5 Stars | Expedia.ca [Old Town Triangle Travel Guide](https://expedia.ca/Chicago-Old-Town-Triangle.dx553248635976809331)[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 Triangle Car Rentals](https://expedia.ca/Car-Rentals-In-Old-Town-Triangle.d553248635976809331.Car-Rental-Guide)[Old Town Triangle Vacations](https://expedia.ca/Old-Town-Triangle.d553248635976809331.Destination-Travel-Guides) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/24000/24578-Chicago-History-Museum.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # 5 Stars Hotels in Old Town Triangle, Chicago from CA $166 ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![](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) ![](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 Triangle 5 Star Hotels Tonight [Oct 25 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=553248635976809331&startDate=2025-10-25&endDate=2025-10-26&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 26 - Oct 27](https://www.expedia.ca/Hotel-Search?regionId=553248635976809331&startDate=2025-10-26&endDate=2025-10-27&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=553248635976809331&startDate=2025-10-31&endDate=2025-11-02&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=553248635976809331&startDate=2025-11-07&endDate=2025-11-09&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Old Town Triangle 5 Star Hotels ![Lobby](https://images.trvl-media.com/lodging/7000000/6310000/6309400/6309326/33b4ff92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/7000000/6310000/6309400/6309326/0ab012f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dinner served, Mediterranean cuisine](https://images.trvl-media.com/lodging/7000000/6310000/6309400/6309326/71f6a2f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/7000000/6310000/6309400/6309326/0c7c3240.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Langham, Chicago Downtown Chicago 9.8/10 Exceptional (1016) "Great place to stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Shawn CA $700 CA $822 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Chicago-Hotels-The-Langham.h6309326.Hotel-Information) ![Bar (on property)](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/209f8cff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Body treatments, body wraps, body scrubs, facials](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/743bf216.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/c35e7743.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Gym](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/4f5517f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Trump International Hotel & Tower Chicago Downtown Chicago 9.4/10 Exceptional (1762) "Very accommodating and friendly staff, brilliant location" ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Aaron CA $604 CA $709 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Chicago-Hotels-Trump-International-Hotel-Tower-Chicago.h1723215.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/1000000/30000/25800/25748/7da48e89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/30000/25800/25748/ee956af2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, minibar, in-room safe](https://images.trvl-media.com/lodging/1000000/30000/25800/25748/56d62feb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/1000000/30000/25800/25748/d00895ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Four Seasons Hotel Chicago Downtown Chicago 9.4/10 Exceptional (999) "Amazing hotel" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David CA $686 CA $805 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Chicago-Hotels-Four-Seasons-Hotel-Chicago.h25748.Hotel-Information) ![Front of property - evening/night](https://images.trvl-media.com/lodging/1000000/590000/581300/581213/f1144862.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/590000/581300/581213/e294b3a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Couples treatment rooms, body treatments, hydrotherapy, aromatherapy](https://images.trvl-media.com/lodging/1000000/590000/581300/581213/6ca152e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Ballroom](https://images.trvl-media.com/lodging/1000000/590000/581300/581213/5616df34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Peninsula Chicago Downtown Chicago 9.8/10 Exceptional (1021) "Great weekend get away" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) craig CA $805 CA $945 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Chicago-Hotels-The-Peninsula-Chicago.h581213.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/3000000/2720000/2717600/2717582/1040fa3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; American cuisine ](https://images.trvl-media.com/lodging/3000000/2720000/2717600/2717582/9baa79de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/3000000/2720000/2717600/2717582/5001f31e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/3000000/2720000/2717600/2717582/cc9f9fd8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Waldorf Astoria Chicago Downtown Chicago 9.4/10 Exceptional (1001) "Simply love this hotel" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) laura CA $660 CA $775 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Chicago-Hotels-Waldorf-Astoria-Chicago.h2717582.Hotel-Information) ![Indoor pool, open 6:00 AM to 9:00 PM, sun loungers](https://images.trvl-media.com/lodging/37000000/36480000/36475600/36475533/486e1134.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/37000000/36480000/36475600/36475533/37b7786f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Designer toiletries, hair dryer, bathrobes, towels](https://images.trvl-media.com/lodging/37000000/36480000/36475600/36475533/ab9e9616.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/37000000/36480000/36475600/36475533/8f021abe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Nobu Hotel Chicago Downtown Chicago 9.4/10 Exceptional (739) "Great location, amenities and staff. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nicholas CA $485 CA $569 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Chicago-Hotels-Nobu-Hotel-Chicago.h36475533.Hotel-Information) ![Suite, Terrace (Water Tower)](https://images.trvl-media.com/lodging/1000000/30000/20700/20695/c7c718ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/20700/20695/ca3d604d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; American cuisine, alfresco dining ](https://images.trvl-media.com/lodging/1000000/30000/20700/20695/6526f50f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite (LAKE MICHIGAN SUITE) | View from room](https://images.trvl-media.com/lodging/1000000/30000/20700/20695/ef2f5d42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Park Hyatt Chicago Downtown Chicago 9.6/10 Exceptional (1000) "beautiful room and hotel great bar!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) ravi CA $693 CA $813 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Chicago-Hotels-Park-Hyatt-Chicago.h20695.Hotel-Information) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/20000/14500/14447/30b68b68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/14500/14447/2fe2113a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom](https://images.trvl-media.com/lodging/1000000/20000/14500/14447/bedaec25.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/1000000/20000/14500/14447/4690ab59.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Ritz-Carlton, Chicago Downtown Chicago 9.2/10 Wonderful (1002) "Great location" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Peter CA $588 CA $690 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Chicago-Hotels-The-Ritz-Carlton.h14447.Hotel-Information) ![2 restaurants, breakfast served](https://images.trvl-media.com/lodging/92000000/91140000/91139000/91138950/0d225744.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/92000000/91140000/91139000/91138950/43b7d4aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/92000000/91140000/91139000/91138950/5bfebb1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Banquet hall](https://images.trvl-media.com/lodging/92000000/91140000/91139000/91138950/bd0f84f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The St. Regis Chicago Downtown Chicago 9.2/10 Wonderful (77) "Nice place " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John CA $662 CA $777 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Chicago-Hotels-The-St-Regis-Chicago.h91138950.Hotel-Information) ![Design Townhome, 3 Bedrooms, Kitchen, City View | Terrace/patio](https://images.trvl-media.com/lodging/116000000/115170000/115163800/115163763/93a33738.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/116000000/115170000/115163800/115163763/c0bd1b1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Design Townhome, 3 Bedrooms, Kitchen, City View | Living area](https://images.trvl-media.com/lodging/116000000/115170000/115163800/115163763/5df59d23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Full-size fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/116000000/115170000/115163800/115163763/6cef91d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Art Villa West Town 10/10 Exceptional (2) " " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) tomonobu CA $378 CA $912 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Chicago-Hotels-Art-Villa.h115163763.Hotel-Information) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2F5Star-Old-Town-Triangle-Chicago-Hotels.s50-n553248635976809331-0.Travel-Guide-Filter-Hotels)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F5Star-Old-Town-Triangle-Chicago-Hotels.s50-n553248635976809331-0.Travel-Guide-Filter-Hotels) ## Explore similar 4-star hotels Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Old Town Triangle. ![Embassy Suites by Hilton Chicago Downtown River North](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/w3840h2859x0y0-5fc518eb_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Embassy Suites by Hilton Chicago Downtown River North 600 N State St, Chicago, IL CA $175 CA $205 total Nov 23 - Nov 24 includes taxes & fees 8.4/10 Very Good! (5,122 reviews) [](https://expedia.ca/Chicago-Hotels-Embassy-Suites-Chicago-Downtown.h11580.Hotel-Information) ![Hyatt Regency O'Hare Chicago](https://images.trvl-media.com/lodging/1000000/10000/5500/5403/46cc150a_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Hyatt Regency O'Hare Chicago 9300 Bryn Mawr Ave, Rosemont, IL CA $165 CA $188 total Nov 24 - Nov 25 includes taxes & fees 8.6/10 Excellent! (2,087 reviews) [](https://expedia.ca/Chicago-Hotels-Hyatt-Regency-OHare-Chicago.h5403.Hotel-Information) ![Warwick Allerton - Chicago](https://images.trvl-media.com/lodging/1000000/30000/25500/25452/w1261h711x0y1-96bd53d1_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Warwick Allerton - Chicago 701 North Michigan Avenue, Chicago, IL CA $106 CA $166 total Nov 24 - Nov 25 includes taxes & fees 8.4/10 Very Good! (2,911 reviews) [](https://expedia.ca/Chicago-Hotels-Warwick-Allerton-Chicago.h25452.Hotel-Information) Still don't see what you're looking for? [See all properties in Old Town Triangle.](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=26%2F10%2F2025&endDate=27%2F10%2F2025®ionId=553248635976809331&star=50) You can also use these popular filters to refine your search. [Pool](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=26%2F10%2F2025&endDate=27%2F10%2F2025®ionId=553248635976809331&star=50&star=50&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=26%2F10%2F2025&endDate=27%2F10%2F2025®ionId=553248635976809331&star=50&star=50&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=26%2F10%2F2025&endDate=27%2F10%2F2025®ionId=553248635976809331&star=50&star=50&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=26%2F10%2F2025&endDate=27%2F10%2F2025®ionId=553248635976809331&star=50&star=50&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=26%2F10%2F2025&endDate=27%2F10%2F2025®ionId=553248635976809331&star=50&star=50&amenities=WATER_PARK) 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 Triangle Hotel Reviews ## Frequently asked questions ### What are the best 5-star hotels in Old Town Triangle? > A world of indulgence awaits at [Waldorf Astoria Chicago](https://www.expedia.ca/Chicago-Hotels-Waldorf-Astoria-Chicago.h2717582.Hotel-Information), [Four Seasons Hotel Chicago](https://www.expedia.ca/Chicago-Hotels-Four-Seasons-Hotel-Chicago.h25748.Hotel-Information) and [The Ritz-Carlton, Chicago](https://www.expedia.ca/Chicago-Hotels-The-Ritz-Carlton.h14447.Hotel-Information). These are among the 5-star properties around the North Side neighbourhood of Old Town Triangle that rate highly with Expedia customers. ### How much does it cost to stay in a 5-star hotel in Old Town Triangle? > How much you pay for a 5-star hotel in Old Town Triangle can vary depending on when you decide to travel and how long you plan to stay, among other factors. Take advantage of our price per night filter and other search tools to score the best deal on a luxurious getaway. > > > > - Search for the lowest price per night from CA $166 ### What makes a hotel 5 stars in Old Town Triangle? > From gourmet dining venues and all-day fitness centres to swimming pools and the finest bedding, the 5-star experience in Old Town Triangle is all about indulgence and comfort. But it requires more than just top-notch amenities to get a 5-star rating. 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[Hotels near Chicago History Museum](https://www.expedia.ca/Chicago-History-Museum-Hotels.0-l6064041-0.Travel-Guide-Filter-Hotels) - [Chicago Hotels](https://www.expedia.ca/Chicago-Hotels.d178248.Travel-Guide-Hotels) - [Downtown Chicago Hotels](https://www.expedia.ca/Downtown-Chicago-Chicago-Hotels.0-n6350699-0.Travel-Guide-Filter-Hotels) - [Hotels near Farm-in-the-Zoo](https://www.expedia.ca/Farm-In-The-Zoo-Hotels.0-l553248621533116592-0.Travel-Guide-Filter-Hotels) - [All Inclusive Resorts and in Lincoln Park](https://www.expedia.ca/Lincoln-Park-Chicago-Hotels-All-Inclusive-Hotel.0-n6059328-0-tAllInclusiveHotel.Travel-Guide-Filter-Hotels) - [Best Western Hotels in Lincoln Park](https://www.expedia.ca/Lincoln-Park-Chicago-Hotels-Best-Western.0-n6059328-0--bBestWestern.Travel-Guide-Filter-Hotels) - [Boutique Hotels in Lincoln Park](https://www.expedia.ca/Lincoln-Park-Chicago-Hotels-Boutique-Hotel.0-n6059328-0-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Business Hotels in Lincoln Park](https://www.expedia.ca/Lincoln-Park-Chicago-Hotels-Business-Hotel.0-n6059328-0-tBusinessHotel.Travel-Guide-Filter-Hotels) - 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[Hotels near North Avenue Beach](https://www.expedia.ca/North-Avenue-Beach-Hotels.0-l6069221-0.Travel-Guide-Filter-Hotels) - [Boutique Hotels in Old Town Chicago](https://www.expedia.ca/Old-Town-Chicago-Chicago-Hotels-Boutique-Hotel.0-n6351828-0-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Old Town Chicago](https://www.expedia.ca/Old-Town-Chicago-Chicago-Hotels-Cheap-Hotels.0-n6351828-0-tCheapHotels.Travel-Guide-Filter-Hotels) - [Historic Hotels in Old Town Chicago](https://www.expedia.ca/Old-Town-Chicago-Chicago-Hotels-Historic-Hotel.0-n6351828-0-tHistoricHotel.Travel-Guide-Filter-Hotels) - [Hotels with a Pool in Old Town Chicago](https://www.expedia.ca/Old-Town-Chicago-Chicago-Hotels-Hotel-With-Pool.0-n6351828-0-tHotelwithPool.Travel-Guide-Filter-Hotels) - [Hotels with Bar in Old Town Chicago](https://www.expedia.ca/Old-Town-Chicago-Chicago-Hotels-Hotels-With-Bar.0-n6351828-0-tHotelswithBar.Travel-Guide-Filter-Hotels) - [Hotels with Free Breakfast in Old Town Chicago](https://www.expedia.ca/Old-Town-Chicago-Chicago-Hotels-Hotels-With-Free-Breakfast.0-n6351828-0-tHotelswithFreeBreakfast.Travel-Guide-Filter-Hotels) - 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[Routes Rental Cars in Lincoln Park](https://www.expedia.ca/Routes-Car-Rentals-In-Lincoln-Park.d6059328-c1101.Car-Rental-Guide-Suppliers) - [Book Hotels in Old Town Triangle on Expedia.com](https://www.expedia.com/5Star-Old-Town-Triangle-Chicago-Hotels.s50-n553248635976809331-0.Travel-Guide-Filter-Hotels)