Title: Sleepy Hollow Vacation Packages | Holiday Packages & Trips 2026/2027 from CA $744 Expedia.ca [Hotels in Sleepy Hollow](https://expedia.ca/Sleepy-Hollow-Chicago-Hotels.0-n6132427-0.Travel-Guide-Filter-Hotels)[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)[Sleepy Hollow Car Rentals](https://expedia.ca/Car-Rentals-In-Sleepy-Hollow.d6132427.Car-Rental-Guide) ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?impolicy=fcrop&w=1200&h=300&q=medium) # Sleepy Hollow Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to CA $1,096 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, book, and manage your trip all in one place ## Top Holiday Package Deals in Sleepy Hollow Price found within the past 48 hours. Click for updated prices. ![Hotel Riu Plaza Chicago](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Riu Plaza Chicago Downtown Chicago CA $744 per person Mar 17 - Mar 21 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) Great breakfast, Clean room, enjoyed the stay Reviewed on Jan 9, 2026 ![Waldorf Astoria Chicago](https://images.trvl-media.com/lodging/3000000/2720000/2717600/2717582/1040fa3a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Waldorf Astoria Chicago Downtown Chicago CA $2,354 per person Mar 14 - Mar 21 found 1 day ago Roundtrip non-stop flight included Montreal (YUL) to Chicago (ORD) 9.4/10 Exceptional! (1,000 reviews) When we arrived at check in time, we were informed that our room was not ready but that we could upgrade at a discounted additional cost to a suite. At first, we didn't want to do that and decided to wait. The host provided complimentary round of drinks and meal for the wait. We decided to upgrade and I'm so glad that we did. The room was incredible and the service, from concierge, staff and valets, here is top notch. We ordered the Waldorf salad and Waldorf chocolate chip cookies because you have to if you stay here. Loved this place and will definitely return. Reviewed on Jan 5, 2026 ![Hilton Orrington / Evanston](https://images.trvl-media.com/lodging/1000000/20000/19800/19722/fbf21c1c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Orrington / Evanston Downtown Evanston CA $847 per person Mar 3 - Mar 8 found 1 day ago Roundtrip non-stop flight included Montreal (YUL) to Chicago (ORD) 7.6/10 Good! (1,002 reviews) yes, courteous and professional. Reviewed on Jan 3, 2026 ![Trump International Hotel & Tower Chicago](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/209f8cff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Trump International Hotel & Tower Chicago Downtown Chicago CA $1,377 per person Mar 17 - Mar 21 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) The location was more than perfect!! Reviewed on Jan 11, 2026 ![Level Chicago - River North](https://images.trvl-media.com/lodging/75000000/74510000/74500500/74500458/668d065a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago - River North Downtown Chicago CA $1,395 per person Mar 14 - Mar 21 found 1 day ago Roundtrip non-stop flight included Montreal (YUL) to Chicago (ORD) 9/10 Wonderful! (766 reviews) We absolutely love staying here! It’s fantastic every time!! Reviewed on Jan 4, 2026 ## Where to stay in Sleepy Hollow Find the best Sleepy Hollow areas and neighborhoods for the activities you enjoy most. [Learn more about Sleepy Hollow](https://expedia.ca/Chicago-Sleepy-Hollow.dx6132427) ![Downtown Chicago showing a city](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/332000/332072-Downtown-Chicago.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Downtown Chicago 5 out of top 10 points of interest in this area The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art. [Find hotel + flight trips in Downtown Chicago](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Downtown%20Chicago&DestID=6350699&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Magnificent Mile - River North](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/24000/24577-Magnificent-Mile.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Magnificent Mile Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service. [Find hotel + flight trips in Magnificent Mile](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Magnificent%20Mile&DestID=800025&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![The Loop - Downtown featuring a river or creek](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/192000/192013-The-Loop-Downtown.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### The Loop 4.5/5(725 area reviews) Chicago's central business district boasts numerous global businesses, retail establishments, and theaters. Explore the Loop Retail Historic District, Chicago Landmark Historic Michigan Boulevard District, and visit iconic attractions like the Art Institute of Chicago. [Find hotel + flight trips in The Loop](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=The%20Loop&DestID=800024&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Default Image](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/543000/543369-chicago.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### River North Artistic spirit thrives here, with art galleries and a design district featuring luxury interior furnishings. Explore Kingsbury Park, enjoy vibrant nightlife on Hubbard Street, and visit the iconic Contemporaine Building. [Find hotel + flight trips in River North](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=River%20North&DestID=6350695&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Chicago which includes rides](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/23000/23717-Chicago.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Theatre District While you're in Theatre District, take in top sights like Michigan Avenue or State Street, and hop on the metro to see more the city at Washington Station or Monroe Station (Blue Line). [Find hotel + flight trips in Theatre District](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Theatre%20District&DestID=651190586167894016&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ## Sleepy Hollow Hotel Deals ![Hilton Chicago](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/274f52b9_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hilton Chicago 720 S Michigan Ave Chicago IL Fully refundableReserve now, pay when you stay CA $193 CA $267 total Jan 17 - Jan 18 includes taxes & fees 8.4/10 Very Good! (2,498 reviews) Great visit Reviewed on Jan 7, 2026 [](https://expedia.ca/Hotel-Search?startDate=17%2F01%2F2026&endDate=18%2F01%2F2026&selected=12570&PinnedHotelID=12570&HadPinnedHotel=true®ionId=6132427) ![Hilton Chicago/Magnificent Mile Suites](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/f21f6764_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hilton Chicago/Magnificent Mile Suites 198 E Delaware Pl Chicago IL Fully refundableReserve now, pay when you stay CA $124 CA $146 total Jan 18 - Jan 19 includes taxes & fees 8.8/10 Excellent! (3,683 reviews) Room and hotel overall very clean. Noted some things that could be updated in bathroom(stopper in sink didnt go all the way down, peeling caulk and some missing grout). Minor updates. Our sink was clogged when we checked in and I called the front desk, housekeeping and the hotel hotline 4 different ... Reviewed on Jan 7, 2026 [](https://expedia.ca/Hotel-Search?startDate=18%2F01%2F2026&endDate=19%2F01%2F2026&selected=18514&PinnedHotelID=18514&HadPinnedHotel=true®ionId=6132427) ![Club Quarters Hotel Wacker at Michigan, Chicago](https://images.trvl-media.com/lodging/1000000/890000/889800/889753/f3eb640d_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Club Quarters Hotel Wacker at Michigan, Chicago 75 E Wacker Dr Chicago IL Fully refundableReserve now, pay when you stay CA $103 CA $121 total Jan 30 - Jan 31 includes taxes & fees 8.6/10 Excellent! (2,042 reviews) Helpful staff Great view of the River Reviewed on Jan 6, 2026 [](https://expedia.ca/Hotel-Search?startDate=30%2F01%2F2026&endDate=31%2F01%2F2026&selected=889753&PinnedHotelID=889753&HadPinnedHotel=true®ionId=6132427) [See all 4,945 properties in Sleepy Hollow](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=12%2F01%2F2026&endDate=13%2F01%2F2026®ionId=6132427) 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. ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ## Frequently asked questions ### How much does a Sleepy Hollow vacation package cost? ### How do I get a cheap travel package to Sleepy Hollow? ### Where should I stay in Sleepy Hollow? ### How far in advance should I book my Sleepy Hollow vacation? ### What does an Expedia Sleepy Hollow travel package include? ### What should I know before booking a Sleepy Hollow travel package? ### Can I choose my airline with a Sleepy Hollow Expedia vacation package? ### If I'm not able to travel, can I cancel my Sleepy Hollow vacation package? ### Discover the most popular places to visit in Sleepy Hollow ![Magnificent Mile - River North which includes signage, a city and night scenes](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/23000/23728-Magnificent-Mile.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Michigan Avenue You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants. [](https://expedia.ca/Michigan-Avenue-Downtown-Chicago.d6156167.Vacation-Attraction) ![Wrigley Field featuring central business district, a city and a sporting event](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/35000/35620-Wrigley-Field.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Wrigley Field Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium. [](https://expedia.ca/Wrigley-Field-Lakeview.d6034754.Vacation-Attraction) ![Navy Pier](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/54000/54738-Navy-Pier-Chicago.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Navy Pier A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district. [](https://expedia.ca/Navy-Pier-Downtown-Chicago.d6069215.Vacation-Attraction) ### Things to do ![Color Factory Chicago Ticket](https://mediaim.expedia.com/localexpert/49191714/feac7bb1-c7ea-4b19-8342-818eafa34e83.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Color Factory Chicago Ticket CA $46 per adult **96%** of travellers recommend [](https://expedia.ca/things-to-do/color-factory-chicago-ticket.a49191714.activity-details) ![Medieval Torture Museum Ticket with Audio Guide and Ghost Hunting](https://mediaim.expedia.com/localexpert/4973725/0b36f3b1-b375-4fa2-8cfd-1a9815dcdcdc.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Medieval Torture Museum Ticket with Audio Guide and Ghost Hunting CA $49 per adult **96%** of travellers recommend [](https://expedia.ca/things-to-do/medieval-torture-museum-ticket-with-audio-guide-and-ghost-hunting.a4973725.activity-details) ![Flyover in Chicago](https://mediaim.expedia.com/localexpert/50023979/095bdacd-a8be-4515-aac0-469239aa8c0a.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Flyover in Chicago CA $52 per adult **100%** of travellers recommend [](https://expedia.ca/things-to-do/flyover-in-chicago.a50023979.activity-details) [See all activities in Chicago](https://expedia.ca/things-to-do/search?rid=6132427) ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - [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) - [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) - [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) - [Hotels near Midway Intl. ](https://www.expedia.ca/Midway-Intl-Airport-Hotels.0-aMDW-0.Travel-Guide-Filter-Hotels) - [Hotels near Pulaski Station ](https://www.expedia.ca/Pulaski-Station-Hotels.d6211019.Travel-Guide-Hotels) - [Flights to Chicago ](https://www.expedia.ca/Cheap-Flights-To-Chicago.d178248.Travel-Guide-Flights) - [Flights to Midway Intl. ](https://www.expedia.ca/Cheap-Flights-To-Midway-Intl.d5719117.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) - [Porter Airlines Ottawa (YOW) to Chicago (MDW) flights ](https://www.expedia.ca/lp/flight-routes/porter-airlines-from-macdonald-cartier-intl-to-midway-intl/pd/yow/mdw) - [Porter Airlines Montreal (YUL) to Chicago (MDW) flights ](https://www.expedia.ca/lp/flight-routes/porter-airlines-from-pierre-elliott-trudeau-intl-to-midway-intl/pd/yul/mdw) - [Porter Airlines Thunder Bay (YQT) to Chicago (MDW) flights ](https://www.expedia.ca/lp/flight-routes/porter-airlines-from-thunder-bay-intl-to-midway-intl/pd/yqt/mdw) - [Flights from Lake Of The Ozarks (AIZ) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/aiz/mdw/lake-of-the-ozarks-to-chicago) - [Flights from Atlanta (ATL) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/atl/mdw/atlanta-to-chicago) - [Flights from Aurora (AUZ) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/auz/mdw/aurora-to-chicago) - [Flights from Bellingham (BLI) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/bli/mdw/bellingham-to-chicago) - [Flights from Boston (BOS) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/bos/mdw/boston-to-chicago) - [Flights from Buffalo (BUF) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/buf/mdw/buffalo-to-chicago) - [Flights from Baltimore (BWI) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/bwi/mdw/baltimore-to-chicago) - [Flights from Sault Ste. Marie (CIU) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/ciu/mdw/sault-ste-marie-to-chicago) - [Flights from Detroit (DTW) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/dtw/mdw/detroit-to-chicago) - [Flights from Newark Liberty Intl. Airport (EWR) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/ewr/mdw/newark-liberty-intl-airport-to-chicago) - [Flights from Fishers Island (FID) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/fid/mdw/fishers-island-to-chicago) - [Flights from Niagara Falls (IAG) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/iag/mdw/niagara-falls-to-chicago) - [Flights from Las Vegas (LAS) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/las/mdw/las-vegas-to-chicago) - [Flights from Orlando (MCO) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/mco/mdw/orlando-to-chicago) - [Flights from Michigan City (MGC) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/mgc/mdw/michigan-city-to-chicago) - [Flights from Minneapolis (MSP) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/msp/mdw/minneapolis-to-chicago) - [Flights from Ogdensburg (OGS) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/ogs/mdw/ogdensburg-to-chicago) - [Flights from Ontario (ONT) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/ont/mdw/ontario-to-chicago) - [Flights from Plattsburgh (PBG) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/pbg/mdw/plattsburgh-to-chicago) - [Flights from Philadelphia (PHL) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/phl/mdw/philadelphia-to-chicago) - [Flights from South Bend (SBN) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/sbn/mdw/south-bend-to-chicago) - [Flights from Seattle (SEA) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/sea/mdw/seattle-to-chicago) - [Flights from Brandon (YBR) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/ybr/mdw/brandon-to-chicago) - [Flights from Edmonton (YEG) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/yeg/mdw/edmonton-to-chicago) - [Flights from Hamilton (YHM) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/yhm/mdw/hamilton-to-chicago) - [Flights from Halifax (YHZ) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/yhz/mdw/halifax-to-chicago) - [Flights from Kelowna (YLW) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/ylw/mdw/kelowna-to-chicago) - [Flights from Ottawa (YOW) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/yow/mdw/ottawa-to-chicago) - [Flights from Peterborough (YPQ) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/ypq/mdw/peterborough-to-chicago) - [Flights from Québec (YQB) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/yqb/mdw/quebec-to-chicago) - [Flights from Windsor (YQG) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/yqg/mdw/windsor-to-chicago) - [Flights from Moncton (YQM) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/yqm/mdw/moncton-to-chicago) - [Flights from Thunder Bay (YQT) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/yqt/mdw/thunder-bay-to-chicago) - [Flights from Sudbury (YSB) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/ysb/mdw/sudbury-to-chicago) - [Flights from Timmins (YTS) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/yts/mdw/timmins-to-chicago) - [Flights from Toronto (YTZ) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/ytz/mdw/toronto-to-chicago) - [Flights from Montreal (YUL) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/yul/mdw/montreal-to-chicago) - [Flights from Vancouver (YVR) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/yvr/mdw/vancouver-to-chicago) - [Flights from Winnipeg (YWG) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/ywg/mdw/winnipeg-to-chicago) - [Flights from Saskatoon (YXE) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/yxe/mdw/saskatoon-to-chicago) - [Flights from North Bay (YYB) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/yyb/mdw/north-bay-to-chicago) - [Flights from Calgary (YYC) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/yyc/mdw/calgary-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) - [Art Institute of Chicago ](https://www.expedia.ca/Art-Institute-Of-Chicago-Downtown-Chicago.d6064021.Vacation-Attraction) - [Broadview Vacations ](https://www.expedia.ca/Broadview.d7064.Destination-Travel-Guides) - [Buckingham Fountain ](https://www.expedia.ca/Buckingham-Fountain-Downtown-Chicago.d6064027.Vacation-Attraction) - [Burbank Vacations ](https://www.expedia.ca/Burbank.d183178.Destination-Travel-Guides) - [Cibc Theatre ](https://www.expedia.ca/CIBC-Theatre-Downtown-Chicago.d553248621563220853.Vacation-Attraction) - [Carbide and Carbon Building ](https://www.expedia.ca/Carbide-And-Carbon-Building-Downtown-Chicago.d553248621555594910.Vacation-Attraction) - [Chicago Riverwalk ](https://www.expedia.ca/Chicago-Riverwalk-Downtown-Chicago.d553248621533116610.Vacation-Attraction) - [Chicago Theatre ](https://www.expedia.ca/Chicago-Theatre-Downtown-Chicago.d6064049.Vacation-Attraction) - [Chicago Vacations ](https://www.expedia.ca/Chicago.d178248.Destination-Travel-Guides) - [Clearing Vacations ](https://www.expedia.ca/Clearing.d6132083.Destination-Travel-Guides) - [Cloud Gate ](https://www.expedia.ca/Cloud-Gate-Downtown-Chicago.d6182888.Vacation-Attraction) - [Ernest Hemingway Museum and House ](https://www.expedia.ca/Ernest-Hemingway-Museum-And-House-Chicago.d6241604.Vacation-Attraction) - [Frank Lloyd Wright Historic District ](https://www.expedia.ca/Frank-Lloyd-Wright-Historic-District-Chicago.d553248634340947645.Vacation-Attraction) - [Garfield Park Conservatory ](https://www.expedia.ca/Garfield-Park-Conservatory-East-Garfield-Park.d6182807.Vacation-Attraction) - [Grant Park ](https://www.expedia.ca/Grant-Park-Downtown-Chicago.d507389.Vacation-Attraction) - [Hometown Vacations ](https://www.expedia.ca/Hometown.d6132133.Destination-Travel-Guides) - [House of Blues Chicago ](https://www.expedia.ca/House-Of-Blues-Chicago-Downtown-Chicago.d6227753.Vacation-Attraction) - [Loretto Hospital ](https://www.expedia.ca/Loretto-Hospital-Austin.d553248635997986962.Vacation-Attraction) - [Marina City ](https://www.expedia.ca/Marina-City-Downtown-Chicago.d553248621533116577.Vacation-Attraction) - [Millennium Park ](https://www.expedia.ca/Millennium-Park-Downtown-Chicago.d6069201.Vacation-Attraction) - [Obama's House ](https://www.expedia.ca/Obamas-House-Kenwood.d553248621533116333.Vacation-Attraction) - [Richard J. Daley Center ](https://www.expedia.ca/Richard-J-Daley-Center-Downtown-Chicago.d6175173.Vacation-Attraction) - [River Forest Vacations ](https://www.expedia.ca/River-Forest.d5986.Destination-Travel-Guides) - [Robie House ](https://www.expedia.ca/Robie-House-Hyde-Park.d6064059.Vacation-Attraction) - [South Loop Vacations ](https://www.expedia.ca/South-Loop.d6130108.Destination-Travel-Guides) - [The East Bank Club ](https://www.expedia.ca/The-East-Bank-Club-Downtown-Chicago.d553248621555594881.Vacation-Attraction) - [The Loop Vacations ](https://www.expedia.ca/The-Loop.d800024.Destination-Travel-Guides) - [United Center ](https://www.expedia.ca/United-Center-Near-West-Side.d6064077.Vacation-Attraction) - [Unity Temple ](https://www.expedia.ca/Unity-Temple-Chicago.d6064079.Vacation-Attraction) - [Willis Tower ](https://www.expedia.ca/Willis-Tower-Downtown-Chicago.d6064069.Vacation-Attraction) - [Ace Rental Cars in Midway Intl. ](https://www.expedia.ca/Ace-Car-Rentals-In-Midway-Intl.d5719117-c2.Car-Rental-Guide-Suppliers) - [Budget Rental Cars in Midway Intl. ](https://www.expedia.ca/Budget-Car-Rentals-In-Midway-Intl.d5719117-c39.Car-Rental-Guide-Suppliers) - [Rental cars Midway Intl. airport ](https://www.expedia.ca/Car-Rentals-In-Midway-Intl.d5719117.Car-Rental-Guide) - [Dollar Rent A Car Rental Cars in Midway Intl. ](https://www.expedia.ca/Dollar-Rent-A-Car-Car-Rentals-In-Midway-Intl.d5719117-c43.Car-Rental-Guide-Suppliers) - [Enterprise Rental Cars in Midway Intl. ](https://www.expedia.ca/Enterprise-Car-Rentals-In-Midway-Intl.d5719117-c15.Car-Rental-Guide-Suppliers) - [Express Travel Group Rental Cars in Midway Intl. ](https://www.expedia.ca/Express-Travel-Group-Car-Rentals-In-Midway-Intl.d5719117-c1124.Car-Rental-Guide-Suppliers) - [Hertz Rental Cars in Midway Intl. ](https://www.expedia.ca/Hertz-Car-Rentals-In-Midway-Intl.d5719117-c40.Car-Rental-Guide-Suppliers) - [Van Car Rentals near Midway Intl. ](https://www.expedia.ca/Van-Car-Rentals-In-Midway-Intl.d5719117-tVan.Car-Rental-Guide-Class) \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.