Title: 4 Stars Hotels in Woodlawn, Chicago from CA $158 - Find Cheap Woodlawn Hotels With 4 Stars | Expedia.ca [Woodlawn Travel Guide](https://expedia.ca/Chicago-Woodlawn.dx6132422)[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)[Woodlawn Car Rentals](https://expedia.ca/Car-Rentals-In-Woodlawn.d6132422.Car-Rental-Guide)[Woodlawn Vacations](https://expedia.ca/Woodlawn.d6132422.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/7d94e81b9801269da869c6a2279a6290.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Richard Remington # 4 Stars Hotels in Woodlawn, Chicago from CA $158 ![](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 Woodlawn 4 Star Hotels Tonight [Oct 23 - Oct 24](https://www.expedia.ca/Hotel-Search?regionId=6132422&startDate=2025-10-23&endDate=2025-10-24&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 24 - Oct 25](https://www.expedia.ca/Hotel-Search?regionId=6132422&startDate=2025-10-24&endDate=2025-10-25&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=6132422&startDate=2025-10-24&endDate=2025-10-26&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=6132422&startDate=2025-10-31&endDate=2025-11-02&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Woodlawn 4 Star Hotels ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/w3840h2859x0y0-5fc518eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/896a6d3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/9b9a583c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily full breakfast](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/0a522c10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Embassy Suites by Hilton Chicago Downtown River North Downtown Chicago 8.6/10 Excellent (5139) "Great place, good breakfast and the location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) NATIA CA $177 CA $208 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Chicago-Hotels-Embassy-Suites-Chicago-Downtown.h11580.Hotel-Information) ![Daily full breakfast (USD 27.76 per person)](https://images.trvl-media.com/lodging/1000000/10000/5500/5403/46cc150a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 Double Beds Premier Tower](https://images.trvl-media.com/lodging/1000000/10000/5500/5403/aa7843d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Presidential Suite Premier Tower](https://images.trvl-media.com/lodging/1000000/10000/5500/5403/87025041.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/5500/5403/57e178a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Regency O'Hare Chicago O'Hare 8.8/10 Excellent (2094) "Had a very nice stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Glenn CA $165 CA $189 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Chicago-Hotels-Hyatt-Regency-OHare-Chicago.h5403.Hotel-Information) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/30000/25500/25452/w1261h711x0y1-96bd53d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/30000/25500/25452/ccacdd84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room](https://images.trvl-media.com/lodging/1000000/30000/25500/25452/22cb8b3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/30000/25500/25452/023ff9a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Warwick Allerton - Chicago Downtown Chicago 8.4/10 Very good (2919) "Nice hotel close to everything Enjoyed our stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Barbara CA $146 CA $212 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Chicago-Hotels-Warwick-Allerton-Chicago.h25452.Hotel-Information) ![View from property](https://images.trvl-media.com/lodging/1000000/990000/982600/982552/8007d2c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/990000/982600/982552/3bea7af7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/990000/982600/982552/95d420ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Library](https://images.trvl-media.com/lodging/1000000/990000/982600/982552/b59ebdf4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pendry Chicago Downtown Chicago 9.4/10 Exceptional (1124) "great stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dr. David R. CA $252 CA $353 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Chicago-Hotels-Pendry-Chicago.h982552.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/1000000/20000/17300/17288/7af111e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/1000000/20000/17300/17288/bebf91fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/17300/17288/fbf72db1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/20000/17300/17288/c8521e1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Swissotel - Chicago Downtown Chicago 9.0/10 Wonderful (2888) "Perfect place to stay!! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gemaline CA $200 CA $276 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Chicago-Hotels-Swissotel-Chicago.h17288.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/40000/34500/34496/69c2e798.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/40000/34500/34496/dffcca17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/40000/34500/34496/ec9ee4a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Serves breakfast and happy hour](https://images.trvl-media.com/lodging/1000000/40000/34500/34496/b2bfe2d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Allegro Royal Sonesta Hotel Chicago Loop Downtown Chicago 9.0/10 Wonderful (2142) "Very kind staff, nice amenities, great location." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) ARRY CA $167 CA $241 total includes taxes & fees Nov 20 - Nov 21 [](https://www.expedia.ca/Chicago-Hotels-The-Allegro-Royal-Sonesta-Hotel.h34496.Hotel-Information) ![Cocktail bar](https://images.trvl-media.com/lodging/1000000/30000/22700/22684/5ea33759.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cocktail bar](https://images.trvl-media.com/lodging/1000000/30000/22700/22684/bab7a943.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/22700/22684/7744cb58.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/1000000/30000/22700/22684/880fa2cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Claridge House Chicago, Tapestry Collection by Hilton Downtown Chicago 9.0/10 Wonderful (1401) "Wonderful Stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) catherine CA $125 CA $188 total includes taxes & fees Nov 5 - Nov 6 [](https://www.expedia.ca/Chicago-Hotels-Claridge-House-Chicago.h22684.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/83000000/82660000/82652400/82652306/55b627dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/83000000/82660000/82652400/82652306/bb272e60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed, City View | View from room](https://images.trvl-media.com/lodging/83000000/82660000/82652400/82652306/c06f4b61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/83000000/82660000/82652400/82652306/1792d463.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### citizenM Chicago Downtown Downtown Chicago 9.4/10 Exceptional (3986) "Great place to stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) sherry CA $171 CA $201 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Chicago-Hotels-CitizenM-Chicago-Downtown.h82652306.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/cc779b7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Snack bar](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/c0ded825.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/2f70f55e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Riu Plaza Chicago Downtown Chicago 9.4/10 Exceptional (2639) "Great place to stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Larry William CA $162 CA $230 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Chicago-Hotels-Hotel-Riu-Plaza-Chicago.h102622712.Hotel-Information) ![2 bars/lounges](https://images.trvl-media.com/lodging/1000000/10000/5000/4903/w3837h2157x3y3-c3ed4c01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 restaurants, breakfast, lunch, dinner served; American cuisine](https://images.trvl-media.com/lodging/1000000/10000/5000/4903/4df3bcb9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Queen Beds, Lake View](https://images.trvl-media.com/lodging/1000000/10000/5000/4903/w3837h2561x3y0-ec3252d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 restaurants, breakfast, lunch, dinner served; American cuisine](https://images.trvl-media.com/lodging/1000000/10000/5000/4903/w3837h2695x3y3-e619dd92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Regency Chicago Downtown Chicago 9.4/10 Exceptional (3352) "Great location and hotel." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Travis CA $255 CA $341 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Chicago-Hotels-Hyatt-Regency-Chicago.h4903.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/20300/20205/35cb1bb8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/30000/20300/20205/89e1318d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/30000/20300/20205/5785af38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/30000/20300/20205/fcdb86cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### InterContinental Chicago Magnificent Mile by IHG Downtown Chicago 9.0/10 Wonderful (2515) "Great location, nice rooms and excellent staff. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Roberto CA $278 CA $372 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Chicago-Hotels-InterContinental-Chicago-Magnificent-Mile.h20205.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/6c1738b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, pillowtop beds, in-room safe, desk](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/a9c979ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lake view](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/5d460cc6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bars/lounges](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/55a8ba7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sable at Navy Pier Chicago, Curio Collection by Hilton Downtown Chicago 9.4/10 Exceptional (2214) "Rooms were clean with a great view of the lake and the city " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nathan CA $178 CA $257 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Chicago-Hotels-Sable-At-Navy-Pier-Chicago.h57651125.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) ![Interior entrance](https://images.trvl-media.com/lodging/3000000/2230000/2222400/2222364/9097f753.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) ### Hotel Felix River North/Magnificent Mile Downtown Chicago 8.2/10 Very good (2293) "Great stay and great location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Wendy CA $100 CA $160 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Chicago-Hotels-Hotel-Felix-Chicago.h2222364.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/274f52b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/bbeef356.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/f2c5642d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/b5bf3aa2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Chicago Downtown Chicago 8.4/10 Very good (2261) "We loved this hotel it was beautiful and convenient . " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Daniel CA $257 CA $343 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Chicago-Hotels-Hilton-Chicago.h12570.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/13000000/12790000/12786700/12786616/74c2f40d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Presidential Suite, 1 King Bed, Accessible | Living room](https://images.trvl-media.com/lodging/13000000/12790000/12786700/12786616/72c3363f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 restaurants, breakfast, lunch, dinner served; American cuisine](https://images.trvl-media.com/lodging/13000000/12790000/12786700/12786616/7aab5ae1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/13000000/12790000/12786700/12786616/6ccd2813.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### LondonHouse Chicago, Curio Collection by Hilton Downtown Chicago 9.4/10 Exceptional (3343) "Great staff, great rooms" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jerome Lawrence CA $235 CA $276 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Chicago-Hotels-LondonHouse-Chicago.h12786616.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/17600/17543/696a55e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Ballroom](https://images.trvl-media.com/lodging/1000000/20000/17600/17543/fa2dd97c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor wedding area](https://images.trvl-media.com/lodging/1000000/20000/17600/17543/ca08eac0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, down comforters, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/1000000/20000/17600/17543/fdd134a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Royal Sonesta Chicago Downtown Downtown Chicago 9.4/10 Exceptional (3004) "Excellent hotel, great staff and perfect location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Farid CA $167 CA $241 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Chicago-Hotels-Royal-Sonesta-Chicago-Downtown.h17543.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/870000/864300/864219/6b3ccd19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Banquet hall](https://images.trvl-media.com/lodging/1000000/870000/864300/864219/b33c86e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Junior Suite, 1 King Bed with Sofa bed, Accessible | Living area](https://images.trvl-media.com/lodging/1000000/870000/864300/864219/cac42afe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Presidential Suite, 1 King Bed | Bathroom](https://images.trvl-media.com/lodging/1000000/870000/864300/864219/6bab11c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sofitel Chicago Magnificent Mile Downtown Chicago 9.4/10 Exceptional (2192) "Nice place polite staff, great location!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stefan CA $263 CA $350 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Chicago-Hotels-Sofitel-Chicago-Magnificent-Mile.h864219.Hotel-Information) ![Breakfast, lunch, dinner served; American cuisine ](https://images.trvl-media.com/lodging/1000000/20000/16000/15937/7e178380.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/1000000/20000/16000/15937/798cdd6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Steam room, body treatments, facials, 2 treatment rooms, massages](https://images.trvl-media.com/lodging/1000000/20000/16000/15937/b376d4df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, down comforters, pillowtop beds, minibar](https://images.trvl-media.com/lodging/1000000/20000/16000/15937/2e9bef56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fairmont Chicago at Millennium Park Downtown Chicago 8.6/10 Excellent (1987) "Great place " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) ognandon CA $263 CA $350 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Chicago-Hotels-Fairmont-Chicago-At-Millennium-Park.h15937.Hotel-Information) ![Rooftop terrace](https://images.trvl-media.com/lodging/10000000/9070000/9069700/9069667/af0ef9e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Egyptian cotton sheets, premium bedding, in-room safe, desk](https://images.trvl-media.com/lodging/10000000/9070000/9069700/9069667/c12c78f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/10000000/9070000/9069700/9069667/0ec157ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/10000000/9070000/9069700/9069667/w3576h2561x0y0-5f9110d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Centric The Loop Chicago Downtown Chicago 9.0/10 Wonderful (2204) "It was an amazing stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kristy S CA $173 CA $203 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Chicago-Hotels-Hyatt-Centric-The-Loop-Chicago.h9069667.Hotel-Information) ![Breakfast, lunch and dinner served](https://images.trvl-media.com/lodging/1000000/570000/565800/565746/19b0236f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/1000000/570000/565800/565746/9378ca8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Queen Bed, Kitchenette](https://images.trvl-media.com/lodging/1000000/570000/565800/565746/01e59f66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Queen Bed, Kitchenette](https://images.trvl-media.com/lodging/1000000/570000/565800/565746/a9bc446d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Club Quarters Hotel, Central Loop, Chicago Downtown Chicago 8.8/10 Excellent (3374) "The room was very nice, and the on-site restaurant was a nice place for both dinner and breakfast." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kathryn CA $135 CA $158 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Chicago-Hotels-Club-Quarters-Hotel.h565746.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%2F4Star-Woodlawn-Chicago-Hotels.s40-n6132422-0.Travel-Guide-Filter-Hotels)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F4Star-Woodlawn-Chicago-Hotels.s40-n6132422-0.Travel-Guide-Filter-Hotels) ## Explore similar 5-star hotels Many 5-star hotels have the same amenities as 4-star hotels. See all 5-star hotels in Woodlawn. ![The Langham, Chicago](https://images.trvl-media.com/lodging/7000000/6310000/6309400/6309326/33b4ff92_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### The Langham, Chicago 330 North Wabash Avenue, Chicago, IL CA $700 CA $822 total Nov 16 - Nov 17 includes taxes & fees 9.6/10 Exceptional! (1,013 reviews) [](https://expedia.ca/Chicago-Hotels-The-Langham.h6309326.Hotel-Information) ![Trump International Hotel & Tower Chicago](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/209f8cff_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Trump International Hotel & Tower Chicago 401 N Wabash Ave, Chicago, IL CA $603 CA $708 total Nov 2 - Nov 3 includes taxes & fees 9.4/10 Exceptional! (1,767 reviews) [](https://expedia.ca/Chicago-Hotels-Trump-International-Hotel-Tower-Chicago.h1723215.Hotel-Information) ![Four Seasons Hotel Chicago](https://images.trvl-media.com/lodging/1000000/30000/25800/25748/7da48e89_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Four Seasons Hotel Chicago 120 East Delaware Place, Chicago, IL CA $741 CA $870 total Nov 2 - Nov 3 includes taxes & fees 9.4/10 Exceptional! (998 reviews) [](https://expedia.ca/Chicago-Hotels-Four-Seasons-Hotel-Chicago.h25748.Hotel-Information) Still don't see what you're looking for? [See all properties in Woodlawn.](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=24%2F10%2F2025&endDate=25%2F10%2F2025®ionId=6132422&star=40) You can also use these popular filters to refine your search. [Pool](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=24%2F10%2F2025&endDate=25%2F10%2F2025®ionId=6132422&star=40&star=40&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=24%2F10%2F2025&endDate=25%2F10%2F2025®ionId=6132422&star=40&star=40&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=24%2F10%2F2025&endDate=25%2F10%2F2025®ionId=6132422&star=40&star=40&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=24%2F10%2F2025&endDate=25%2F10%2F2025®ionId=6132422&star=40&star=40&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=24%2F10%2F2025&endDate=25%2F10%2F2025®ionId=6132422&star=40&star=40&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 Woodlawn Hotel Reviews ![Warwick Allerton - Chicago](//images.trvl-media.com/lodging/1000000/30000/25500/25452/w1261h711x0y1-96bd53d1_y.jpg) ### Warwick Allerton - Chicago 10/10 Excellent "Great location. Excellent staff. Great prices for the area and in comparison with nearby competitors hotels" [](https://expedia.ca/Chicago-Hotels-Warwick-Allerton-Chicago.h25452.Hotel-Information) ![Hotel Riu Plaza Chicago](//images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f_y.jpg) ### Hotel Riu Plaza Chicago 10/10 Excellent "fresh breakfast attentive and pleasant staff" [](https://expedia.ca/Chicago-Hotels-Hotel-Riu-Plaza-Chicago.h102622712.Hotel-Information) ![Freehand Chicago](//images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/3b3ade3c_y.jpg) ### Freehand Chicago 10/10 Excellent "Love the live jazz and vibe in the cafe and cocktail lounge. Overall, as expected for an upscale youth hostel. " [](https://expedia.ca/Chicago-Hotels-Freehand-Chicago.h9418281.Hotel-Information) ![Embassy Suites by Hilton Chicago Downtown River North](//images.trvl-media.com/lodging/1000000/20000/11600/11580/w3840h2859x0y0-5fc518eb_y.jpg) ### Embassy Suites by Hilton Chicago Downtown River North 10/10 Excellent "Parking was terrible and expensive. Recommend valet parking. Staff, very hard to talk to and i arrived at 3:30 scheduled to check in at 4 pm. Room wasn't available until 4;30. Staff wasn't to concerned." [](https://expedia.ca/Chicago-Hotels-Embassy-Suites-Chicago-Downtown.h11580.Hotel-Information) ![Sable at Navy Pier Chicago, Curio Collection by Hilton](//images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/6c1738b5_y.jpg) ### Sable at Navy Pier Chicago, Curio Collection by Hilton 10/10 Excellent "Location, location, location" [](https://expedia.ca/Chicago-Hotels-Sable-At-Navy-Pier-Chicago.h57651125.Hotel-Information) ![The Royal Sonesta Chicago Downtown](//images.trvl-media.com/lodging/1000000/20000/17600/17543/696a55e6_y.jpg) ### The Royal Sonesta Chicago Downtown 10/10 Excellent "The room was great, view gorgeous and all the hotel staff were welcoming and helpful! Location of the hotel is perfect to walk or take the metro. The restaurant had limited choices for breakfast but was nice enough and convenient." [](https://expedia.ca/Chicago-Hotels-Royal-Sonesta-Chicago-Downtown.h17543.Hotel-Information) ![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 "It was a beautiful property in a spectacular location. Close to transit, and walkable to everything in the loop. Would definitely stay again. " [](https://expedia.ca/Chicago-Hotels-The-Allegro-Royal-Sonesta-Hotel.h34496.Hotel-Information) ![Hilton Chicago](//images.trvl-media.com/lodging/1000000/20000/12600/12570/274f52b9_y.jpg) ### Hilton Chicago 10/10 Excellent "Very convenient to all things. " [](https://expedia.ca/Chicago-Hotels-Hilton-Chicago.h12570.Hotel-Information) ![citizenM Chicago Downtown](//images.trvl-media.com/lodging/83000000/82660000/82652400/82652306/55b627dd_y.jpg) ### citizenM Chicago Downtown 10/10 Excellent "Great spot next to the pendry" [](https://expedia.ca/Chicago-Hotels-CitizenM-Chicago-Downtown.h82652306.Hotel-Information) ## Frequently asked questions ### What are the best 4-star hotels in Woodlawn? > [Sophy Hyde Park](https://www.expedia.ca/Chicago-Hotels-Sophy-Hyde-Park.h22355297.Hotel-Information) gets top marks from Expedia guests. This 4-star hotel located around Woodlawn promises an inviting guest experience and plenty of handy amenities. ### How much does it cost to stay in a 4-star hotel in Woodlawn? > With Expedia's sort and search filters, landing a top deal on a 4-star hotel in Woodlawn just got easier. Start by entering your chosen arrival date and length of your getaway. Then sort the results by price and pick a hotel that best matches your style and budget. > > > > - Search for the lowest price from CA $708 ### What's the difference between 5-star and 4-star hotels in Woodlawn? > Give yourself the luxury treatment during your Woodlawn vacation by choosing a 4-star hotel. As well as featuring upscale surroundings, these retreats are usually filled with amenities like bathrobes, large beds and more. A 5-star hotel will go above and beyond to make your trip an even more indulgent and memorable one. 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