Title: Sleepy Hollow Vacation Packages & Trips 2025 from CA $493 | 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. ![Hilton Grand Vacations Club Chicago Magnificent Mile](https://images.trvl-media.com/lodging/38000000/37650000/37641700/37641670/843f6e73_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Grand Vacations Club Chicago Magnificent Mile Downtown Chicago CA $493 per person Nov 24 - Nov 26 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.2/10 Wonderful! (291 reviews) Food price was high but everything was fine Reviewed on Oct 4, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-24/2025-11-26/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=37641670&paandie=true&dealMarker=1qy9L2f9MnB3Zlaf3cNbvlxAforiZTzxo0mGQWruPNgFZwFX_V07CPlN7Rz9BkrZ) ![The Westin Michigan Avenue Chicago](https://images.trvl-media.com/lodging/1000000/30000/21100/21055/dcfbf36b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Westin Michigan Avenue Chicago Downtown Chicago CA $1,012 per person Dec 24 - Dec 29 found 20 hours ago Roundtrip non-stop flight included Edmonton (YEG) to Chicago (ORD) 8.8/10 Excellent! (1,046 reviews) One bad part -drain in tub very slow. Called to fix it but even afterwards still slow. Also room was not cleaned one day, had to call to get it done. Reviewed on Oct 2, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-24/2025-12-29/?FromAirport=YEG&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=21055&paandie=true&dealMarker=6CuNs0vxu2uILjtBFDt_OxznqKC6Y5Jsj7dc5AE5G_9EAWtBG6CcADT-t4ZH4Y3K) ![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 $1,258 per person Dec 15 - Dec 19 found 1 day ago Roundtrip non-stop flight included Edmonton (YEG) to Chicago (ORD) 9.4/10 Exceptional! (1,716 reviews) I stayed at the Trump International Washington DC, and this one pales in comparison to be honest. The staff was friendly/excellent, but the hotel itself was pretty standard. I expected the same level as the old Washington DC hotel. The shower was plugged up and drained as slow as frozen molasses. Reviewed on Oct 6, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-15/2025-12-19/?FromAirport=YEG&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1723215&paandie=true&dealMarker=q82CN2n13NUTAYSDQ7OVEoodEnv8ERvxpuKizgqGQdNmrygVGQ8lqEGlmLDZLP7L) ![Pendry Chicago](https://images.trvl-media.com/lodging/1000000/990000/982600/982552/8007d2c6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Pendry Chicago Downtown Chicago CA $707 per person Dec 15 - Dec 19 found 1 day ago Roundtrip non-stop flight included Edmonton (YEG) to Chicago (ORD) 9.4/10 Exceptional! (1,085 reviews) The bed was extremly comfortable Staff was very attentive. Highly recommend Reviewed on Oct 7, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-15/2025-12-19/?FromAirport=YEG&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=982552&paandie=true&dealMarker=q82CN2n13NUTAYSDQ7OVEt_ucKPcw06RoTKW-AOex9QZgcth9PmToE80TTWpR9x4) ![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 $1,565 per person Dec 15 - Dec 19 found 16 hours ago Roundtrip non-stop flight included Edmonton (YEG) to Chicago (ORD) 9.4/10 Exceptional! (1,002 reviews) Simply love this hotel Reviewed on Sep 18, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-15/2025-12-19/?FromAirport=YEG&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=2717582&paandie=true&dealMarker=n5HdZvsqH8RXHZEDY1p-0WkiSj2lkEm62fCIphX2V6tGi6U6ponE8o9h7NQITUlQ) ## 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 modern architecture and a city](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/54000/54398-Chicago.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Lincoln Park 5/5(20 area reviews) Upscale national retailers, boutiques, and bookstores abound in this affluent area, alongside numerous restaurants and coffee shops. Must-see attractions include Lincoln Park Zoo, Chicago History Museum, and North Avenue Beach. Easily accessible via CTA transit and major roads. [Find hotel + flight trips in Lincoln Park](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Lincoln%20Park&DestID=6059328&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ## Sleepy Hollow Hotel Deals ![Congress Plaza Hotel](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/a9ee91b7_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Congress Plaza Hotel 520 South Michigan Avenue, Chicago, IL Fully refundableReserve now, pay when you stay CA $179 CA $210 total Nov 2 - Nov 3 includes taxes & fees 7.8/10 Good! (9,342 reviews) "We did not use laundry service, and the front desk staff did not mention any availbale services" Reviewed on Oct 7, 2025 [](https://expedia.ca/Hotel-Search?startDate=02%2F11%2F2025&endDate=03%2F11%2F2025&selected=6452&PinnedHotelID=6452&HadPinnedHotel=true®ionId=6132427) ![Freehand Chicago](https://images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/3b3ade3c_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Freehand Chicago 19 East Ohio Street, Chicago, IL Fully refundableReserve now, pay when you stay CA $95 CA $137 total Nov 11 - Nov 12 includes taxes & fees 7.8/10 Good! (2,426 reviews) "Excellent location, clean and good room partners" Reviewed on Oct 6, 2025 [](https://expedia.ca/Hotel-Search?startDate=11%2F11%2F2025&endDate=12%2F11%2F2025&selected=9418281&PinnedHotelID=9418281&HadPinnedHotel=true®ionId=6132427) ![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=340&ch=150) ### Embassy Suites by Hilton Chicago Downtown River North 600 N State St, Chicago, IL Fully refundableReserve now, pay when you stay CA $213 CA $250 total Nov 9 - Nov 10 includes taxes & fees 8.4/10 Very Good! (5,072 reviews) "The onsite parking is worth the money compared to other lots. Walk where you can. The Embassy is in the perfect location for a lot of attractions." Reviewed on Oct 9, 2025 [](https://expedia.ca/Hotel-Search?startDate=09%2F11%2F2025&endDate=10%2F11%2F2025&selected=11580&PinnedHotelID=11580&HadPinnedHotel=true®ionId=6132427) [See all 4,740 properties in Sleepy Hollow](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=12%2F10%2F2025&endDate=13%2F10%2F2025®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? > Get your credit card ready, because a getaway to Sleepy Hollow starts from a tempting CA $493. When you bundle your flights, hotels and more into a package, you'll land the lowest prices. ### How do I get a cheap travel package to Sleepy Hollow? > Book everything in the one place with our Sleepy Hollow vacation packages. We have incredible bargains on hotels, flights, tours and more that'll keep your travel budget happy and your adventurous spirit alive. And, with more than 550 partner airlines and 1,000,000 hotel options around the world to pick from, there are endless opportunities to mix and match as you like. ### Where should I stay in Sleepy Hollow? > There's plenty to do in Sleepy Hollow, so stay near its best attractions and spend more time sightseeing. Balzekas Museum of Lithuanian Culture is one spot to put on your must-see list. ### How far in advance should I book my Sleepy Hollow vacation? > Reserving your flights early with Expedia means one less thing to worry about. A number of air carriers advertise prices up to 12 months in advance. This is usually the cheapest time to book. If circumstances have left you booking late, fantastic last-minute deals to Sleepy Hollow sometimes emerge a few weeks before departure. ### What does an Expedia Sleepy Hollow travel package include? > Expedia has everything you need to lock in Sleepy Hollow trip, but what goes into your package is your call. Select from any combination of rental cars, flights and hotels. Chasing some experiences or tours to keep you on the go? Once you've made your booking, you can add them on too. No matter your style, there's a package to meet your needs. ### What should I know before booking a Sleepy Hollow travel package? > Booking all the parts of your getaway together is a great way to save. Bundle your airfares, rental cars and hotels into a neat package. But your options don't end at hotels. Expedia has all kinds of properties, including vacation rentals like beachside villas and city apartments. You've got choices galore! ### Can I choose my airline with a Sleepy Hollow Expedia vacation package? > Expedia has access to more than 550 airline partners worldwide, so you definitely can. Simply select the carrier that suits you and craft your ideal Sleepy Hollow getaway. ### If I'm not able to travel, can I cancel my Sleepy Hollow vacation package? > Certainly, and we'll help you every step of the way. You may be able to cancel or amend your Sleepy Hollow vacation package at no cost if you booked in the last 24 hours. But you may incur a fee from your hotel, airline or car rental company for older bookings. If your travel plans unexpectedly change, have a look at our [Customer Service Portal](https://www.expedia.ca/service/?langid=4105) for more information. ### Discover the most popular places to visit in Sleepy Hollow ![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) ![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) ![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 ![River tour boat in Chicago](https://mediaim.expedia.com/localexpert/170432/2ab44ef1-1211-4f4f-9436-ce9a14d4241f.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Architecture River Tour CA $67 per adult **96%** of travellers recommend [](https://expedia.ca/things-to-do/architecture-river-tour.a170432.activity-details) ![Relax and enjoy the view](https://mediaim.expedia.com/localexpert/46106377/6686561e-a3aa-4cbf-9e71-f553bde2fa06.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Chicago Architecture Center River Cruise aboard First Lady CA $77 per adult **96%** of travellers recommend [](https://expedia.ca/things-to-do/chicago-architecture-center-river-cruise-aboard-first-lady.a46106377.activity-details) ![Color Factory Chicago Ticket](https://mediaim.expedia.com/localexpert/49191714/1b6e1be3-a6ba-4b3d-8e57-4d0336c3fd23.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Color Factory Chicago Ticket CA $47 per adult **94%** of travellers recommend [](https://expedia.ca/things-to-do/color-factory-chicago-ticket.a49191714.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. 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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.