Title: 5 Stars Hotels in Southwest Side, Chicago from CA $270 - Find Cheap Southwest Side Hotels With 5 Stars | Expedia.ca [Southwest Side Travel Guide](https://expedia.ca/Southwest-Side.dx553248635976475403)[Hotels in Southwest Side](https://expedia.ca/Southwest-Side-Hotels.d553248635976475403.Travel-Guide-Hotels)[Vacation Rentals in Southwest Side](https://expedia.ca/Southwest-Side-Vacation-Rentals.d553248635976475403.Travel-Guide-VacationRentals)[Flights to Southwest Side](https://expedia.ca/Cheap-Flights-To-Southwest-Side.d553248635976475403.Travel-Guide-Flights)[Southwest Side Car Rentals](https://expedia.ca/Car-Rentals-In-Southwest-Side.d553248635976475403.Car-Rental-Guide)[Southwest Side Vacation Packages](https://expedia.ca/Southwest-Side.d553248635976475403.Destination-Travel-Guides) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/495000/495661-chicago-il-mdw-midway-intl.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # 5 Stars Hotels in Southwest Side, Chicago from CA $270 ![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 Southwest Side 5 Star Hotels Tonight [Sep 27 - Sep 28](https://www.expedia.ca/Hotel-Search?regionId=553248635976475403&startDate=2025-09-27&endDate=2025-09-28&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Sep 28 - Sep 29](https://www.expedia.ca/Hotel-Search?regionId=553248635976475403&startDate=2025-09-28&endDate=2025-09-29&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=553248635976475403&startDate=2025-10-03&endDate=2025-10-05&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=553248635976475403&startDate=2025-10-10&endDate=2025-10-12&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Southwest Side 5 Star Hotels ![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) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/4465cc02.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 (1745) "Beautiful hotel centrally located" CA $643 CA $754 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Chicago-Hotels-Trump-International-Hotel-Tower-Chicago.h1723215.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/7000000/6310000/6309400/6309326/33b4ff92.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) ![Club Suite, 1 Bedroom, Lake View](https://images.trvl-media.com/lodging/7000000/6310000/6309400/6309326/9a653c17.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) ### The Langham, Chicago Downtown Chicago 9.8/10 Exceptional (1011) "Great place to stay. " CA $758 CA $889 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Chicago-Hotels-The-Langham.h6309326.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) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/590000/581300/581213/acbf2aab.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) ![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 (1013) "Amazing hotel will be back for sure!" CA $871 CA $1,022 total includes taxes & fees Sep 28 - Sep 29 [](https://www.expedia.ca/Chicago-Hotels-The-Peninsula-Chicago.h581213.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) ![Interior entrance](https://images.trvl-media.com/lodging/1000000/30000/25800/25748/d00895ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/25800/25748/fc796025.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) ### Four Seasons Hotel Chicago Downtown Chicago 9.4/10 Exceptional (1006) "Amazing hotel" CA $801 CA $941 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Chicago-Hotels-Four-Seasons-Hotel-Chicago.h25748.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) ![Courtyard](https://images.trvl-media.com/lodging/3000000/2720000/2717600/2717582/c47ab94b.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 (1006) "Simply love this hotel" CA $804 CA $944 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Chicago-Hotels-Waldorf-Astoria-Chicago.h2717582.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) ![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) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/20700/20695/3c600fe1.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) ### Park Hyatt Chicago Downtown Chicago 9.6/10 Exceptional (1003) "beautiful room and hotel great bar!" CA $871 CA $1,022 total includes taxes & fees Sep 28 - Sep 29 [](https://www.expedia.ca/Chicago-Hotels-Park-Hyatt-Chicago.h20695.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) ![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) ![Terrace/patio](https://images.trvl-media.com/lodging/37000000/36480000/36475600/36475533/37b7786f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Nobu Hotel Chicago Downtown Chicago 9.4/10 Exceptional (729) "Great location, amenities and staff. " CA $595 CA $698 total includes taxes & fees Sep 28 - Sep 29 [](https://www.expedia.ca/Chicago-Hotels-Nobu-Hotel-Chicago.h36475533.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) ![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) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/14500/14447/2fe2113a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Ritz-Carlton, Chicago Downtown Chicago 9.2/10 Wonderful (1007) "Beautiful place " CA $871 CA $1,022 total includes taxes & fees Oct 5 - Oct 6 [](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) ![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) ![Lobby lounge](https://images.trvl-media.com/lodging/92000000/91140000/91139000/91138950/43b7d4aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The St. Regis Chicago Downtown Chicago 9.2/10 Wonderful (77) "Nice place " CA $871 CA $1,022 total includes taxes & fees Oct 5 - Oct 6 [](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) ![Full-size fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/116000000/115170000/115163800/115163763/3b336ff1.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) ### Art Villa West Town 10/10 Exceptional (2) " " [](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-Southwest-Side-Hotels.s50-0-d553248635976475403.Travel-Guide-Filter-Hotels)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F5Star-Southwest-Side-Hotels.s50-0-d553248635976475403.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 Southwest Side. ![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 $259 CA $305 total Oct 5 - Oct 6 includes taxes & fees 8.4/10 Very Good! (4,975 reviews) [](https://expedia.ca/Chicago-Hotels-Embassy-Suites-Chicago-Downtown.h11580.Hotel-Information) ![Hilton Chicago O'Hare Airport](https://images.trvl-media.com/lodging/1000000/10000/8100/8058/ce2102d4_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Hilton Chicago O'Hare Airport O'Hare International Airport, Chicago, IL CA $282 CA $331 total Oct 25 - Oct 26 includes taxes & fees 8.2/10 Very Good! (2,145 reviews) [](https://expedia.ca/Chicago-Hotels-Hilton-Chicago-OHare-Airport.h8058.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 $237 CA $270 total Oct 4 - Oct 5 includes taxes & fees 8.6/10 Excellent! (2,018 reviews) [](https://expedia.ca/Chicago-Hotels-Hyatt-Regency-OHare-Chicago.h5403.Hotel-Information) Still don't see what you're looking for? [See all properties in Southwest Side.](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=28%2F09%2F2025&endDate=29%2F09%2F2025®ionId=553248635976475403&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=28%2F09%2F2025&endDate=29%2F09%2F2025®ionId=553248635976475403&star=50&star=50&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=28%2F09%2F2025&endDate=29%2F09%2F2025®ionId=553248635976475403&star=50&star=50&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=28%2F09%2F2025&endDate=29%2F09%2F2025®ionId=553248635976475403&star=50&star=50&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=28%2F09%2F2025&endDate=29%2F09%2F2025®ionId=553248635976475403&star=50&star=50&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=28%2F09%2F2025&endDate=29%2F09%2F2025®ionId=553248635976475403&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. ## Learn more about Southwest Side Explore attractions like Balzekas Museum of Lithuanian Culture and Union Stock Yard Gate as you discover things to see and do in Southwest Side. [See all hotels in Southwest Side](https://www.expedia.ca/Hotel-Search?startDate=2025-10-11&endDate=2025-10-12&adults=2®ionId=553248635976475403) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/495000/495661-chicago-il-mdw-midway-intl.jpg?impolicy=fcrop&w=900&h=506&p=1&q=high) Photo by by Midway Intl Airport ## Top Southwest Side Hotel Reviews ## Find out more about Southwest Side Luxury is the name of the game at the best 5 Stars hotels in Southwest Side. If you want to vacation like a true VIP, these are the places to go; from spacious resorts to boutique-inspired hot spots, the top Southwest Side 5 Stars hotels are dedicated to immersing you in the ultimate experience. Want to relax with a serene treatment at a designer spa? These properties offer them. Interested in tasting delicious dishes from top chefs? The gourmet restaurants at the 5 Stars Southwest Side hotels have you covered. You’ll even find first-class hotels near the city’s must-see attractions and most upscale entertainment districts. Plus, when you book your trip with Expedia.ca, you’ll get access to fantastic rates and seasonal discounts, so you can take advantage of a cheap deal on 5 Stars hotels Southwest Side without giving up even an inch of quality. Everything your heart desires (and a few perks designed to make it skip a beat): That’s what’s on offer when you plan a trip to the hotels with 5 Stars in Southwest Side. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [1 Star Hotels in Chicago](https://www.expedia.ca/1Star-Chicago-Hotels.s10-0-d178248.Travel-Guide-Filter-Hotels) - [1 Star Hotels in Far Southwest Side](https://www.expedia.ca/1Star-Far-Southwest-Side-Hotels.s10-0-d553248635976475353.Travel-Guide-Filter-Hotels) - [1 Star Hotels in Gano](https://www.expedia.ca/1Star-Gano-Chicago-Hotels.s10-n6132380-0.Travel-Guide-Filter-Hotels) - [1 Star Hotels in Grace Abbott Homes](https://www.expedia.ca/1Star-Grace-Abbott-Homes-Chicago-Hotels.s10-n6132393-0.Travel-Guide-Filter-Hotels) - [1 Star Hotels in Sheffield and DePaul](https://www.expedia.ca/1Star-Sheffield-And-DePaul-Chicago-Hotels.s10-n553248635976474890-0.Travel-Guide-Filter-Hotels) - [1 Star Hotels in South Englewood](https://www.expedia.ca/1Star-South-Englewood-Chicago-Hotels.s10-n6132433-0.Travel-Guide-Filter-Hotels) - [2 Star Hotels in Chicago](https://www.expedia.ca/2Star-Chicago-Hotels.s20-0-d178248.Travel-Guide-Filter-Hotels) - [2 Star Hotels in Downtown Chicago](https://www.expedia.ca/2Star-Downtown-Chicago-Chicago-Hotels.s20-n6350699-0.Travel-Guide-Filter-Hotels) - [2 Star Hotels in The Loop](https://www.expedia.ca/2Star-The-Loop-Chicago-Hotels.s20-n800024-0.Travel-Guide-Filter-Hotels) - [3 Star Hotels in Chatham](https://www.expedia.ca/3Star-Chatham-Chicago-Hotels.s30-n6132318-0.Travel-Guide-Filter-Hotels) - [3 Star Hotels in Chicago](https://www.expedia.ca/3Star-Chicago-Hotels.s30-0-d178248.Travel-Guide-Filter-Hotels) - [3 Star Hotels in Chicago Ridge](https://www.expedia.ca/3Star-Chicago-Ridge-Hotels.s30-0-d89160.Travel-Guide-Filter-Hotels) - [3 Star Hotels in Lincoln Park](https://www.expedia.ca/3Star-Lincoln-Park-Chicago-Hotels.s30-n6059328-0.Travel-Guide-Filter-Hotels) - [3 Star Hotels in Magnificent Mile](https://www.expedia.ca/3Star-Magnificent-Mile-Chicago-Hotels.s30-n800025-0.Travel-Guide-Filter-Hotels) - [3 Star Hotels in The Loop](https://www.expedia.ca/3Star-The-Loop-Chicago-Hotels.s30-n800024-0.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Chicago](https://www.expedia.ca/4Star-Chicago-Hotels.s40-0-d178248.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Downtown Chicago](https://www.expedia.ca/4Star-Downtown-Chicago-Chicago-Hotels.s40-n6350699-0.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Lincoln Park](https://www.expedia.ca/4Star-Lincoln-Park-Chicago-Hotels.s40-n6059328-0.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Magnificent Mile](https://www.expedia.ca/4Star-Magnificent-Mile-Chicago-Hotels.s40-n800025-0.Travel-Guide-Filter-Hotels) - [4 Star Hotels in The Loop](https://www.expedia.ca/4Star-The-Loop-Chicago-Hotels.s40-n800024-0.Travel-Guide-Filter-Hotels) - [4 Star Hotels in West Bucktown](https://www.expedia.ca/4Star-West-Bucktown-Chicago-Hotels.s40-n553248635976472789-0.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Chicago](https://www.expedia.ca/5Star-Chicago-Hotels.s50-0-d178248.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Douglas Park](https://www.expedia.ca/5Star-Douglas-Park-Chicago-Hotels.s50-n553248635976384191-0.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Downtown Chicago](https://www.expedia.ca/5Star-Downtown-Chicago-Chicago-Hotels.s50-n6350699-0.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Lincoln Park](https://www.expedia.ca/5Star-Lincoln-Park-Chicago-Hotels.s50-n6059328-0.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Magnificent Mile](https://www.expedia.ca/5Star-Magnificent-Mile-Chicago-Hotels.s50-n800025-0.Travel-Guide-Filter-Hotels) - [5 Star Hotels in North Riverside](https://www.expedia.ca/5Star-North-Riverside-Hotels.s50-0-d6132147.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Ranch Triangle](https://www.expedia.ca/5Star-Ranch-Triangle-Chicago-Hotels.s50-n553248635976474882-0.Travel-Guide-Filter-Hotels) - [5 Star Hotels in River North](https://www.expedia.ca/5Star-River-North-Chicago-Hotels.s50-n6350695-0.Travel-Guide-Filter-Hotels) - [5 Star Hotels in The Loop](https://www.expedia.ca/5Star-The-Loop-Chicago-Hotels.s50-n800024-0.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Archer Heights](https://www.expedia.ca/Archer-Heights-Chicago-Hotels-Cheap-Hotels.0-n6132347-0-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels with Free Parking in Archer Heights](https://www.expedia.ca/Archer-Heights-Chicago-Hotels-Hotels-With-Free-Parking.0-n6132347-0-tHotelswithFreeParking.Travel-Guide-Filter-Hotels) - [Romantic Hotels in Archer Heights](https://www.expedia.ca/Archer-Heights-Chicago-Hotels-Romantic-Hotel.0-n6132347-0-tRomanticHotel.Travel-Guide-Filter-Hotels) - [Archer Heights Hotels](https://www.expedia.ca/Archer-Heights-Chicago-Hotels.0-n6132347-0.Travel-Guide-Filter-Hotels) - [Hotels near Ashland-63rd Station](https://www.expedia.ca/Ashland-63rd-Station-Hotels.d6211065.Travel-Guide-Hotels) - [Hotels near Bridgeport Art Center](https://www.expedia.ca/Bridgeport-Art-Center-Hotels.0-l553248621533116324-0.Travel-Guide-Filter-Hotels) - [Boutique Hotels in Brighton Park](https://www.expedia.ca/Brighton-Park-Chicago-Hotels-Boutique-Hotel.0-n6132396-0-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Brighton Park](https://www.expedia.ca/Brighton-Park-Chicago-Hotels-Cheap-Hotels.0-n6132396-0-tCheapHotels.Travel-Guide-Filter-Hotels) - [Brighton Park Hotels](https://www.expedia.ca/Brighton-Park-Chicago-Hotels.0-n6132396-0.Travel-Guide-Filter-Hotels) - [Canaryville Hotels](https://www.expedia.ca/Canaryville-Chicago-Hotels.0-n6132307-0.Travel-Guide-Filter-Hotels) - [Chicago Hotels](https://www.expedia.ca/Chicago-Hotels.d178248.Travel-Guide-Hotels) - [Beach Hotel Hotels in Chicago Lawn](https://www.expedia.ca/Chicago-Lawn-Chicago-Hotels-Beach-Hotel.0-n6132188-0-tBeachHotel.Travel-Guide-Filter-Hotels) - [Boutique Hotels in Chicago Lawn](https://www.expedia.ca/Chicago-Lawn-Chicago-Hotels-Boutique-Hotel.0-n6132188-0-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Family Hotels in Chicago Lawn](https://www.expedia.ca/Chicago-Lawn-Chicago-Hotels-Family-Hotel.0-n6132188-0-tFamilyHotel.Travel-Guide-Filter-Hotels) - [Hotels with a Pool in Chicago Lawn](https://www.expedia.ca/Chicago-Lawn-Chicago-Hotels-Hotel-With-Pool.0-n6132188-0-tHotelwithPool.Travel-Guide-Filter-Hotels) - [Hotels with Bar in Chicago Lawn](https://www.expedia.ca/Chicago-Lawn-Chicago-Hotels-Hotels-With-Bar.0-n6132188-0-tHotelswithBar.Travel-Guide-Filter-Hotels) - [Lgbt Friendly Hotels in Chicago Lawn](https://www.expedia.ca/Chicago-Lawn-Chicago-Hotels-LGBT-Friendly-Hotel.0-n6132188-0-tLGBTFriendlyHotel.Travel-Guide-Filter-Hotels) - [Romantic Hotels in Chicago Lawn](https://www.expedia.ca/Chicago-Lawn-Chicago-Hotels-Romantic-Hotel.0-n6132188-0-tRomanticHotel.Travel-Guide-Filter-Hotels) - [Spa Hotels in Chicago Lawn](https://www.expedia.ca/Chicago-Lawn-Chicago-Hotels-Spa-Hotel.0-n6132188-0-tSpaHotel.Travel-Guide-Filter-Hotels) - [Chicago Lawn Hotels](https://www.expedia.ca/Chicago-Lawn-Chicago-Hotels.0-n6132188-0.Travel-Guide-Filter-Hotels) - [Downtown Chicago Hotels](https://www.expedia.ca/Downtown-Chicago-Chicago-Hotels.0-n6350699-0.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Englewood](https://www.expedia.ca/Englewood-Chicago-Hotels-Cheap-Hotels.0-n101911-0-tCheapHotels.Travel-Guide-Filter-Hotels) - [Englewood Hotels](https://www.expedia.ca/Englewood-Chicago-Hotels.0-n101911-0.Travel-Guide-Filter-Hotels) - [All Inclusive Resorts and in Gage Park](https://www.expedia.ca/Gage-Park-Chicago-Hotels-All-Inclusive-Hotel.0-n6132375-0-tAllInclusiveHotel.Travel-Guide-Filter-Hotels) - [Business Hotels in Gage Park](https://www.expedia.ca/Gage-Park-Chicago-Hotels-Business-Hotel.0-n6132375-0-tBusinessHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Gage Park](https://www.expedia.ca/Gage-Park-Chicago-Hotels-Cheap-Hotels.0-n6132375-0-tCheapHotels.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Gage Park](https://www.expedia.ca/Gage-Park-Chicago-Hotels-Luxury-Hotel.0-n6132375-0-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Gage Park Hotels](https://www.expedia.ca/Gage-Park-Chicago-Hotels.0-n6132375-0.Travel-Guide-Filter-Hotels) - [Hotels near Garfield Station](https://www.expedia.ca/Garfield-Station-Hotels.d6210926.Travel-Guide-Hotels) - [Inns in Garfield Station](https://www.expedia.ca/Garfield-Station-Inns.d6210926-aaInns.Travel-Guide-Accommodation) - [Motel 6 Hotels in Glendale](https://www.expedia.ca/Glendale-Chicago-Hotels-Motel-6.0-n6132385-0--bMotel6.Travel-Guide-Filter-Hotels) - [B&B in Halsted Station](https://www.expedia.ca/Halsted-Station-Bed-And-Breakfast.d6211063-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Hotels near Halsted Station](https://www.expedia.ca/Halsted-Station-Hotels.d6211063.Travel-Guide-Hotels) - [Hotels near Marquette Park](https://www.expedia.ca/Marquette-Park-Hotels.0-l507385-0.Travel-Guide-Filter-Hotels) - [Boutique Hotels in McKinley Park](https://www.expedia.ca/McKinley-Park-Chicago-Hotels-Boutique-Hotel.0-n6132389-0-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Four Seasons Hotels in McKinley Park](https://www.expedia.ca/McKinley-Park-Chicago-Hotels-Four-Seasons.0-n6132389-0--bFourSeasons.Travel-Guide-Filter-Hotels) - [Ski Hotels in McKinley Park](https://www.expedia.ca/McKinley-Park-Chicago-Hotels-Ski-Hotel.0-n6132389-0-tSkiHotel.Travel-Guide-Filter-Hotels) - [Mckinley Park Hotels](https://www.expedia.ca/McKinley-Park-Chicago-Hotels.0-n6132389-0.Travel-Guide-Filter-Hotels) - [Hotels near Midway Intl.](https://www.expedia.ca/Midway-Intl-Airport-Hotels.0-aMDW-0.Travel-Guide-Filter-Hotels) - [B&B in Midway Station](https://www.expedia.ca/Midway-Station-Bed-And-Breakfast.d6211025-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Hotels near Midway Station](https://www.expedia.ca/Midway-Station-Hotels.d6211025.Travel-Guide-Hotels) - [Motels in Midway Station](https://www.expedia.ca/Midway-Station-Motels.d6211025-aaMotels.Travel-Guide-Accommodation) - [Beach Hotel Hotels in New City](https://www.expedia.ca/New-City-Chicago-Hotels-Beach-Hotel.0-n6132388-0-tBeachHotel.Travel-Guide-Filter-Hotels) - [Boutique Hotels in New City](https://www.expedia.ca/New-City-Chicago-Hotels-Boutique-Hotel.0-n6132388-0-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Hotels with a Pool in New City](https://www.expedia.ca/New-City-Chicago-Hotels-Hotel-With-Pool.0-n6132388-0-tHotelwithPool.Travel-Guide-Filter-Hotels) - [Lgbt Friendly Hotels in New City](https://www.expedia.ca/New-City-Chicago-Hotels-LGBT-Friendly-Hotel.0-n6132388-0-tLGBTFriendlyHotel.Travel-Guide-Filter-Hotels) - [Luxury Hotels in New City](https://www.expedia.ca/New-City-Chicago-Hotels-Luxury-Hotel.0-n6132388-0-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in New City](https://www.expedia.ca/New-City-Chicago-Hotels-Pet-Friendly-Hotel.0-n6132388-0-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [New City Hotels](https://www.expedia.ca/New-City-Chicago-Hotels.0-n6132388-0.Travel-Guide-Filter-Hotels) - [Hotels near Pulaski Station](https://www.expedia.ca/Pulaski-Station-Hotels.d6211019.Travel-Guide-Hotels) - [Cheap Hotels in West Englewood](https://www.expedia.ca/West-Englewood-Chicago-Hotels-Cheap-Hotels.0-n6132412-0-tCheapHotels.Travel-Guide-Filter-Hotels) - [West Englewood Hotels](https://www.expedia.ca/West-Englewood-Chicago-Hotels.0-n6132412-0.Travel-Guide-Filter-Hotels) - [Luxury Hotels in West Lawn](https://www.expedia.ca/West-Lawn-Chicago-Hotels-Luxury-Hotel.0-n6132413-0-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in West Lawn](https://www.expedia.ca/West-Lawn-Chicago-Hotels-Pet-Friendly-Hotel.0-n6132413-0-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [West Lawn Hotels](https://www.expedia.ca/West-Lawn-Chicago-Hotels.0-n6132413-0.Travel-Guide-Filter-Hotels) - [Hotels near Zhou B Art Center](https://www.expedia.ca/Zhou-B-Art-Center-Hotels.0-l553248621533116323-0.Travel-Guide-Filter-Hotels) - [Flights to Chicago](https://www.expedia.ca/Cheap-Flights-To-Chicago.d178248.Travel-Guide-Flights) - [Flights from Midway Intl.](https://www.expedia.ca/lp/airports/mdw/flights-from-midway-intl-airport) - [Porter Airlines Toronto (YTZ) to Chicago (MDW) flights](https://www.expedia.ca/lp/flight-routes/porter-airlines-from-billy-bishop-toronto-city-to-midway-intl/pd/ytz/mdw) - [Flights from Toronto (YTZ) to Chicago (MDW)](https://www.expedia.ca/lp/flights/ytz/mdw/toronto-to-chicago) - [Flights from Toronto (YYZ) to Chicago (MDW)](https://www.expedia.ca/lp/flights/yyz/mdw/toronto-to-chicago) - [Flights from Toronto (YYZ) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yyz/ord/toronto-to-chicago) - [Visit Back of the Yards](https://www.expedia.ca/Chicago-Back-Of-The-Yards.dx553248635976382392) - [Visit Brighton Park](https://www.expedia.ca/Chicago-Brighton-Park.dx6132396) - [Visit Canaryville](https://www.expedia.ca/Chicago-Canaryville.dx6132307) - [Visit Chicago Lawn](https://www.expedia.ca/Chicago-Chicago-Lawn.dx6132188) - [Visit Englewood](https://www.expedia.ca/Chicago-Englewood.dx101911) - [Visit Gage Park](https://www.expedia.ca/Chicago-Gage-Park.dx6132375) - [Car rentals near McKinley Park](https://www.expedia.ca/Car-Rentals-In-McKinley-Park.d6132389.Car-Rental-Guide) - [Rental cars Midway Intl. airport](https://www.expedia.ca/Car-Rentals-In-Midway-Intl.d5719117.Car-Rental-Guide) - [Book 5 Star Hotels in Southwest Side on Expedia.com](https://www.expedia.com/5Star-Southwest-Side-Hotels.s50-0-d553248635976475403.Travel-Guide-Filter-Hotels)