Title: Book the Best SHOPPING Hotels in Clearing 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)[Clearing Car Rentals](https://expedia.ca/Car-Rentals-In-Clearing.d6132083.Car-Rental-Guide)[Clearing Vacations](https://expedia.ca/Clearing.d6132083.Destination-Travel-Guides) ![Default HTG hotel image](https://media.expedia.com/media/content/shared/images/travelguides/sem-hotels-tablet.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Shopping Hotels in Clearing, IL from CA $210 ![](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 Clearing Shopping Hotels Tonight [Oct 13 - Oct 14](https://www.expedia.ca/Hotel-Search?regionId=6132083&startDate=2025-10-13&endDate=2025-10-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 14 - Oct 15](https://www.expedia.ca/Hotel-Search?regionId=6132083&startDate=2025-10-14&endDate=2025-10-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=6132083&startDate=2025-10-17&endDate=2025-10-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=6132083&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Clearing Shopping Hotels ![Banquet hall](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/a9ee91b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Junior Suite, City View | Living area](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/cc919354.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Suite, 1 King Bed, Lake View, Lakeside](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/e932b9a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/e43f096f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Congress Plaza Hotel Downtown Chicago 8.0/10 Very good (9405) "Beautiful hotel!" CA $179 CA $210 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Chicago-Hotels-Congress-Plaza-Hotel.h6452.Hotel-Information) ![Ballroom](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/7f542141.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Ballroom](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/8318473d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/9d783fbd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/aaad0ec5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Palmer House a Hilton Hotel Downtown Chicago 8.4/10 Very good (2014) "Great place to stay." CA $251 CA $329 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Chicago-Hotels-Palmer-House-A-Hilton-Hotel.h8079.Hotel-Information) ![Snack bar](https://images.trvl-media.com/lodging/19000000/18060000/18057400/18057374/4844f60a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/19000000/18060000/18057400/18057374/w1584h1367x232y0-c5298bdc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast and dinner served](https://images.trvl-media.com/lodging/19000000/18060000/18057400/18057374/81d45e8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/19000000/18060000/18057400/18057374/edbd6260.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cambria Hotel Chicago Loop - Theatre District Downtown Chicago 8.8/10 Excellent (1426) "Great stay" CA $208 CA $244 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Chicago-Hotels-Cambria-Hotel-Chicago-Loop-Theatre-District.h18057374.Hotel-Information) ![American cuisine, alfresco dining ](https://images.trvl-media.com/lodging/8000000/7070000/7063300/7063210/ab309a05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/8000000/7070000/7063300/7063210/36960d65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Rooftop bar, alfresco dining, open daily](https://images.trvl-media.com/lodging/8000000/7070000/7063300/7063210/df696474.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, in-room safe, desk](https://images.trvl-media.com/lodging/8000000/7070000/7063300/7063210/a073ef3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Godfrey Hotel Chicago Downtown Chicago 8.6/10 Excellent (1898) "Attentive staff, great location " CA $173 CA $236 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Chicago-Hotels-The-Godfrey-Hotel-Chicago.h7063210.Hotel-Information) ![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) ![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) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/9b9a583c.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 (5101) "Great place, good breakfast and the location " CA $214 CA $251 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Chicago-Hotels-Embassy-Suites-Chicago-Downtown.h11580.Hotel-Information) ![Room, 1 King Bed, Corner](https://images.trvl-media.com/lodging/1000000/160000/151200/151139/w3837h2249x3y0-2724cf53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/160000/151200/151139/w3837h2584x3y3-d51aee41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/160000/151200/151139/461957e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/160000/151200/151139/w3840h2557x0y3-a19ef5e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Centric Chicago Magnificent Mile Downtown Chicago 9.0/10 Wonderful (1037) "Great place to stay" CA $232 CA $313 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Chicago-Hotels-Hyatt-Centric-Chicago-Magnificent-Mile.h151139.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/430000/424200/424187/d51caee8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/430000/424200/424187/b9be2277.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/430000/424200/424187/59baefbb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/430000/424200/424187/5e299c2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Chicago Downtown/Magnificent Mile Downtown Chicago 8.4/10 Very good (4077) "Clean room , staff were friendly, a lot of restaurants in the area." CA $237 CA $279 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Chicago-Hotels-Hilton-Garden-Inn-Chicago-DowntownMagnificent-Mile.h424187.Hotel-Information) ![View from room](https://images.trvl-media.com/lodging/1000000/30000/21100/21055/dcfbf36b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/30000/21100/21055/72429a8d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/21100/21055/ae36f870.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio Suite, 1 King Bed](https://images.trvl-media.com/lodging/1000000/30000/21100/21055/2fbef424.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Westin Michigan Avenue Chicago Downtown Chicago 8.8/10 Excellent (1069) "Great location and wonderful staff" CA $220 CA $300 total includes taxes & fees Nov 13 - Nov 14 [](https://www.expedia.ca/Chicago-Hotels-The-Westin-Michigan-Avenue-Chicago.h21055.Hotel-Information) ![Room, Multiple Beds (The Drake Residence) | Living area](https://images.trvl-media.com/lodging/1000000/20000/15100/15092/w3840h2550x0y3-037e0eb4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/20000/15100/15092/7715e6da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 restaurants, breakfast served](https://images.trvl-media.com/lodging/1000000/20000/15100/15092/bdaa578c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/15100/15092/e945085d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Drake Downtown Chicago 8.8/10 Excellent (1314) "Great historic hotel " CA $270 CA $317 total includes taxes & fees Nov 6 - Nov 7 [](https://www.expedia.ca/Chicago-Hotels-The-Drake.h15092.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1120000/1110100/1110039/86b2dc93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1120000/1110100/1110039/289caf93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, coffee/tea maker](https://images.trvl-media.com/lodging/2000000/1120000/1110100/1110039/0d2b3bd2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Tapas bar](https://images.trvl-media.com/lodging/2000000/1120000/1110100/1110039/e6c4a358.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### AC Hotels by Marriott Chicago Downtown Downtown Chicago 8.8/10 Excellent (1005) "Great location. " CA $206 CA $242 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Chicago-Hotels-AC-Hotels-By-Marriott-Chicago-Downtown.h1110039.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=2025-10-28&endDate=2025-10-29®ionId=6132083&adults=2&location_highlights_explore=shopping&sort=RECOMMENDED&openPlayBack=true) ## Top Clearing Hotel Reviews ![Congress Plaza Hotel](//images.trvl-media.com/lodging/1000000/10000/6500/6452/a9ee91b7_y.jpg) ### Congress Plaza Hotel 10/10 Excellent "Staff was outstanding. Very helpful. " [](https://expedia.ca/Chicago-Hotels-Congress-Plaza-Hotel.h6452.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 "Excellent location for visiting Chicago, near major attractions, walking distance to mig mile and Chicago river. Subway station is beside the hotel. Many restaurants are around. Hotel is a little old but condition is good and the price is reasonable. Staffs are very friendly. " [](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 service." [](https://expedia.ca/Chicago-Hotels-Hilton-ChicagoMagnificent-Mile-Suites.h18514.Hotel-Information) ![InterContinental Chicago Magnificent Mile by IHG](//images.trvl-media.com/lodging/1000000/30000/20300/20205/35cb1bb8_y.jpg) ### InterContinental Chicago Magnificent Mile by IHG 10/10 Excellent "The bell hops were awesome!! If i needed to know anything, all i had to do was ask them. " [](https://expedia.ca/Chicago-Hotels-InterContinental-Chicago-Magnificent-Mile.h20205.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 "This was the best hotel I ever stayed at! I did not want to leave. It was very clean and the cleaning staff was attentive and thorough. The staff at the desk were friendly and knowledgeable, and never acted disgruntled or impatient. The bellhops were excellent and trustworthy and anticipated our needs. The hotel was just beautiful and clean in the lobby with boutique atmosphere and art. The room was spacious with comfortable bed and furnishings. The coffee was excellent and the bathroom felt luxurious. We just loved everything! The restaurant food was great quality and not overpriced. And, our location downtown couldn’t be better, near Riverwalk and Michigan Avenue. We thoroughly enjoyed our stay. Thank you, Sonesta!" [](https://expedia.ca/Chicago-Hotels-Royal-Sonesta-Chicago-Downtown.h17543.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 "Clean.Comfortable beds. Great location .Includes a great breakfast." [](https://expedia.ca/Chicago-Hotels-The-Whitehall-Hotel.h17903.Hotel-Information) ![Freehand Chicago](//images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/3b3ade3c_y.jpg) ### Freehand Chicago 10/10 Excellent "All the staff had great energy and were very helpful. Nice bar/lounge area and cozy space. I had a private room and though it wasn’t huge, it was exactly what we needed for our staycation." [](https://expedia.ca/Chicago-Hotels-Freehand-Chicago.h9418281.Hotel-Information) ![Warwick Allerton - Chicago](//images.trvl-media.com/lodging/1000000/30000/25500/25452/w1261h711x0y1-96bd53d1_y.jpg) ### Warwick Allerton - Chicago 10/10 Excellent "Everything was great. It was awesome being back in Chicago again. " [](https://expedia.ca/Chicago-Hotels-Warwick-Allerton-Chicago.h25452.Hotel-Information) ![Holiday Inn Chicago Dwtn - The Mart by IHG](//images.trvl-media.com/lodging/1000000/10000/5500/5467/2806d344_y.jpg) ### Holiday Inn Chicago Dwtn - The Mart by IHG 10/10 Excellent "Great hotel - great location. It's a bummer that the view from the restaurant/bar isn't as cool as it used to be, because of the new buildings in front of it, but it's still pretty - and the drinks and food are very good. Room was very nice and clean. 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[Waterpark Hotels in Downtown Chicago](https://www.expedia.ca/Downtown-Chicago-Chicago-Hotels-Waterpark-Hotels.0-n6350699-0-tWaterparkHotels.Travel-Guide-Filter-Hotels) - [Winery Hotels in Downtown Chicago](https://www.expedia.ca/Downtown-Chicago-Chicago-Hotels-Winery-Hotel.0-n6350699-0-tWineryHotel.Travel-Guide-Filter-Hotels) - [Downtown Chicago Hotels](https://www.expedia.ca/Downtown-Chicago-Chicago-Hotels.0-n6350699-0.Travel-Guide-Filter-Hotels) - [Aparthotels in Forest View](https://www.expedia.ca/Forest-View-Apart-Hotels.d6132093-aaApartHotels.Travel-Guide-Accommodation) - [B&B in Forest View](https://www.expedia.ca/Forest-View-Bed-And-Breakfast.d6132093-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Chalets in Forest View](https://www.expedia.ca/Forest-View-Chalets.d6132093-aaChalets.Travel-Guide-Accommodation) - [Guest Houses in Forest View](https://www.expedia.ca/Forest-View-Guest-Houses.d6132093-aaGuestHouses.Travel-Guide-Accommodation) - [Luxury Hotels in Forest View](https://www.expedia.ca/Forest-View-Hotels-Luxury-Hotel.0-0-d6132093-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Forest View Hotels](https://www.expedia.ca/Forest-View-Hotels.d6132093.Travel-Guide-Hotels) - [Resorts in Forest View](https://www.expedia.ca/Forest-View-Resort-Hotels.d6132093-aaResortHotels.Travel-Guide-Accommodation) - [Townhomes in Forest View](https://www.expedia.ca/Forest-View-Townhomes.d6132093-aaTownhomes.Travel-Guide-Accommodation) - [Cheap Hotels in Garfield Ridge](https://www.expedia.ca/Garfield-Ridge-Chicago-Hotels-Cheap-Hotels.0-n6132357-0-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels with Free Parking in Garfield Ridge](https://www.expedia.ca/Garfield-Ridge-Chicago-Hotels-Hotels-With-Free-Parking.0-n6132357-0-tHotelswithFreeParking.Travel-Guide-Filter-Hotels) - [Romantic Hotels in Garfield Ridge](https://www.expedia.ca/Garfield-Ridge-Chicago-Hotels-Romantic-Hotel.0-n6132357-0-tRomanticHotel.Travel-Guide-Filter-Hotels) - [All Inclusive Resorts and in Hickory Hills](https://www.expedia.ca/Hickory-Hills-Hotels-All-Inclusive-Hotel.0-0-d6132128-tAllInclusiveHotel.Travel-Guide-Filter-Hotels) - [Casino Hotels in Hickory Hills](https://www.expedia.ca/Hickory-Hills-Hotels-Casino-Hotel.0-0-d6132128-tCasinoHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Hickory Hills](https://www.expedia.ca/Hickory-Hills-Hotels-Cheap-Hotels.0-0-d6132128-tCheapHotels.Travel-Guide-Filter-Hotels) - [Ski Hotels in Hickory Hills](https://www.expedia.ca/Hickory-Hills-Hotels-Ski-Hotel.0-0-d6132128-tSkiHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Justice](https://www.expedia.ca/Justice-Hotels-Cheap-Hotels.0-0-d120367-tCheapHotels.Travel-Guide-Filter-Hotels) - [Historic Hotels in Justice](https://www.expedia.ca/Justice-Hotels-Historic-Hotel.0-0-d120367-tHistoricHotel.Travel-Guide-Filter-Hotels) - [Farmstay in Lyons](https://www.expedia.ca/Lyons-Agritourism.d183188-aaAgritourism.Travel-Guide-Accommodation) - [B&B in Lyons](https://www.expedia.ca/Lyons-Bed-And-Breakfast.d183188-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Chalets in Lyons](https://www.expedia.ca/Lyons-Chalets.d183188-aaChalets.Travel-Guide-Accommodation) - 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[Mccook Hotels](https://www.expedia.ca/McCook-Hotels.d6132272.Travel-Guide-Hotels) - [Hotels near Midway Intl.](https://www.expedia.ca/Midway-Intl-Airport-Hotels.0-aMDW-0.Travel-Guide-Filter-Hotels) - [Hotels near SeatGeek Stadium](https://www.expedia.ca/SeatGeek-Stadium-Hotels.0-l6131157-0.Travel-Guide-Filter-Hotels) - [Farmstay in Summit](https://www.expedia.ca/Summit-Agritourism.d177671-aaAgritourism.Travel-Guide-Accommodation) - [Aparthotels in Summit](https://www.expedia.ca/Summit-Apart-Hotels.d177671-aaApartHotels.Travel-Guide-Accommodation) - [B&B in Summit](https://www.expedia.ca/Summit-Bed-And-Breakfast.d177671-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Chalets in Summit](https://www.expedia.ca/Summit-Chalets.d177671-aaChalets.Travel-Guide-Accommodation) - [Guest Houses in Summit](https://www.expedia.ca/Summit-Guest-Houses.d177671-aaGuestHouses.Travel-Guide-Accommodation) - [Hostels in Summit](https://www.expedia.ca/Summit-Hostels.d177671-aaHostels.Travel-Guide-Accommodation) - 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[Flights to Chicago](https://www.expedia.ca/Cheap-Flights-To-Chicago.d178248.Travel-Guide-Flights) - [Flights to Lyons](https://www.expedia.ca/Cheap-Flights-To-Lyons.d183188.Travel-Guide-Flights) - [Flights to McCook](https://www.expedia.ca/Cheap-Flights-To-McCook.d6132272.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 Buffalo (BUF) to Chicago (MDW)](https://www.expedia.ca/lp/flights/buf/mdw/buffalo-to-chicago) - [Flights from Detroit (DTW) to Chicago (MDW)](https://www.expedia.ca/lp/flights/dtw/mdw/detroit-to-chicago) - [Flights from Toronto (YTZ) to Chicago (MDW)](https://www.expedia.ca/lp/flights/ytz/mdw/toronto-to-chicago) - [Flights from Winnipeg (YWG) to Chicago (MDW)](https://www.expedia.ca/lp/flights/ywg/mdw/winnipeg-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) - [Rental cars Midway Intl. airport](https://www.expedia.ca/Car-Rentals-In-Midway-Intl.d5719117.Car-Rental-Guide)